rbucks.com

My Life in AI

2025-12-29T10:00:00-08:00

I haven't written anything here about artificial intelligence, even though I use it every day. My work life is entirely dependent on it now. Being without it would feel like doing my job with no internet.

The main tool for me is Claude Code. I run a tech company, and we have far more tech problems than we can solve. I carve out the ones that I'm best equipped to tackle:

Unknown ROI: It's probably not worth it for one of our engineers to go spelunking down an uncharted path. There are plenty of known positive ROI problems that they can solve.

Requires full context: Doing the job well requires some detailed knowledge about the entire company. Only a few of us here have that breadth of perspective.

Is modular: Despite needing full context, it's not really part of the existing infrastructure and can be tinkered on without impacting anything in production.

I love these kinds of projects. It's like going from 0 to 1 all over again, but within Shovels, so I have a lot of resources. I have servers, databases, and smart people I can ask when I get stuck.

Most importantly, I have Claude Code.

I've been messing around with web applications for about 15 years now. I understand web frameworks and database architecture. I've built Ruby on Rails and Python Django apps from scratch. Looking back, those were hard times. It was slow. When I ran into the inevitable errors, I had to Google them and scroll through Stack Overflow answers until I found the one that worked. On the plus side, I actually learned how to build.

With Claude Code, I punch far above my weight. Instead of writing code, I prompt for output. When I know the destination, I can have Claude do the hard work of setting up the Python code structure and writing all of the modules. For my projects that meet the criteria I laid out above, "vibe coding" is fine. I don't need to read every line. Eventually, if the project is successful, somebody else on my team will do that. While I'm spelunking, code quality matters much less.

As I write this, I'm having Claude Code confirm that a data migration worked. It noticed that there were 244 files out of some 200,000 that appeared to have not transferred. This particular challenge is interesting because we just acquired a company, and they stored about 190gb of files in Google Drive. The founder wanted me to sync that drive to my laptop. No way, I thought. We need this in S3, and I need to translate all of his code to Python.

Over 24 hours, I had Claude learn everything about this project. I gave it access to the founder's GitHub data processing and website repositories and a Google Drive that ties it together. Claude had to analyze PowerShell scripts with sparse notes about the data processing flows. Claude asked me clarification questions and made me think. I took breaks to make sure I was nudging Claude in the right direction, but I had to rely on it to tell me what all of these scripts do. Together, we learned the founder's process. We looked at the git history and metadata on his files to see what's been kept up to date and what's obsolete. The pieces started to fit together, and we came up with a plan that simplifies a lot of what the founder was doing and sets us up to efficiently take over operations.

This would have taken me days, maybe weeks, because I wouldn't have been able to focus on it. It would have required a lot of context switching, and as a result, the process would have slowed down significantly. Instead, Claude Code is a focused process. It can run on a single task while I toggle back and forth between Slack and email and other daily items. Claude can wait patiently for an answer, for hours at a time, and pick up immediately once I provide a response. This is not human, and it's wonderful.

For someone like me, doing the projects I'm actually best equipped at my company to be doing, Claude Code is perfect. It's the ultimate complement to my regular work brain. It loves to chew through complex, modular projects that need a lot of context. It makes me feel 100X more productive to outsource most of this deep thinking to Claude.

I don't know what the future holds, but I do know I'll be able to influence it more with this tool.

Thinking a lot about community

2025-12-21T12:00:00-08:00

My dog is named Charlie. I kind of wish we spelled it differently. She could be Charley, the same spelling that Steinbeck used in "Travels with Charley." But that's not the way we spelled it when we named her. I live with this mistake every day.

Charlie likes to be near me, but not next to me. She wants to be in the same room, or the near vicinity, but not really in touching distance. If I go outside, she goes outside but keeps her distance. When I come back inside, she goes to the other room and lies down in the dark. This is how she shows her affection.

Her community is us, the Buckley family, the kids of Manzanita Court, and the handful of dogs and dog owners she has come to know well in the 10 months since we got her. It has me thinking: what's my community? Who's in it? And how did they get here?

My community is my family, of course. That's obvious. I could say everybody has this but I know that's not really true. People who don't have families find it elsewhere: in sports, at church, or the bar. Older people are more likely to not have family.

Neighbors are my community. I somehow landed in this great neighborhood where I ended up enjoying the company of just about everybody within 20 houses of my own. There's a single woman a few houses down who drives too fast, has earphones on whenever I see her, and has barely said a word to me in five years. We have neighbors across the street whose kids play with my own nearly every day but have I said a word to them recently? Nope.

Then there's the neighborhood dads. For the last 5 years and maybe the next 2, we meet at the bus stop and chat like the old men at Starbucks. How's the snow report? What are your vacation plans? What, this Friday they're letting the kids out early? I live for it. I shuffle my kids out the door because I don't want to be late and miss the chatter. It's six minutes of standing around talking about nothing. I have Charlie with me, in my vicinity, because now she's used to this routine too. We both need that hit of community every morning.

My community is also the people I work with. Unlike my neighbors, who I liked out of luck, I get to design my work community. Being the CEO lets me influence my work community far more than I'd otherwise be able to. So of course I really like my coworkers. This is an important community. I'm going to spend more time with them than my neighbors and on some weeks, even more than my family. We're a community by choice, not by convenience. It feels good that we're all opting into it.

When I think about my place in these communities, I wonder if I'm like Charlie, in the vicinity of it, wanting to be near it, but not in the middle of it. Or do I want to be the center of attention, the orchestrator, the mayor of the community? I think my neighbors may put me closer to the mayor bucket. My coworkers certainly would. My wife is the mayor of the family. I think I'm happy to observe. I want to be known and noticed, but I'm not a center of attention kind of guy. I play the part when I have to, but I like assembling communities more than I like being in the center of them.

Some people build communities so they can be the center of it. The purpose of the community is to be that stage on which they perform. Others build community because that is their gift. Their satisfaction is seeing the community take on a life of its own.

I think I'm in that latter camp. I like to see my neighbors get along. I don't have to do much, and I played a more proactive role when I first moved here; now the social fabric has moved on. In my business, I'm a de facto orchestrator, but it too has assumed a life of its own. In my family, I'm important, but my wife is clearly in the middle of it.

I'm happy to be in the vicinity.

Where the Red Fern Grows

2025-09-30T12:00:00-07:00

I have been reading Where the Red Fern Grows, one chapter each night, to my kids. I can't take credit for this idea; it was my wife's. I've been the one keeping it going, though.

I love this book. It was first recommended to me by my Aunt Harriet some thirty-ish years ago. I remember reading it at my grandparent's house. I was probably 9 or 10 at the time. When I got to the end, I became a complete sobbing mess. I really let myself go. My grandparents must have been out or asleep, because I distinctly remember going to the bathroom to look at myself in the mirror and being shocked at the snot-nosed, red-eyed mess looking back at me.

It was the first time a book broke my heart. Even now, as I read it, those raw emotions come rushing back. I get teary-eyed at Billy's grandpa, the store owner who helped him order his coon hounds, and at the sheriff who protected him from the bullies in town. Every little anecdote plucks a string in me. I don't know if it's because I saw myself in that young boy or because I saw my grandpa's dog Bowie in Old Dan and Little Anne. Maybe it's because the little cabin in the Ozarks reminded me of Pinecrest.

As a narrative arc, it has all the elements that I love:

An old person reminiscing. You see it in The Sandlot, Fried Green Tomatoes, The Titanic, and A River Runs Through It. This well-worn literary device has my number. I'm 43, I'm still young, in the prime of my life, but I know (I mean, I hope) that one day I'll be old and that wears on me. All the movies of old people telling stories about their youth make me feel my age, and sometimes it hurts.
A boy on an adventure. There's a hero's journey element to this story as well. A boy craves dogs. He struggles to obtain them. He rejoices, and then tragedy strikes, and he finds redemption. I immediately care about the boy. I can see myself in him.
Faithful dogs. I don't know if my love of dogs came before this book or because of this book. But it's there, and this is a book for people who love dogs.

I read this book for the first time when I was around the age of the protagonist, the boy named Billy. Thirty some-odd years later, I'm the age of his dad, Papa, and I'm reading it to my kids, who are a few years younger than Billy.

I see more of the story through Papa's eyes now. What was it like to raise three children on a ranch in the middle of the wilderness? How did it feel when Billy took off on a multi-day to pick up his pups without telling anyone? These are the reflections of a parent. I'm less concerned about Billy's desire to buy the dogs and more interested in what his Papa thinks and feels about all this hunting.

Maybe that's what makes a book a classic. You can read it at different ages and capture a different set of feelings and impressions. I can see that my own kids, who also love dogs, are most drawn to the descriptions of how hard Billy worked to buy, pick up, and train them. They can feel that relationship. I can still feel that too, but it's not my only focus. That's what age does to your perspective, I suppose.

I'm halfway through the book. More adventure awaits, and I know the end is coming... but I'm looking forward to it anyway.

Twenty-five years since I graduated high school

2025-08-03T15:00:00-07:00

Today I went to my high school reunion. I went because I wanted to go, and also because I organized it. Why did I organize it? I don't know. I'm writing this post to figure that out.

I'm a sucker for nostalgia. I wrote about it in my post about 1994 music. My teens, the 90s, were a special time in my life.

I didn't appreciate it then as much as I do now, but having all the time I wanted to just be is a tremendous gift. My mom provided everything I needed to live a normal adolescence. I'm grateful for it. I think back on the 90s and feel warm and fuzzy.

Part of it is not having any fear of missing out. I was perfectly content with my neighborhood. Between roller hockey and music, my weekend plans were filled. There was always something to do, some place to go, and a 7-11 or Jack In The Box to stop by at on the way. There must have been dull days, but I don't remember them. This was a time of my life that just worked.

I must have been craving that feeling when I posted on the Facebook group that my class created many, many years ago. There had been some chatter about doing a reunion but plans never materialized. This year is our 25th year after high school and I knew this year would come and go unless someone said something about making a reunion happen.

One night a few months ago, that's what I did. I said this needed to happen, and I suggested we do it towards the end of summer but before school starts for most families. Either of the first two weekends in August should work, I figured, and I also decided that we should do it at a public park in the middle of the day. I love a barbecue and the potluck picnic format would make it family-friendly.

I suggested it! And people responded. We got 33 RSVPs and a bit more than half of them showed up.

What does a reunion have to do with my 90s nostalgia? I think it's being in the presence of artifacts of this time in my life. These people were there too. They are proof that the 90s happened, that this time in my life was real, because they lived it too. It's the difference between seeing a work of art online and visiting it in the museum. When you're there, live, it feels different.

That's the same feeling I get with my classmates from Los Altos High School. I knew a few of them well. Most were vaguely familiar faces. But all of them gave me that feeling. We did that together. You were there too. And now we all miss the 90s.

We can all be nostalgic together.

Maybe the museum is a bad example. It's more like a concert. Here's a perfect example: Tonight, my sister-in-law and her husband went to see the Backstreet Boys at the Sphere. Talk about nostalgia. It's one thing to listen to "I Want It That Way" streaming on your headphones and remember that middle school dance. It's a completely different experience to be in the same building as not only the Backstreet Boys themselves, but thousands of other people having the same experience at the same moment.

My reunion today was a Backstreet Boys concert. It was all of us being nostalgic together, in awe of the passage of time, and grateful to still be alive to witness it.

0 to 1, 1 to 10

2025-06-29T00:00:00-07:00

About six years ago I announced on this very blog that I was done with venture capital. Kaput. Over. I was going out on my own, bootstrapped, never to rely on another dollar of VC money.

Things can change.

Shovels announced a $5M Seed round earlier this month. I'm proud of it. I wanted it. I still want it, and I still don't regret it, and I don't think I ever will. We will need this money and we will turn this $5M into many multiples of market value. It's invigorating.

So, what happened between 2019 and 2025?

To put it succinctly, Shovels happened.

I'll start from the beginning.

Coming off of MightySignal, where I took over leadership, I was convinced that I wanted to start another data business. I decided three things would have to be true about this next data business:

It needed to be related to the real, physical world.
It needed to be helpful to climate companies.
It needed to be a big idea. Like, really big.

I could determine the first two points on my own, but how would I know if the idea was big enough? There's an obvious answer: get validation from VCs. I'll know it's big enough if I can raise money for it!

For the pre-seed, which I raised when we had no revenue, I just got lucky. Zach Coelius from Coelius Capital knew me (or really, just knew of me, but that was good enough!) So, I was able to raise the $1M I set out to raise when I wrote my business evaluation of Shovels.

My takeaway from pre-seed, btw, is that it's a crapshoot. You're pitching the highest of high-risk investors. These guys are the definition of crazy. To find one to lead your round, you just have to get lucky. Here's what needs to be true, all at the same time:

The investor likes you
The investor already believes the business opportunity
The investor is currently investing

For all three to be true, lightning has to strike. You get lightning to strike by continuing to pitch. You get intros, you prepare, you meet and pitch. You follow up.

When you get the right investor, it moves fast. Don't waste time with the slow ones. Don't waste time with the ones who don't already believe that your market is massive.

That's my pre-seed advice.

Now here's my seed advice. I call it "O to 1, 1 to 10".

The first phase, 0 to 1

Every entrepreneur starts with a 0 to 1 idea. There's no other choice. Your first idea is the most practical version. It has to make the most sense because you've rolled that thing around in your head like a rock tumbler and what comes out is smooth and... practical.

Practical is a good thing. It helps you focus on making money, inch by inch, step by step. You have to break it all down into small pieces or you'll choke.

Now here's the thing. Most 0 to 1 ideas can be bootstrapped. You probably don't need money to do it. Or maybe you need some, but you certainly don't need millions of dollars to build your practical idea.

If you did need all that money, it wouldn't be practical!

This is the irony of fundraising in this stage -- you know you're supposed to ask for money, but you know deep down that you don't really need it. Sure, you want to pay yourself and your co-founder, but what's that? $250 or $500K for one or two years? You can't pitch the big guys with that small of a raise.

So you struggle with the slides because there's a little voice asking you why you're asking for so much money. You find ways to convince yourself that you need it and hope to find an investor who believes you.

To be clear, this is all perfectly normal. I've been here many times. Shovels was here once too, but I got lucky and pitched a 0 to 1 idea to someone who saw the path from 1 to 10. I'll explain this part now.

The real phase, 1 to 10

The 1 to 10 is what happens if your practical idea is successful. The earlier you figure out what this is, the better.

It can take a while, though, so be patient and listen to your customers. At some point, the pattern will emerge and you'll realize your perfectly practical idea was really just one piece of a much larger puzzle.

You'll be amazed. The investors you pitch will be flabbergasted. Everybody will love it! This is when you can recruit top talent, raise a ton of money from the best investors, keep everyone around you motivated. This is the 1 to 10 phase.

I learned this the hard way.

When Shovels was doing well, growing at a healthy clip, I decided to raise what we now call a "seed" round. Our first was $1.5M, a healthy "pre-seed." I decided that with more than $350K of annual subscription revenue, I was ready to open up a round and let everyone give me money.

I struggled with the deck. It was very... practical. There was nothing wrong with it, but it didn't sizzle. I got plenty of meetings but I couldn't close anybody. Even my super excited lead pre-seed investor was out. He didn't think I had the vision yet.

I was confused and disheartened.

Then I went to New York City for Climate Week and had a bagel with one investor who focuses on story. That's his value-add -- messaging and story -- and he told me about a company that he loves that helps police departments identify patterns in retail theft. Since thieves (shoplifters, primarily) operate across police jurisdictions, it's not easy for them to catch the scent when there's a stealing ring. So he invested in a startup that solves this problem for police departments.

"Isn't that boring?" I asked. "And isn't that market size really small? How can they build a big business selling software to police?"

"Police departments is just the start," he said. "By figuring out how to solve this problem and get police on board, they had all the social proof and learnings they needed to sell direct to retailers."

Software for police departments to see misdemeanor patterns across jurisdictions is the 0 to 1.

Once there, they can expand to every retailer in the country. That's the 1 to 10.

I understood what he was telling me. My current vision for Shovels, to find more ways to sell permit data, was actually still the 0 to 1. There was another missing step, and it was holding my story back. I needed to find it before he or anyone else would invest.

That was September. By October I had the scent. My team flew in for our twice-yearly summit, and at our final session I shared with them my vision for the future of Shovels: local government data, all of it.

Permit data is the 0 to 1.

Everything else is the 1 to 10. By establishing ourselves as the leading provider building permit data, we unlock the opportunity to sell everything else. And by getting everything else, we create a data network, which also becomes a valuable moat.

I closed our $5M seed round the first time I pitched it. True fact.

I believe that at least right now, today, this is the way to fundraise. It could change tomorrow, but right now, even if you're raising a pre-seed, include something, anything, even just a guess about what your 1 to 10 will be.

I guarantee that it will help you close!

My best advice for entrepreneurs

2025-04-27T20:57:00-07:00

Hey, I've been writing.

It's been too long since I've posted here, but I've been writing on the Shovels blog, writing to my investors, and writing gobs and gobs of emails. I spend my evenings clearing my inbox or writing code.

Tonight, however, is different. I feel like making my first rbucks post in a while. It's because I have something to share.

I'll throw this up on LinkedIn eventually, but my good news humblebrag here is that Shovels broke $80,000/mo in revenue last week. That's $80K MRR in startup-speak. That's shorthand for a million dollars per year in revenue! (I know, the real number is $83,333, but we'll round that down.)

It's a big deal. It's the thing every startup dreams of when they first launch: let's make a million dollars. Let's clear that bar. At $80,000 per month you have a real business and you can support some real employees. There's NO DOUBT that the business has legs. The only question now is how far you can take it.

It took us 20 months to get here, and I have to admit that for the first time in my entrepreneurial career, I never doubted that this would happen. I knew Shovels felt different. I felt different. Together, we felt different. It was the right idea at the right time for me. This trilogy is important. However, if I had to pick one from the three that matters most, it'd be the idea.

And that's what I want to share here: the importance of idea.

When I interviewed to teach at DVC, I had to put a lesson plan together. I decided to do it on ideation. I still have my notes. I decided that tonight I need to turn this double-sided piece of paper into a blog post.

What's an idea?

An idea is a thought or suggestion as to a suggested course of action or a concept / belief. That's what the dictionary says.

Entrepreneurs call an idea a way to solve an unmet need.

Unmet need! This concept is important.

Let's use an example: the light bulb.

What's a light bulb? Is it an idea? Or a solution? What's the purpose of a light bulb and whom does it benefit? A light bulb might solve several problems; which is the most important? Most of us have never thought of a light bulb like this.

The scientist says, "My idea is to create light from electricity."

The entrepreneur says, "My idea is to make people more productive indoors and at night."

A "business idea" takes an "idea" a few steps further. Let's explain this using our ideation selection framework.

How do you choose an idea?

You should evaluate an idea by considering each of these attributes:

Criteria	Evaluation
Target market	Size
Existing solution	Penetration
Unmet need	Urgency
Key benefits	Strength
Defensibility	Technology

For each of the criteria, you want more of the evaluation. A good idea should be positive in every evaluation.

An efficient way to evaluate is to turn the table above into a sentence. For our light bulb, it would go like this:

For anyone dissatisfied with candles and kerosene lamps due to dimness, flicker, and inconvenience, I'm creating a light bulb that is bright, constant, portable, and electric, and is also difficult to manufacture.

This one-liner also makes a great pitch! When you have a strong idea, your pitch is also strong. They always go together.

Shovels made it to $80K MRR because it was a good idea. That's the bulk of it. It helped that I was motivated, that I had the perfect co-founder, and I was able to get a great team together. Those aren't small things, but none of it would have been impactful if the idea was bad.

So while I celebrate this moment, and I've been glowing about it all week (enjoying it while it lasts), I'm simultaneously humbled by the simple fact that I'm at the mercy of the idea.

Companies work because ideas work.

Entrepreneurs are merely vectors for good ideas.

Short post of appreciation

2025-02-17T21:07:00-08:00

I'd like to think that I take nothing for granted, that I'm always present and appreciative and live life to the fullest. None of this is true, of course. I get caught up in what I'm doing or the exact opposite, caught up on my screens, oblivious to what I or anyone around me is doing. Either way, I get sucked into the vortex.

One thing I can say with certainty is I have held myself to one standard: when my kid asks for my attention, I give it to them, and when they ask me to do something with them -- anything with them -- I do it.

Today is a holiday, President's Day, so my kids were not in school, but my wife and I worked. After dinner I did what I usually do while my kids are noodling around the house: I worked. I think I was editing a Snowflake query when I heard those magical words, "Dad, will you play chess with me?"

I did the right thing. I closed my MacBook and walked to the kitchen table where I keep a chessboard for this exact reason. While I played chess with my 8-year-old, my 10-year-old was practicing "Let It Be" on the piano. She was playing on the Yamaha Clavinova that I bought to replace the Baldwin piano that I inherited from my grandpa. Chess and piano. These are not the pieces of the puzzle that my wife brought to the picture. These are both mine, two hobbies that my kids adopted and seem to really enjoy.

For the rest of their lives, they'll know how to play chess. They'll appreciate the game. And at least one of my kids will know how to find middle C and play an A minor chord on piano.

I did that, and it took work. It took leading by example and showing interest when they showed interest.

I'm thinking about this tonight because yesterday my wife learned that her good friend was going through something awful. Her husband is on life support, perhaps from a heart attack, but we don't know. He's been in a coma for a week. They have two kids and a third child is due in five months. He may not make it. It's a tragedy on every dimension. I can't think of anything positive about this.

I can't help but think, "What if it was me?" What would I regret? What would my kids remember?

Most of us hope to die surrounded by family. I still read the obituaries and most of the time that's what they say. There must be a reason for it. Family is in our DNA, ever present in our thoughts, a safe place in our souls.

Our friend's husband might die surrounded by family. He may not know it. He also might break the coma and live another healthy fifty years.

Time will tell, but in the meantime, I take this moment to appreciate what I've done well and what I'll still improve. Take it day by day, try to be present, and appreciate everything I love.

Thoughts on building a brand

2024-12-25T09:06:00-08:00

Marketing is increasingly central to who I am and what I do as an entrepreneur. This is not what I expected.

When I started in entrepreneurship, I was the operations guy, not the CEO. I liked to think about how things worked. I dealt with the accountants, the lawyers, the recruiters. It was fun and I was good at it. When my first business failed, I remember meeting with a top-tier VC who funded us. He asked what I was going to do next. I said I didn't know.

"Every company needs a Ryan Buckley," he said.

"Thank you," I replied, unsure of exactly what he meant.

The conversation stuck with me ten years later. That was my personal brand back then: The guy who works behind the scenes and gets things done. A capable workhorse with some leadership potential.

My brand is different now: The CEO of Shovels who writes about entrepreneurship and building permit data. For my LinkedIn followers, I hope it's also about thoughtfulness and authenticity. For my new investors, I hope it's about determination and transparency.

Of all the definitions of what a brand is, I like Seth Godin's concept of a promise. A brand a promise. It's a set of expectations tightly bundled together into this thing that we call a brand. The rbucks.com blog brand is some authentic content (not AI), well-written (I try to minimize typos), about topics that I find interesting. The Shovels brand is high quality construction data accompanied with helpful customer service. The Saranap brand (my neighborhood) is walkable, family-friendly, charming area with lots of young kids.

A brand promises that these expectations are met. If the promise is broken by unmet expectations, the brand loses value. It gets tarnished. The best brands in the world have accumulated greater and greater expectations over the years, and the years themselves produce compounding value. This is how brands become incredibly valuable.

One important note: a brand is not a logo. A logo is not a brand. A logo can represent a brand, and a beautiful logo can enhance a brand on the margins, but the logo itself doesn't make the brand. Here are some examples:

American Express: Just a light blue square with the name of the company
Gap: Just a dark blue square with the name of the company
Bass: Just a red triangle above the name of the company

Yes, the fonts are distinctive, but that's the effect of decades (or in the Bass case, nearly 250 years) of presence in society. A logo can be very, very simple, and the brand can still represent a wide variety of complex associations and expectations. Brand development takes hard work, years of consistency, and a dedicated staff to ensure that expectations are always met. Logo development just takes a consultant. I care about brands far, far more than I care about logos.

My final point ties brand to culture. It's hard to imagine a great brand without a great culture, because you need that culture for the brand to consistently meet expectations. Years of achieving excellence cannot be driven by an outside consultant, a beautiful logo, or the perfect website with optimized copy. It's culture. Culture makes the brand work and that's why it's so important. Culture makes the product great, the support friendly, the documentation current. It's all of the things that allow a company to fulfill and even exceed the promise that the brand represents. I truly believe this.

I've had to think a lot recently about the Shovels brand. What does it mean to our audience? Is it meeting and exceeding expectations? Are the logo and website good brand ambassadors? It's been brought up to me more than once that we should consider a rebrand, make the Shovels guy and logo a bit more polished and serious. We should hire consultants to "rebrand" us. On the one hand, I can see that: make the logo more serious, get more serious customers! But on the other hand, it didn't sit right with me. Logos don't make companies. Logos don't make brands. Logos don't delight customers.

So I squashed it. We need design help, but we don't need a rebrand. And to the extent we need to rethink our positioning, that's work we have to do in-house.

I'm not a great slide designer, so I hired someone who can make great slides. They're not trying rebrand us. They're taking our content, our logo, and working with our brand to make a sales deck that looks nice. I'll translate the design over to the website and make it look nicer. These are useful exercises that are part of building our brand.

We'll always keep rethinking what we do and how we describe it. But WE need to be the ones doing it because that's how WE entrench the culture that makes our brand work.

I believe there's such thing as a "good enough" logo. The three logos above fit that mold. They're not beautiful. They're just logos, and they're good enough. What makes the three brands stand the test of time is everything else. That's what I'm focused on.

The process

2024-09-29T11:04:00-07:00

I started fundraising again for Shovels. Not because I need to -- because I want to. The process of fundraising and being fully transparent with my team throughout has revealed to me that this process, my process, is the way that I do most things. Seeing it reflected back to me in our #investors Discord channel has got me thinking more about my process.

My process is messy. I don’t mean disorganized; it’s organized to the tilt. I track every conversation, set reminders for myself, and keep a file on every VC and angel I’ve ever talked to. The messiness is shown in the evolution of my strategy. I let myself get excited about new ideas that come up in conversation. I allow myself to be impressed by the founders of these venture capital firms and feel lucky to have their attention. I want to be persuaded that their vision for my company is superior to my own.

As a result, I swing. I go from here to there based on the last conversation I had. We’re a data company, no, we’re a software company, actually, we’re both! My fully-remote team and I meet for an hour twice a week and I relay my thinking in near real-time. For them it’s like a soap opera, new characters entering and leaving the stage, falling in love, breaking up. I post notes like journal entries for myself and my team on the Discord channel almost every day.

I know this is unusual. Most CEOs don’t do this, even when the team is very small. I do it because my team was originally against the fundraise and, as it turns out, they might have been right.

We have the opportunity to become profitable and never fundraise again – why not do that? It sounds great, sure, but being profitable is not my goal. I want the option to be profitable, but I don’t necessarily want to exercise that option. I’d rather grow fast. Fast growth, market share, and rapid innovation are a stronger strategy than burn minimization.

What I'm finding, though, is that it's a lot easier to fundraise when the path is set. We have product-market fit and we can prove it by the demand we're seeing for our products. When we first launched, making product was easy and making sales was hard. All of a sudden, making sales is easy and making product keep up with all the sales is hard.

The job of the CEO is to not run out of money. Outside of that, I think my job as CEO is to keep my team invested, and rather than tell my teammates what to believe, I’d rather show them. Being so transparent about the fundraise and the evolution of my thinking is my way of showing them how rich our opportunities are.

So many things to do! And look, we can get smart finance people to give us money to do them!

So as I scroll back in time over the last eight weeks I see how much has changed over the course of this fundraise process. I’m learning as I go and trying to find patterns in the reactions of the people I’m pitching. I’m also paying attention to how I feel as I go through the motions. I’m finding what resonates and what falls flat. I’m digesting the feedback even when it’s hard and trying to decide how much weight to put on a negative reaction. Even when I don’t know, I paste the whole rejection email into the #investors channel. I want my team to see it too.

Eventually I will have seen enough. I’ll have looked at all sides and taken my own perspective from doing this for nearly two years and I’ll make a decision about our fundraise and what Shovels will be two years from now.

I’ll run my process by getting my hands dirty and sharing it with my team.

It’s the only way I know how to do it.

The vertical approach

2024-09-01T20:03:00-07:00

I wrote about the difference between platforms versus point solutions a while ago. I explained why I would proactively try to make Shovels a platform. Point solutions are critical parts of the technology ecosystem, but they're not where the value goes. Value accrues to the platforms and I want Shovels to be a platform.

That's all fine and good and even a bit obvious. It gets more interesting when I ask the question that I've asked myself so many times before: what if it can be both?

Why point solutions remain point solutions

Here's my argument. Yes, it's possible to be both, but it has to be done in a particular order. A company must be a platform first and then add on point solutions, not the other way around.

It is very hard for point solutions to become platforms. I'm sure it's been done but the problem with finding examples is the only folks who know this transformation occurred are the founders and maybe an early investor or two. They had to do it early, deliberately, and sustain a major change in business direction without breaking everything. This is hard. The odds of success are quite low. If that was part of the original story, it's not what they would be known for today.

It's hard for point solutions to become platforms because it requires a major shift in the company DNA. In a typical tech example, a point solution is a data service. They collect data first-hand, do a bit of manipulation, perhaps, and send the data to other companies that do more transformations and shuttle it off to a broader market. Those companies that buy data from point solutions are the platforms. They're buying from multiple point solutions, squishing the data together, and reselling it in some sort of software solution for a specific high-value customer.

This is MightySignal (my last data company which focused on narrow type of mobile data) getting acquired by Airnow (which had an ad platform and many types of mobile data). This is also SafeGraph, perhaps the largest point of interest database, selling data to Placer.ai, which helps stores choose the best retail sites.

My argument is that even though MightySignal and SafeGraph know that Airnow and Placer are in a better strategic position to capture the most value, they won't change. Being a good point solution is a good, safe place to be. You won't grow, but you can run profitably until you wear out. That's one force keeping them sitting still. The other is that by the time they recognize their poor position, they've slowed down while the platforms have sped up, making the difference too far and hard to overcome.

I remember this feeling at MightySignal. I'd look at Airnow, Data.ai, Apptopia, and think, "Man, they have so much data. We just have this little bit. Oh well, I guess we'll just keep doing what we're doing."

And that's how it went until we sold the company to one of them.

Being both a platform and a point solution

It's a lot easier to go the other way around, to build a platform and then add point solutions. I've seen it happen.

Platforms usually add point solutions by acquiring them. They don't lose their status as platforms; they expand vertically. They may determine after a couple of years of buying a dataset that there are myriad uses for it and they want more control over it. They have to decide whether to buy or build, but for platforms this is an easy answer: they buy. That's their DNA.

For example, Data.ai already had the type of data that MightySignal offered. I was curious how they got it; it seemed to come in-house because I'd never heard of another point solution selling to them. I knew them all. I learned that they bought this data for a while and then eventually acquired the entire company. Now they own the data provider, so they would never need to be a MightySignal customer and they wouldn't want to acquire us either.

Closed lost. On to the next one.

I was envious then and I'm very strategic now. I think this platform-first approach is smart and the right way to go. Have a platform mentality from the beginning. Be scrappy about how your resources are spent (both time and money) and set out early to build a broad base of data products. Buy, trade, and swap your way into a portfolio of datasets. Use those data to build products for a defined niche and make those customers very happy. Let them tell you where to expand. Get those datasets the same way you got the first ones. Keep going.

At some point you'll have enough power and influence to acquire entire companies instead of just buying their data. You do this in order to have strategic control because at this point you have that option and the stakes are a lot higher.

The value-maximizing option

Platforms capture the most value and are the most resilient to market changes. They're a portfolio of assets (like datasets, software products, or brands) and by having a portfolio approach, they get to "feel" out different market opportunities. When a great one comes along, they have the option to double-down on it, go deep into that niche, and mine all the value. This is the point-solution emerging from the platform.

In my field, data products, the point-solution manifests in two ways: below the data and above the data. Below the data is the extraction process. Above the data is the software.

Today, Shovels is investing in software. We don't need to buy someone else's software products; software is cheap. We're investing in the point solution of having visibility into building permits and contractors in specific markets. Eventually, through software, we can explore other point solutions too.

There's a possibility Shovels could also expand below the data. I'm open to it, and we will definitely do it if we need to expand into an area where there are no data vendors. For now, I'm relieved that we were able to build a good business in a market where we can acquire the data rather than extract it ourselves.

It has made all the difference.

I'm down with ICP

2024-07-05T08:24:00-07:00

I became a better entrepreneur in the last few months. I have never thought so hard about ideal customer profiles (ICP), had so many conversations with marketing experts, or written so much about this to my investors.

The net result: it's another superpower. I'm finding that thinking hard about ICP, having the stamina to keep doing it and the skill to do it well, is special. It sets an entrepreneur apart and puts their business on stronger footing. In short, figuring out your ICP is akin to seeing the future.

The Shovels ICP: A case study

I've been doing all this ICP work for Shovels, of course. I never thought twice about the ICP for my side projects; the stakes were too low. Who cares? Just build and let the chips fall where they may.

Shovels is too interesting. It's too big, there's too much surface area to look at. With Shovels, I want to get it right. It's my baby, my reputation, my investors' money on the line. I have a co-founder and a team this time. I want to go all the way. Figuring out the ICP for Shovels has been a struggle but I think we may have it figured out now.

The hard thing about ICP is that it's multidimensional. I think of see ICP on two axes: the what and the who.

The what

For example, here are just a few of the ways I have described the "what" of Shovels:

An API for building permits
A database of permits and contractors
A building contractor directory
A list of contractor recommendations
A marketing solution for construction companies
Permit histories on any address
A sales intelligence platform

The "what" is meant to be what we offer. It's the actual thing that people buy. I can spin Shovels in a lot of ways on this axis. It changes based on who we talk to, what we're building, and what I'm most excited about at the time.

The who

Tho "who" is who's buying. It's the "profile" in ICP. Fortunately, I can look empirically for this answer. I have hundreds of registrations and dozens of customers to base this answer on.

Unfortunately, there is no majority. Among the many profiles are:

Climate tech companies
Construction tech companies (who sell to contractors)
Property tech companies (who sell to homeowners)
General contractors
Banks
Financial tech companies that work with banks
Building materials suppliers
Real estate data aggregators
Energy utilities
City managers

The list goes on. It's nuts. We use to watch this list grow in awe. It made me feel good -- so many different types of customers see value in Shovels! We're onto something!

While true, it also makes messaging a challenge. Each of the profiles has a specific twist on what we're building. They may share some fundamentals, but on the edges they are different, and you can't please everyone.

The matrix

As I said in the beginning, an ICP is where the "what" meets the "who." A nice simple ICP structure, a one-sentence tagline, is something like "Shovels is the what for who."

The challenge, as you might have guessed, is that the "what" is different for each "who." I could create a two-dimensional matrix with each "who" on the y-axis and each "what" on the x-axis. Where the who and the what intersect is a match.

For example, I know that climate tech companies (the who) want an API for building permits (the what). I also know that construction tech companies (the who) want a contractor directory (the what). Many profiles want more than one thing.

Shovels can provide a lot of things to a lot of profiles. So, are we "an API for building permits and a contractor directory for climate tech and construction companies"?

That's clunky, but it's a place to start.

However, with many of these intersections to consider, we'll have to prioritize, and I've learned that it's best to prioritize on the "who." Products can change; profiles can't.

We've been working with a couple of market strategists to get this right and I learned there are a few ways to prioritize our profiles:

Number of them in the market
Total combined revenue
Distribution of revenue (ideally there are a lot of big ones rather than a few super massive ones)
Urgency to use us
Familiarity with our use case

If I look at each of our profiles through this lens then it gets a lot easier to see the differences.

The choice

We can rank our profiles across these priorities as low, medium, or high. Here's a start.

It gets us closer, but you can see there's not an obvious winner. We have a few options to sort this out further. We could weight the priorities on top. I'm assuming that they're worth the same; they probably aren't. We could add more priorities and more profiles. Maybe I need to be more specific (e.g. "climate tech companies who work with heat pumps").

This is where the work comes in. It's an ongoing process to drill in, refine, zoom out, and see where we're at.

Conclusion

We spent a lot of time doing this and I think we've landed in a good spot. We have a BIG profile. They understand our product and they have urgency. We have some proof points in our pipeline and I suspect that we'll have our first paying customers in this category very soon.

What is this profile, exactly? Not telling! It will emerge in our marketing over time, but I don't want to make the announcement yet. We still have more work to do.

A short essay on free will

2024-06-11T19:20:00-07:00

My most pretentious title yet! 🥳

Whatever. I’m not a philosopher, but neither are my friends. So here goes.

I believe in free will. Put me in the camp that says my choices today were not dictated by the cosmic explosion 14.3 billion years ago. I believe there is randomness in the world. I believe in chance.

Furthermore, I believe this truth to be self-evident. I’ll try to briefly explain using a short proof that the free will argument is flawed.

The logic goes like this:

If we don’t have free will, then chance does not exist
If chance does not exist, then everything can be predicted
If everything can be predicted, then time does not exist
If time does not exist, then we don’t exist (consciousness, space, everything falls apart)
Since we do exist (just ask Descartes), then we must have free will

To fully give these ideas the inside-out analysis they need is beyond my ability. I don’t have the time to get caught up on all the philosophy already written on these concepts. I won’t enjoy writing about it, either.

What I’m sharing here is a thought that I can’t shake. It’s my best attempt at explaining why it’s completely abhorrent to me that we should throw our hands up and believe we have no choice. That world sounds so dull. I don't want to live in it.

To not have free will implies the existence of a plan, a god-like creator who set the dominos tumbling. I don’t like this at all. It’s too religious, so I reject it on those grounds too.

Regardless, I will briefly explain the five parts of my counterfactual argument. I'm going to argue against the existence of free will in order to prove that it does in fact exist. I'm trying to prove that free will leads to a conclusion that we all must agree could not be possible.

If we don't have free will, then chance does not exist

Yeesh, what a place to start.

If I don’t think too hard about this one, it appears quite simple. With no free will, everything is pre-ordained. Let's be clear here: we are not special. We are made out of the same star dust as tectonic plates and asteroids. If we don't have free will, then nothing has free will. We have to apply the same rules to the entirety of the universe.

Thus everything happens for a reason, and that reason is built into the very fabric of our universe. Every law of physics, biology, and chemistry is describing the perfect order that was set from the beginning of time. If you wound back the clock and replayed the big bang, every single little thing, from the flicker of a butterfly's wing to the last presidential election, every war, murder, crash of a wave, earthquake and cosmic explosion would happen in exactly the same way at exactly the same time.

That's what no free will means.

Therefore, if there is no free will, then chance cannot exist, because all the cards were dealt 14.3 billion years ago.

If chance does not exist, then everything can be predicted.

It’s important to note that this argument doesn’t need to explain how everything is predicted. The point is the mere possibility of perfect omnipotent prediction. Without chance, we leave open the possibility that every single little and large event can be predicted. I find that the anti-free will argument requires this to be true.

Indeed, this argument flows logically from the last one. If everything is preordained, if the cards are dealt and the game proceeds by fixed rules, then if you know all the cards, you can predict everything. I'm not shaken by the idea that nobody can know all the cards. That fact doesn't matter. What matters is that if the cards are known then the future, the entire future can be predicted.

I think this argument flows logically from the last one.

If everything can be predicted, then time does not exist

Here we start to get into the heart of what I'm trying to say.

In the game of Hearts, this is where you see me slough a diamond instead of a heart or the queen of spades. You get suspicious of what I'm up to.

Indeed, this here is the crux of my argument. Everything hinges on this point. If you want to attack my line of reasoning, this is where you should start. I'll try to support my position knowing I've left my kidney exposed.

In a universe where the future is perfectly predictable, we have no need for time. Given this as fact, time makes no sense. Therefore, it must not exist.

I'll briefly explain. If I have the cards, I can play out the future. As I perfectly predict the future, time compresses. I bring the future forward and time loses meaning. It's only when the world is unpredictable that time is necessary. You need time for chance to be chance, for unpredictability to exist.

If you can predict everything, you don't need time. Therefore, time isn't required. If time isn't required, then it won't exist. If it won't exist, then it does not exist.

If time does not exist, then we don’t exist

It follows. If we have no need for time, then we have no need for anything.

Time builds our reality. Without it, there's nothing.

So if we have no chance, we have no time, and we have... nothing.

I'll just end that line of reasoning there.

Since we do exist, then we must have free will

Here's my other vulnerable point. I'm presupposing that we exist. I'm anchoring on Descartes, the one shoulder I stand on. I assume this to be truth, therefore the argument that we have no free will must be false.

The other way to turn this around is to say that those who are anti-free will are also anti-consciousness and anti-Descartes. They must believe that we are living in a grand simulation, connected to the matrix, that we all took the blue pill and are in a dream world controlled by intelligent machines. The AI overlords have already taken over and we're all just pawns on their grand chess board.

I reject this wholeheartedly. I just can't believe it. It's fatalistic. That is wrong and I think I've proven it.

Wouldn't you agree?

Doing it the slow way

2024-06-11T17:40:00-07:00

I have not written here in a few months. This break happens whenever I teach. My classes absorb what time I have left after Shovels. In the evening, when my family is in bed and the quiet house is my writing muse, I have emails to answer and papers to grade.

The sun rises and sets over and over again… and I don’t write. Ho hum.

I just read my last post, What I want in 2024. Some things are going well. Shovels is good but we haven't found product-market fit yet. My fitness is great. My friendships are strong. Teaching was hard; I got tired at the end of the semester. I stopped playing chess; just couldn't fit it in.

But it is summer now and the days are longer. I’m not teaching live classes and I’ve adjusted my fall semester schedule to have more time to work on Shovels. I felt comfortable enough to hire another Shovels employee.

It’s time to rock and roll, but I want to do it slowly.

I don’t like to go fast. I like a steady, even jog. I’m a marathoner, not a sprinter. I can ride my bike 135 miles in one day and enjoy it. I like the climbs more than the descents. Going too fast makes me nervous -- the faster you go, the harder you stop.

This is not typical entrepreneurship advice. The consensus is to move fast and break things. Grow, grow, grow! And then grow faster.

The problem is that growth is not free. Fast growth means building and selling fast, and that usually means hiring lots of people. People are expensive, so growth means spending a lot of money.

When the money runs out, then what? You stop. Hard.

My approach with Shovels, now about a year and a half into this journey, is to grow steady. Not fast, not slow. Steady. Keep the burn rate reasonable in the context of our product market development. Don’t overspend, but also don’t be afraid of spending. Not spending enough can hurt you too.

Some say slow is bad. I don’t think they’re wrong. I will start slowly and gather speed over time. I’ll treasure our cash and only spend when I see a return. My investors gave me money to invest into Shovels. Every dollar we spend should be building this business up, making it stronger, fortifying the defenses, and helping it move faster.

Slow can be strong. In a long race, I’ll bet on the jogger, not the sprinter. The goal at this stage is to not burn out before we break even. Once that happens, we can start investing in speed.

I want to assure my investors (at least one of whom reads this blog!) of one thing -- if I found a cheap way to move fast, I would be all over it. I'm skeptical of silver bullets, though. I'm learning that product-market fit is a rare bird. You can spend your life looking for it and then all of a sudden it perches on your windowsill. I'm not suggesting that I set around do nothing! It takes hard work to get lucky, but it also takes time. We've got to keep the windows open and the lights on.

In the meantime, I continue jogging. I like a long run, probably more than most people, and I don't mind the soreness. For the eighteen months I've been battling all kinds of running pains: a sore right knee, then left hip, then left achilles. I ran around Pinecrest Lake yesterday and felt nothing. It was magical.

You push through the pain. It just takes time.

What I want in 2024

2024-01-01T18:02:00-08:00

If I do this right, the way I want to do it and believe that I can do it, this will be a big year for me. Maybe the biggest.

As I shared a couple of blog posts ago, I turned 41. Age is only a number, but it has become a symbol on a map. It's the sign post on the road, a ticking clock. Turning 41 in 2023 meant a lot to me. It meant roots, friendships, patterns, and routines. It meant kids that are getting older and more independent. It meant a marriage that lasted many times longer than the one between my mom and dad.

I wanted financial stability when my kids were young and we had a mortgage on our house and then a major remodel. Now it's different. I feel like I can dream big again. This past year set the stage. This next year is when I go for it.

Shovels to find product-market fit

For me, this is going to be the year of Shovels. I've already gone all-in on this idea. I've raised $1.3M to date, and likely will raise another $200K more before hitting the upper limit on how much dilution we can take in this round.

While the fundraising is important because we need it, the goal is to build a big business. Big to me, right now, is $10M ARR (annual recurring revenue). That's the target, and I'm willing to fight tooth and nail to get there.

The path that we'll take is selling to the enterprise. We have to sell bigger deals to bigger companies. The ability for me to hire a sales team depends on it. We'll still take the smaller customers -- I want to support climate tech startups -- but we can't spend time handholding them through the process. The product itself will need to do 99% of it.

We have 10 small customers. Our MRR (monthly recurring revenue) is already higher than my last two bootstrapped companies. This business is inherently different.

The big deals are in my pipeline, and I'm attracting an elite team to help me find more. It's all very clear to me. It just makes sense. It's like I can see the future.

When I think about Shovels, I feel a combination of pride, excitement, and anticipation. It's a potent mixture. I think the last time I had it was in college. Everything worked out as planned (I went to grad school at Harvard) and I have many reasons to believe that my dreams for Shovels will come true too.

I'll know if it's working by the start of summer.

Teaching to be rewarding

When I'm not doing business, I'm teaching it.

This spring I'll teach a couple of supervision and management courses that I've never taught before. I'm looking forward to it. I did most of my course preparation last week in Hawaii. Poolside, palm trees swaying in the breeze, the Pacific Ocean in the distance. Kids playing in the pool. It could be worse.

I decided to introduce cases into my teaching. Every week, we'll discuss a case and I'll let the students work on their responses in class. The supervision and management cases are interesting. We'll discuss Uber and Netflix, how cultures form, and how important leadership is throughout the lifecycle of a business. As Shovels grows up, examples like these will take on new meaning. It's the perfect time for me to study management, supervision, and leadership.

I'm living these lessons as I teach them, and for me this has become something of a superpower. I really enjoy interacting with students in class. I like extemporaneous speech. I look forward to grading. Perhaps someday it will get tiring. Maybe I'll find that I can no longer be an entrepreneur while I teach entrepreneurship. I'm not so sure, though. For now, I'm finding that doing and teaching at the same time has a positive amplifying effect on both. If that ever changes, I'll deal with it then.

Friendships to matter

A couple of weeks before I turned 40, I took a group of guys up to Pinecrest. We hiked, we swam, we grilled, and we played Cards Against Humanity. It was awesome.

I remember vividly one moment at the end of the weekend. Only two guys remained, and since I was their ride home, they helped me put the cabin back together. We were sweeping the front deck when my career came up, and I lamented that I wasn't sure exactly what I was going to do next. I had some ideas but I was uncertain which one to pick. I told them I really wanted to be a climate tech CEO.

"That makes all the sense in the world," one of my friends said. The other agreed emphatically. On the drive home, I decided my building permit idea was the best one and hired a couple of programmers on Upwork to start scraping permits in Contra Costa County the following day. This was the start of the chain reaction that would become Shovels. It happened because of my friends.

I'm making more friends as a result of the work I'm doing on Shovels and at DVC. I'm also hearing from more old friends than any time in recent memory. I find it very rewarding, and it tells me that I'm doing something right. My network grows when I'm most productive.

Fitness to keep improving

I'm in the best shape of my life. It's true. I credit a combination of my daily core routine, training for some endurance races, and doing a triathlon which really was about forcing myself to swim laps. Now a typical workout week for me looks like this:

5 mornings of 10 minute core. Mondays I do a 5 minute straight arm blank. Tuesday through Friday I do 4 minutes on my elbows. The rest of the workout is various crunches, stretches, squats, and 40 pushups.
A couple of 5.5 mile runs. Plus one 10+ mile run or a 35 mile bike ride.
1 mile swim at a pace of about 2 mins per 100 yards.
1 Peloton workout. My favorite is a 20 minute ride followed by a 20 minute full body strength

The morning core routine, which I've now been doing for more years than I can track, is table stakes. It's always there, so I don't think about it. This means I work out twice on most days. It feels normal. In fact, on days when I don't work out at all, I get restless. That's when I head out to the backyard cottage where we have our Peloton stuff and knock one out. I have to exercise every day or I don't feel right.

When I was younger, I remember thinking one sweaty exercise a week was all I needed. Maybe that was true at the time. A few years ago, I got into a rhythm of exercising every third day. One day on, two days off. It felt like work, but I stuck to it. I've been narrowing that gap in off days ever since, and it's now to the point where even on vacation I have to get my workouts in. The only days I didn't exercise in Hawaii were the days spent packing and flying.

I'm proud of my Strava profile. I want to keep it going.

To take chess more seriously

Chess is a different kind of release. It's what I do to ramp into work mode. It's also what I do to reward myself for getting work done.

I happen to be on a really good clip right now. My chess is strong, but I've been playing long enough to know that it's cyclical. This could last another two weeks or maybe another two months. Then I'll hit a losing streak and drop about 200 points. Right now, though, I see the board and accurately anticipate my opponents' moves. I know this because they slow down in response. It's thrilling.

I play 5-0 and 3-0 games. That means five minutes, no increment, or three minutes, no increment. These are fast games. I like using the clock as a weapon. No incremental time after each move (alternatively, you can get 2 or 3 seconds back after each move).

A different personality comes out when I play chess. I talk shit (chat it, actually). I'm hyper-competitive. I allow myself to dislike my opponent. I'm mean!

If I had to critique my entrepreneurship, it's that I tend to be too nice. It's great for building a network, but it's probably bad for sales and negotiation. I want to pull parts of my chess personality into my entrepreneur personality. That's one goal for this year, especially as each new Shovels enterprise deal becomes a negotiation.

That's five good goals for me to keep in mind going into this year.

I'm ready 😁

The importance of mentors

2023-11-05T20:35:00-08:00

"Are you mentoring anybody?" my old mentor asked me a few weeks ago.

"No, I'm not." And I stopped to think about that for a minute. I don't have a mentor right now.

Lisa Bauer is my old mentor. I worked for her in college, but it felt like she was also my partner. She guided me through the politics of UC Berkeley, helping me understand the incentive structures that make the university tick. Our interests were aligned: I was a capable and hungry 18-year-old interested in environmental policy, and she was an ambitious and underfunded 40-year-old running the campus recycling and refuse program. She needed help. I needed a project.

I didn't know this then, but I also needed a mentor, and she was the perfect fit.

Through Lisa and the other students she cultivated, I joined a cadre of great organizers. They knew how to execute an idea and keep it running. They were smart in the right ways, and I discovered I also had a natural talent for navigating the campus bureaucracy. The truth is, I liked it, and the people I met on campus seemed to like me. It was easy, and it didn't feel like work. When I ran into problems, Lisa helped. I remember feeling back then that I made her proud.

We stayed in touch off and on after I graduated, reconnecting over a meal at her house in Berkeley every few years. It was easy to stay friends despite the long gaps in communication. When she sent a group email recently about wanting to find a renter for her house in Berkeley, I replied and suggested we meet again. After some back and forth, I offered to visit her ranch way out in the Anderson Valley.

It had been years, but we hit off like old times. We chatted while Lisa and her husband, Doug, cooked dinner. It occurred to me that I'm at the age now that Lisa must have been when we worked together 20 years ago. I told her that even in retrospect, with the decades washing away the loose memories, I still consider the projects we worked on the most important part of my Berkeley experience. That type of work, the organizing, politicking, networking, planning, strategizing... that's what I love to do. Doing this under her tutelage was a masterclass. It definitely helped me get into the Harvard Kennedy School, and MIT Sloan, and there's a straight line between all of that and meeting my wife, becoming an entrepreneur, and building the life I'm living today.

The mentor relationship is unique. It's personal and professional. These days that's a sensitive topic, but I liked that Lisa often treated me and her other student employees like peers. She said what was on her mind. She gave us relationship advice. The work was serious and important, but when we worked, it was casual and often funny. Most importantly, we knew that she cared both about the mission of making our little piece of the planet more sustainable and about nurturing and helping us.

I don't have that now. I have friends, connections, formal and informal advisors, but I don't have an older, wiser coach in my corner checking in and making sure I'm doing my best work. I don't have someone opening doors for me, feeding me ideas and opportunities. I no longer have an advocate and I want to get that back.

Having a mentor seems to be effective. I keep running into these relationships in the biographies of successful people. Here are a few that I remember:

Arnold Schwarzenegger had Joe Weider to help him navigate the American bodybuilding circuit and get his first acting role
David Beckham had Sir Alex Ferguson as his coach and surrogate father for many years while he played for Manchester United
Albert Einstein had Max Talmud, who introduced him to math, science, and philosophy.

Is it ever too late to get a mentor? I hope not. When I think across all of my professional relationships, I have the individual pieces that make up a mentor. I have a lot of people supporting me through my current projects. I have to work to solicit the output and cull the ideas. I don't have it all in one person the way I did with Lisa so many years ago.

I miss that.

![Lisa and Doug at ranch]({static}/images/2023/10/DSCF0096_0046-1.jpg) ![Ranch visit photo]({static}/images/2023/10/AA0B9D9B-E6AF-4FD1-AFDE-9F9DDA1E5915_1_105_c-1.jpeg)

Happy 41st birthday to me

2023-08-25T19:13:00-07:00

There's a million things I haven't done... and probably never will. That's okay.

I slept in today. My wife's alarm went off at 5:40am, as it always does, and we dozed for another 30 minutes. Murphy hopped onto the bed at 6:10am and then I was awake. I didn't do my regular core routine (which involves a 4 minute forearm plank -- a daily feat that I'm quite proud of) because today is my birthday, and I decided to go on a bike ride instead.

I made coffee, as usual, and my girls wandered out of Norah's room. They slept together last night because my wife and I were out late, and it would be easier on the babysitter if they slept in the same bed. We had a lovely dinner at Julia's Restaurant in Berkeley and saw Weezer at the Greek Theater. I pumped my hands in the air and sang along to the songs from 1994. I thought about playing roller hockey in the parking lot in front of Eric Rosales's house, his Sony boombox blasting Weezer's Blue Album, the open CD case somewhere on the steps by his front door.

I was happy then. I'm happy now. I'm grilling a ribeye at my happy place so thick I can cook it sideways. My Alvarez guitar, the upgrade I gave to the cabin two summers ago, is leaning on a stump. The sun is setting on the ridge across the lake. Murphy is lying down in front of me. And I'm writing this post on my laptop because of an upgrade we added this summer: a Starlink satellite dish.

I turned 41 today. I'm happy. I feel good because I have a family that loves me, neighborhood friends who I love to spend time with and work that I love to spend my time doing. I love entrepreneurship, and I love teaching, and I get paid to do both. I found a way to be successful at wearing all of my hats. Everything seems to fit.

I didn't have this ten years ago. I was happily married, but there was no community, no roots. I was living in an apartment in San Francisco, trying to build Scripted, looking forward to a sense of stability and above average mediocrity. Those were my goals back then. My friends were my coworkers, and those were real friendships, but we didn't share a story beyond the company we were trying to build. In a real community, the story is shared at a fundamental level. When I see my neighbors at the bus stop, I'm proud. We're doing this thing together. We have similar routines, similar challenges, and similar goals. It's not about building a company or making money; it's about finding fulfillment as we raise our kids together. That's a big deal, and whether we acknowledge it or not, that story is huge.

I didn't know this when we moved to the suburbs. It's probably been the most delightful surprise of my adulthood. To go through this stage of life with really good people is such an incredible gift. I had no idea.

I became a husband at 27, a dad at 32, a homeowner at 33, and a teacher at 38. I think I was always an entrepreneur. Those five roles: husband, dad, homeowner, teacher, and entrepreneur are the five that most define my life at 41. I'm other things: a son, a nephew, a son-in-law, and a blogger, but those roles don't define me or influence most of my days. The first five I mentioned are with me all the time.

It's been a year since I last reflected on a birthday. My life hasn't changed that much since I turned 40. I started Shovels. I'm teaching some new classes. I learned some new guitar songs. But I'm still the same person doing the same things. And that is good.

A few things I learned from watching Einstein

2023-08-02T06:43:00-07:00

A friend suggested that I watch the first season of Genius series, which profiles Albert Einstein. I checked to see how many episodes there were and how long each one was, as I always do when somebody recommends a new series to me.

Ten episodes! Each one 45 minutes! I hesitated at the commitment but took the plunge. Fortunately, I was not disappointed. The acting: phenomenal. I thought I was witnessing the actual Albert as a young man struggling with his place in the universe. I enjoyed seeing old Albert as a dirty old man, fondling his secretary. And in between, we get to know the wire-haired caricature Eintein, sometime in his 40s and 50s, as an unconventional physicist, unafraid to yield to his libertarian tendencies.

All of this was brilliant because it presented Albert Einstein as a complex, flawed, deeply insecure human being. His brilliance and creativity as a physicist were also on display, but his success was merely a backdrop to his personal life, which was not brilliant at all.

The tragedy around most, but not all, of his personal relationships was not due to social awkwardness. On the contrary, Albert was outspoken, charming, and funny. He had much to say and, famously, much to ask. Curious people are fun to be around, and Albert had many friends. He had a typical relationship with his own family, his parents and his sister. He struggled with an unapproving dad, but that's not unusual.

We witness his curiosity getting him into trouble in school, ultimately leading to expulsion. He had to find his own way into college, forcing his way to the Polytechnic Institute in Zurich, where he excelled at math and physics but had no patience for other subjects. We begin to see the iconoclast emerge in the classroom. His ability to break with conformity was a pattern throughout his life. I admire and respect him for that.

He also chose not to conform as a typical husband and father when he got his girlfriend pregnant. The series presents this relationship as an honest, true love. I remember a scene when Albert tells Mileva, "I am madly in love with your mind." They agree to marry, but the relationship turns tragically toxic. They have two boys together, and Albert is an inconsistent father. Mileva, his intellectual equal at the Polytechnic Institute, gave up her career to raise their family and support Albert's research while he worked at the patent office. It's unclear how much she contributed, but there are several scenes where Albert professes his indebtedness to her hard work and insights. Nonetheless, he never formally credited her on his papers.

He was a doting father when he was with the boys, but when he needed to work, he focused only on his work. As his relationship with Mileva soured, he spent less time at home, and the boys suffered. Albert recognized the impact of his decisions but shrugged it off as the sad byproduct of a bad marriage.

He was also a philanderer. He met Mileva while in a serious relationship with another woman. He couldn't bring himself to tell her and kept his long-distance relationship alive while courting Mileva. Similarly, he fell in love with Elsa, a distant cousin, while his marriage to Mileva dissolved. And while he was with Elsa, he had numerous affairs: a secretary, an artist's wife who was a Russian spy... those are two I remember. Albert was either a man of the times (apparently, wives expected this behavior) or felt compelled to display his iconoclastic stripes in all parts of his life. The show didn't editorialize Albert's conscience.

All of this happens against the backdrop of the rise of Hitler and the Third Reich. Albert is weary of Hitler's rise to power but refuses to believe that Germany will fall completely under the Nazi regime. He holds out, even as antisemites publicly disparage his research as "Jewish science." Eventually, he conceded that Nazism would overtake Germany, and he and Elsa moved to Princeton. The presentation of this tension is masterful.

The show ends with Einstein struggling to maintain the mental stamina he had as a young man. He needed to solve the unified field theory, which would unify much of his earlier research, but he was unsuccessful. He succumbed to age as any old man will. He was merely human, after all.

I admire Albert Einstein for making huge bets on himself many times throughout his life. He willed his way to success, and he paid for it personally, but history has paid him back.

Could he have been a good dad and a great physicist? Without his foibles, would he maintain his brilliance? These are the questions I'm left asking. I want to believe it's possible.

Why are some communities in Contra Costa County unincorporated?

2023-06-20T05:56:00-07:00

When we first bought our little house in the suburbs out here in Contra Costa County, I'd never heard of "unincorporated" communities. Our city address was Walnut Creek and I just assumed that we were Walnut Creek residents. As it turns out, we are not!

Case in point: In 2019, some of my neighbors asked the county to consider changing the mailing addresses to Lafayette in the parts of Saranap covered by the Lafayette School District. After years of meetings and one successful appeal, the change was granted. And just like that, my mailing address works as both Walnut Creek, CA and Lafayette, CA. And yet we technically "belong" to neither city.

Here's the text from the county website.

Any change on the property tax roll associating your property with Lafayette, rather than Walnut Creek, will be in name only. It will not move your property into the City of Lafayette and the Zip Code of your property will remain the same. Mail will continue to be sorted at the Walnut Creek Post Office and continue to be recognized by the United States Postal Service (USPS) when addressed as either “Walnut Creek” or “Lafayette.”

In other words, we're still unincorporated. We belong to neither Walnut Creek nor Lafayette. When we call the police, we're routed to the county Sheriff. The county handles our permitting. All that usual stuff you go to City Hall for is handled for us at the county level. My closest elected official is a County Supervisor.

I haven't run into any issues with this setup. In fact it's been beneficial. We get all the benefits of living close to Lafayette and Walnut Creek without dealing with the red tape or paying extra taxes. It feels a bit like cheating.

So this begs the question: Why do unincorporated areas exist? Why aren't we annexed by Walnut Creek, or Lafayette, or heck, even Alamo (Alamo is also unincorporated!) And why doesn't Saranap, all 5,000 of us, form a town, elect a mayor and town council, and set our own rules?

To answer these questions, let's start with the fictional history of a fictional little town.

People settle in an area. What do you need when you form a town? A store, a church, and a post office, pretty much. The people who live closest to the downtown will tend to be most involved in it. They'll organize, handle disputes, and discuss plans for growth and security. In essence, they form a government and a police force. That's real work, and real work needs real pay. Who's going to fund all this?

The people who live further from the downtown don't want to be bothered. They don't need the town services. They carve their own roads and build their own fences. The shotgun by the door is all the police force they need. They only want to deal with the grocer, the postman, and the priest, so they opt out of everything else. They become unincorporated. Meanwhile, the homes closer to town form a city, collect taxes, and together deal with all the local politics ("Old Man Jones hacked the head off Mr. Johnson's rooster for waking him up at 5am after a heavy night of drinking...")

However, at least in California, every unincorporated area still belongs to a county. You can bypass the town or city, but you can't bypass the county. This family with the shotgun by the door still has a Supervisor and county rules to deal with. They also have to deal with special districts. There are schools, sewage, water pipes, roads, and trash collection to pay for. Being unincorporated is a far cry from being "off the grid." It simply avoids the tip of the spear in local government.

Let's take this back to Saranap. Like I said, we're right between Lafayette and Walnut Creek. We have no side walks or street lamps. Like many suburbs, we were once part of a big ranch, and it eventually was carved up into hundreds of little parcels. It kept its semi-rural flavor, though, and has remained in its in-between state for the last seventy-five years.

It remained so because it's too expensive for Saranap to be annexed to Lafayette or Walnut Creek. The neighborhood would be out of compliance with the current planning codes of both cities. We have no streetlights and nobody wants to pay to put them in. We have no sidewalks, and nobody wants to give up their yards to accommodate them. With no urgency or desire from either the residents or surrounding cities annex, Saranap is probably just gonna Saranap for the long run.

So if Saranap is gonna Saranap, why don't we form our own government? The other idea of incorporating itself is an interesting one. To get a glimpse of how this might work, we can turn to the Town of Moraga.

Moraga is only 10 square miles and has a population of 16,000, about three times the population of Saranap. It incorporated in 1974 when the three towns of Moraga Town, Rheem, and Rheem Valley decided to merge in order to prevent overdevelopment.

Today, Saranap could do this by petitioning our Local Agency Formation Commission, or LAFCO. These commissions are unique to California, which has 58 of them, and they are able to form and dissolve cities within their jurisdiction. To start a new city, the journey begins here.

But first, we must ask the question: Why would anyone want to form a new city? To answer this, let's look at what city does versus what a county does.

A city can:

Handle law enforcement and fire protection
Set planning rules (land, zoning, building inspections)
Manage public works like streetlights, potholes, drainage, water and sewer, etc
Make public services like libraries and parks
Deal with animal control

A county will typically:

Handle welfare and child protection
Manage the criminal justice system, like courts and jails
Handle elections
Collect and distribute taxes
Do other health services
Manage regional parks

So, if the residents of Saranap felt potholes were going unfixed, buildings were in shambles, and the community wasn't served by libraries and parks, we could incorporate and deal with these issues ourselves! But where would this money come from? The share of revenue that went to the county, of course! But what about the stuff that the county will still handle for us? We'd still have to pay for it!

And this is what the bulk of the incorporation documentation deals with: the comprehensive fiscal analysis. It sounds so messy, the LAFCOs give it its own acronym: the CFA.

The LAFCO's main responsibility is to ensure that the county isn't worse off by the incorporation and that the new city is fiscally sound. If the analysis is sound and the voters approve it, the new city is born. For more on how it works, this incorporation guide by the CA Governor's Office of Planning and Research was really helpful.

Data transformation >> data extraction

2023-05-26T13:51:00-07:00

The ETL (Extract, Transform, Load) data framework has been around for a long time. Its roots formed in the early days of data warehousing in the 1970s and 1980s when solid-state drives (SSDs), which use a technology commonly known as flash memory, first hit the market. You might remember the computer hard drives that buzzed, clicked, and hummed when you loaded a program. That technology involved a rotating disk with an arm like a record player that read and wrote data to the disk. It was relatively slow and impossible to scale down. There'd be no "thumb drive" version of this technology.

The SSD revolution quickly drove down the price of storage, and with it, emboldened companies to grab and retain more and more data. The ETL framework evolved as a logical way to deal with this mass of information. You take raw data (in the Extract stage) and make it useful (in the Transform stage) and ultimately throw it into some publicly accessible API or feed (in the Load stage).

You take raw data, wrangle with it to make it nice, and then put some sort of interface on it so other people or companies can use it. That's all pretty obvious. What's less obvious, and what I've come to appreciate in the last few years, is that these steps are not valued equally by the markets.

({filename}mightysignals-new-leadership.md), the last company I ran, was an extraction company. We extracted the type of software running in mobile apps. We also transformed and loaded it, but we did so in a way that kept it in the same extracted context. That's a bit nuanced, but suffice to say, I'd still put MightySignal squarely in the extraction bucket even though we did some transformation and loading for our customers.

MightySignal acquired AppMonsta. This was also an extraction company that took app details off of the app store pages and loaded it into an API. Yes, there was also a little T and a little L here and there but primarily AppMonsta was an extraction company.

An extraction company is one that spends most of its resources on extraction. Even if it does some T and some L, if most of its resources are spent on extraction, then it's an E company and has the mixed bag of pros and cons of doing data extraction.

The critical insight I want to focus on here is that E companies don't produce as much enterprise value as T and L companies. Enterprise value is shorthand for the valuation of a company, which is a function of the company's revenue, market, and growth rate. The factor that I'll focus on here is revenue. I argue that E companies don't make as much revenue as T and L companies and therefore have a lower enterprise value.

There are a few reasons why E companies don't make as much revenue. Let's break them down.

Extracted data is a commodity

There's nothing special about extracted data. It's usually hard to get, and I'll consider that difficulty later on in this post, but once you have it, it's a commodity: it looks just like everyone else's extracted data. That's the nature of extraction. Anyone can do it, but not everyone wants to do it. Once you've extracted the data in its raw form, it's going to be the same product as if I'd done the extraction myself. You may be better at it than me. You may write better scrapers or have a better server architecture, giving you a competitive advantage, but the end result is going to be the same as if I scraped it myself.

Therein lies the challenge. Raw, extracted data is a commodity. It's undifferentiated; I could buy it from multiple sources, and likely will choose the source based purely on price. In a mature market, quality is going to be the same between sources, so consumers buy the cheapest option.

Markets with pricing pressure are difficult environments to produce enterprise value. Investors don't like them. They are the realm of nail salons and convenience stores in the real world. In tech, they are data extraction and, increasingly, B2B SaaS companies. These can make great lifestyle businesses, but they're not likely to produce venture-scale returns. When competing products start to look the same, it's time to either innovate or accept a lower valuation.

Data extraction is a distraction

Data extraction companies have a very hard time being great at both extraction and transformation. The complexity of data extraction is a bit of a moat; it's why I'd rather buy than build, so there's a business to be had, but once you're in the extraction business, it's hard to leave it.

Running an extraction operation is playing non-stop wack-a-mole. The fire drills are constant. There's no time for transformation when all of your resources are focused on keeping the scraping operation alive and expanding it in a constantly evolving landscape.

This distraction makes it hard, if not impossible, for an extraction company to also do the creative, innovative work of transformation that creates unique additional value. All the attention has to be on extraction because it's so darn complicated and fragile.

Tying this back to revenue, it means that extraction companies have a hard time adding value that they can use to justify higher prices. It's hard to grow revenue without increasing prices.

Data extractors sell to data transformers

I have some experience with the nature of this market. Like I said, both MightySignal and AppMonsta were extractors. We both sold to businesses that transformed our data into new products by combining datasets, exposing them in interesting ways, and adding user management and billing features required by enterprise customers.

As a result, our customers grew much faster than we ever could. By creating a unique data product and enterprise features, they were not price-constrained. By not being price-constrained, they could innovate. By innovating, they could continue to drive enterprise value upward with higher prices. This is the positive cycle that we lacked as a data extractor.

Data transformers need data extractors. They don't want to do the extraction themselves for the reasons I described above. This creates the market for data extractors, but it also keeps them at lower valuations than data transformers.

As I've ({filename}platforms-versus-point-solutions.md), Shovels will be a data transformer. In that blog post, I described this same idea in terms of a platform versus a point solution. Here, I would describe data transformation companies as platforms and extraction companies as point solutions. I want Shovels to be a platform, a transformer, a unique provider of data, but without commodity pricing pressure. I want to innovate and create enterprise value that is attractive to venture capital firms.

I recently our April 2023 newsletter in the Shovels blog that we raised $1M. I wouldn't have been able to raise it without describing Shovels as a transformation company. I know this because my original pitch was extraction. I didn't know we had the option to buy permit data, so I had to lead with this extraction focus. I could get first meetings, but none of the investors wanted follow-ups. When I discovered that raw permit extraction was available to buy, I changed our pitch to be transformation-focused. Investors leaned in and we pretty quickly identified our lead. Angels followed, and then more funds. The transformation pitch was far more compelling than the extraction pitch.

To be clear: I'm glad data extraction companies exist! I'm grateful for them and I have nothing but love and respect for the ones that do it well. They're important and they can make great businesses for the founders, but I have other ambitions this time.

An exploration of deep exhaustion

2023-04-08T20:59:00-07:00

This month I plan to push my endurance to the outer limits. I rode my bicycle 142 miles in just under 12 hours a week ago.

A week from now, I will do it again, but with twice the vertical climb. It will be my second year in a row doing the Belgian Waffle Ride California, a day-long ride on road, gravel, and sandy dirt trails in the hills above San Marcos, California. It's a silly 135 miles and 11,000 feet of climb. That's the equivalent of riding around the base of Mt. Diablo twice and hitting the summit three times.

Who does a ride like that? Me, apparently. It's becoming clearer to me why I like doing it.

The term "deep exhaustion" comes to mind when I think about why I do this. I googled it. Deep exhaustion has mostly negative connotations, like when you hit a wall of fatigue and can't break through it.

That's not the deep exhaustion I'm referring to. This type of exhaustion sits in your bones but drives you forward. You somersault through the fatigue and come around to the other side of it. You find energy in the heavy cloak. Somehow, incomprehensibly, the deep exhaustion actually feels good. It's comforting because it's supposed to be there, and the thrill lies in seeing how long and how far you can carry it with you.

From the start of my 142-mile loop, it took about 40 miles and a bit over two hours for me to ride from my house in Lafayette to the estuary on the eastern side of the Dumbarton Bridge. That's when I got my first taste of tiredness. I stopped there and stretched. I filled my water bottles at a little trailhead visitor center structure. I took this picture there.

I was still feeling good. I stretched my legs, felt a twinge of cramp coming on but shook it off. I hopped back on and kept going. At 50 miles, I took a picture at the peak of the bridge span. I took my last picture as I entered Martinez from the north ninety miles later.

![Peak of bridge span at 50 miles]({static}/images/2023/04/IMG_4208.jpeg) ![Entering Martinez from the north at 90 miles]({static}/images/2023/04/IMG_4216.jpeg)

I planned to circle the bay and cross five of the seven bridges (I couldn't fit San Mateo in and the Bay Bridge has no bike lane on the western span.) From the Dumbarton Bridge, I headed north up the western shore, through San Mateo, Redwood City, Belmont, and into SFO. The stretch along the airport is a drain. It's long and windy. Eventually, I crossed the freeway and hit another windy stretch opposite Candlestick Point, near the Cow Palace. This is the threshold between South San Francisco and SF proper. The Bayview / Hunter's Point district is not my favorite part of the city. I push up and then down the hills and onto the Chase Center and Oracle Park. I followed the Embarcadero around to the Golden Gate Bridge. This is about 85 miles from home. I cross into Sausalito, and a quick twenty miles later, I'm on the Richmond Bridge span. This is my third bridge with a wide, protected bicycle lane. I got a little lost (Garmin fail) between the Richmond Bridge and the Carquinez Bridge (the fourth), but I finally found it about 125 miles into the ride. Fifteen miles later, I hit the fifth bridge. Mission accomplished!

Deep exhaustion hit me right around mile 60. I carried it for another 80 miles. I'm proud that I lasted that long. It took work and preparation to do this. I trained by exercising regularly. I run, I swim, and I bike. I generally do one of them every other day. So my base fitness was good going into this monster ride. I stopped, stretched, and ate every 20 miles. I mentally rode in 5-mile increments, each one a step closer to my next break. At the sixty-mile mark, I was somewhere in Belmont and stopped at a Roam burger restaurant. I ate like a champion. Feeling better but still quite tired, I kept going.

Twenty miles later, I was on the Embarcadero, tourists everywhere. I pulled to the side and forced a few handfuls of trail mix down my throat. I was tired, but I wasn't any more tired than I was at mile 60. That awareness gave me strength. I crossed the century mark in Larkspur. Again I wasn't any more tired than before, and I was excited to head back to the east bay. More energy. At mile 120, I was just north of Rodeo. I stopped on a bikeway right along the bayfront. I could feel my energy waning with the afternoon. I was about ten hours into the ride at this point, and I was concerned I wouldn't make it home before dark.

Mile 140 was a short stop in Benicia. I fed myself, but I wasn't feeling great. The deep exhaustion was starting to wear me out. I crossed the Martinez Bridge and was already in the evening shadows. The sun was still up, but the hills to the west hid it. The temperature never broke 60F the whole ride, but I felt cold for the first time here. I rode a quiet street through a refinery to get to the main road connecting Martinez and Concord. I was uncomfortable, jittery, and hungry, but I couldn't eat any more of the food in my little backpack.

I peddled forward, finally reaching the commercial stretch of Pleasant Hill. I saw a McDonald's and decided to stop. I ordered my food and sat haggardly, my helmet and gloves still on. I filled a cup with Dr. Pepper and ate my Big Mac. The evening turned to dusk, and I wasn't going to leave that McDonald's on my bike.

I took the last seven miles home in an Uber.

I survived. No close calls, no near collisions. I didn't let foolish pride get in my way of a safe ride home. At that point, I was in no condition to ride in the dark. I was able to push my limits without breaking them.

I think that's what deep exhaustion is to me. It's the point where I push my endurance outward. I'm not a weightlifter, but I understand that muscle gets built on slow, consistent reps with heavier and heavier weights. Perhaps endurance works the same way. You grind your way to the outer limits, and you carry its heavy load in order to extend your stamina runway. Parts of the process are painful, but for the most part, it's fine. It's just a steady exertion for a long period of time. At some point, you can't go any further, but until then, you're just tired. Being tired, in the right context, can feel really good.

I'm looking forward to the Belgian Waffle Ride next weekend. I know it will be hard. I know I'll bump up against the limits of my exhaustion. I'll do a better job with nutrition and fluids. I'll stop at every checkpoint, relax my body, eat, drink, and stretch. I'll take as much time as I need and try to enjoy the process for what it is: an exploration of deep exhaustion.

And boy oh boy, I'll look forward to eating dinner afterwards.

1994: A year in music

2023-03-28T20:23:00-07:00

I was twelve years old in 1994. I was in 7th grade and just started learning guitar. I played roller hockey after school, wore braces, held hands with my girlfriend, and competed with the other overachievers.

It was a good year.

Next year is the thirtieth anniversary of 1994. Thirty years! The Beatles put out their first album in 1964. In 1994, that thirty-year leap was ancient history. Today, 1994 feels much closer.

I now understand how my mom felt in the 90s, reminiscing about her teenage years with the Beatles. Distance changes with time.

The 90s music scene of my youth fell into two camps: grunge and rap. I liked some of the rap, but I loved grunge. It's worth noting that In Utero, Nirvana's last studio album, came out the same year as Doggystyle, Snoop Dogg's first, in late 1993. Both albums were edgy, mature, and full of emotion. I consumed them with curiosity and awe. As an almost-teenager, these albums were portals into adulthood. Kurt Cobain and Snoop Dogg couldn't have been more different, but they shared with me the mysteries of adolescence. Listening to them made me feel older.

I owned In Utero. I cherished it. I don't think my mom would have let me buy Doggystyle. I'm not sure I ever asked. Instead, I listened to that album at my best friend's house. We laughed at all the sexual references and pretended to understand the lifestyle that Snoop Dogg rapped about. We two suburban white boys couldn't have been further from South Central LA, but something about the stories, the bravado, and the sound of that music made us listen and feel it anyway.

I'll put Doggystyle on sometimes. I play it loud when my family is out of the house. I recall those feelings of my 12-year-old self like an old smell.

The Blue Album by Weezer and Dookie by Green Day also came out in 1994. These album covers to me are the definition of nostalgia. These were our roller hockey soundtrack. We'd listen to the entire albums on my friend's battery-powered Sony CD boombox. In the parking lot in front of his condo, in the basketball courts at the closest elementary school, we'd listen to Weezer and Green Day and play hours of schoolyard puck.

When we weren't playing hockey, we were jamming at someone's house. I'd lug my guitar and amp up and down Montecito Avenue, sweat marks on my back from the strap of my guitar bag. Weezer and Green Day were heroes to us. Their songs were sweet, angsty, and the musicality was profound. They weren't as deep as Nirvana, but sometimes we wanted a light beer rather than a smokey scotch (a metaphor I wouldn't appreciate until the early 2000s). These two albums were the bright hues against the darker backdrop of In Utero and Doggystyle.

Stone Temple Pilot's Core and Soundgarden's Superunknown were not in the regular rotation with my friends. These were the albums I would play when I needed to take a break from the rest. They were good fillers then, and I appreciate them more today than I did thirty years ago. Scott Weiland of STP and Chris Cornell of Soundgarden are the two best grunge rock singers of the 1990s. Eddie Vedder of Pearl Jam would be a close runner-up, and I suppose Layne Staley of Alice In Chains should be in the mix too. Critics may disagree, but I found the biting power of Weiland's and Cornell's voices to be unlike any other. It almost made the music too hard for me to associate with. Kurt Cobain's voice for Nirvava was pure energy; he's not really a singer. Billy Joe Armstrong of Green Day sounds like a choir boy, and I would go on to spend four years of choir in high school, so I must have liked that sound. Rivers Cuomo of Weezer was like Billy Joe, sweet and normal.

Weiland and Cornell are gods in comparison. There's nobody like them. They're the Freddy Mercury, Robert Plant, and Steve Perry of the 1990s.

Finally, I have to give a shout-out to the two best albums from the MTV Unplugged series. Nirvana's came out in 1994, seven months after Kurt Cobain's death. Eric Clapton's Unplugged was released in 1992. Both albums got a lot of radio and air time on MTV, and each won a Grammy.

Fun trivia fact. Although Nevermind, released in 1991, was a HUGE album, it didn't win anything. MTV Unplugged was Nirvana's only Grammy award.

Knocking your NOx off

2023-03-18T12:35:00-07:00

I just started learning about nitrous oxide (NOx). When we electrified our home, we did it to burn less carbon. I signed up for MCE renewable energy so our share of energy usage would come from renewable sources. I felt good about paying extra (the notorious "green premium") for our all-electric home appliances.

I feel even better now. Nitrous oxide pollution has long been recognized as a significant contributor to air pollution and climate change, posing a threat to both human health and the environment. To address this pressing issue, the Board of Directors of the Air District held a public hearing on March 15, 2023, to consider the adoption of proposed amendments to Regulation 9, which addresses inorganic gaseous pollutants. These proposed amendments include the introduction of zero NOx standards for space and water heating appliances and an ultra-low NOx standard for furnaces, which would have a profound impact on reducing NOx emissions.

The amendments were approved!

The Need for Stronger NOx Standards

NOx emissions are produced by various sources, including transportation, industrial processes, and building appliances, such as natural gas-fired boilers, water heaters, and fan-type residential central furnaces. NOx pollution contributes to the formation of ground-level ozone, smog, and fine particulate matter, which are associated with respiratory and cardiovascular health issues, particularly in vulnerable populations such as children, the elderly, and people with pre-existing health conditions. Additionally, NOx emissions have been linked to adverse environmental impacts, including acid rain, eutrophication of water bodies, and the depletion of stratospheric ozone.

The amendments to Rules 9-4 and 9-6 are a vital step in mitigating these harmful effects. By implementing a zero NOx standard for both space and water heating appliances and an ultra-low NOx standard for furnaces, the amendments will significantly reduce NOx emissions from residential and commercial buildings. These new standards are set to be enforced from 2027 to 2031, depending on the appliance, providing a clear timeline for manufacturers and consumers to transition to cleaner and more efficient technologies.

Addressing Concerns

While the Draft Environmental Impact Report (EIR) for the proposed amendments concluded that there would be potentially significant and unavoidable impacts associated with utilities, services systems, and noise, it is important to put these concerns into perspective. The increased energy demand resulting from the replacement of existing natural gas-fired appliances with electric ones can be mitigated by continued investments in renewable energy sources and improvements in grid infrastructure. Moreover, the benefits of reducing NOx emissions, such as improved air quality and reduced greenhouse gas emissions, far outweigh the potential challenges associated with increased energy demand. Furthermore, I believe the market will solve grid demand issues and supply will ramp up over time to bring prices down.

Similarly, the noise impacts associated with certain zero NOx equipment can be addressed through technological advancements and proper installation techniques. In many cases, the noise levels of these appliances can be reduced to acceptable levels, ensuring that they do not pose a significant nuisance to residents. My heat pump water heater is louder than my old gas one, but we put it in the garage and don't hear it. Plus, the cold air it blows as exhaust is amazing in the summer.

Conclusion

I'm glad the BAAQMD passed the amendments to Regulation 9. By adopting these stricter NOx standards, we can significantly reduce air pollution, protect public health, and mitigate the impacts of climate change.

Mobile homes are a piece of the housing puzzle

2023-02-20T06:58:00-08:00

*Note: this is my first blog post written with an assist from ChatGPT. It was fun! *

Oh, the housing crisis. Let me dip my toe in.

I am a YIMBY. I want to see new housing built close to BART and freeways. I'd much rather see downtowns built up than open spaces built out. Housing has been a problem for years. We've all read about how the high cost of living and a shortage of available housing has left many folks struggling to find affordable places to live. While many factors contribute to the crisis, mobile homes are an interesting part of the solution.

Here are five reasons we should support mobile homes as a solution to the housing crisis in California.

- **Cost**: Mobile homes are more affordable than traditional homes, making them an attractive option for people struggling to afford housing in California. With the high cost of living in the state, mobile homes can provide a relatively low-cost alternative that can help ease the burden on people's finances. Cost per square foot of a mobile home is less than one-fifth the cost of a house.
- **Ownership**: Since costs are lower, mobile homes offer a pathway to homeownership. I learned in my college political science classes that homeowners are more likely to vote, volunteer in their communities, and participate in public discourse. Plus, they gain the benefits of home equity.
- **Flexibility**<span style="font-size: 1rem;">: Mobile homes are prefabricated and can be assembled quickly. They can be deployed quickly to areas that need additional housing. They are also relatively easy to move from one location to another, which provides flexibility in responding to changing housing needs in different counties. With enough warning, mobile homeowners can move their dwellings away from risks of fires and floods.</span>
- **Environmental sustainability**: Mobile homes have a smaller environmental footprint compared to traditional homes. They are often built using sustainable materials and are designed to be energy-efficient, which can help reduce energy consumption and greenhouse gas emissions.
- **Community**: Mobile home parks provide community and belonging for residents. Mobile home parks are built as dense neighborhoods with homes nestled tightly together. This setup helps residents meet and support each other. Some communities offer common facilities like a pool or community center.

I think this is an interesting solution. Land isn't cheap in California, but if we can find a way to produce more mobile, affordable, sustainable homes, it's a step in the right direction. While they are not a complete solution to the complex issue of housing, they offer some benefits that should be considered as part of a comprehensive approach to addressing the housing crisis in California.

Why I'm taking a break from parallel entrepreneurship

2023-02-09T07:22:00-08:00

When I described what I'm doing now to a good friend, he chuckled and said, "Guess you're going to have to write a new forward for your book!"

The book he referred to is The Parallel Entrepreneur, of course. It's hosted free on this blog and generates most of my organic traffic. I still believe in the premise. Side hustling should always be an option for any entrepreneur. However, it's not the right approach for me right now.

My entrepreneurial philosophy evolved a lot over the past year. It probably started with the realization that climate tech is my next big thing. A climate business could not be a side business. The problem is too great, the complexity too rich, and the opportunity too massive. I've learned over the years that if you treat a business like a side business, that's probably all it will be. Most businesses don't expand and explode by their business physics like a supernova. Most startups require determined, disciplined nurturing over a long while. I decided not to neglect my climate tech baby if I were to conceive one.

Then, slowly, I started to wrap up my side businesses. One by one, I sold or shut down each of them. My Heroku bill got smaller and smaller. Two years ago, I sold EmailFinder, Name2Domain, and Name2Profile to Live Data Technologies. Those web applications generated a few thousand dollars per month in aggregate. I still had eNPS.co and MyKidColors.com. I built eNPS in 2017, inspired by my HR experience at Scripted, when I needed to send quick surveys to our employees every quarter automatically. That business probably made $20,000 over its lifespan. MyKidColors scraped coloring pages from the web and organized them better. It never made money, but the organic traffic came quickly. I never monetized it and never got around to incorporating generative AI to produce coloring book content (I still think this is a great idea!)

I thought I would feel sad when I let these little dreams go. I didn't. Instead, I felt relief. Even a small weight lifted releases energy that I can put into Shovels, my new company, the one I'm more excited about than all of my past projects combined. It's that conviction that I've found the one, the idea that will become a company that will grow and grow and grow and make a real impact in the world. That conviction overrides everything! No regrets.

Entrepreneurs need to evolve. When starting a company, we grow and learn quickly. The highs are higher, and the lows are lower. We incorporate these lessons into our business psyches. It makes sense that our perspectives should change too. I'm not burdened by my book titles.

I've justified my ability to change my approach. Now I'll explain why I'm changing it.

I want to build

I sent an email a few weeks ago to a friend I made through this blog, a professor in Europe who found me by googling "parallel entrepreneurship" and then discovered we had other things in common. I was deciding whether to fundraise, coming down to the final decision about whether to take outside money for Shovels or bootstrap it.

I told him these two questions are related: whether to fundraise or side hustle. The answer boils down to what I most like to do: build. I made the point that bootstrapping or side hustling is a relatively quick building process. The code is simple (if I follow the parallel entrepreneur formula), so I can usually get to the first release and first revenue within a few months. After that, it's all launch marketing and long-tail SEO. Then it's customer support and bug fixes. I don't add features or think much more about what else the application should do.

These are running activities. I don't love running companies as much as I love building companies. I can't build a complex side hustle application because of the maintenance requirements and the fact that, if I'm being honest, I'm not that great of an engineer. As a solo entrepreneur, my engineering skillset tapers off quickly as complexity increases. To get to the next level, I'd need to learn to write tests and incorporate javascript, and neither excites me.

On the other hand, raising money expands my ability to build. I won't do the hard stuff myself; I have an amazing co-founder for that! Instead, I can continue to build marketing and revenue operations, send emails all day to potential customers (as I did for the first half of this week!), and think strategically about product-market fit. Fundraising means we have a much longer build ramp. We spend more time building, and if we keep fundraising and the business keeps gaining momentum, we never stop building. This is what I want. I want to spend my time building!

I want a team

The other critical difference between bootstrapping and fundraising is pulling a team together.

For years I've been bootstrapping alone. It served a purpose then: my kids were young, my businesses were small, and I could do whatever I wanted. I could work full-time on someone else's company and keep my little apps running in the background. I could teach. I could go on long bike rides, play piano, go to lunch with my wife, and deal with an entire school year of COVID protocols. My solo lifestyle afforded me all of this. Now I neither need nor want it.

I don't want to be solo on Shovels. It wouldn't work. It's too big. I needed a co-founder, and my co-founder and I need a small team to get this off the ground. Fundraising allows us to do this, and I'm confident the economics will work out. We'll sprint toward profitability, get there, and then take some big calculated risks. Having a team allows me to maximize the opportunity.

I want to win

Finally, I want to win. I wouldn't say this about my side projects. My little companies were meant to be little, make a little extra revenue, and just... be little. I had no ambition other than to keep them alive.

This time is different. I want to win! I want to compete with the other construction data companies and work harder and faster and smarter than all of them. I want Shovels to do stuff nobody else is doing or even thought about. One benefit of being a novice in the field is that I'm not tied down by industry norms.

To win, I need to build, and to build, I need a team. That's how this all relates. This is a marathon, and we've just started running it.

My trip to NYC with Lily

2023-02-06T06:22:00-08:00

A long time from now, with any luck, I will be very old. I will look back on my experiences as a young father: in the delivery room, first steps, first words, first days of school, ice skating rinks, hot dogs, board games, bicycle rides, dinners, friends' houses... all of it.

I have a feeling, though, that one of those memories will unfold like an origami kaleidoscope. My mind will pass by it and feel something a little bit different. I'll stop and look. Then I'll remember the million little details of my trip to New York City with Lily in November 2022.

"I want to go to New York City," my oldest daughter, all of eight years old, announced. I pondered it. How long could we stay? Would it be safe? Would we all go or just me and Lily?

"I'll go," I said. "Let's see what mom thinks."

My youngest daughter still associated flying with earaches, and the hour-long trip to Burbank airport in Los Angeles was the longest flight she'd take. It was settled: it would be just Lily and me, and all we needed were the dates. My wife checked her work calendar, and we settled on the second week of November. I would take Lily to New York, and to even out the score, she would take Norah to Monterey for a night or two.

Lily was ecstatic! New York! We talked a lot about the trip. I asked her to research hotels, her first Google research project. She needed to find three options under $500 per night, choose one, and tell me why she chose it. We ended up booking the Marmara Park Avenue, an affordable boutique hotel just a few blocks from the Empire State Building.

Next, I needed to book our flights. Lily understood that when the flights were booked, the trip would happen. She checked on my progress daily. I had recently negotiated a small sale of eNPS.co, one of my many side projects that never took off. I'd written this one off, shut it down, zipped up the code, and tucked it away. Then, out of the blue, someone asked if I would sell it. Conveniently, the offer was just enough to cover two round-trip first-class tickets to New York.

So, I splurged when that wire came through. For the first time in my 40 years, we flew first class. It was amazing.

This was the beginning of my much-anticipated five-day adventure to New York with my oldest daughter.

We arrived at Newark airport in the late afternoon. It was getting dark. The cab crawled towards Manhattan in long lanes of traffic. Lily's face was glued to the window the whole time. I sat proudly, stoically, pleased with myself for making this trip happen, and nervous about whether it would meet my already wild expectations. But at that moment, I was relieved. We were doing it. Lily and I were in a cab, driving into Manhattan, and Lily was safe and happy. I swelled with pride.

The hotel lobby was small. There was a bar with a few stools and some scattered tables. This was not the Fairmont. Our room was great, though. It had a balcony! I took my Nescafe outside every morning and gazed up at the Empire State Building while Lily watched Spongebob Squarepants from bed. These are the little bits of routine that make traveling fun.

We settled into our room and went out. Lily was excited to see New York. We walked toward Times Square and stopped at a boutique hamburger restaurant. It was quintessential New York: small, crowded, expensive, and... vegan. Oh well! We stayed.

I took this picture of my dinner date that night. She doesn't look seven years old to me here. This could be Lily at 20. I felt many more moments like this. Here's another picture from the subway during our many uptown and downtown trips.

There are moments when I feel like I'm watching my child grow up fast-forward as if every day were a month or a year. I had this sensation throughout our trip. It would make sense to feel this after not seeing my kid for a while, like after a long work trip. Ironically, I felt this repeatedly during this short period when Lily and I were inseparable.

My greatest fear was losing track of her in New York. I worried about being distracted when a large crowd passed between us. I worried she would duck into a store or turn a corner when I wasn't looking. We talked about what to do: find someone she could trust, like a mom or a police officer, and have them call me. I triple-checked that she had memorized my phone number. Fortunately, we never lost each other.

The days were long. We stayed awake until midnight or later, sticking to our Pacific timezone internal clocks. I would wake her up most mornings by 9 am local time, sometimes earlier. Lily was usually fast asleep.

We went to the Statue of Liberty the first morning. She was most excited about this activity. We took the subway to Battery Park and boarded the ferry.

I bought the special tickets that allowed us to climb the pedestal and get right underneath the statue. The view was incredible. We bought her a cheap digital camera so she could take pictures too.

And then we walked. I wanted to see the 9/11 memorial and had tickets reserved using CityPass. We walked through the museum and talked about what had happened there. I didn't want to make her afraid of flying, but I did want her to recognize that we have both lived charmed and protected lives.

We then walked through Wall Street and headed back to the subway and then uptown to our hotel and the Empire State Building.

We loved the Empire State Building. I thought the touristy elements were thoughtfully laid out and interesting. I couldn't believe the building was already 90 years old. It went up the same year my great-grandpa built our cabin at ({filename}my-happy-place.md).

The next day, the rain showed up. It poured. I didn't want to let her watch Spongebob all day, which she would have happily done. Instead, I booked tickets at a slime museum. I paid extra to have slime dumped on us. Marginally worth it. The best part was all the tactile slime bins. We both enjoyed sticking our hands in every one of them.

When the rain passed, we went to Rockefeller Center and used our tickets to Top of the Rock, and caught a lovely view of Central Park and mid-Manhattan. With no plans until the afternoon, I suggested we walk back to the hotel and see what happens.

We popped into Saks. Why not? We also walked through Saint Patrick's Cathedral. It was Lily's first time in a church, and she was full of questions. She knew that our neighbors go to church, and she'd asked me about it in the past, but this was an opportunity to get into more of the complicated detail. We made donations and lit votive candles. We watched people pray. I told her they were trying to answer the hardest questions.

We went by the Met. I didn't have tickets, but we talked about what was inside. She was happy to skip this museum. We just kept walking.

I was anxious to get back to the hotel, and she was too. We cheated and took the subway for the last stretch. I let her watch television while I got changed, answered emails, and put on the nicest clothes I had packed. We were going to see Hamilton!

The show was fantastic, of course. I booked reservations at Del Frisco, a fancy steakhouse nearby, for dinner. It was great, but I've learned over and over again that I can grill better cuts of ribeyes with ({filename}buckleys-grilled-cowboy-rib-eyes.md). Still, a date with Lily is a date with Lily, and I was very happy to be there.

Then we gave ourselves another treat. The night was clear, so we returned to the Empire State Building for the nighttime view. It was very special.

The next day, our only activity was the iconic Museum of Natural History. I'm sure I'd been once before, but I forgot how big and cool it was. We spent a couple of hours wandering around. I could have stayed a lot longer.

This was our last full day in New York City. I was already feeling nostalgic. The next morning we would be off to the airport, back in our first-class seats, and headed home to the old routine. A friend I met through a climate Slack group joined us for lunch, and we slowly made our way back to the hotel.

Lily was still excited to be in New York. I have many videos of her skipping along and running ahead. We both embraced the carefree feeling of being on vacation, and the endless possibilities of being in New York. Even if the plan was just to walk back to the hotel, we enjoyed doing it at our own pace.

Our last dinner in New York was perfect. I found a little Italian restaurant nearby. We sat at the bar and shared a pizza. I overheard a conversation between the owner of the restaurant and one of the regulars. The food was great. We weren't ready to call it quits on New York yet, so I suggested we head down to Greenwich Village. Lily was game for anything. We wandered Washington Square park, watched the skateboarders, and returned to the hotel when we both got cold.

And then it was over.

Lily and I are good travel partners. It helped that we did everything she wanted, and maybe a couple of things I wanted too. It also helped that I gave us the budget to do it all. Most importantly, we got along really well. We listened to each other and we both appreciated that being in New York together was special.

One of my students at DVC told me that she also took her daughter to New York City when she was eight. She told me they still talk about it decades later. She recalled many details of that trip: which museums they visited, how her daughter complained about it, and how much fun they had together. She was very happy for me.

I'll always remember this trip. I think Lily will too. And if she doesn't, well, there's always this blog post to remind her of it.

Business evaluation: Slo Carbon

2023-01-24T06:32:00-08:00

A little while ago, I made a website for Slo Carbon. I picked the name because it was available. I didn't love it, but it was there. So I picked it.

The problem this hypothetical company tries to solve is also described in a different ({filename}business-evaluation-clime.md) for Clime. The "green premium" for carbon-free appliances is too damn high. It needs to come down, so I thought maybe there's a way to do that with carbon credits (carbon misspelled is cabrón, which is kinda funny).

Cabron credits (I did that on purpose) are kinda funny, too. They represent the idea that carbon intentionally not emitted is worth something. That something ranges from $3 to nearly $3,000 per ton. If there was a way to subsidize using less gas with the environmental benefits of using less gas, then... boom. That could be big.

That's what Slo Carbon is about and worth diving into.

The Problem

Like I've said before, residential gas consumption is ({filename}the-importance-of-electrification.md). It needs to come down. Here are the books that validate the last two sentences.

Speed & Scale by John Doerr
How to Avoid a Climate Disaster by Bill Gates
Electrify by Saul Griffith

These books show that 25% of our greenhouse gases come from residential energy usage. The math is pretty simple, and the result is easy to remember. Twenty-five percent of the stuff causing or at least contributing to the climate upheaval we've all been feeling is due to residential energy consumption. That's a big enough lever to focus on.

Homes need to decarbonize. The company I'm building, Shovels, came to fruition out of that premise. As I wrote, the decarbonization need got me looking into building permits and contractors, and the messiness of that data led me to the business behind Shovels.

Slo Carbon asks a different question: Can we use the stream of future CO2 not emitted to create a security that can be sold to subsidize the purchase of an electric appliance? In perhaps a more confusing way to ask the same question, Can we use carbon offsets to offset the cost of decarbonization?

We need homes to decarbonize. The problem is clear. The solution is less so.

The Solution

Slo Carbon would use carbon offsets to offset the cost of appliance purchases. A consumer shouldn't need to front the cash. The ideal flow would look like this:

A homeowner decides to decarbonize. It could be a standalone project or part of a remodel. This typically means replacing the gas HVAC furnace with a heat pump system, the gas water heater with a heat pump water heater, and maybe the gas range with an induction range.
The homeowner hires a consultant or general contractor (GC), or both. They get estimates for parts and labor.
The consultant or GC fills out some official paperwork with Slo Carbon to quantify the reduction in CO2. This should include copies of recent energy bills.
Slo Carbon securitizes the CO2 into an offset to sell in the carbon markets. Slo Carbon estimates what price it will fetch and pays a slightly lower amount to the homeowner. Ideally, this amount offsets the "green premium" or the higher cost of the carbon-free appliance. The homeowner purchases the equipment, and the GC gets to work installing it.
To complete the contract, the GC submits the final install specifications and pictures or other proof to Slo Carbon. Perhaps they also send energy bills for the next six months. Slo Carbon stores this data for anyone who wants to audit the CO2 security.

In this scenario, everybody wins! The homeowner gets a heat pump system. The atmosphere gets less CO2 (yes, even if your electricity is coal or gas-powered--I'll explain). And the homeowner didn't need to pay any extra thanks to the Slo Carbon offset.

The Complications

Oh, there are so many complications here. I wish this were easier. I might have taken a swing at it.

The grid

Okay, climate skeptics. True, we switch to electric appliances, and that draws more electricity which might be generated by gas or coal, especially at night. I can't deny that! However, I learned from Saul Griffith's book that electric appliances are more efficient. They use less energy. It comes down to physics. Electric appliances use about one-third less energy to operate when you measure the input energy, whether it's gas or electricity, and compare it apples to apples. That saving translates upstream to the power generator, whether a solar grid or a natural gas plant. Simply put, electric appliances use less total energy, so it's always a good idea to switch away from gas appliances.

The grid will get cleaner over time. There's too much political momentum for it. We'll go nuclear before we build another coal plant. The cost of renewable energy has declined. Even if the electricity coming into your home is gas or coal-powered now, it will be less so in five and ten years. Our grid will inevitably have no fossil fuel inputs in thirty or forty years.

The cash

The harder problem for me to reconcile is the cash. The cash flow problem here is intense. Let me explain.

About a year ago, I was a homeowner amid a remodel trying to make a green appliance purchase. There's a whirlwind of activity and if I wasn't motivated to do it, we wouldn't have made the switch. I had to do the research, convince my GC to make it work, and hope my wife agreed to spend the extra money. Fortunately, we had the funds (barely), but the stars here needed to align.

Slo Carbon is meant to streamline this decision process for homeowners. Slo Carbon would tell them what to buy and give them the cash to subsidize the extra cost (since the electric appliance is several hundred to several thousand dollars more expensive). The problem is this: Where does that cash come from? Slo Carbon needs to front a lot of money at scale, and each "loan" is of some indeterminant length.

Going back to the Solution flow above, let's hone in on the last two bullets. The homeowner is under pressure to make fast appliance decisions. The GC doesn't want any delays. We need this transaction to be fluid! So, the GC concludes what size heat pump water heater and HVAC to get and Slo Carbon, presumably, determines the total green premium by comparing the heat pump products against the gas alternatives.

Here's where Slo Carbon cuts a check to the homeowner. Straight-up cash. It's either delivered just before the purchase or as an immediate premium reimbursement (probably works better) so we can use receipts as proof of purchase. Regardless, cash moves from Slo to the homeowner. In exchange, we get a signed document that provides Slo the exclusive legal right, or title, to the stream of carbon offsets from these appliance purchases. Through some software that we'd have to develop, that title gets securitized and offered up on one of the many carbon offset exchanges. Then, we wait for someone to buy it and hope the price holds.

Herein lies the other risk. When we paid the homeowner, we relied on an expectation of future carbon market pricing. We took the size of their system, calculated how much carbon would not be emitted over the 20 year life of the appliances, and put a price on that carbon. That price is a guess. If it's a bad guess, and the price of carbon drops, we could lose money on the transaction when the security is sold.

Let's put some numbers down to illustrate this and make it clearer. Using my own gas usage data pre- and post-electrification remodel:

Sep-Mar 2021: 523 therms
Sep-Mar 2022: 157 therms
Savings: 366 therms

Each therm is 12 pounds of CO2, so I'm saving 4,392 pounds or about 2.2 tons of CO2 per year. That sounds like a lot! The problem is that the normal carbon market values each ton between $3 and $100. That's likely the long-term stable price. There are some initiatives where companies are willing to pay far more, but I wouldn't count on long-term rates over $1,000. The price spread is due to many factors, among them the reputation of the seller, the carbon exchange it's listed on, and government or private certification of the offset.

We spent at least $20,000 extra ({filename}the-importance-of-electrification.md) our house. We're a bit of an extreme case, though. Our HVAC heat pump system is fancy. If the typical green premium is half that, and the savings are roughly equivalent, then it still requires 50 years to pay back. Like I said, the most we could offer is 20 years, the appliance's lifespan. Two tons per year at $100 per ton would give $4,000. That's not nothing, but it may not cover the total green premium.

And then there's still Slo Carbon's cut. We'd need to eat into homeowner payment; Slo Carbon needs to make money!

Messy, see? And that's assuming this is a legitimate offset in the first place.

The offset

I looked. These offsets don't exist, perhaps for good reasons. I'll list a few of the reasons here:

The California Air Resources Board doesn't even have a category for residential offsets. We couldn't sell these in the official carbon market in California.
There's no concept of bundling future carbon offsets. Offsets look backward, not forward. It's compensation for carbon already sequestered, a forest not cut down, stuff like that. The idea of promising to use less carbon in the future is alluring but not practical.
The hardest nut to crack is "additionality." This concept refers to the notion that we shouldn't subsidize behavior that would happen anyway. Take us, for example. We opted into electrification. Should we be able to bundle our offsets and sell them one year later? Experts say no. For this to be a valid offset, it should create behavior that saves carbon that would not have otherwise happened. In other words, don't pay people to do things they would have done without subsidy. But it's hard to prove or predict intent.

The net of it is this: The validity of the offset is a major obstacle.

Conclusion

I wanted this company idea to pencil out. I met a lot of great people while I explored this idea and every nook and cranny of the offset market. Many of these folks are now friends and rooting for my success with ({filename}business-evaluation-shovels.md). I'm glad I spent so much time looking into Slo Carbon.

Unfortunately, the idea is just not tenable. It's fraught with legal and financial risk. I couldn't see how this company makes money, grows, and becomes a big deal worth spending a large chunk of my 40s on. So I bagged it.

Then I heard about WattCarbon. To my delight, I learned the CEO lives in Lafayette. We met for beers. McGee is awesome and I love his business. He may have solved the challenges I wrote about here! I will write an evaluation on WattCarbon next.

Is it okay to be a nice CEO?

2023-01-04T08:43:00-08:00

As I take the CEO helm again with ({filename}business-evaluation-shovels.md), I've been thinking more about what kind of CEO I want to be. Am I some visionary leader with all of the answers? A hard-nosed drill sergeant making sure we stick to our deadlines? A coder? A product whiz? Or the Chief Sales Officer?

I simply plan to be thoughtful and nice. Thoughtful makes sense. I should be thinking two or three steps ahead. Besides managing cash, the most obvious job of the CEO is to have a plan. Being thoughtful requires... thought. I think best when I write, so I've been blogging a lot more since I started Shovels. Being thoughtful makes it easier to talk to my team, potential customers, and investors. If I'm thoughtful enough, I'll have already thought of all the answers when I'm asked smart questions.

What about being nice? Why is that so high on my list? Some of my favorite entrepreneurs are nice CEOs. Many have raised hundreds of millions of dollars, taking their companies public and proving that investors like nice CEOs, too. One of them, the nicest CEO I know, recently sold his company for enough money to put $1M into his pocket. Pretty nice, eh?

Mean CEOs do well too. There's the old news about bad-boy-CEO Travis Kalanick and his company's massive IPO but subsequent flop (alongside others in the ride-sharing market). However, for every Travis, there's a Logan (CEO of Lyft) who is equal parts nice.

Here are the good and bad points about being a nice CEO:

The Good

Culture comes from the top. Nice CEOs yield nice cultures, which makes recruiting and retention much easier.
Nice CEOs get more favorable media coverage or at least avoid negative coverage.
Nice CEOs, provided they’re meeting revenue expectations (see below), are less likely to be fired.
Customers like nice CEOs. I've always heard that Box's enterprise customers loooove Aaron Levie, and he seems like a nice guy.

The Bad

Nice CEOs usually struggle with hard personnel decisions like layoffs. They are prone to make these tough calls too late in the game. (({filename}the-story-behind-our-layoffs.md).)
Nice CEOs may be unwilling to move aggressively against competition. They may be unwilling to be the bad guy in order to win a market, so they're vulnerable to being undercut by CEOs willing to take the low road.
Similarly, nice CEOs can have difficulty negotiating on behalf of the company on vendor agreements, term sheets, and salaries.
Nice CEOs tend to over-promote and over-pay their employees. They also are more prone to give in to requests for additional perks.
Nice CEOs tend to avoid conflicts, even when the conflict is important. This was not a problem for Steve Jobs.

The Analysis

I still favor the "nice CEO" model, but I'm biased. I can't be any other way. Since being ({filename}mightysignals-new-leadership.md) for a company that I didn't start, I've been thinking a bit more about this question. Am I actually too nice? What does that even mean? Really, all that I or anyone else should be worried about is results. It's the data that truly tells the story.

The problem with trying to be analytical about this is "niceness" is impossible to quantify. So I took it upon myself to look at the performance of 20 public companies and the Glassdoor reviews of the CEOs in the lifetime-ago pre-pandemic era.

Here's the list of the worst rated CEOs in 2019 and a chart plotting their Glassdoor rating against their stock growth in 2019.

Top 10 Worst CEOs

Micheal Kasbar (4% rating) – World Fuel Services
Mary Barra (6% rating) – General Motors:
Christopher Crane (8% rating) – Exelon
Noel White (8% rating) – Tyson Foods
James Gorman (9% rating) – Morgan Stanley
A. James Teague (9% rating) – Enterprise Products Partners
Richard Hume (9% rating) – Tech Data
Stefano Pessina (23% rating) – Walgreen Boots Alliance
Michael Tipsord (34% rating) – State Farm Insurance
Larry Merlo (35% rating) – CVS Health

Top 10 Best CEOs

Donald Layton (100% rating) – Freddie Mac
Larry Page (100% rating) – Alphabet (Google)
Albert Bourla (100% rating) – Pfizer
Richard Fairbank (99% rating) – Capital One Financial
Hugh Frater (99% rating) – Fannie Mae
Mark Zuckerberg (99% rating) – Facebook
Michael Dell (97% rating) – Dell Technologies
Kelcy Warren (97% rating) – Energy Transfer
Satya Nadella (97% rating) – Microsoft
Samuel Allen (96% rating) – Deere

Doing some unsophisticated statistics, I find a slightly positive correlation between Glassdoor rating and stock returns. The average 2019 return among the highly-rated (my proxy for "nice") Glassdoor CEOs is 54%. The average for poorly rated ("mean") CEOs is 31%. The Pearson correlation between the Glassdoor Rating and the 2019 stock return is 0.19.

Looking at the chart, you see some outliers that bring up my nice CEOs' performance. It's convenient in my analysis that Alphabet's CEO at the time, Larry Page, scored 100% on Glassdoor. There's also some noise here: employees are likely to rate a CEO poorly when stock is underperforming regardless of how nice or mean they are.

However, to consider Larry Page for a bit, at least in public appearances, he seems like a legitimately nice guy. He's one of the founders, a Stanford Ph.D. student who accidentally became a billionaire and had the leadership skills to ride the CEO seat to the top. If Larry Page was an asshole, I don't think he would have made it as far.

My takeaway is this: I can be nice so long as I can deliver. More to the point, if being nice helps me deliver, then this is an easy answer: Be nice.

Taking advantage of the Inflation Reduction Act in Contra Costa County

2023-01-03T12:00:00-08:00

After the success of Diablo Valley Tech Innovation conference, for which I chaired and did the bulk of the organizing, I was approached by a friend in the local sustainability community. She asked me if I'd like to help organize a conference focusing on green tech in Contra Costa County. I enthusiastically said yes!

There's a lot to chew on around this topic. To summarize the three massive spending bills passed by the Biden administration in 2021 and 2022:

$550 billion in new spending over the next five years in the Infrastructure Investment and Jobs Act (IIJA)
$280 billion in the CHIPS and Science Act
$390 billion for clean energy in the Inflation Reduction Act (IRA)

This all amounts to "industrial policy," long considered the third rail in national politics for market meddling. But here we are, post-pandemic, with billions of money itching to be spent on green infrastructure. It's precisely the boon my fellow climate tech entrepreneurs have been waiting for. I want Contra Costa County, the county where I serve on commissions where I live, to take advantage of this. I want a green economy to grow and flourish in Contra Costa County. The question is: How do we take advantage of this windfall?

The funds for climate come from the IRA and the IIJA. We'll start with the IIJA.

The IIJA includes $21.5 billion for clean energy demonstrations and research hubs. There's $8 billion set aside for clean hydrogen. $2.5 billion for advanced nuclear, and $10 billion for carbon capture, direct air capture, and industrial emission reduction. The $1 billion allocated to demonstration projects in rural areas probably won't slide here, even though much of Contra Costa remains in its 19th-century state.

So the real industrial oomph comes from the IIJA. The IRA, which gets most of the attention in the media, provides nearly $400 billion in tax credits for consumers and businesses to adopt clean technology. McKinsey summarized these credits as:

$4,000 consumer tax credit for the purchase of a used electric vehicle
$2,000 consumer tax credit for the purchase of heat pumps, heat pump water heaters, biomass stoves, and boilers
$3 per kilogram for the production of clean hydrogen
$15 per megawatt-hour for power produced at a qualifying nuclear facility

I would love to see a renewed manufacturing sector in Contra Costa County. We're perfect for it. I'd argue we're better equipped than Fremont with its Tesla factory. We're closer to rail, the Central Valle, Highway 5, and shipping ports, and we have "cheaper" housing. Our network of community colleges is perfect for supplying the labor for the advanced, high-skilled manufacturing industries to support the green economy.

We need to attract these businesses. But how? Contra Costa County has refineries but not much appliance manufacturing. We have a strong services sector, especially in the financial, medical, and real estate industries. We also have highly-trained tradespeople for building construction and maintenance. Diablo Valley College and our other local community colleges provide much of that training.

So, where does Contra Costa stand to benefit from the IIJA and IRA funds? I would look here.

Services industries:

EV charger installation and maintenance
Heat pump installation and maintenance
EV and heat pump permitting, inspection, and construction management
Financial advice to access EV and heat pump incentives
Real estate management to execute these retrofits and promote green buildings to tenants and buyers

Government sector:

Streamline EV charger permits
Streamline water heater and HVAC permits
Electrify government buildings and fleets

Manufacturing industries:

EV chargers
Heat pumps
Solar panels

A stretch goal is to create a green technology manufacturing sector. For this to happen, we will need to get services going first and use that advantage to attract the industry. There's a lot of research to do here, starting with understanding if these appliances are built anywhere in California. I suspect not. Suppose there's an economic rationale or the possibility of an incentive provided by these federal dollars directly or through the state. In that case, I hope our county leadership will be aware and make noise about getting our share.

How big is our share? According to this announcement from the governor's office, California will receive more than $16 billion from the IIJA. Allocated by population, Contra Costa should receive about $400 million. Then there's the $47 billion multiyear infrastructure package already in the state budget. Our share of that budget is over $1 billion. So we have $1.4 billion potentially to work with, and more if we can be creative and put good proposals together.

The media calls this a once-in-a-generation event. Unlike the similarly-described extreme weather we've been experiencing, I agree that this funding won't come again next year.

This is the case for organizing a Green Economy Conference in Contra Costa County. We need our representatives to see this window of opportunity, a critical period when economic incentives strongly align with environmental needs. A boom in green economic output could transform this county, producing the change I've been working towards through the Diablo Valley Tech Innovation organization.

I can continue to leverage my connection to Diablo Valley College, which will play a key role in connecting workforce development initiatives to the green economy. I'll also bring in the connections and perspective I've gained recently from my work on Shovels. This will be fun!

Platforms versus point solutions

2022-12-30T10:30:00-08:00

This winter break has been a big one for Shovels. Despite having my kids at home, trekking out to Hawaii, and getting swept up in the Southwest chaos getting to and from Disneyland, I put a lot of deep thought into Shovels. This exercise brought out some gut-wrenching paranoia, deep frustration and confusion, and then a bit of euphoria coming out the other side.

It was a critical exercise, and I don't do this nearly enough, perhaps because it hurts and takes a lot of energy.

Here are the insights from my platform exercise.

We are not alone

First of all, I learned once again that good ideas have company. I was quite certain two months ago that nobody else was scraping building permits. That notion came crashing down hard over the last couple of weeks. We are not alone.

BuildZoom: nationwide permit database but no API
HazardHub: nationwide permit database with some key dates we need and an API
Construction Monitor: nationwide permit database
Builty: nationwide permit database with an API and a data feed AND INSPECTIONS

BuildZoom was the first permit database I came across. I was confused at first because they appear to be a marketplace for contractors. Their data page is hard to find on their website. It's as if they intentionally buried this link on their homepage. The more I thought about that, the more it bothered me. In newspaper parlance this is called burying the lede. Why would they hide the very product that I was planning to build a business around? WHY? What was I missing??

That thought nagged at me as I dove further into BuildZoom's public data. I looked up addresses in cities that had no electronic permit system. They had permit data. Lots of it. I looked up addresses in Contra Costa County, where I had our own data to compare. They had more records than us. I looked up an address in Livermore, where there is an electronic permit system but the permit details are very sparse. They had more data than the city's own electronic permit system. This was a miracle. It made no sense. And yet they were actively trying NOT to advertise their data product. Whyyyyyy?

Luka pointed me towards HazardHub. I started an email thread with the founders. I was very open about Shovels and what I'm doing and they shared that they built custom scrapers, thousands of them, to collect building permits from every city and county that issues them. They gave me access to their API. It's fast and thorough. I was impressed once again. We are not alone.

The ultimate find was Builty. I didn't find them in all of my Googling. They came to me in a conversation with the founder of PermitFlow, a permit processing startup. He listed off the building permit databases he looked at, encouraging us to try to build something better. I didn't recognize the name when he said Builty. I asked him to spell it, and then I took a note to look into them later. I'm so glad I did.

Builty, as it turns out, is Shovels. They're doing exactly what we said we're going to do. It's uncanny. There's not a whole lot on their website, but it was enough to give me the shivers. I reached out through their contact form and asked if they have inspections. The CEO wrote back to me right away and she said they did have inspections. They grabbed them whenever they're available.

She put a phone number in her email signature so I called it. We talked for 30 minutes. At the end of our conversation I was equal parts elated and defeated. Elated because it seemed we don't need to do the permit scrape ourselves. Defeated because I was still holding onto the notion that we had an original idea.

Fortunately, in retrospect, I think both are true.

Platforms versus point solutions

Before I get into why Builty could be such a meaningful relationship, I want to set some context around platforms versus point solutions.

A point solution is a product that does one thing very well. I like point solutions. I've built and sold several of them, and they make some good money for a solo entrepreneur. Toofr, my first point solution, made about $250K per year at its peak. MightySignal was a point solution that topped out at around $1M in revenue per year. AppMonsta was also a point solution, and it made around half that much. All of these businesses stopped growing and were acquired. There's nothing wrong with building and selling a small business. But that's not what I'm trying to do now.

Platforms, however, are like a bunch of point solutions tied together. I've seen that platforms are worth more than the sum of their parts. There are synergies (yes, that word), and network effects that make the platform exponentially more valuable as new features get added. In the mobile data universe of MightySignal and AppMonsta, the platforms were App Annie (now Data.ai), Apptopia, and 42matters. Each of them was orders of magnitude greater in revenue, number of customers, and valuation. They all did what MightySignal and AppMonsta did, but they also did a bunch of other stuff. They had other data and mixed them all together to make a killer app that was far more useful than each of the individual point solutions combined.

I've seen this elsewhere in my career. I remember talking to the founders of Sendbloom, an email marketing software, in their office many years ago. They were growing slowly and watching a couple of competitors, Outreach and Salesloft, take on ambitious product roadmaps. Sendbloom decided to focus on a single feature, drip campaigns. They were confident that Outreach and Salesloft would implode under their ambition, that they couldn't possibly execute drip campaigns, and contact management, and prospecting, and more. In short, Sendbloom chose to be a point solution rather than a platform.

Here's what happened: Outreach and Salesloft raised TONS of money, over $700M between them. Ambition attracts capital, and capital attracts talent. They hired great engineers and product managers, and they both succeeded. They became colossal tech companies with multi-billion dollar valuations. Sendbloom was sold to LinkedIn for an undisclosed amount. I figure it was enough to make the founders some money but only a fraction of the valuation that Outreach and Salesloft are now.

Point solutions don't grow like platforms. They don't accrue value and become big companies. I don't want Shovels to be a point solution!

Shovels as a platform

Builty is a point solution, and from my conversation with the CEO, she's happy to remain that way. She doesn't want investors. She wants to build the best building permit scrape and enable us and others to create products (platforms) on top of it. When I asked her why she said what I'd quietly feared as Shovels moved down this path: the scrape is hard enough. They don't have the bandwidth to figure out what to do with the data. Making the data accessible is all they can manage.

If Shovels wants to be a platform, it must avoid being a point solution. It should not be Builty. When my mind took me here yesterday, I had to sit back and laugh. All that mental struggle over the last few weeks, all that googling and searching and frustration that other companies were already scraping building permits, all of it was a blessing. We don't need to do that. We can be Data.ai, Apptopia, Salesloft, and Outreach rather than MightySignal, AppMonsta, and Sendbloom.

This means we can start building the platform... NOW.

Here's the data we need to mash up together to become the most interesting real estate and construction data platform:

MLS/Zillow for property detail and sales history
Builty for permit and inspection detail
Census for demographic information

With this data we can build products like:

Public contractor profiles with ratings
Time to permit and permit fees by permit type and city or county
Property valuation and square footage adjustment using detail from permits
A new green home rating using detail from permits
CRM for contractors pre-populated with their permitted jobs and leads based on permit history

And with other data that I'm not aware of yet, we'll be able to build even more. This is the beauty of being a platform.

The clouds part when we don't have to do the scrape ourselves. Now we can be creative!

The platform exercise

This got me thinking: could I have landed here sooner? Is there a lesson here about thinking beyond the initial problem?

The platform exercise could be like this:

State the current problem and solution you want to build
Now assume that the solution already exists and the original problem is solved
What's the next big problem? **<-- This is probably where the money is! **

Point solutions solve problems for platforms. Platforms solve problems for the market.

I want my next company to be big, so Shovels should be a platform.

Business evaluation: Alumnify

2022-12-29T21:03:00-08:00

I like B2B data businesses. I learned how to write web applications by building Toofr.com (now FindEmails.com -- they kept my "oo" logo after I sold it). Toofr found email addresses for business contacts. I wrote a book, The Parallel Entrepreneur, about my experience building, running, and selling Toofr while I kept a day job as co-founder of Scripted.

I took some time off after selling Scripted and built a few more B2B data companies. TrackJobChanges automated some clever Googling to figure out current employment status and alert when a business contact changed jobs. EmailFinder did what Toofr did, but better, and in bulk. Name2Domain found the right website for a company name. TrackJobChanges made the most revenue and it utilized both EmailFinder and Name2Domain. In fact, Name2Domain powered EmailFinder's domain identification. If I entered "Bill Gates" at "Breakthrough Energy" into EmailFinder, Name2Domain would be called on to turn "Breakthrough Energy" into breakthroughenergy.org, and then the email finding trial and error would begin.

It was fun stuff, but it was a grind. After a few years at this, I decided to sell all three apps to Live Data Technologies. I was already friendly with the CEO and he invited me to continue working on a retainer to pump up their combined revenue. I ended up spending most of my time on EmailFinder, helping to shore up its resources. Live Data operated on a scale orders of magnitude larger than me. That was challenging work and it required all of my creativity. We made it happen though, and I learned how to use Heroku workers to scale a web app to previously unimaginable levels.

When my year was up after the acquisition, I re-focused my energy on MightySignal and teaching at DVC. That didn't last long; after a few months, I was back on with Live Data, this time to focus on TrackJobChanges (it now redirects to a similar but better Live Data app) and launch something we're calling Live Data Labs. I'm excited to share our progress!

The first app in the Live Data Labs portfolio is Alumnify. Alumnify taps into Live Data's trove of tens of millions of real-time B2B contacts. The idea is to focus on alumni of companies and schools. Why? I'll get to it.

Let's now evaluate Alumnify.

The Problem

The problem, I suppose, for most B2B data companies is that LinkedIn won't share employment data. If LinkedIn opened up its API, a lot of B2B data companies would go out of business. I don't see this happening, though.

Here are the two sharpest pain points that Alumnify addresses:

Nobody is tracking college and university alumni. Alumni associations can't access registrar records due to privacy constraints. They need to get a list of past and recent alumni to invite into the association, but it doesn't exist.
College and company alumni both make great marketing segments, but LinkedIn doesn't provide a way to download a comprehensive and accurate list.

The two problems are distinct. The first, felt primarily by alumni association directors, is truly core to the job. Figuring out who is an alum of a college or university is a painstaking process. I know this first-hand as a board member on the DVC Foundation. We're creating a new alumni association and the data is sparse. Alumnify would help a lot!

The second is a problem that every online marketer will know. There's always a need for more data, more targeting, more lists. Sending marketing material to every Harvard or UT Austin alum is a compelling offer. There's no way to do this now. Recruiters feel this pain too. If they want to recruit from Goldman Sachs or Stanford, they can do it manually on LinkedIn, but they can't scale that effort up.

How big is this problem? I don't know. It could be huge. It might be small. It's not nothing, though. It feels to me like this is a big enough problem to put some effort into solving.

The Solution

Alumnify is already live: alumnify.ai. It takes a company name or school name and provides summary information about the alumni of that institution. It gives a sense of where they are and what they're doing. For a fee, it allows a marketer to purchase a list of everyone who worked at the company or went to the school.

The technology behind it is crazy. I still don't know exactly how Live Data does it, but they've found a way to combine multiple data sources to produce an accurate profile of employment and education history on 70 million people. I've been assisting in identifying emails for all of them and thinking up more compelling ways to present this information.

So that part of the solution is technical. The rest is a marketing challenge: how do we package this data and make it accessible? This is what we're in the midst of figuring out now.

Customer Profiles

Alumnify needs a growth hack. There's one in here... somewhere. I have a few ideas, but let's break this down into who the ideal customer profiles for Alumnify.

College Director of Alumni Relations

The head of alumni relations at a college or university is responsible for staying in touch with graduates. They usually are fundraisers, building relationships over time and developing an annual fund. To do this work well, they need an ever-growing list of alumni to contact. Since the registrar can't share this list, the alumni relations teams put a lot of effort into reaching students while they're on campus. Once the students leave campus, Alumnify will be the best tool to track their professional updates.

Head of Digital Marketing

The head of digital marketing for a startup is responsible for finding more leads in an ever-competitive environment. Since past employment and education work as proxies for all sorts of things -- ambition, interest, geography, income -- alumni lists offer useful targeting. Alumnify will give names, current employment, LinkedIn profile ID, and an email address. This data should be sufficient for digital marketers to build lookalike models in Facebook or Google to further expand reach.

Recruiter

This profile might be the most obvious. A recruiter at Goldman Sachs might want to headhunt people currently at Citi, and vice versa. Doing this at any kind of scale can't be done easily on LinkedIn, so Alumnify has an opportunity here.

Growth Hack Ideas

The question is: how do we quickly and efficiently get Alumnify in front of all of these profiles? One way is to use Alumnify itself to find them.

In a cold email to an alumni relations director, call out what school they went to. Tell them they could send messages just like this to all of their alumni.
Send a message to a newly-hired digital marketing director congratulating them on their new position and suggesting that they check out Alumnify.
Pitch recruiters a list of all Google alumni who went to Stanford.

Then there are the associations, the opportunities where we can hit a bunch of these guys at once. There's an Alumni Relations Institute that would be a perfect audience for Alumnify. There's a million LinkedIn groups and YouTube and blogger influencers looking for new growth marketing hacks. I could offer them free usage in exchange for a testimonial or pitch. For recruiters, I'd also look for LinkedIn groups and try to win a few over with InMail and social media hits.

On the organic side, I've already started to make the company and school detail pages more SEO-friendly. Alumnify needs marketing pages, though. It needs help showing off how it works. The way I built it, Alumnify is able to link directly to a company or school detail page. I should show off a few on the homepage.

SEO isn't really a growth hack, but it's important nonetheless, and forms the basis of any good growth recipe.

Conclusion

I like Alumnify. It was fun to build. It should exist in the B2B sales and marketing data ecosystem and Live Data should be the company to put it there.

Meet Murphy

2022-12-24T07:19:00-08:00

I wrote only two posts about Blue Boy here about Blue Boy, our first dog, a lovable chocolate Labrador who left us too soon. But if you had access to our photo album, you'd see that he's in nearly every video and every picture. Once you notice his round brown shape, the sound of his walk and shake, you can't miss him. Scrolling through the last seven years, he is everywhere.

That's what dogs do. They permeate the background, sometimes the foreground. You smell them and hear them even when you can't see them. It's a lot. It can be overwhelming, and when Blue left us, the empty was nice.

So I was surprised at how quickly we all wanted another dog. Our first reaction was to apply to be a host on Rover, a dog-sitting service, like Airbnb for dogs. We passed and started getting hits immediately. We hosted a half-dozen dogs. We met a hyper-energetic 11-year-old German Shepard. He was too much. We met a really old Irish Setter. His breath was terrible and he somehow made it down to the creek and wandered downstream before I caught up with him. That was a big scare.

Our favorite guests where the doodles, the new trendy "designer dogs" that are usually a cross between a Labrador and a poodle or a Golden Retriever and a poodle. My girls took to both of the doodles right away. The asked me to have them stay with us again. Then a neighbor we'd frequently see on our way to the bus stop in the morning walking her doodle asked us if we'd babysit. My girls were very excited.

Before I knew it, we were sending adoption applications to shelters for pre-approval. The one we liked the best, Homeward Bound Golden Retriever Rescue, approved our application after speaking to my wife. They had a young doodle, Mini Murphy, who was six months old and already passed through two families. He was staying at a foster house while they found a permanent home for him.

The foster parent wasn't sure about us. The last family had young kids and he was too much for them, but she agreed to let us meet him. We drove out to Sacramento hoping for the best, that we'd meet our new friend and fall in love at first sight. What happened was pretty darn close.

Murphy is old for his age. He has puppy vibes, but he calms down quickly, and then a happy old man comes out. He likes to nap. Scratch that, he needs to nap. He loves to cuddle as close to his humans as possible. He gets scared when he hears a new sound. Importantly, he sleeps through the night, quiet as a mouse. And he doesn't shed!

It's early for me to claim victory; we've had Murphy for all of three days. I can tell my wife and my girls have feelings for him. Is it love? Maybe, but it's certainly heading that direction. I'm happy for Murphy, and I'm happy for us. So far this is a great fit.

I'm fundraising this time -- and here's why

2022-12-22T06:36:00-08:00

If you read this blog, I mean really parse through it and find my stuff from 2017 and 2018, you'd be surprised to know that I'm eagerly, enthusiastically, passionately fundraising for my startup this time around.

Yes, me, the guy who wrote ({filename}dont-make-a-mountain-of-a-sand-hill.md). I wrote that. I'm not ashamed. As Jay-Z would say, "It's just what I was feelin' at the time..."

And this time is different. I'm working on different things, thinking different thoughts, seeking different outcomes. This time I'm not interested in a side hustle that I can grow to ten or twenty thousand dollars a month with very little work. I've been there, and it's great, but it's not what I want now.

This time I want big, and to get big, I need capital.

The case for capital

My new startup, ({filename}business-evaluation-shovels.md), is not a small project. It's a monstrosity. It's far too much work for me, or me with a co-founder, or even me with a team of 20 engineers. Shovels, at scale, is a lot of people doing a lot of different things. That's what I love about this idea.

When it takes money to make money, you have a case for capital. This is the purpose of financing. You need to spend money now to make money later. You deploy money upfront, in a strategic manner, to produce more later. The expectation, of course, is that you make more money than you originally deployed.

In startups, we talk about seeds. This is a good analogy. You by seeds at a store. Seeds cost money. You plant seeds in your yard. Yards cost money. You water them. Water costs money. The seeds, the land, the water, it all costs money, and you haven't grown a thing yet. But when that seed sprouts and fruits, the harvest yields back a multiple of the fixed cost (the seed and land) and the stream of variable costs (the water). This is why businesses need capital.

I didn't need capital for my personal projects. I could build the seed myself, plant it, water it, and grow it. I didn't need to borrow anyone's money or sell any equity. Even when I was surreptitiously offered it, I turned it down. But those were small ideas with small outcomes. I know this now because I've exited my side projects.

I told myself that what I ({filename}climate-tech-is-my-next-big-thing.md) would have three ideal attributes:

Be big: have a chance to be very large in scope, having real impact in the world
Be green: move our climate crisis response forward in some meaningful way
Be local: have an impact on my local community or somehow be involved in it

I explored a ({filename}climate-tech-is-my-next-big-thing.md). I talked to a lot of people. I worked for free. But none of them quite fit. An idea might tick two of the boxes and the missing third one would continue to bother me.

Finally, I hit upon Shovels.

It's big: on multiple levels, but for one, this dataset doesn't exist anywhere and it will take a TON of work -- that alone proves its size to me
Be green: our first two customers are climate tech companies
Be local: building permits are inherently local -- better yet, it incorporates local government, which I also care about

Since our revenue will be tied directly to our ability to gather local building permits, we have the chicken-and-egg problem required to justify a capital infusion. And since Shovels will one day be huge, we have what we need for the loftiest of all money: venture capital.

The case for venture

If angel investment is a used Honda, venture investment is a Formula 1 race car. The idea is to move fast, as fast as possible, and get all your growth-hampering mistakes out of the way early. The VC firm gives you an F1 team, coaching, and credibility to raise even more capital.

What I disliked about venture in the past was this vicious cycle of ever-higher valuations, burn rates, and the constant pressure to fundraise. It felt like our business was to fundraise rather than to build and sell product. I see now, years later, that this was a case of bad fit. We got in a fundraising cycle and couldn't get out, and that led us to crash and burn. The company was over-capitalized.

Knowing this, and knowing what austerity feels like too, I want the venture capital. I have conviction that what I do next will be big. If I can't convince a VC that my idea is big enough, then I need to reassess my pitch or, worse, reconsider my idea. Venture capital has become a yard stick for me this time. I want VC to prove that my idea is big enough.

Playing devil's advocate for a moment, can I be wrong about this? Aren't I putting too much weight on VC, hinging my perception of my idea on what one group of people think? I could argue that VC is too short-sighted, not creative enough, too focused on shiny objects (web3! AI! NFT!) but I don't think that's true. I read this post from Y Combinator calling for climate tech companies, and it's one of the most thoughtful pieces about the climate tech opportunity. It reassured me that VCs get it.

Climate is mainstream, and construction tech is coming up. Shovels is positioned between two big market opportunities that will attract a lot of capital. The constraint, therefore, is my ability to pitch and position what we're working on. If I'm not successful in partnering with a VC firm, it's my fault, not theirs.

The typical case for not taking venture capital is the expense. VCs take equity, upwards of 20% in a single round, and that capital can ultimately cost millions or even billions of dollars. Why bother with that when a loan would cost a fraction as much? The answer has to do with risk. VCs get rewarded for accepting the risk (80%+, they would say) that they won't make their money back. This is why equity financing is so expensive.

The case for debt

I want to briefly touch on the case for debt. I'm reading a great book right now, Debt: The First 5,000 Years. My takeaway so far (just 11% in, according to Kindle) is that debt is a natural relationship between members of society and society itself. Debt is ancient, and it's necessary. It's unavoidable too; taxes are a form of debt payment.

So, would I take out a loan to build Shovels? Not right now, no. There's too much risk in this early stage and I don't want the obligation to pay the loan back or the risk of suffering the consequences of bankruptcy. Shovels doesn't have enough revenue to de-risk taking a loan. I would be very open to this form of financing at a later stage, though.

I'm on a mission now. I want take a venture capital firm on this journey with me. Along the way, I'll probably start with an incubator or a small, specialized VC. Then we'll go after the brand names. I have a good feeling about this strategy this time.

Climate tech is my next big thing

2022-11-26T09:12:00-08:00

This has been a wild year. I guess I'll start from where I left off on that children's book post about a year ago.

Coming into 2022, I was doing really great. MightySignal was acquired and was enjoying the process of moving into our remodeled house. I'd spend my evenings in the cottage (which wasn't described at all in that long blog post -- an accidental oversight) working on a web3 project and listening to loud music (thank you, Sonos home theater system.) I was really happy.

Then I started teaching and my routine completely changed. As soon as I finished prepping for one class, another one was around the corner. Spring semester this year I taught thirteen units in five sections across four classes. Two of the sections were 90-minute lectures, back-to-back. It was a lot!

I figured since I was working from home that I could fit this all in: my startup obligations, family life, exercise, creativity, and yes, teaching. A whole shit-ton of teaching.

I was wrong, of course. What suffered was my creativity. I never missed a work call, rarely missed my share of walking my kids to the bus or taking them to practice, and even managed to do a lot of cross training so I wouldn't wreck myself on the Belgian Waffle Ride California. I got into the best shape of my life, actually, and would knock out 13 miles trail running, or 2,000 yards of swimming, or 50+ miles with some major climbs on my road bike, on a whim. I could wake up feeling like doing several hard hours of exercise and totally crush it. I found a way to make that all work. But I stopped writing for fun. I didn't have anything left in the tank for that.

Meanwhile, my first year under Airnow was rapidly approaching. I figured I would stay a while because I really liked my team and I wanted to take MightySignal "all the way" -- basically to see it become something of a big deal in the mobile data industry. Airnow, it seemed, would get us there.

But as the post-COVID boom collapsed, inflation soared, and the war in Ukraine reigned in global economic optimism, a new reality set in. There would be no huge victory party for us in 2022. MightySignal was still in a stagnant growth pattern and it wasn't clear to me how the rest of Airnow's business units were doing. The last few months have been hard.

So, in the midst of all my teaching, I started to think about what I would do next. It was an aggravating experience. I sent a few feeler emails out and got some responses, eventually leading to a couple of offers. One in particular was fantastic: an opportunity to lead another B2B SaaS company, build on my resume as a hired CEO, and take its $4 million revenue and $1 million net income startup into double digit millions. I could work from home, get good equity, and increase my salary by 40 percent. It was a virtual phone service company, a solid business with room to grow.

The only problem was I didn't want it. It took me a month to figure that out. When I turned it down, they offered me more money, and I turned it down again. "What kind of asshole turns down a job like this?" I texted a friend.

But I was relieved. It felt good to make a decision symbolic of what I really truly want to do next: work in climate tech.

It's time. It's time for me to take another big risk. It's time for me to work on something that I actually care about. It's time for me to combine my extracurricular interests with my day job.

I didn't always see it this way. The turbulence en route stemmed from the recognition that a job doesn't need to mean everything. I don't need to love mobile data to work in it. If I'm passionate for something else, I can do it in my free time, which I'll probably get more and more of as my kids get older and older. So why not take a job that checks every other box and just let my job be my... job?

Well, I suppose, the answer is it's just not that simple. Not for me, at least. I won't do my best work unless I can get truly excited about it, and I know I've been diluting my focus these last few years because I don't really care about the companies I've been running. The companies are functional means-to-ends, unfortunate necessities to allow me to volunteer and teach and do other community stuff that makes me happy.

But all along I've had the nagging question: why can't my day job also do this?

So I'm going to find out. I've been telling people around me, including the guy who owns that virtual phone service company, that I'm doing climate tech next. It feels great! And along the way I've been networking with new people and re-networking with old contacts and beginning to sense where in the space I'm going to land. I've settled on two approaches: the well-funded startup and the unfunded idea, both in the residential retrofit space.

There is an incredible amount of work happening in climate tech. Here are just a few of the most interesting companies I've found:

Twelve, which makes critical chemicals from air
Brimstone Energy, which makes carbon negative Portland cement at market cost
BlocPower, which finances residential and commercial property decarbonization
Carbios, which uses enzymes to break down plastics
Climeworks, which absorbs CO2 from the air and stores it underground
WattCarbon, which sources carbon offsets from buildings

It's all fascinating, incredible stuff. I would love to work at any of these companies and be on the frontlines of growing a business that is poised to make a lot of money while preventing humanitarian crises. I could see having boundless enthusiasm for this work.

But it's competitive, and being ten years out of the professional environmental game, I'm not anyone's top pick for a senior role. I've tried and failed to get some of these interviews. I'll keep trying, but I also have another way to get in. I can build a company myself.

I thinking seriously about a couple of ideas. One was around financing residential decarbonization using carbon offsets. I wanted to find a way to use the market value of the future unused CO2 to subsidize carbon-free renovations. It seemed like there should be a way to do this, but the pathway is far from clear. Nobody has figure it out yet, but WattCarbon seems to be the closest. My revenue model would be an arbitrage between what the company pays to homeowners for their carbon credits and what the credits sell for in the market.

My other idea was to quantify how green a home is. This would be a pure software play, or possibly with some hardware if partners don't cooperate. This company would ingest indoor temperature and air quality, thermostat and water heater usage, smart device usage, and any other home-related data streams we can access. Besides analyzing this data to give tips for living greener, it would be a database of households' "home stacks," or the specific appliances that they use. The revenue model would be freemium -- free to use with some paid upgrades on the consumer side and possibly some paid advertising on the business side. This is a variant of the Clime idea I evaluated previously.

The possibilities are endless, and I'm relieved to have finally settled on one idea, Shovels, which is not purely a climate business but one that fills a critical gap in the climate data puzzle.

Now the way I describe what I do and why I chose to work on Shovels is that I found the intersection, after a lot of hard work, between B2B data and climate technology. Shovels is both and it's exciting and hard and... perfect for me.

In the coming years I will learn a lot about real estate and construction. I'll take another run at venture capital and running a high growth business that has to spend ahead of revenue. I can do it right this time and I'm very excited to use my scar tissue to my advantage. The current economic climate is also ideal for an entrepreneur with my background.

I've known excess. I've known frugality. The ground in the middle is very fertile.

Business evaluation: Shovels

2022-11-22T12:04:00-08:00

TL;DR I'm now working on Shovels.

I’m going to evaluate a business that I’ve already started working on. Perhaps I should have done this earlier, but for better or worse, this project has evolved far faster than expected!

To back up a bit, I’ve been looking for a good idea for a while. I was obliged to stick with MightySignal for a year after Airnow acquired it. I set a timer in July 2021 thinking it would be easy to figure my path out in the following year.

But COVID dragged on, I continued ({filename}im-now-an-adjunct.md), and life simply just kept moving. The year was up before I knew it. I wrote ({filename}business-evaluation-clime.md) in June 2022, just four months ago. In it, I said I’m a “general manager in search of an idea” and that I wanted my next idea to be a “B2B climate tech solution that solves an enormous problem.”

The idea was elusive, to say the least. I crawled through the thousands of posts on Work on Climate, social media-stalked my contacts launching their own climate tech companies, and went deep on at least three co-founder opportunities. I came close to joining an electric vehicle manufacturer (micro-mobility, like golf carts), a carbon-free steel technology, and a programmatic interface for carbon accounting.

None of them worked out. Either I fell out of love with the idea, the CEO/co-founder I was courting chose someone else, or momentum waned and sputtered out.

And then, out of the ether, I started thinking about home construction and contractors. My wife and I did a big remodel and it went really well. Our neighbors had the opposite experience. I felt bad for them, angry at the guys they hired, and wondered what the difference was between the contractor we hired and the one they went with. I started to look around and idea began to materialize.

There’s public data about building permits and the inspections that are required for a permit to be signed off. There’s a ton of this data, in fact, but it’s hard to get. Despite being public, there’s no standardized, simple interface to interact with it. There are a dozen different softwares among the jurisdictions that post the data online. Many simply don’t have it on the Internet.

A little antenna went up in the back of my head. This is why there’s no single, central, public database. This data is super fragmented and painful to get. I like fragmented data. I like relentlessly painful scraping projects. I can do this!

For a month or so, I did nothing. I told my neighbors about it and they nodded in appreciation of my excitement if not for the brilliance of the idea itself, and then as has happened for my preceding forty years, life just rolled along.

A change happened in mid-August when I brought a group of friends to Pincerest for a weekend. It was a short trip, just one night for most of the group. Two close friends stuck around while I put the cabin back together and as I swept the deck they gave me a very consequential pep talk.

I don’t remember exactly what was said, but I remember what I took away from it:

I can be a great CEO. I can lead and navigate a business.
I can assemble a great team. Great people will follow me.
I can fundraise. People will trust me with their investment.

They gave me a big pat on the back and said they both see me being a successful CEO of a climate tech company. “It makes all the sense in the world,” one of them said. They agreed that I should chase after this dream. I sighed, smiled on the inside, and kept sweeping.

I returned home invigorated. I reached back out to a couple of the co-founder conversations I still had open. They both quickly ended. Undeterred, I posted a project on Upwork to get help building the permit scraper prototype. It felt great to start moving.

Then I reached out to a contact at Teamworthy who I’d known for years. He had also encouraged me to pursue my own company rather than working for anyone else, including another turn as a hired CEO. I sent him an email to reconnect and told him about the carbon credit accounting opportunity and my idea to harvest building permit data. A week later, the carbon accounting deal was off the table and I was left with my permit data idea.

I scheduled a meeting with my Teamworthy guy. He told me that to be competitive with their process I needed a co-founder. Fortunately, I had the perfect person in mind.

I met Luka for the first time in February 2020 when I organized a MightySignal retreat in Las Vegas. We rented out the “Real World Suite” at the Gold Spike in Downtown Las Vegas so everyone could stay in the same place and get more opportunity to connect (in retrospect this only worked because we were all guys).

Luka arrived last due to a harrowing sequence of flight delays. He ended up traveling nearly 24 hours from Slovenia to Las Vegas. I felt terrible for him but he was chirpy as ever, just glad to be there, and went immediately to sleep.

That trip almost didn’t happen for another reason — in order to get Luka there, I needed to close the acquisition of AppMonsta, the company he was running at the time. Legal delays forced Luka to hop on a plane uncertain if the parties would have everything signed by the time he touched down in Vegas. That too had a photo finish. Docs were executed and the wire triggered just hours before Luka took the elevator up to the suite.

I would come to admire Luka and Cata, his support engineer, greatly over the coming years. They worked hard, constantly putting out fires as the goal posts were in constant motion.

The goal posts, in this case, were the Google Play and Apple App Stores. AppMonsta performed daily scrapes of both, each with millions of pages. Doing this at scale, non-stop, with monitoring and redundancies, is a really difficult task. That AppMonsta could do this with such a small team was truly remarkable. As an important plus, both Luka and Cata fit very well culturally with my small crew at MightySignal. I was grateful that they both stayed with me through our Airnow acquisition about a year and a half later.

Due to some issues at Airnow, Luka left a few months ago. We lost touch for a bit and I reached out in late August 2022 to ask him for help with my permit scraper. We had a brief chat and then a few weeks went by. Unsure if Luka was interested, I continued to work with my freelancers.

We finally reconnected at the end of September and I told him that I put him in my pitch deck as a co-founder. He didn’t object, and we’ve been working together since.

Now, long backstory aside, let’s dive into the actual business.

The Problem

As I wrote in the introduction to Shovels, there’s an agency problem in the trades. Contractors have far more knowledge about their skill level and fit for a job than the people who hire them and the banks who fund them. As a result, there is an inefficient market with a lot of bad deals. This is how my neighbors ended up with their awful contractors.

Which contractors are active in my area and which of them are the best fit for my project? The answer today is “nobody knows!” This is what we call the contractor agency problem. Everyone looking to hire a contractor, whether they’re a homeowner with 2,000 square feet or a real estate builder with 2 million square feet, has this problem. The financial institutions who loan money to builders have this problem, too.

There’s another problem, and it’s faced by planners and data aggregators who want to understand building trends in a specific geography. The geo could be a zip code, county, state, or even just a single address.

What specific type of building activity is happening now and has happened in the past in this area? The answer, again, is “nobody knows!” I spoke to an executive at a very large home improvement website recently. These guys have raised hundreds of millions of dollars and should have the resources to acquire any dataset they want. He told me they are looking for a way to get permit histories on any address in the US. He said it’d be a really big deal for them to get this.

But it doesn’t exist… yet.

The Solution

Shovels (did I mention that’s what we’re calling this business?) figures out where construction work is happening and who’s doing it. We pull together and analyze millions of records of public data on building permits and inspections. From this data we can measure and therefore predict performance for every contractor, and we also see what work has been done on every address.

What we’re seeing already is not surprising. The data is messy: it’s incomplete, it’s inconsistent, it’s rife with human error. It's every dirty data problem wrapped up in one incongruous mess. Luka and I remind each other that this is our moat. This is the essence of the problem: decentralized data with different schema maintained by different organizations.

This is why the world needs Shovels.

But more specifically, the world needs Shovels because the world needs more information about who the good contractors are. By analyzing inspection data, we're able to introduce a couple of new metrics into the contractor hiring process. As I describe on the Shovels website, our first two new metrics are:

When we make a histogram of all of the inspection pass rates for contractors in Contra Costa County, it produces a beautiful bell curve.

This is exactly what I'd hoped to see. The standard deviation is about 13 points on either side of the mean. Those contractors beyond the standard deviation are the best (right side) and worst (left side) of the bunch, and we can raise that flag to anyone looking to hire them. It doesn't necessarily mean they're awful, but it does mean that hiring or funding them has additional risk.

Beyond this positive/negative rating system, we can also match contractors to future jobs by showing specifically which type and size of projects a contractor tends to excel at completing. We're able to grab all the metadata along with the permits to visualize the types of projects a contractor has done recently. We also can share how many jobs they tend to do at once. This is useful to make decisions about both hiring and funding.

Our solution addresses the data transparency problem in construction. Specifically, provide visibility into what construction activity has been happening. By looking at that problem, we also end up with info about contractors, so we can solve the contractor agency problem.

We are building this database for the first time. It doesn’t exist today, and to me, this is really, really exciting. My past projects involved rearranging existing technologies and commoditized data. This is the first time I’m building something truly original.

So that’s the problem and what Shovels does to address it. Now let’s dive into the business itself.

Business Model

Here I'll explain how Shovels grows to $10 million annual recurring revenue (ARR).

We sell data to banks, builders, and construction data aggregators and make it accessible through a web application. We price based on geography. Here's our current rate card:

Single jurisdiction (county or city): $500/mo
Ten jurisdictions (bundled by us or custom): $2,500/mo
All jurisdictions: $500,000/year

Our base fee will include one year of historical data. We will charge additionally for all historical data, which might go back 10 years or more. We also charge additionally for API and data feed access.

With an average contract value (ACV) of $10,000 per year, we can get to $1 million ARR with just 100 customers. If ACV stays constant, it will take 1,000 customers to hit $10 million ARR.

So, how do we get to 1,000 customers? There are about 3,000 counties and 350 metropolitan areas in the United States. Revenue should scale with geography, so if we were in only 100 counties, we'd need to get an average of 10 customers in each one. If we focused on the major metro areas, say the top 10, we would need 100 customers per metro.

This requires real work on both the sales and engineering sides of the house, but it is reasonable. Plenty reasonable. And it doesn't take into account the likelihood of signing some major nationwide contracts that would each be worth 50X our ACV.

The harder question is how we get to $100 million ARR. This revenue level is approaching IPO territory and one where Shovels could be valued at $1 billion or more. This breaks down as follows:

Data coverage in 100% of metro areas
Data coverage in 90%+ of counties
10 national customers at $1M per year = $10M ARR
50 customers in each metro at $5K per year = $90M ARR

It adds up fast! The trick, of course, is that we need to be in each metro before we can collect revenue. Thus, we'll have to absorb engineering spend ahead of revenue. This is our primary case for venture capital.

Use of Funds

I used to struggle with this section in my previous companies. The use of funds was never clear-cut. I felt like I had to make up reasons to spend money. For most of my projects, the software was not ground-breaking stuff. We attempted to turn it into some very complicated work, but in retrospect very little of it was necessary.

Likewise, on the sales and marketing front, we built up expensive sales teams and purchased expensive marketing software long before found product-market fit. We did this because we could, because the money was there and we were expected to spend it.

Shovels is different. There's a clear connection between engineering and sales expense. We need to harvest data (engineering) in order to sell it (sales). The two work in tandem, at least until we have complete coverage. Even then, there will be more local datasets to harvest, integrate, and analyze. I can see engineering and sales working together well into the later stages of this business.

I'd like to raise $1M sooner than later. Here's how I'd spend it.

Initially, Luka and I figure a team of 3 engineers can add five jurisdictions every quarter. A jurisdiction is a city or county that manages permits (most cities outsource this to the county; very few run their own permitting operation). A good benchmark for a metro area is five jurisdictions, so this engineering trio can add one new metro area to Shovels each quarter.

Our engineers, a couple of revenue folks (sales development representative and marketing manager, perhaps) plus founders would take us up to about $1M per year in expense. Now, we back into the four metro areas and 20 jurisdictions we'll have in Shovels at this point, and assuming the $10K/year ACV holds, we need each metro to contribute $250K per year, or about $20K per month.

That's 20 customers in each of these four metro areas. Think about how many banks and construction companies there are in San Francisco, Chicago, Tampa Bay, and Dallas. Can we get to 20 customers in each one? You betcha.

I want to raise $1M in order to get $1M ARR. That's the ratio I would promise to investors. Every dollar raised gets a dollar of ARR within 12 months.

That's my north star as CEO. Since I think we can achieve it, I'm all-in. LFG!

The Descent of Blue

2022-11-06T21:18:00-08:00

Everybody who met Blue said he was the best dog they'd ever met. Everybody was right, of course.

In the years since The Ascent of Blue, which I wrote about five years ago, Blue became his own establishment, a pillar of our little neighborhood, as recognizable as any street sign.

He was out all the time, accompanying us on walks, jogs, and bike rides through every nook and cranny of Saranap. And when he wasn't out and about, he was in front of our house, watching the cars roll up, hoping to see his favorite UPS driver so he could tour the truck and get another treat and pat on the head.

Our mutual comfort with him free-roaming in front of the house peaked when we traveled to Colorado this spring and couldn't find a full-time dog sitter. As a last resort, we hired our neighbor to feed and play with him a couple of times a day while we were gone.

The calls came quickly: Blue was howling, whining, crying, carrying on and making a huge fuss. I relented and told my neighbor next door to open the side gate and let him out front. I told the teenage dogsitter to leave the gate open after he fed Blue. The howling stopped, and there Blue stayed without a leash or a collar for three more days until we returned home. When the Uber driver pulled up to our house, Blue was on the porch, curiously watching until he recognized us, and then he trotted down the driveway to welcome us back.

In fact, the only time he was leashed was when I'd sneak a free ride, letting him pull me along on a bicycle or rollerblades. That was a long time ago. The rest of the time, he was off-leash, trotting alongside or slightly in front of me, slowing down only to see if he guessed correctly where I'd turn at an intersection.

Yes, I was that guy running with his 100-pound chocolate lab through downtown Lafayette and Walnut Creek and everywhere else with no leash. People would either stare at me or not care at all. A few smiled and nodded in respect. They knew this was a special dog.

The mark of any great partner, I suppose, is trust. Other dogs can be good, kind-hearted animals that love their people with every fur in their coats. But you wouldn't trust them on a busy street, or in a room full of elderly people, or with a hot steak resting on the counter.

Blue was great because I could trust him. I could trust that he would make good decisions, that he could read the room, that he would know when to slow down and stop at the edge of the sidewalk on a busy street.

This was peak Blue, between ages 3 and 5. In his "middle age", he was perfect. No problems at all.

Starting about two years ago, it started to change, and then it all went downhill in a heartbreaking hurry.

I remember when he started to slow down. Quite literally: I could no longer run with him. The days of him pulling hard enough on his leash to drag me around the neighborhood were a dusty dream.

I started to jog long distances a few months before the start of the pandemic. My neighbor Neil would invite me out, and we'd hit anywhere from 5 to 10 miles in the hills and all around our rolling suburbs. Blue used to keep up, even staying a bit in front. Neil was amazed that Blue's big frame would take it all in stride. I beamed proudly. Yea, Blue was my boy.

Over the course of the following year, as the pandemic rolled on, Blue fell further and further behind us during our jogs. It was subtle at first. I blamed his feet or maybe something he ate that morning. As the allergies gave him ear, eye, and skin infections around his face, he looked older, and I thought maybe his knees or hips were giving out.

Blue with his itchy eyes.

In retrospect, I think it was his paws. He'd spend a lot of time licking the webbing between his toes, and they would get really red. It wasn't comfortable for him to jog, so I eventually stopped inviting him.

He used to get so excited when I would put on my jogging shorts and then my socks and shoes. He would watch me intently, waiting for me to get to the door, and with a single nod of my head, he would go racing out.

That was Blue before.

The Blue after would lie down just outside the front door, his paws hanging over the step, still watching me but not interested at all in joining. I could see him lower his head to his front paws as I jogged away. That's the way it was for the last couple of years of his life.

I remember the first time he got a really bad ear infection. I didn't know what it was, so I didn't pay much attention. He shook his head all the time, which we'd gotten used to, but also, in retrospect, this was a bad sign. I didn't act, and I let his ear infection get so bad his ears puffed out like little balloons. They got thick and stiff, and I could see green and yellow puss in both of his ear canals.

That was an expensive vet visit. They loaded him up with antibiotics, anti-fungal shampoo and lather, and antihistamine pills for the itching. He also got a thorough ear cleaning, which led to his deep fear of vet hospitals. After that first ear cleaning, he hated going to the vet. Blue is not one to have strong negative feelings about anything, but boy, did he try to avoid going into that vet hospital ever again. I had to drag him out of the car multiple times when that pesky ear infection returned.

I eventually learned that this condition was seasonal. Winters were good times. The months between October and March were generally clear. Blue's coat would soften up, his ears wouldn't swell, and he wouldn't scratch and lick and chew his skin during the winter. But I could tell that spring was coming as the head shaking and non-stop scratching came back. The skin around his eyes would dry out, and he'd scratch the hair off of his chest, leaving a red oozy welt that had a hard time healing up. It was painful for all of us.

The vet bills piled up, and I gambled on one final treatment, a visit to the animal dermatologist in Oakland to get an allergy panel and immunotherapy treatment. The doctors figured out what dusts and pollens Blue was most allergic to and told me to inject him with trace amounts of those allergens every month for a year. I did, and the symptoms became far less severe.

The ear infections never went completely away, but the skin problems eventually subsided. For that, I was relieved. Blue lived the last couple of years of his life in relative comfort with his skin. The ears would get stinky but not puffy as they did before. It was a smell we just had to get used to.

And then came the seizures.

He had his first one in June 2021. We were in the midst of a home remodel and living down the street in a rental house. Blue was sleeping in our girls' room, where they had bunk beds. Around midnight we heard a loud noise, a thump, and then more bumps and thrashing. My wife jolted out of bed and went to see what was happening in their room.

"Ryan! Something's wrong with Blue!" she said hurriedly.

I remember seeing a huge animal, completely out of its mind, saliva dripping from its mouth, a blank stare across its face, convulsing on the floor next to the bunkbed where my daughters were still sleeping. It didn't click for a moment that this was my dog.

Blue continued to seize. I grabbed both of his legs and dragged him into the hallway, and shut the bedroom door. I told Melissa to go into our bedroom and shut the door too. I thought Blue was either rabid or about to die. I had no idea what to do, but I stood by the front door, watching him come out of his post-seizure malaise. He stared back at me; his head cocked, ears perked as if seeing me for the first time.

I coaxed him out of the house, relieved that whatever had gripped him was wearing off and called the emergency vet. I drove him over and talked to the nurse. She came out to the car and looked at him, and after hearing me describe this event as some sort of exorcism, she shrugged and said he had just had a seizure.

"A seizure?" I asked.

She explained that it can be caused by anything and that medicines can help. She said he was probably fine to go back home but that we should try to see a vet soon. It's impossible to know when the next seizure will hit.

I made Blue sleep outside that night, a pattern that we would get used to with his nighttime seizures. He'd usually get amped up after his seizure, making it hard for all of us to go back to sleep. We had to tune out his whining to be let back in. That part was as hard as the seizure itself.

Then there was the cleanup. He peed a lot during the seizures. Sometimes he defecated too. This would be messy, not the ideal activity at 12 or 1 or 3 or 4 in the morning. It would happen at all hours of the night.

And then it started happening during the day, too. One morning, when we were moved back into our house but still finishing the paint in some rooms, our painter came to the front door, knocking hard. He said something was wrong with Blue. Another seizure.

One time Blue was resting on our bed, which we let him do sometimes in the mornings. He started having a seizure. Instinctively, I shoved him off the bed with my feet. He started scratching the brand-new walls. I had to move him again and wait for it to stop. He peed on the carpet. Ugh.

Eventually, we determined that we'd have to block Blue in the living room and put padding and blankets down every night, so we did. Sometimes we caught the seizure, making cleanup a lot easier. Other times we didn't since Blue had a habit of finding the cool spots on the wood floor in the summer and sleeping there instead of on a blanket. Other times we just made him sleep outside. My wife would feel bad for him and let him in as soon as she woke up.

This is the downside of having a dog. It's a commitment, in sickness and in health, up to a point. And I was getting tired of it.

A little more than a year after he started having seizures, we hit the final straw.

I took Blue down to the creek behind our yard. He loved the creek and I'd take him down during my casual work phone calls. I threw rocks, and he chased them into the deep bend where it was deep enough to swim. He just loved it.

I threw a rock for him to chase and turned and looked for more rocks. When I saw Blue coming towards me, I noticed that he had a limp. He didn't seem bothered by it. In fact, he started barking at me to throw another rock. I figured he had a stick in his paw, and he'd run it off if I threw a few more rocks, so I did. When he approached me again to bark for more rocks, the limp appeared worse.

I turn around and headed back towards the trail that led up to our backyard gate, knowing he would follow. I could see he was having trouble with his left leg. Oh boy, I thought. This could be bad. Blue made it up to our yard, limping the entire way without putting any pressure on that leg.

The vet told me the worst-case news. The X-Ray didn't show anything wrong with his leg bones or hips. That meant the problem was ligaments and that it was most likely a torn ACL (the dog version). The remedy was an $8,000 surgery and a long rehabilitation. This was a price in time and money that I wasn't willing to pay.

We came home to have a think.

This was hard. I saw the writing on the wall, but I didn't want to read what it said. I could acknowledge what it meant, but I didn't want to understand it, digest it, or plan for it.

Blue was a mess. My friend, the dog I picked and brought home and took on miles and miles of runs and hikes had reached his limit, passed it even. Maybe I was to blame, maybe it was all those jogs. I thought about that, too, asked myself if I had pushed him too hard. I didn't know then. I still don't.

I do know that he was happy during those golden years. He loved being with me, and I wanted him to be right there too.

After sitting on it for two months, I made the call. I found a veterinarian who did house visits to gently put my Blue down. I scheduled it after my 40th birthday party and a dad's weekend at my family's cabin in Pinecrest. I wanted Blue to partake in all of that, and I wanted me to embrace the limited time I had left with him.

It's a weird thing to have a doomsday clock, a knowing that a life was going to end on a specific date at a specific time. The days went by. I talked to Blue. I spent more time with him at night. I told my daughters to tell Blue they loved him. They could tell he wasn't feeling well and that his lame leg was bothering him.

I brought Blue to the bus stop the morning that the vet came. I made sure my girls gave Blue a big hug before they went to school. That was hard.

The rest of the morning was shot. I paced. I sat. I held Blue's big smelly head in my hands and kissed him. The minutes moved slowly until, finally, I received a text that the vet was on her way. I brought Blue outside and waited.

The process was pretty simple. She started with a strong sedative to make Blue go to sleep. It took a while. She had to increase the dose before he finally became drowsy, eyelids droopy, and put his head down to rest. We fed him and talked to him. I think he liked all the extra attention and fought the sleep.

Once he was down, the vet gave us a few minutes to say goodbye. This was it. My old friend, loyal as a shadow, was going away forever. How do you say goodbye? I patted his head and nodded to the vet. I walked away and leaned my elbows on the fence overlooking the creek where he and I spent so much time together. I cried like a baby.

And then it was done.

I had spent the prior two days digging a grave for Blue under our huge oak tree. I read that it needed to be three feet deep, and Blue's frame was long. This was a lot of dirt and the summer dirt was hard. I had to pause to buy a hatchet to cut through some thicker roots. The vet helped me wrap Blue in a sheet and place him into the grave. Then she quietly and politely let herself out.

I know Blue's body is still there, breaking into smaller and smaller pieces.

But I like to think his spirit, the essence of who he was, now is in some outer ether, re-living this love that he got from all of us, but especially from my two girls.

They loved him. We all did.

You're my boy, Blue

So this is 40

2022-08-24T21:26:00-07:00

I'll try to briefly recap the last day of my thirties.

I woke up a bit groggy, which is not at all unusual because my wife hops out of bed at 5:30 am every morning to work "East Coast hours" because her boss, the CEO, lives and works in Connecticut. She lets Blue out of the living room (aka "Blue's Room") where he's fenced in so we don't hear him romping around on the hardwood floors all night and he diligently jumps onto our bed to help me wake up.

At this point, I look over at the clock and it's always within five minutes of 5:45 am. Today was no exception.

This morning my wife worked from Blue's Room. Sometimes I see her in the office, but since she had no early morning calls, she was there. I kissed her and removed the pads from the couches which indicate to Blue that he doesn't belong on this furniture. I folded up the fences, set them aside, and proceeded to make coffee.

We religiously drink whole bean Peet's French Roast, ground up just seconds before brewing. Today was no exception.

With the coffee brewing, I headed upstairs to the luxurious media room with the massive sectional couch we purchased from Ethan Allen after agonizing amounts of research. I walk up here and it makes me happy every time. We nailed it. Everything about this room is fantastic. I'm starting to perk up at this point, about 6:00 am, and I switch on our massive Samsung The Frame television and toggle over to the NBC app to watch the previous night's Nightly News with Lester Holt. I don't particularly like this show, but it goes ten minutes exactly before the first commercial break and that's exactly how long my morning core workout takes.

So I start the show, begin tracking a Core Workout on my Apple Watch, and assume the plank position, elbows down, for four minutes. This usually is long enough to get through the Trump segment and something about police brutality. Today was no exception.

I just listen because four minutes in an elbow plank is hard even though I've been doing it now for months. I don't need the extra strain to try to see the TV up on the wall to my right.

I'm just starting to sweat as 3:45 roles around and I try not stare at my watch for the last 15 seconds. Finally, I do bird dogs, star crunches, some isometric holds, and close out with a few leg stretches and rolling plank pushups. I usually go just over ten minutes, more if one of the stories grabs my attention and I end up watching for 30 seconds in between moves. These short breaks are an indulgence.

Another indulgence awaits -- sweet cream in my coffee! I used to drink coffee black, like my wife, and I still like it black, but I really love it with sweet cream. Rather than buying it from the store, I've found I get the flavor and the creaminess simply by mixing syrup and milk into my coffee. That's it, and it's wonderful.

At this point, it's about 6:15 am. My wife is still working, in the midst of emails or whatever. She usually doesn't talk to me at this time in the morning. On my best days, I'll avoid my laptop and instead head outside where some compassionate person dropped off today's East Bay Times on my driveway. It still tickles me that every day I get this delivery for practically nothing.

Then I sit, in Blue's Room, and read the paper while my wife does her emails or whatever. At some point she'll stop working and chat, or one or both of my daughters will emerge from their slumbers, cuddle up to us and start talking about breakfast. I'm pretty sure that happened today around 6:30 am. They both came out and asked what's for breakfast. We answered that question with some poppyseed muffins from Costco and a couple of bowls of Honey Nut Cheerios. I partook in both.

We all get dressed after breakfast. The girls brushed their hair and teeth and I put on some chinos and a polo shirt since today was a teaching day at DVC. Normally I walk the girls out promptly at 7:25 am to their bus stop but today my wife offered to take them. I obliged and continued playing guitar on our porch, as I'm prone to do on most weekdays in the 15 minutes before we leave for the bus stop. Today was no exception.

I practiced the lyrics to Suzanne by Leonard Cohen and got on a MightySignal sales team call. After that, I headed to DVC, calling in an order to Morucci's for sandwiches from the road. I needed to pick them up on my way back and they get very very busy during lunchtime.

From 9:35 am to 11 am at DVC this morning I taught Introduction to Marketing. It was my second day of class today and I had a lot of participation. We talked about the Marketing Mix, Marketing Envirnoment, and Marketing Orientation. I told them about Lee Iacocca, the legendary President of Ford and CEO of Chrysler during the 70s and 80s, and we talked about the automobile industry marketing mix and environment in the context of the period. It was a great discussion. I thoroughly enjoyed it and recognized that 15 years after my last formal education I've continued to learn a lot.

The lecture went quickly, which I've learned is always a good sign, and after fielding a few logistical questions from my students after class, I sped home, picking up those sandwiches on the way. I also went by our local liquor store and got some Campari, Gran Marnier, sparkling wine, and a fancy expensive liqueur I'd never heard of, but it looked old and Italian so I bought it. Sonny was behind the counter again and I know he appreciates my boozy shopping sprees.

At home I went to work, setting up my audio equipment for the soundcheck my friend and I planned to prepare for my birthday party concert this weekend. The gear looks like this:

Two mics and stands- Two guitar stands- Two music stands- A four-track Mackie mixer- A super simple PA with two channels in- Tube amp (Peavey Classic 30)- My best two guitars (Webber and Fender Tele)

My friend showed up just as I finished prepping the sandwiches, at 12:30 pm. Minutes later, we got our outdoor furniture delivery, a nice set of two wicker lounge chairs and a couch, as well as a nice teak coffee table. We sat on our brand new furniture and ate Morucci's sandwiches.

For the following two hours, we played music. He did most of the lead vocals and I played more electric guitar than I expected I'd play. It just sounded so good. I was happy with the harmonies I added and again loved the fact that he plays harmonica so well. It's such a wonderful addition to the mix of sounds.

At 3:00 pm, he headed home to Novato, and I turned my attention to the many parts of the basketball backboard that I purchased online to replace the one that our contractors damaged during the home addition and remodel. After a bunch of trial and error, I figured out that the best way to attach the backboard to the original pole mount was to take part of the pole mount apart. With some WD-40 and a couple of pliers, I was able to detach it, making the assembly process a lot easier.

Another thing I've noticed, as I've approached 40, is my confidence in figuring out these silly handy projects has increased dramatically. I know to expect things not to match up perfectly, for the instructions to be wrong or a part to be missing. I embrace that part of the challenge.

This project was no exception. My mounting bracket is old; the angles don't match up to the new backboard very well. I didn't buy a new mounting bracket, so I used my hammer to solve the problem.

At 5:00 pm our neighbors and their two boys came over. I was happy with my progress on the backboard and went into our kitchen to make a Campari spritz using the ingredients I bought from Sonny. My wife was enjoying the new outdoor couch, listening to music on the outdoor speakers, looking as beautiful as ever. We sat for a while, letting the kids play upstairs in the TV room where I did my core workout this morning. At 5:30 pm I fired up the grill and slathered the salmon my wife bought earlier today with olive oil and a lot of sea salt.

The grill was hot. I put the salmon flesh-side down and watched the flames come up. I tried to put them out, turned down the heat, and tried again. Eventually, the grill settled down and I lowered the lid and set a timer for six minutes. I talked to our neighbor friends, trying to keep an eye on the grill to put out more flare-ups. I flipped over the salmon, put them up on the roasting rack, and closed the lid again. Two minutes later I took off the salmon and brought it inside, most of it golden orange, a few bits blackened from the flames.

Our friends stayed until 8:00 pm. The grilled salmon tacos were delicious, a real treat. We finished the Campari spritz and the bottle of wine they brought. I admired the beautiful cleaver they gave me for my birthday. We put pajamas on our kids and helped them fall asleep. At 9:00 pm I talked to my wife for a few minutes and then came up here to write this post.

I turn 40 tomorrow.

What have I learned? Well, let me count the ways:

I always enjoyed grilling. I enjoyed it in my 20s. I'm better at it now because I can afford nicer meats.- I made lasting friends in college, at my first job, and at grad school. Today, most of my friends are my neighbors. I'm totally fine with that. - I always wondered, growing up, what it would feel like to be able to spend up to $100 on groceries or dinner or whatever and not even care about it. I've known this feeling for a while now, and it's a wonderful feeling, and I'm still grateful to feel it. I hope I stay that way. - Relationships take work, moreso as you get older. - Being fit takes work, moreso as you get older. - Disposable income and disposable time are a great combination.

I don't feel 40. I recognize that I am 40 and I don't fight it. But the "40" that I thought of growing up is not the 40 that I see in me today. I have all the enthusiasm and hopes and dreams that I had at 20. I'm in better shape, probably in much better shape, and I'm more established and with far more financial stability. By these metrics, I'm better at 40 than at 20. I believe that. I hope it's still true at 50.

So I leave my 30s tonight with this blog post, a glimpse into a day not unlike most of the days of my 30s, and probably not unlike many of the days I will have in my 40s.

I'm happy and excited.

Today was no exception.

Why it's good to befriend your competitors

2022-07-07T20:13:00-07:00

Here's a bit of contrarian advice: Be nice to your competitors. In fact, befriend them, because you just might make a pile of money as a result.

I've always taken this road and it has never backfired. I'm going to describe a bunch of examples here and then generalize the approach for your own situation.

Scripped: Got the competitor to invest in us

You wouldn't think that two browser-based screenwriting apps would launch within a month of each other from opposite coasts, but that's what happened. Scripped and Zhura both came onto the market in 2011 to all the glitz and glam that Hollywood could offer. Super Bowl commercials, endorsements from the Oscar stage, digital banners in Times Square.

Just kidding. Nobody noticed, except perhaps a few screenwriting geeks and our respective teams.

I couldn't believe it, actually. Zhura was a much better product. It worked better, it looked better, and I was intimidated by the team: an MIT-educated engineer and a wealthy entrepreneur teaming up to do the exact same thing we were doing: take box screenwriting software into the Internet age. We were fresh out of grad school, with no funding, and outsourced our software development to some guys in Canada. The Zhura engineer built that product himself.

But what we had was hustle, and my co-founder Sunil was great at pulling all the strings in LA, where he was living, and leveraged that as the one advantage Zhura seemed very unlikely to take away. We had geography on our side.

Why would anyone want to use a screenwriting product from Boston?

So that's how it went for a while. We each put up competitor matrices, passive-aggressively poking each other in the ribs. We'd compete against each other on Google Ads. And we figured out that Zhura had public URLs for their users, and that the user IDs were sequential, so if we wanted to know how many screenwriters signed up, we just had to find the highest member URL that didn't give a 404 error. If I recall correctly, we usually had more users than them.

But it was a slog. This was not a great market to be in and every little pivot we made led to another dead end. We hit $15,000/mo in revenue and stalled out. At some point, I convinced Sunil to let me reach out to Zhura. It would be the first of many times I contacted my direct business competitors.

That first email is lost to history, but I remember being very frank. I sent it directly to Eric MacDonald, the wealthy CEO, and complimented him on building a great product. I even acknowledged that the technology was better than ours, and I hinted that I knew we had more users (those public user URLs disappeared shortly afterward). I also asked if maybe there was a way to work together against a common enemy (Final Draft, in our case).

Eric responded with a thoughtfulness that I would come to appreciate and know well. One conversation led to another, and soon we talked about joining forces. In another show of magnanimity, he accepted that the combined entity would use our name, and even offered to invest another $100,000 to give us the resources we'd need to grow.

And that's how one honest email to a competitor led to a merger and a $100,000 investment.

We hired our first full-time developer and got to work combining the assets.

Scripted: Saw the writing on the wall

Scripped eventually did one final pivot over to what became Scripted. We sold the remnants of Scripped to another competitor, WriterDuet (still the redirect target from Scripped.com), and focused on our new content marketing marketplace.

Things went really, really well for a while. We raised a ton of money, hired a great team, and managed to build a meaningful brand in the content marketing space. We positioned ourselves in between Upwork (Elance/Odesk at the time) and a Madison Avenue marketing agency. The idea was to offer software-powered high-quality writing that paid well, respected the writing process, and could scale up.

We weren't alone, of course. Just like our screenwriting launch with Zhura, another east coast competitor sprung up at the same time we launched Scripted. Contently was based in New York and focused their writer recruiting on journalists rather than screenwriters. They allowed public writer profiles and ours (at the time) were private. They charged a hefty annual subscription and we just took a percentage of the fees. They were positioned upmarket from us but close enough that it made me nervous.

We coexisted peacefully, though, skirmishing a bit on the Google Ads front as most competitors do. I didn't reach out to them early on because they didn't come up on our sales calls. We had very different customers. There were plenty of others to worry about, especially Zerys and WriterAccess.

Conferences make it easy to meet the competition, and I remember the first time I went to Outbound, the big HubSpot user conference in Boston. They were all there and I sheepishly went up to their booths. I remember the Zerys founders were very reserved. They squinted at my badge and when they recognized my company they backed away, offended that I would even approach them. I tried to make small talk. They wouldn't have any of it. I walked away feeling mad.

WriterAccess was the opposite. Byron, the happy-go-lucky founder, was happy to meet me. He mentioned that he didn't see our booth. I had to admit that we didn't have one. He had a million questions for me. I probably shared too much, but he gave me some useful information about their revenue and growth prospects and how hard they've tried to get an official endorsement from HubSpot as THE marketplace for writers. Importantly, we shared a distaste for the Zerys guys. Once again, the common enemy strategy worked.

I stayed in touch with Byron over the years, making a point to have a heart-to-heart at each HubSpot conference. He called me after one of our fundraising announcements and said he was exploring a sale. His expectations were far too high and we never looked hard at it. A couple of years later the tables turned and I asked him if he would buy Scripted. His is a cash flow business. He had no VCs backing him, so coming up with millions of dollars was a non-starter. Instead, we explored merging for the sake of selling to a larger entity, making us both more valuable in a 1+1=3 approach. Ultimately, it didn't pencil out.

What I realized through these and similar conversations is that Scripted, like Scripped, was in a really hard business again with customers that simply don't want to pay a lot. Switching costs were too low; it was too easy for a customer to bounce around to all the writer marketplaces, leaving behind a trail of churns.

I eventually used my MIT Sloan connections to get the meeting with HubSpot's CEO and head of M&A. I told them about Scripted and what I thought made us different than the rest. Brian, the CEO, leaned back and reflected on the number of agencies and marketplaces just like us that buzz around HubSpot. Brad Coffey, my Sloan classmate, concurred and asked why no one was winning. It seemed we were all struggling in the low millions of annual revenue.

I didn't have an answer for him, and that conversation marked the first time I saw the writing on the wall.

How could we have raised all this money, have the backing of great VCs, and still be competing with the likes of WriterAccess, a bootstrapped company without the benefit of fancy MBAs and Silicon Valley engineers? I didn't have an answer back then. I still don't.

I did eventually reach out to Contently and tell them that we're looking to sell. They offered to take a look but very politely declined and wished me the best. We were in different markets, after all, and the lift our revenue would give them wasn't significant enough.

This ending wasn't so happy, but the relationships I built with our competitors only helped. It was a useful perspective and I'm glad I got it.

Toofr: Made friends and got offers

Toofr.com was my very first web app. I built it first in CodeIgniter (PHP) and then switched to Rails (Ruby) and there it has stayed ever since. It started as simply a reason to learn how to program for the web. It evolved into a source of passive income and then I basically wrote a book about it. All because I wanted to learn how to code.

Toofr is an email-finding app. Punch in a person's name and what company they work at and it will try really hard to get the right email address for them. For sales and marketing people it's gold. Toofr wasn't the first to do this but it was one of the first. That early start helped drive organic customers and spur the competition. Most similar apps that came online afterward knew about Toofr.

Hunter.io was and still is the best in the business. I was always impressed and intimidated by them. I reached out a few times over the years. I think they ignored me once or twice but we did have a friendly exchange when I finally told them I wanted to sell Toofr and shared my numbers. They concluded it wasn't worth the hassle.

FindThatLead and Lusha are two others I got to know. I got along particularly well with Gerard at FindThatLead. He was hilarious, happy to joke around, throwing out compliments about how great I am, and Toofr is, and how they could never afford to buy it. I don't know how serious he was but I enjoyed that relationship. The Lusha guys were more serious. I'm pretty sure they reached out to me, perhaps checking my interest in acquiring them, but Toofr was a cash-flow business and couldn't buy anything. When I flipped it around and asked if they would buy Toofr, I learned they were in a similar situation.

I eventually sold Toofr to a private equity shop that operated a competing product. Once again, I shared a lot of detail and was entirely vulnerable and it paid off (until it didn't, but that's another story). My friends, technically my competition, were happy for me. They asked for advice about how they could get similar exits.

I told them to be friends with everybody.

MightySignal: Talked to everyone until I found a buyer

MightySignal, a B2B company that deals in mobile software data, is the first company I've run that I didn't start. It feels different to come in from the outside. I didn't have to deal with culture shock because none of the original employees were there. The private equity firm that hired me to run it gave me a company without a team. I knew nothing about mobile data so I had to learn everything. It was a good excuse to make a list of the competitive environment and reach out to people.

The first person I contacted was Scott Milliken at Mixrank. I knew him and his cofounder because, in addition to mobile data, they also have B2B contact information. It crossed into Toofr territory. It turned out that he and the MightySignal founders had a healthy "frenemy" thing going and he thought it was pretty funny that I wound up as MightySignal's new CEO.

We stayed in touch, sometimes meeting at Samovar Tea in San Francisco. He was coy but helpful. Later on, when I was certain that MightySignal needed to sell, he put a Letter of Intent together and sent it to me. Although my bosses turned it down, it was a really nice gesture. He correctly noted that having an LOI would help me get other offers, and it did help move some conversations along.

Ultimately, to get this deal done at a multiple my board would accept, I need to talk to everyone. I mean everyone. Friends, enemies, and everything in between. I made a list (actually had my virtual assistant do it) and set about the long, arduous process of building relationships with CEOs where I had a specific end in mind. I ultimately wanted to have an M&A conversation but I knew I couldn't open with that. I needed to have a relationship first and then make that ask.

So that's what I did. I set about building relationships knowing that I had around a year to become friends and try to get a deal done. I tracked my conversations, noting how long it's been since my last outreach. I had a bunch of calls, demos, and emails with other CEOs and founders. For the most part, they were great. Very friendly, helpful, and in a few cases it led immediately to partnership opportunities. Our marketing teams connected and we did joint webinars and email campaigns. These activities made it easier to talk M&A later on.

MightySignal eventually sold not to Mixrank but to Airnow, a product that was very complimentary to MightySignal. The relationship began more than a year before when I reached out about a data product we wanted to incorporate into MightySignal. It turned out they wanted our data too, and then it turned out they'd rather buy the whole company than lease the data. this acquisition announcement.

How to make useful relationships with competitors

I've just shared several specific examples where befriending competitors worked out for me. Now I'm going to generalize the approach so you can try it.

First, though, I want to address what some entrepreneurs might be thinking: This is dumb. It's way too risky. People will walk all over me if I do that. It looks weak.

That's the paranoid approach. I could be more generous and call it "safe" or "measured" but at the heart of this argument is paranoia. I think paranoia is a sign of weakness or lack of confidence or both.

Sure, it's possible that one of the relationships you might form could backfire. They could use that information to spread gossip, solicit your customers, or spread fear to your investors. Those founders are the exception, not the rule. And though it may happen, I believe the cost of not having any relationships with competitors is far greater.

Don't give in to your fears. Reach out and see what happens. You will be rewarded.

Here's the approach I recommend.

Build a good list. Use a VA to do the research.- Make your approach with authentic curiosity. - Check in quarterly to maintain the relationship.- If they want to dance, then dance. - Wait for the right time to make the direct ask.

Build a good list

Don't allow yourself to succumb to research paralysis. When I first looked down the barrel of all the work I would have to do to find a buyer for MightySignal, I froze. It was overwhelming, and for a while, I did nothing because I just didn't want to do another LinkedIn search. My answer was simple: Then don't. I hired Phani, a virtual assistant I found somewhere on the Internet many years ago, to do it for me.

I set up a Google Spreadsheet with the following headers:

Company Name- Company URL- HQ Location- Employee Count- Revenue- Funding- CEO Name- CEO Email- CEO LinkedIn

I gave him access to my Crunchbase (company data) account and upgraded his LinkedIn account. I gave him a few examples of companies that I wanted him to add. For MightySignal, it was our direct competitors and also complementary products. Anyone who touched mobile data was a potential acquirer. In all, he probably found 50 companies and CEOs.

Having this list made it much easier to do what I actually kind of liked to do: write cold emails to other CEOs.

Make an authentic approach

Like any good sales pitch, you can't just copy and paste some boilerplate template. I took time to get familiar with the CEO and the company and crafted a custom but very short email. I mentioned some things we had in common, perhaps a school or place we lived, or the size of our companies and the time of launch. If they were also a hired CEO, I mentioned that. Throw in a tiny bit of flattery and you have an excellent first message.

Here's an example.

Hey CEO_NAME,


I saw your latest funding round. Congrats! I know it's hard to do.
I've been watching COMPANY from the sidelines, of course, and was always secretly impressed with what you guys built. We're in a tough industry and I respect teams that do it right.
Would you be willing to chat for a few minutes, just to compare notes? I've been meaning to connect.
Thanks,

Ryan

Even though this is strategic, it's still completely authentic. You can be both cunning and genuinely curious. I wanted to get to know these guys. I had real questions for them and I think that came through. My response rate was really high. Close to half of the CEOs engaged with me in some way. A few flat out said no, not interested, but most of them were curious in return. We had good, genuine conversations as a result. They didn't share all their secrets and desires, but neither did I. It was still fun to connect and chat, leader to leader. Sometimes we identified a common enemy/competitor. That helped. Other times the common enemy was Google and Apple or the market as a whole which made our jobs really hard. We lamented not working in an easier field. I remember how refreshing it felt to talk to some guys who intimately understood everything, the highs and the lows, of what we were doing. Even though we were fighting for the same customers there was still something like a fraternal bond there. It was real. ### Check in quarterly Staying in touch, once I had broken the ice, felt natural. I'd share some news with them. "Have you seen this?" I'd ask and send a link to an article or a tweet. That's all it took to rekindle the relationships. I used Pipedrive to track how long it had been since I reached out to them. I made sure that it was never longer than three months. There's a really nice view that Pipedrive offers so you can stay on top of these relationships, emails and phone call notes included. I reported it to my board every month. I don't know what happens if you do this more or less frequently. I picked quarterly because it felt right. Two quarters is too long. One month is too soon. A quarter is just long enough to sort of forget about the relationship but be able to recollect it really fast. That's what I wanted. Just long enough to be refreshing but not so often as to be annoying. ### Do the dance Eventually, after enough check-ins and Zooms, the dance begins. The dance can last a moment or it can last months, but it usually starts like this. - "Hey, did you ever think of selling?"- "Tell me about your board composition, again?"- "Remind me what valuation range your company was acquired at (or invested at) last?"- "If you ever sold your company, would you want to stay on?" At some point, the conversation turns to M&A. You can prompt it by asking one of those questions yourself, but it's always best of course to wait until they bring it up. Then you know they're ready to do the dance and probably have someone important pushing them onto the dance floor. Look for these queues, and when they're offered to you, take them. Be open, honest, but don't give the farm away. Answer in incomplete truths. For example, to the last question above, I might say, "Well I'd want to be there for my team." And leave out the fact that I'd be happy leaving after a 30 or 60-day transition period. Since you don't know what they want to hear, I highly recommend answering honestly while not giving away too much. Sometimes they'll drop it after one questions. Other times there will be multiple questions and they'll say something like, "Maybe next time we should include Ben who runs our business development. He'd like to learn more about what you guys do." The business development (BD, for short) approach is a shortcode for M&A (mergers & acquisitions). It's a less presumptuous way of saying it. Keep an ear out for that too. ### Make the ask At some point, you have to make the ask. The ask sounds something like this. - "So, would you ever buy us?"- "Is your board looking for a solution like ours?"- "If the price was right, do see an M&A opp here?"- "My board actually wanted me to see if you're interested in partnering with us." You choose your ask based on the type and tenor of your relationship. You don't want to come on too strong but you also want to make sure they understand that the dance is over and you're asking them about the status of this relationship. It's the awkward "So... are we girlfriend/boyfriend...?" stage of the relationship. You need to know so you can invest your time and set expectations to your board appropriately. Making the ask can be jarring but if you've invested sincerely in the relationship then it won't damage anything. They can say no. Plenty have said no to me, and the relationship survives. You fall a bit more out of touch but it's not damaged. The ones that engage are the ones you'll focus on next. You start filtering out the flirts, the non-committal ones who maybe just enjoy the conversations but have no interest in getting hitched. That's fine! That's going to be most of them. At some point, though, you need to sell your business and move things along. You can't do that without making the ask. --- This is how I sold Scripted, Toofr, Track Job Changes, EmailFinder, and MightySignal. It's a good approach and I stand by it. Even if you don't want to sell, having these relationships will pay off at some point. I'm sure of it.

Business evaluation: Ahoy

2022-06-28T15:24:00-07:00

*Edit: Ahoy is now live so I've included links. *

I'm still working on the web3 project I ({filename}my-foray-into-web3.md). In November 2021 I wrote a white paper of a fundraising tool that I hoped could be used to influence votes on climate legislation. Rather than collecting signatures, this project would collect cash, real dollars, and release that cash conditionally on voting outcomes. It would function like a PAC but exist in broad daylight, meant to "put our money where our mouth is" and quite literally pay for votes.

The same approach could be used for election results. Candidate A could have a primary election fund and a general election fund. If they lose the primary, then the general election donations get refunded in full. A soaring balance in the general election fund could indicate momentum and maybe change voting behavior because people would want to back the person with the most to lose.

In fact, this idea of paying for somebody to do something and keeping that value locked up in a contract until they do it, at which point it gets released, or refunded if they fail to do it, is a general bounty problem. Earlier this year a couple of guys working on that general bounty problem read my November 2021 project description and loved it. They reached out and I've been talking to them ever since.

They call their bounty app Ahoy.

Ahoy isn't live yet. I'll link to it once it's available to the general public (which should be soon, I'm told). Ahoy! For this business evaluation I'm going to describe the business opportunity of Ahoy generally and my political fundraising idea specifically.

The Problem

Ahoy solves a few problems, some more real and applicable than others. I'll list them in no particular order.

All online fundraising requires exorbitant amounts of trust- Our climate is changing and that is already massively disruptive- The will of the people isn't always expressed in the law- Blockchains aren't used to do enough interesting things in the real world

Please indulge me in an expansion of each of these points.

Trust in fundraising

Let's say you get an email from a non-profit organization asking for a few of your hard-earned dollars so they can continue doing their work. You can trust that they're a non-profit; it's possible to look them up on third-party websites. You can trust that they do good work; you can find articles and testimonials. It would require a lot of effort to spin up all this online evidence to support a fake NGO, and the payoff would be questionable. So the fact that the NGO exists and does real work can be trusted.

However, as a donor you have no visibility into their fundraising. They could be backed by bilionaires and still come out asking for your money. NGOs don't have to disclose their fundraising reports the way politicians do. You simply don't know if the $250 they ask for is a meaningful addition or a drop in the ocean. Is your donation going towards rent at their swanky New York headquarters or actually helping hungry children? You don't know because you can't see their bank account balance. You don't know what goes in or what goes out.

It gets more interesting when we consider the popular "matching grant" fundraising technique. Here's a letter from an organization I admire, the Environmental Voter Project. Note the highlighted circle at the bottom.

There's no way for me to know if this matching donor actually exists. It could be simply a marketing technique, and I suspect that most of the time that's all it is. It's hard to fundraise. There's a lot of competition for attention and donations, especially in this climate of falling stock prices and rising inflation. Donors could be misled out of desperation. It's still not ideal for those of us who donate.

The climate is changing and I hate it

There was no wildfire season when I grew up in Mountain View, California. I've been going to ({filename}my-happy-place.md) in the Sierra Nevada mountains my entire life. I used to spend the month of August up there with my grandparents. I never caught a whiff of a wildfire. Not once.

We don't go to the cabin at Pinecrest Lake in August anymore. We can't plan our vacations around the uncertainty of being smoked out. It's happened the last two years in a row. Before that, ashes fell on the lake during the Ring Fire near Yosemite. I can't say it clearly enough: This is not normal. My grandpa wouldn't recognize it.

You're crazy, Ryan, you might argue. Wildfires have been happening for millions of years. What do you mean it's not normal?

*https://sierranevada.ca.gov/2021-another-historic-sierra-nevada-fire-season/ *

It's not normal.

The will of the people is not expressed in law

Books have and are being written on this topic. I'll just brush the surface here, focusing on the cause and the symptoms.

The reason why unpopular laws get passed is the same reason why unpopular presidents get elected: we put extra weight on the voices of rural America. This philosophy probably traces its roots all the way back to King George III and the founding fathers' revulsion to rule by aristocracy. Wealth tends to aggregate in the cities so the framers ensured that rural, less populous states get an equal vote. This is why we have the Senate.

The Electoral College was set up specifically to handle the presidential election. It distributes electoral votes by the sum of the House and Senate seats in each state. The two extra Senate-based votes may not seem like much but it has tipped the scales against the popular vote more than once (Bush v Gore in 2000 and Trump v Clinton in 2016). Case in point, Wyoming influences the presidential 3X more than other states:

On average a state is awarded one electoral vote for every 565,166 people. Wyoming has three electoral votes and only 532,668 citizens (as of 2008 estimates). As a result each of Wyoming's three electoral votes corresponds to 177,556 people. Understood in one way, these people have 3.18 times as much clout in the Electoral College

https://www.fairvote.org/population_vs_electoral_votes

Is that fair? Doesn't seem like it. Is it by design? Youbetcha.

As much as I'd like to see Electoral College reform, primarily because it's an antiquated institution put in place when literacy rates were much lower and information about presidential candidates was harder to come by, I know it won't happen. The very system that gives rural states their voting power would need to be used to strip that power away.

In other words, we're stuck with it.

Blockchains aren't used to do enough interesting stuff in the real world

Right now blockchains are used to do two, maybe three things.

Speculate on cryptocurrencies- Prove custody of certain digital properties- Become a modern baron

Unless you really never read a newspaper or watch a Super Bowl ad, you've become familiar with the rise and fall of cryptocurrency prices. You have coworkers, family members, and friends who struck it rich or lost it all on Bitcoin, Ethereum, or whatever the flavor of the month is on Coinbase. This crypto casino is the #1 use of blockchain right now.

The last year also saw the rise of non-fungible tokens (NFTs). These are basically transferrable contracts that have some unique digital asset associated with them. These days, that asset is a funny looking, unnecessarily pixelated artwork of some animal doing something silly, like smoking a cigar. There are more interesting examples but I'm very biased against NFTs and can't think of anything nice to say about them.

Finally, and this is more sensitive because some of these barons are my friends, but crypto has become a very efficient way for entrepreneurs to get absurdly rich. Mind-bogglingly, insanely rich, in a very short amount of time. I met my first billionaire when I was an MBA student. I figured I'd never meet another one. Now I know about five who made billions of dollars in three short years.

Put in perspective, my most successful MBA friend (probably the most successful for several years on either side of our graduating class) started his company in 2009, went public in 2017, and is worth only a couple/few hundred million dollars.

How does this make sense? It doesn't. It defies logic, but then again, who am I to say what's logical? I'm probably just jealous, as I've ({filename}above-average-mediocrity.md).

Regardless, I'm quite certain none of this is great for crypto. We need more real-world, rising tide-style uses for blockchain where the winners don't stand on the backs of the losers.

The Solution

Going back to where we began, the founders of Ahoy reached out because they loved the idea of using bounties in politics. If you do X, we pay Y. It's fundraising based on results rather than promises. You only get the money when you show us the goods.

This solves the problem of trust that I led with up top. On a blockchain the wallet balances are public. You can see every ledger transaction. You know when and where a transaction goes, and if the wallet has some public identity, then you know who it goes to as well.

If politicians used crypto wallets exclusively we wouldn't need quarterly reporting. It would already be public, available in real-time.

If an NGO wanted to set up a matching grant campaign, we could see both wallets, the NGO and the matcher. When I donate to the NGO, I could see its balance go up 2X my donation and watch the matching wallet drop by the amount I donated. I could verify that my donation is matched. And if the NGO claimed to have a $10,000 match, I could see that in the matcher's wallet balance, clear as day. It would be completely trustless.

There's something really clean about this approach for NGO campaign fundraising. It gets messier for politics. If everyone knows there's $5M in a wallet and those funds will get distributed automatically to every senator who votes in favor a bill, that will make the opposing side uneasy. I argue, though, that this is what already happens. The only difference is we're being transparent about it. Glaringly transparent. If that makes you uneasy then let's call back another Supreme Court decision and stop giving companies "freedom of speech" in political donations.

I think it will be useful to have this debate.

In the meantime, we can use Ahoy to influence climate change legislation by doing direct legislation bounties or fundraising for elections. In fact, any law that is widely unpopular (two that are timely: abortion prohibition and gun rights) is fair game here. If a majority of the American people believe one thing and the laws state another, then we wound up here because something tipped the scales against the majority.

Let's use Ahoy to tip it back.

And this way we use a blockchain to actually do something useful.

The Business Model

This time I'm adding a new section here because it's not obvious how Ahoy itself or anyone involved with the bounties makes money. I'm a capitalist at heart. I believe even the best intentioned still need to make a buck. And as I told my Intro to Business class many times over: without profit, a business dies. No exceptions.

We want Ahoy to survive, so we need it to make money.

There are a few tried and true business models that we can discuss here. Ahoy could implement one or all in order to keep the lights on and incentivize its most valuable users.

Setup fee- Transaction fee- Subscription fee- Tokenomics

Setup fee

A setup fee is a bit like a deductible in health insurance. Sure, it generates some money, but the real value to the company is setting a buy-in so neither side wastes their time.

There's a whole social science behind deductibles but the basic theory states that pure subsidies are prone to abuse. If you make healthcare cheaper, people will use more of it. We don't necessarily want people to use more of it, we just want them to be able to afford healthcare when they need it. The deductible sets that bar for need.

A setup fee could work the same way. To make sure that only serious people use Ahoy, we could implement a $200 or even a $2,000 setup fee. Only the people who look at that and think it's worth it will pay. And then Ahoy filters out the chaffe and knows that each user is real.

Setup fees generally aren't the core of a business revenue model and I wouldn't expect it to work really well for a mostly consumer play like Ahoy.

Transaction fee

So maybe we don't want to filter anyone out. Maybe it's worth it to us to deal with some tire kickers because they might go and tell more people about Ahoy. It's hard for something to go viral if it's gated.

In this case, we charge a transaction fee. For every dollar that passes through Ahoy via a bounty, Ahoy takes three cents, or five cents, or a quarter. Transaction fees can work on a schedule, scaling up or down with volume. This model is how the whole financial system makes money. It's how Uber and Scripted, Amazon and Apple worked. Transaction fees are great so long as you have liquidity in the marketplace and funds keep moving. Low volume means low revenue. If it never picks up, you never make money. But when it works, it works wonderfully. You get rich.

The trick, like any pricing game, is to make the take rate just high enough to maximize revenue without turning people off and trying to go around you. That's the risk at Upwork, for example. If I like a freelancer, maybe I'll offer them 5% more (since Upwork takes 10%) to work with me directly. Same with Ahoy, if we charge too much, they may try to pay the bounty target directly.

Subscription fee

I love me subscription business models (monthly recurring revenue). We could charge bounty creators a monthly fee for hosting the bounties or even for promoting them. Once Ahoy becomes large enough, there will be a need to rank the bounties on the homepage and include them in email marketing. This could be pay-to-play scheme, prioritizing those who are subscribers.

As with most SaaS businesses, a free tier is usually best practice. We want the tire kickers, after all. But if we're clever with certain features and promotional opportunities, we can probably entice a fraction of the creators to pay a fee.

MRR is nice because it's predictable. With predictability comes stability and confidence that the company can invest ahead of growth. Investors love it too. While you can still become a huge company without MRR (looking at you, Stripe) it's harder to do that these days. You need massive volume to make up for the lack of predictable revenue.

Tokenomics

Finally, we get to the wild card. Tokenomics is the idea that a project can create its own cryptocurrency and use it cleverly to incentivize behavior that benefits all token holders. We can turn using Ahoy into a little game. Create a bounty, get some tokens. Raise $10,000, get some tokens. Get enough tokens, join the special Ahoy governance council.

Then you make the tokens transferrable, throw some up on a decentralized exchange, and let people buy them. A price gets set by the market, and that stash of a million (or five million) tokens you set aside for yourself is all of a sudden worth... millions. Don't believe me that this happens? The top 20 wallets for ConstitutionDAO have millions in value (more like $1.5M just a few months ago). The top handful are worth tens of millions. I can't know for certain but I assume these are the founders' wallets.

These guys are the modern crypto barrons, the people at the top of the totem pole who are able to literally print their own money. It's (mostly) unregulated, certainly nothing like the stock market where companies have to jump through hoops to print more of their own paper.

So it's fun when you're one of the lucky few who make it to this position. It could be a great way for Ahoy to make money, and others would surely benefit along the way. It's not just the founders of these early tokens who got rich. Many others did too, but the founders got the richest... by far.

My recommendation

I like a transaction fee and tokenomics. Setup fees and subscriptions are too heavy for a consumer play like Ahoy. We need volume. Everyone wins if there's volume. Transaction fees and tokenomics depend on it. If we win, we win big. That's the kind of game I want to play right now.

I don't own Ahoy. I'm not even an official advisor. To the extent I've written "we" above, it's just because I feel some sense of ownership over how we do the political stuff.

I'll recommend this to the founders of Ahoy and I'll post the link here when it's live. And maybe I'll get some tokens.

See you at the top.

Business evaluation: Clime

2022-06-22T09:37:00-07:00

I recently read this great short article about how to get startup ideas by Jared Friedman, a partner at YC. In it he describes a recurring theme across the thousands and thousands of startup pitches they see. They call it SISP, or "a solution in search of a problem." It's an idea that has no practical use in the market. I'll come back to this.

Me, I'm a GMISI, or a "general manager in search of an idea." I'd love to start something new in climate tech. To be clear, I'm still happily plugging away at MightySignal, but the shiny object flickering at me in the distance is a B2B climate tech solution that solves an enormous problem. What this is exactly, I simply don't know. But I'm searching for it.

One of the first ideas that I went down the rabbit hole on is Clime. Clime is, unfortunately, a technology in search of a problem. In this blog post I make a case for how cool this technology is and how challenging it will be to commercialize it.

The Problem

This much I know: residential energy consumption is a major climate issue. Gates, Doerr, and every actual scientist of academic merit who has looked at the numbers agree. We don't need to use so much gas at home. In fact, we don't need to use any. We want to cook at home like we're Bobby Flay but it's just not necessary.

(Nobody needs to cook like this)

As I've described elsewhere on this blog, I'm no climate saint. After our remodel, we kept three gas appliances: our gas clothes drier (which we'll swap for a heat pump drier when it poops out), our gas fireplace (which I love but use only in the winter) and our gas grill (which I use for maybe 45 mins a week, tops). We got rid of the major gas guzzlers: the air furnace, the water heater, and the cooktop range. As a result, we use about 100 therms less per month in the winter than before, a reduction of about 2.5 tons of CO2 per year. Just in our little house. (Note: we pay ~$50 per year extra for 100% renewable electricity.)

But enough about me. The problem is not everyone is making this change and we need everyone to do it. People opt not to go gas-free because even though the electric appliances are better (as I've written before) they are also significantly more expensive. Higher price means lower adoption. So we have to do something about the price.

The Solution

Clime is a product that helps homeowners understand the price of inaction. It does this in two ways:

Clime has access to proprietary software that detects the leakiness of the house using only a temperature log. Energy leakage is money wasted. That's heat leaving the house in the winter and entering the house in the summer. Space heating and cooling is always the highest household expense. Clime tells you if your house is too leaky.
Clime takes the data feeds of other Internet-connected appliances and provide suggestions for how to lower their usage cost. For example, noting the price of gas and electricity and how much hot water is consumed, it could demonstrate how swapping out the gas water heater will pay for itself within 18 months. Combining with the leakiness data, it could show how lowering the thermostat by one degree in the winter could save $150 over three months. For many Americans, this is real money.

So Clime attacks the pricing problem by exposing opportunity cost. It shows, counterintuitively, that the price of a new gas-free appliance is actually lower than the price tag because the cost of not upgrading is real. It's there; most people just don't see it. Clime exposes it.

The Problem with The Solution

To describe the problem with the solution, I'll go back to the article that I linked to in the beginning. Jared lays out three ways to evaluate an idea:

Is the problem really big?
Is there founder/market fit?
Is the solution timely?

I'll tackle these in reverse order because the first point is the hairiest one for Clime.

Is the solution timely?

YES. Emphatic YES. The solution is timely for two main reasons:

The proliferation of IoT devices in the market. Everything is Internet-connected and it's getting easier to connect those devices that are not yet online. Even water meters are coming into the Internet age.
Climate solutions entered the zeitgeist. The price of natural gas is higher than it's been for the last 10 years. Extreme weather events are all over the place. EVs are everywhere too. Everyday people are starting to come around to the cause/effect relationship between greenhouse gases and climate instability.

I'm confident that consumers have a different mindset now than they did before. I see it with my own two eyes. This combined with amazing developments in household appliance technology make this solution possible.

Is there founder/market fit?

YES. I'll just copy the bios I put for myself and my friend and potential co-founder Howard Chong. We're complimentary. He's the Ph.D. and I'm the M.B.A.

Is the problem really big?

MAYBE. I wish I could say YES. I really, really do. But I just don't know.

Although the environmental problem is really big, the consumer problem may not exist. Our solution attacks the problem with information. It doesn't actually solve anything. Maybe information is enough of a solution, but I doubt it. A lot of people may be happy to pay the extra money to keep their leaky house extra wram. They don't want the hassle of a remodel, of being out of water while the plumber swaps out their water heater. Putting new insulation in the walls is disruptive. Putting new windows in the house is expensive and loud. There's nothing fun about going through this.

So to the typical consumer, this may not be a problem at all. Homeowners may not be our target market after all, and I've been struggling to find another customer. I've considered real estate agents, contractors, inspectors...

I'm searching... for a problem. A solution in search of a problem.

I want a problem so obvious it just smacks me across the face. I should feel the sting for days. Clime doesn't have that. Unfortunately. But I learned a lot while studying it.

Next steps

I still want to work with Howard on something. It's possible Clime could evolve into that something. I'll keep looking into the price problem. I have another idea that attacks price directly, actually lowering it for consumers. I also have information from local contractors showing that about a third of people doing remodels are opting for heat pump space heating and cooling systems. The other two thirds will eventually come around by mandate; it seems inevitable that cities will stop approving new gas meters and may start requiring gas caps during major remodels. This will create new opportunities for heat pump evangelists. Maybe I'll start looking there too.

Exercising the writing muscle

2022-06-21T20:18:00-07:00

Okay, here we go. I'll write as many mostly unedited words as I can before I give up and turn on Better Call Saul.

These days I have a rule. I can watch my Netflix show if I've read a book for an hour during the day. This rule has led to a wonderful habit: laying in my bed in the afternoon with the fan circling above me as I indulge myself with some prose or nonfiction. I'm reading a lot more and it's lovely. I've been averaging almost a book a week. I read Catalyst in a weekend, having picked it up at the airport after forgetting to pack a book for our trip to La Jolla. The weekend after that I read The Happiness Project on the plane to Colorado. I knocked the whole thing out, cover to cover, on each leg at 30,000 feet.

Tonight, for whatever reason, I've decided I also have to write before Netflix-ing. So here I am.

I've been playing piano too. Moonlight Sonata is my new jam and I already know that I'm going to miss learning it once I have the piece memorized. It's such a beautiful work of art. Each measure is ripe with emotion and pretty easy to play. I'm adding only a few bars each week. It's slow progress, but like I said, I'm enjoying it. I don't want it to end.

For a while I was writing more too. Sitting down like this, usually between 8 and 9pm, to compose something thoughtful. This routine has been harder to keep up... for no good reason at all. I just haven't prioritized it.

So tonight I'm doing what the books tell me to do. I'm writing nonsense for the sake of writing. Just get the words down, edit later or throw this away. Who cares? Not me. I'm just doing this so I can enjoy my Netflix in a few minutes.

There are three windows above the stairway. Through them I can see what looks like a pine tree but it must be an oak. We don't have any pine trees in our cul de sac (aside: did you know the plural of cul de sac is culs de sac?)

Tonight my girls were in fine form. They ran around like lunatics, yelping and screeching, chasing each other on the big couch I'm sitting on now. They get along very well these days. As Norah gets older she plays better and longer. There are far fewer tears than there were even just a few months ago. I can see her shed off her younger tendencies and approach her growth with something close to grace. I am grateful for this. Lily never gave me any concerns; Norah was not always so easy to read. But for now this ship is sailing on course. I like where it's headed. I'm excited for the journey.

I have two girls who love me very much. It's good to be a dad.

In fact, the closer I get to 40, the more I see myself looking like 40, the easier life becomes. There are fewer expectations of what's coming, more enjoyment of what's here and now. I still look forward to the future, still believe in the promise of more achievement, but I no longer dwell on it. It doesn't eat me inside. I can do both. I can deeply, sincerely appreciate what's before me and await anxiously what comes next.

I'm not afraid of time anymore. I'm grateful for every day.

Whatever, that's enough.

Hacking for climate sales

2022-06-05T10:23:00-07:00

About a million years ago I wrote a blog post called "Hacking for Sales." I posted it on the Scripted blog and didn't think about it again until this guy Max Altschuler from Udemy contacted me about running a course on it. I demurred and ultimately declined, but he and I stayed in touch. Later, we got some other people interested in the intersection of engineering, automation, and sales together for monthly dinners and meetups in San Francisco. He turned it into the Sales Hacker conference, website, and community, and ultimately sold it to Outreach.

That was my education in sales. Recently, I wrote and taught an accredited course at Diablo Valley College on tech sales and invited my network to guest lecture. Many of them were friends from the Sales Hacker days. As I've recently rediscovered my interest in climate science and begun to get immersed in climate technology, I've been asking myself: Is there a role for sales hacking in climate tech?

Selling climate tech is different than selling regular B2B tech. There’s a mission-driven element to the product sale that makes it much more powerful and easier to sell, but you have to do it the right way.

There’s a mimetic desire element here too. By capitalizing on the buyers’ idealized vision of themselves, you can appeal to better natures as well as the standard painkiller strategy.

Mimetic desire (see René Girard's work and Luke Burgis's book) is the idea that all desire comes from external models. It doesn’t come from within. You don’t chose to want things. Your desire is entirely influenced by others.

This idea is more than just Michael Jordan selling you Hanes briefs. It’s more nuanced than that. It’s fitting in, it’s fear of missing out, it’s viewing yourself as someone who should wear Hanes.

How does this relate to climate sales? We need people to see themselves as climate warriors, contributors to the solution. We need today’s heat pump water heater to be yesterday’s victory garden. We do that by slowly but deliberately building mimetic desire for climate technology.

There are a few ways to tackle this:

Climate technology is high-end (Tesla! Rivian!)
Climate technology is mysterious and magical (Induction cooktops!)
Climate technology is for really smart people (Gates! Doerr! Musk!)

These models are setting a new standard for what it means to live virtuously. I can see the New Yorker cartoon now: A man at the Pearly Gates getting asked, “Tell me about your carbon footprint?”

If we can get there, we’ve made it. Climate technology and the idea that everyone has a role to play will have gone mainstream. Climate tech entrepreneurs will be the titans of business. Climate tech will be referenced in pop culture: sitcoms, movies, and podcasts. If you still water your lawn, have a combustion furnace, or cook on a gas stove, you’ll be out of touch, old, anachronistic.

The path to get here is not yet clear. It requires basic selling techniques as well as the latest research on influence. Here’s a best practice on selling climate technology.

Explain the costs of status quo. Eventually you will need to adopt. Might as well do it soon! It’s like waiting to buy a plane ticket until the day before. You’re going to pay more and get a worse seat. Better to make the change early.
Sell the sparkle. Climate tech is new, it’s faster, better, easier to maintain, cheaper to operate. That’s why it costs more.
Offer a choice. There are hybrids. Heat pump water heaters still have a pure electric mode. Put an induction cooktop in your kitchen and a gas grill outside. Get the best of both. You choose where to start.
Decarbonize a bit at a time, no need to do it all at once.

Not everyone will be onboard, of course, but I think there will be more climate heroes than villains, more people influenced by green models than gray ones (gray: the color of smoke and gas). That's all we need.

For example, I still eat red meat. I love a seared rib-eye, medium rare, crust so salty it makes your mouth water. Will I ever go meat-free? Doubt it, but I'll be aware of what I'm doing and offset that rib-eye by not eating meat the rest of the week, taking shorter showers (or fewer, especially in the summer when we're at the pool almost every day), and being willing to pay a lot more for local, grass-fed beef.

I also cook that meat on a natural gas grill and in the winter, we heat one room with a natural gas fireplace. Why? Because I love it. I'm willing and able to pay more for it.

My goal is to be a climate hero, not a climate saint. If most people are closer to me than environmental activist Julia Butterfly Hill, then perhaps I can analyze my own mimetic models to anticipate how the desires of other people are formed.

For me, it is the Gates and Doerrs and Musks, the technologists who use their money, ingenuity, and general management to invest in or build climate tech and make a ton of money in the process. They have nice things and do nice things. I want to model that.

So climate tech is a tool that gives sympathetic people a way in. It can give a CEO of a B2B SaaS that does nothing climate-related an opportunity to model climate heroes by helping employees telecommute or offset their business travel CO2. It can give suburban parents a way to buy something that looks and feels high-end with extra benefit of being electric, recycled, or compostable.

The point is, climate tech sales is appealing to both emotions and pain points. It's a unique combination of these two selling techniques and it also makes the sales rep feel good about the deal.

I look forward to exploring this further.

A summary of our first home projects

2022-05-30T20:28:00-07:00

This is a prequel to the longer post about our ({filename}how-we-did-our-home-addition-and-remodel.md).

Look, our house wasn't that bad. Friends and family would come to visit and more or less say the same things:

"Your place has such nice energy!"

"Everything feels so calm..."

"There are good vibes in this house."

This, of course, was true. When our kids were fed and happy and we had nothing else on our minds, there was indeed a nice vibe in our 1500 square feet of 1951's finest pock-marked walls and squeaky floors. But at six in the morning when we tried to sneak past the kids' rooms without waking them up; when the outlet by the dining table just stopped working; when you could hear the mice in the walls at night... we were reminded that the house was old. Well-loved and lived-in, for sure, but damn old.

I met our house for the first time late in 2015. We were deep in our housing hunt at this point, having already made offers on three other places, narrowly missing a $1.3 million offer by just $5,000. My ({filename}remembering-meredith.md) was getting sick and we knew the end was near. It just happened to also be our house-hunting time, and for a few months we considered buying his house near Acalanes High School from my family.

On October 18, 2015, I went with my friend Eric to see two houses in Lafayette and visit my grandpa at his outpatient clinic. The first house we saw was on Upper Happy Valley, a very well-to-do street in a well-to-do neighborhood. I didn't like it. It was at the top of our budget and the road it was on was too narrow and the cars drove by too fast. I couldn't imagine teaching my daughter to ride her bike there. I shook my head as we left. I was not going to live there.

Then we went to this house at the end of a cul de sac in unincorporated Saranap. The curb appeal was nothing to scream about. The inside was not staged... at all. The owner's stuff was everywhere. I'd learn later that she was actually there, at the open house, which is really unusual. I saw piles of her stuff in the garage. The deck at the rear of the house was in bad shape. But the yard was HUGE. There were oak and bay trees everywhere. And I liked the people I saw. They were normal and seemed happy. I talked to a few and learned they were neighbors, just checking out the house.

Here are a few pictures from that day.

![Interior view of house]({static}/images/2021/07/9975D10C-0AA6-4BF3-96E7-F34220979EAE.jpg) ![Kitchen view]({static}/images/2021/07/F7EF082E-508B-47FA-828F-3E85BADA58D0.jpg) ![Living room view]({static}/images/2021/07/9FB72A98-A375-4F0C-A89B-AA2EBEA05170.jpg) ![Bedroom view]({static}/images/2021/07/C2A59BDA-A8DC-41FF-B340-85C47B685CD6.jpg) ![Bathroom view]({static}/images/2021/07/9AC7E3EF-E24B-4B6B-8DBC-36FB708E309B.jpg) ![Back deck view]({static}/images/2021/07/51DD33D2-B101-4FBB-A87E-47EEDE7FE2A9.jpg) ![Backyard view]({static}/images/2021/07/ACD4246A-4C85-463A-8A61-23D5830E9867.jpg) ![Another yard view]({static}/images/2021/07/B7F997A9-D56F-4359-AC80-8D9D20592FD7.jpg) ![Trees in yard]({static}/images/2021/07/FB7C9DF6-C828-4945-B72C-6DFEA8636BB0.jpg) ![Another interior view]({static}/images/2021/07/0ACB7452-E547-4B29-A85F-B7CDF6DBD6AF.jpg) ![Final interior view]({static}/images/2021/07/9BC16C12-83DB-4951-9840-571631394938.jpg) ![Another exterior view]({static}/images/2021/07/6F80352A-8168-436B-9C7E-E37B0E62D7D2.jpg)

I was smitten. This is what I wrote on Redfin to my wife about the house.

I could see the potential and something about the neighborhood spoke to me. I knew I'd be happy living on a court and being able to enjoy its safety and security. I could definitely see my daughter learning to ride a bike right in front of my house. And as it turned out, I witnessed both of my daughters and the two boys next door learn to ride bikes, scooters, roller blades, and skateboards in the six years since we moved here. "Court life" is the single thing I've loved most about living at this house.

My daughter entering the court on her scooter.

Over the years we made a lot of improvements. We added fake grass to the front yard. And then some hardscaping. This was a big DIY project, in large part with my father-in-law. I wore out a Collins pick axe doing this thing. I remember succumbing to my wife's suggestion that we hire some local kids to dig up the yard (you need to go down 6-8 inches to accommodate the fine and rough gravel under the grass). I did, and they sucked. It took three of them all day to dig up a quarter of the yard. I did the rest myself the following day. Then my father-in-law helped me roll it out and seam it. Voila!

![Front yard before artificial grass]({static}/images/2021/07/F00566F2-E7E2-4BDD-8F06-BE7F2703070C.jpg) ![Front yard after artificial grass]({static}/images/2021/07/7A5BE747-92C5-4F24-8444-14B3F2AC62E6.jpg) *Here's the before and after! You can barely see the seam tying the two rolls of grass together (it runs straight toward the chimney). Not bad for a first-timer's job. *

![Hardscaping project start]({static}/images/2021/07/97C09582-A14B-4E79-BECF-A9B9D2762FFB.jpg) ![Adding slate and pebbles]({static}/images/2021/07/474952B8-8542-49DA-AA00-0898C67E4C4F.jpg) ![Finished hardscaping]({static}/images/2021/07/1A2297DC-8C14-471C-AC3C-2F6237A562BE.jpg) ![Final front yard landscaping]({static}/images/2021/07/2E9DBFDD-41DF-4B19-A2F9-022B07D39239.jpg) *Later, we added slate and pebbles surrounding the grass. It looked pretty, but I learned too late that pebbles on a sloped front yard mean pebbles in the rain gutter. This was a ton of shoveling and wheelbarrowing just to wind up scooping pebbles out of the curb every week. *

Then we got the house painted "Bachelor Blue" to protect the siding and get rid of the weird off-yellow color the house was when we bought it. The purplish blueish color popped nicely against the white trim. I'm pretty sure the trim was Kelly Moore "Swiss Mocha."

![House painting in progress]({static}/images/2021/07/EA9D6A00-98C6-43EB-ACC0-5A45E3C453FE.jpg) ![Painters at work]({static}/images/2021/07/1D8157A8-9F7C-4836-8CA0-33C780A97DCB.jpg) ![House painting nearly complete]({static}/images/2021/07/8BE7B251-91D7-4A15-9AC0-8F2B8C494E27.jpg) *We hired painters to do the job right, obviously. There was no way I was going to roll the whole house. The pros used a spray. Watching them work was when I came to appreciate that "painting" is 90% prep and 10% actually painting. *

![Finished painted house]({static}/images/2021/07/09F59AEB-90DF-458D-A7C2-37AA5C680532.jpg) ![House with Bachelor Blue paint]({static}/images/2021/07/20B3793C-44DC-429E-A3AF-9DF5DFDDC569-1.jpg)

We also replaced the ratty old deck, opting for some top-of-the-line Fiberon planks rather than redwood. They clean up well and look great, and the deck should easily outlive us. The house really shined.

After that, I took on a huge DIY backyard hardscaping project. I really wanted a sitting area and a decomposed granite path to our cottage. With the new deck in place, it made sense to finish the job and complete the backyard.

![Backyard hardscaping start]({static}/images/2021/07/015D4E0C-8209-45F5-BDDB-918A7784E7DA.jpg) ![Moving materials for backyard]({static}/images/2021/07/760D36DF-690D-4C40-90F0-BB78ED3B6A94.jpg) ![Backyard project in progress]({static}/images/2021/07/79DD5FAF-4972-4077-B520-E924CFE649D8.jpg) ![Completed backyard sitting area]({static}/images/2021/07/E1E254A9-9522-4C19-89B3-FB52E382C90B.jpg)

It looks great, but I'm telling you, this was a fuck-ton of shoveling. Something like ten cubic-yards of gravel and decomposed granite. It may not sound like much, but try doing it yourself. It'll wear out your wheelbarrow. My forearms looked like Popeye's by the end of this job.

![Backyard path construction 1]({static}/images/2021/10/08730EB9-CBC4-46EB-8506-A80E962368AA.jpg) ![Backyard path construction 2]({static}/images/2021/10/B46C18D9-1608-427F-9A49-6B790AF42630.jpg) ![Backyard path construction 3]({static}/images/2021/10/E7DC90DE-CBF9-4973-B1C3-0022D099AB2F.jpg) ![Materials for backyard project]({static}/images/2021/10/B53924F5-0F58-4DD0-8E0A-0A737FC517C9.jpg) ![Backyard project progress]({static}/images/2021/10/7397EAF0-E3DC-4252-9A26-0FD0A80AFDEE.jpg) ![Decomposed granite path]({static}/images/2021/10/2423D2D3-3295-4D0A-9F39-42E445DF2F44.jpg) ![Completed backyard hardscaping]({static}/images/2021/10/3F37FCFE-ACEA-4711-9E69-46F4E9974289.jpg)

Then we remodeled the kitchen. It was a drab, old galley kitchen with some weird red tiling on the floor and odd blue tiling on the counter. Here's the before pic.

Then, somewhat abruptly, we went for it. We found a local kitchen company and ordered a quartz slab. They removed the old countertop and put in some new boards, measured the sink, and cut a hole for it right in our driveway. I still remember this old guy with a cigarette hanging from his mouth making those cuts. He did a beautiful job.

Then we used Thumbtack to find someone to do the tiling job. He ripped out the old tile, smoothed over the wall to bury all the old adhesive, and then... bounced. He never came back. We purchased the tile from the clearance shed at Heath in Sausalito and I wasn't about to go and find another contractor to do it.

So I did it. I tiled and grouted this here kitchen, and it was good. The irregularities you can see where the faucet is hail from the uneven wall surface. He didn't mud it right and I didn't fix it. So the tiles didn't lie perfectly flat. I was still proud of this job.

![Kitchen tiling work in progress]({static}/images/2021/07/57033683-BFEC-4EE7-9636-DE8C35F84863.jpg) ![Kitchen tile installation]({static}/images/2021/07/621316BB-1632-428E-A09A-D07DD058F03C.jpg) ![Kitchen countertop work]({static}/images/2021/07/FA9D59E6-B067-40E2-831A-12DFB94B30FF.jpg) ![Kitchen backsplash tiling]({static}/images/2021/07/3AC13E36-C1EE-4059-9A86-A38C5128FBF1.jpg) ![Kitchen renovation progress]({static}/images/2021/07/D6AC93FF-722A-449A-AC49-E10CD982D697.jpg) ![Kitchen tile work detail]({static}/images/2021/07/F0D6B56B-7C8B-4FAD-99EE-2B901C759678.jpg) ![Kitchen remodel near completion]({static}/images/2021/07/E0A47B5C-BD05-4E5B-A863-1E7C655AC53D.jpg)

Oh, then we decided to paint the cabinets. This took forever. We sanded, we primed, and we used two coats of special cabinet paint. Front and back. This took about three weeks because we only worked in the evenings after the kids were down. It must have been grueling, but when I look back on it now, it sounds kinda fun.

And finally, we added another counter and cabinet system, courtesy of IKEA, to the bare wall by the garage door. We purchased everything and hired a guy on Craigslist to put it all together. He did a really nice job. There was no way I was going to figure all this out.

At long last... our dream kitchen!

(sarcasm)

There were many more projects, come to think of it, but I don't have pictures of all of them. We redid two bathrooms, we added new Marvin windows throughout the house, added on to the treehouse, knocked down a chimney, replaced a fence, and I placed some nice tongue and groove planks under the eave that wrapped around our house.

It was 1500 square feet, and we used all of it. These were good times.

![Neighborhood kids playing]({static}/images/2021/07/0C70A548-76F6-4347-8428-C1C735D2F82E-1.jpg) *Impromptu neighbor playdates* ![Family time in backyard]({static}/images/2021/07/8080B237-E3EB-4484-B86F-BA02FB3F90EC.jpg) ![Kids playing outside]({static}/images/2021/07/8DBF5CA9-4590-47A4-8CE5-D417A8946848.jpg) ![Family enjoying the home]({static}/images/2021/07/6FD43CBD-7BF2-4B50-964A-5F536097DE9E.jpg)

({filename}how-we-did-our-home-addition-and-remodel.md).

The lives people live

2022-04-27T08:35:00-07:00

I met an old friend for lunch in Malibu. He had a decent exit from his marketplace startup and had become a leadership coach. When we compared notes, we discovered that we both felt an undercurrent of inadequacy. I've written about above average mediocrity.

We each had friends become far richer and more famous and influential than us. We didn’t want to care, but we did. A vicious cycle ensued: feeling bothered about being bothered made us feel even more bothered.

On the surface we were aware that once you reach a certain threshold of income, the returns in utility decrease rapidly. We thought about what we would do if we were “rich.”

I had a few answers:

Fly first class exclusively
Stay in really nice hotels when I travel
Make bigger donations to UC Berkeley and Diablo Valley College

I couldn’t think of anything else. Is that really the difference between me right now and me as a hundred-millionaire?

If I had a magic credit card right now with an unlimited balance, what would I be super excited to buy? I couldn't think of anything, and I'm embarrassed by that. Do I really have every material thing that I want? I could always buy more stuff, but I don’t like clutter. I could upgrade things like my road bike or car, but I don't like throwing things away.

When presented with this thought experiment, I realized I don't need to be "rich." Or, perhaps more honestly, I already am.

What about the first class flights and nice hotels? $10,000 for that flight into Heathrow? Another $10,000 for that penthouse at the Ritz? I could do that now, I suppose. I wouldn’t, but I could, at least for a little while.

Maybe my point is that being “rich” means $20,000 feels like $20 and maybe what I think I'm missing out on is that I’d like to know how that feels.

Why? I dunno. Just because.

My friend had similar answers. We felt better about ourselves after this chat. We paid for our $30 breakfasts and went our separate ways. I told him I’d write a blog post about that conversation. Here it is.

I think people have six ambitions in life. These are the layers on top of the basic stuff: be healthy, be social, give and receive love, and protect your family.

When those bases are covered you get to ask yourself an important question: now what? The answer is going to be one of these six ambitions.

Live a simple life
Have more impact
Be more interesting
Gain more influence
Make more money
Have more fun

You don’t need to pick only one. Most people start with #1 and are content to stay there, but would probably level up to #2 (Have more impact) given the opportunity.

Our working years are fraught with demands from children, bosses, and financial advisors. We raise families while struggling to compile sufficient assets to retire for twenty years or more. The goals here are obvious: happy kids and lots of savings.

Upon retirement, volunteering comes into the picture. This is level #2. Lions and Rotary Clubs, substitute teaching, things like that become possible. You work to have some freedom, and when you have freedom, you try to give it away.

If you’re good at making an impact, then you might discover that people find you interesting. You get good at telling the story about how much impact you’re having. Now you have a following.

With a following comes influence, #4 on my list. You discover that the impact you had, which made you interesting, now makes you influential. Social media becomes useful to you as people begin to follow you because you’re interesting. Your list of friends grows as you get invited into more social circles. This social acceleration begets more influence.

Money naturally follows influence. There are books to be written, speaking and teaching fees to be had. You get interviewed on podcasts and then start making TV appearances. You write a book, do consulting, advise some startups in exchange for equity, maybe invest in some of them directly. This is how fame breeds fortune. Now you’re playing #5, the make more money game.

When you have money you can optimize for fun. You fly first class, join country clubs, attend expensive charity dinners, and go on fancy cruises. You meet more interesting people, which compounds your influence, money, and fun. It’s a virtuous cycle.

I see these people on Twitter. I read their blogs. I know some of them from grad school and beyond. I’m sure I look at this from the outside through rose-tinted glasses but I think I have it right. They're having fun, meeting interesting and influential people, and making a positive social impact.

It still starts with the simple life, which, again, is "simple" because all of the basic needs are already met. From here they get absorbed into the other games, working their way up, often intentionally, and sometimes by accident.

They don’t have to start with the simple life, though. It's possible to enter the game at any level. Some may try to cheat the game by having the most fun while living the simple life. This is where #1 and #6 converge. Some people can bend the game to the point where the two ends meet.

This achievement requires a uniquely wired psyche. These are the monks, the Franciscans who level up to a plane above and beyond the rest of us. I don’t know how to get there and I believe those who figure it out have a different physical properties than the rest of us. It can’t actually be taught but meditation and mindfulness probably get us close. I think the melding of #6 and #1 is what nirvana is all about.

Conversely, money is necessary but not sufficient to have fun. Plenty of people with lots of money are unhappy and therefore don't have fun. They have influence, they make impact, and they’re interesting, but they are deeply unhappy because they’re not having any fun. They could have fun but the momentum of their own mimetic demons keeps them from doing what would actually make them happy. They’re so busy looking around at everyone else’s money that they aren’t able to enjoy their own.

Enough of the hand-wavy stuff. Let’s name some names to bring this down to brass tacks.

Who is having more fun (#6)

Dave Grohl is the former drummer of Nirvana (prescient, perhaps?) and current leader of the Foo Fighters. He is beyond wealthy and seems to have remained in his prime for the last twenty years at least. By all accounts, he’s a nice guy and a wonderful dad (watch this YouTube video of him cooking with his daughter — it’s so, so genuine). He tries to meld the simple life with rock and roll stardom and although it must be an impossible task, he makes it look easy.

Keanu Reeves is nice. He’s generous. He comes off like a regular guy. I’ve read accounts on Twitter and Quora about him crashing a wedding and actually showing up. He makes sure the under-appreciated staff on his movie sets get paid. I include him because being nice is the perfect proxy for having fun. You can’t have fun if you’re not happy. You can’t be happy if you’re not nice. I believe this.

Barack Obama seems like he’s always been comfortable in his skin. And now, as a former president, wealthy from his books and celebrity, he can have fun. From what I read, he is doing that well. I know one person who knows Obama well and the picture he paints is one of a man who has found his place in the universe. Life can’t be simple for a former president, but I don’t hold that against him.

Oprah just has to be on this list. I mean… right?

Others I think are here: Bruce Springsteen, Stephen King. They all reached self-actualization: the virtuous cycle of being able to do what you’re “meant to do” all the time and have a lot of fun in the process.

Who makes money and doesn't have fun (#5)

The list of people who reach #5 but are unhappy and therefore stuck below #6 is long and tragic. I put Donald Trump, Tiger Woods, Bernie Madoff, Tom Brady, and many the lesser-known wealthy people in the “unhappy rich” category here. We all know a couple of them.

They seem to be self-actualized, but they're not. Is it because money allows them to pursue their fun and surround themselves with a glossy rich-colored wrapper?

If you truly love your job, can you reach a steady-state of self-actualization, so long as you still have your job? When Michael Jordan stopped playing basketball, was he still self-actualized? Where does Tom Brady fit in? Many of these guys can’t let go of sport. Let's start with Tom Brady.

Tom Brady is, by account of most critics who care about American football, the G.O.A.T. He has more Super Bowl rings and MVP trophies than anyone in NFL history. As a quarterback he has the most passing yards and passing touchdowns. To cement his virtuosity, he proved that he could do it without his long-time Patriots and head coach Bill Belichick by taking the Tampa Bay Buccaneers to the Super Bowl and winning it in 2020, when Brady also was named the MVP at age 39, the oldest honoree in NFL history.

So why is it so hard for Brady to retire? Why put his body -- and his family -- through this ringer again? Just a few months ago, in the middle of the season, his supermodel wife, Gisele Bündchen, filed for divorce. Brady returned for another season after receiving a hero's reception at his retirement party. Apparently, for Bündchen, it was the final straw.

Applying the 6 levels framework here, I rationalize Brady's decision by assuming that he can only have fun as a quarterback. He's self-actualized only when he's the starting QB of an NFL team. He must love it more than anything else. More than his legacy, more than his family, more than his health. He was already on top -- where else is there to go but down? Sadly, that appears to be the reality of the current Buccaneer season.

Brady is not fulfilled by money, influence, or impact. He's clearly not able to live the simple life. Because he defined fun so narrowly, he made a deeply damaging decision to return for another season. I will be curious to see how he navigates life after the NFL, which he will inevitably be forced to do.

Donald Trump is, by all accounts, an unhappy person. He appears to have fun sometimes, but but most of his public time is spent lamenting his victimhood. He has influence, impact, and money. My armchair analysis (I've never met the guy, obviously) is that he had the most fun as the leading role in NBC's The Apprentice, and in fact the success of the show catapulted his political career.

Was Trump happy as president of the United States? Not from what I have read, certainly not the way that Bush, Clinton, and Obama had fun. He was fixated on the press, his detractors, and then distracted by COVID and the subsequent economic fallout. I don't recall seeing any footage of him having fun, except perhaps a telescopic picture or two of him on the golf course.

Trump, like Brady, is seeking a sequel. Why? The answer for Trump is different. While Brady had fun on the field, I believe Trump conflates the exorbitant amount of influence and impact he gets as president with fun. He is seeking an end that he cannot reach with the means at his disposal. In the quest for #6 he fills up his time seeking copious amounts of #5 and #4. That's what his recent third run for the oval office is about.

The list here goes on and on. It's every wealthy, over-worked, divorced professional who drives an expensive car, lives in a fancy home, and is a member of the best country club. And yet they are deeply unhappy. We work with them, we went to school with them, and we hear about them on podcasts. They have everything in the world, but they're not having fun.

Thought experiment: the remedy

Can you have self-actualization while doing nothing? Lao Tzu would say yes.

Picture a man in a box: no social media, no FOMO or reference points. He’s given a menu of 1,000 unique tasks he can do to earn money. Over time, he discovers a few that he really likes doing. He eventually settles on one of those tasks and gets good at it. Maybe he tries one of the others again but discovers he really does prefer to do the one task. He keeps doing it and keeps being rewarded with "money" that he believes can be traded for future fun.

In this hypothetical universe, does he ever stop working? If so, when? If work is work, and not meant to be fun, when is enough, enough? With no reference points, the man in the box probably accumulates enough money, based on some exchange rate, to last a long time. Then he stops working and trades money for fun. He should be happy.

We know from studying human psychology that we can't help comparing ourselves to others. This is the mimetic desire I read about in the book Wanting. We are programmed from an early age to mime those around us, and that very much includes material possessions. If we can short-circuit that tendency, we find happiness faster.

Personal takeaways

I'm in the vicinity of #3 right now. That's not to say I'm not having fun. I am! But I haven't reached "peak Ryan" yet so I can't claim the mantle of #6. I'm working my up to it and enjoying the process. It is fun, it's just not that kind of fun. The pinnacle takes time, for me at least, and I won't feel it until my professional career is more mature and I've done a lot more writing.

I know I'm not content with the simple life, #1. This may be a foible. I want to make an impact. I want my impact to be appreciated, making me interesting. I see myself as someone who can be influential -- should be influential -- but I also recognize that I need to work for it. I expect that influence to coincide with even more money, and I imagine that having impact, influence, and money will bring me ultimate fulfillment.

As I write this, I present myself with the question: can I not have "ultimate fulfillment" without impact, influence, and money? That seems like a sad state to be in. Is there no fun without #6?

Of course there is. My 6 steps are not a hierarchy, each level up being better than the previous. Rather, it's a sequence I see from observation. It's not a hard and fast rule. The melding of #1 and #6, for example, is very real. The same could be said for #2 and #6, and so on.

I'm still working my way through this thinking, finding my bits of impact and influence along the way, and, of course, trying to have some fun.

Ode to the wheelbarrow

2022-03-10T20:49:00-08:00

The wheelbarrow cleverly combines two ancient technologies, the wheel and the lever, into a very useful device. Elegant and efficient, it's a beauty to behold.

I mean really, look at this thing.

The leverage you get comes from the long handles. Keeping the load near the fulcrum allows you to lift the load off the ground with less effort. Since the purpose of a wheelbarrow is to move a load along a plane, not lift it up high, its design is perfect.

I once needed to move a 450 pound boulder about 20 feet up a slight grade from the street to my front yard. I ended up watching a bunch of YouTube videos with grizzly-haired men talking about how ancient Egyptians built the pyramids. They relied on leverage and the efficiency of rolling and dragging rather than lifting and carrying. I got this boulder into my wheelbarrow, built a ramp to get it up the curb, and plopped that sucker onto its final resting place without herniating a disc.

![Boulder moved with wheelbarrow]({static}/images/2022/11/IMG_3856.jpeg)

I have repaired this wheelbarrow many times. I've replaced and tightened many screws. I even had to buy a new wheel, a solid rubber variety that won't be susceptible to nails and rocks. It just keeps on giving.

I've lent it to my neighbors to move stumps and branches and piles of dirt around their properties. I've used this wheelbarrow to move stacks of pavers and bricks, cubic yards of dirt and decomposed granite, and even to transport gallons of water to a withering oak tree.

Sometimes engineering is so perfect, so elegant, that it appears boring. I'm grateful for this instrument, and I appreciate it.

Thank you, wheelbarrow.

How I wrote my children's book

2022-02-20T21:22:00-08:00

"Children's book author" is not something I aspired to put on my resume. It never crossed my mind. Not once.

But then, one night, I wrote a poem.

It was November 29, 2021. A Monday. We had just wrapped up a long holiday week. My wife's family visited us for several days, culminating in a large family Thanksgiving dinner with my parents joining the party. We hosted everyone, putting to use every inch of our newly remodeled home.

They all left on Friday, we took a breather on Saturday, and on Sunday we did it again with my dad's side of the family. I called it the "Buckley Holiday Dinner" on my calendar. I roasted a four-bone prime rib complete with hand-grated horseradish sauce and big pot of mashed potatoes. It was fun to show off the place and eat too much one more time.

I must have been feeling a little nostalgic the following day. Maybe even a little old. It's a big, grown-up thing to do to host family in this way, and I also felt proud and grown up for owning a house that can handle it. Maybe on that Monday night I was thinking about how my own kids might see me. Maybe I recognized that their perception of me might be completely different than my own.

That little spark lit a fire that hasn't burned in a long time. I used to love writing poems. I don't write them anymore. I wrote one that night, probably on accident. I just needed to feed the flame.

I opened up a blank page on my computer and wrote, "I Remember." Then I wrote this early draft of the poem:

Below it, I made these notes for myself: - Left side of page is first line, from perspective of the child (genderless, a girlish looking boy, maybe) remembering their larger-than-life dad- Right side of page is the dad, answering honestly- Illustrations should be simple and sketch-like, a la Shel Silverstein. Left side should be exaggerated and large with bold colors. Right side should be plain and simple with pastel colors.- Is it a grown daughter talking to her dad on his deathbed? Is it a conversation over Thanksgiving? Is it just the thoughts of a dad missing his kid? Who knows? That's why I like it. That was Monday. I remember wiping away tears the first time I read it through. I went to bed happy with myself for stirring up so much emotion in so few words. As I lay in bed that night, it hit me. I was going to turn this into an actual children's book. The following morning, during a lull in my work schedule, I decided to find an illustrator. I looked in the only place I knew to look: Reddit. I browsed [the HungryArtists subreddit](https://www.reddit.com/r/HungryArtists/) and scrolled and searched around for people doing line drawings and portraits. One in particular caught my eye. It was only an hour old. *My comment is still there:* ![Reddit comment screenshot]({static}/images/2022/02/Screen-Shot-2022-02-20-at-8.46.41-PM.png) I thought it was funny that OP (that's the gender-neutral Internet slang for "original poster" -- the person who started the thread) said they don't draw people but would do it if I didn't mind them being strange. For a kid's book, I figured strange was good. Strange was special, unique, and memorable. I didn't want anything too polished, and I really liked the art in OP's portfolio, so I left that comment. I must have caught [Jolene's attention](https://www.jreneart.com/) because she wrote back a few minutes later on Reddit's direct message service. She offered to get started right away and do a drawing just to make sure I liked her style. I agreed to pay her whether or not I liked it. That was it for Tuesday. On Thursday, this is what she sent. ![Child's perspective of father playing piano]({static}/images/2022/02/Screen-Shot-2022-02-20-at-8.54.33-PM.png) *I remember you were so good at playing piano when I was growing up* ![Father's perspective learning piano]({static}/images/2022/02/Screen-Shot-2022-02-20-at-8.54.01-PM.png) *I was only learning for the first time* I loved it! Plus I was amazed: How did the Internet let me do this? Some random person I just met on Reddit was helping me turn this poem into a children's book. Having spent my entire career online, this shouldn't be a shock to me, but I'm glad it doesn't get old. I'm just grateful that I found Jolene and she turned out to be the perfect illustrator for my book. This partnership continued for the next three months. I revised the poem. A word here, a phrase there. I went on a run with my neighbors and their kids. At the elementary school where we stopped to let the kids play there was a short basketball hoop, about six feet high. He dunked in front of his one-year-old son and joked that he hoped his son would remember him being able to do that. *Bingo*, I thought. *There's another page! *It's in the final version.

In December, I reconnected with the [book designer](https://dtperfect.com/) I used for *[The Parallel Entrepreneur](https://rbucks.com/the-parallel-entrepreneur/)*. She told me she would be busy after January, so I started a new email thread with her and Jolene. Together, they made sure that the art would be in the right format and resolution for the 8.5 inch square book layout. By the end of January, Jolene was done with the poem spreads and we spent a few days with the cover. I made sure Jolene was paid in full and worked the final steps with the book designer. All of a sudden, I was done. I received the final set of files on February 10, 2022. I published my book on Kindle Direct Publishing (ebook, paperback) and IngramSpark (hardcover) the same day. Now I'm working on marketing my book. I hired my long-time virtual assistant to find parenting blogs and reach out to them. We're getting decent response, so I'll continue with that effort and maybe pay for some sponsored content on the larger blogs. My out-of-pocket costs here so far are about $1,700. I didn't plan to spend this much when I started this project in late November, but I can't think of a better way to spend that amount of money. My kids are proud. My neighbors appreciated it. And now I'm the author of an independently-published children's book. That's money well-spent. Regardless, I'm confident that over time I'll make it back, just as I did with *The Parallel Entrepreneur*. I'm not in this game for the money, though. It's a labor of love, and if my oldest daughter has a say in it, I'll be doing this again soon.

My first month of real teaching

2022-02-10T21:58:00-08:00

I leave Diablo Valley College each Tuesday and Thursday exhausted but on the equivalent of a mental high. Teaching two Introduction to Business sections back-to-back is a full body+mind workout that I've never experienced before.

My classroom

I'm three weeks in with thirteen more to go until the end of the semester. I've learned a few things, but before I go into that, let me provide some context.

I described my motivation for teaching in a previous post. I still believe all of it. My heart is 100% still in this. I love the community college atmosphere, the type of students I teach, and the subject itself. My first two semesters were, like so many educators, a shallow pit of Zoom office hours and online quizzes. It was fine but not particularly rewarding. I did all that work upfront and merely shepherded the course along as the weeks went by. I didn't feel like I was teaching. I was just the facilitator.

When the Business Administration Department asked me to teach the only two in-person sections of Introduction to Business, a course that every business student needs to take, I eagerly accepted. This would be my moment! I could finally don my elbow-patched tweed blazer, smoke my pipe, and wax poetical before a chalkboard in front of enamored students.

So, late last year, I chose my textbook and began to imagine how my lectures would go. My sections would be Tuesday and Thursday at 9:30am and 11am. Each is 80 minutes. I wanted to believe I could give an enchanting lecture every time, peppered with tails of my business experience, maybe incorporating something interesting and current from MightySignal and AirNow. Thinking back on my favorite lectures at UC Berkeley, I admired most the professors who could riff on current events and tie them back to the reading.

I've been trying, desperately, to be that professor. I'm not sure I'm doing it right, but I do think I'm getting better.

So, let's get back to what I've learned.

Authenticity is rewarded

I play Grateful Dead at the start of each class.

I always get to class early, and since I use my own laptop for some slides and other multimedia, I figured I should play music the way it's played at a concert venue before the opening act.

I chose Grateful Dead because it's calming (for me, at least) and unique. When I first started doing this a student in each of my sections called me out.

"Is that the Grateful Dead?" they asked.

"Yup," I said.

They nodded in quiet appreciation. I'd like to think they'll enjoy the class better now.

I also am quick to say when I'm not sure about an economic or business concept. It's not easy to riff on the news and relate it to the reading. Sometimes I talk myself into a corner, make a mental note and admit my confusion, and Google it as soon as I get home. I'm learning new things this way.

I can actually feel myself getting a lot smarter. My own learning is driven by being curious, exploring the chapter concepts, and trying to teach it by drawing connections to current events. Sometimes it works better than others, but when I get it wrong, I recognize that's an opportunity for me to learn too.

It's good, and I believe my students reward me for it.

Preparation is paramount

I can't improvise a lecture. It would not be fun. I would stumble, feel awkward, and also feel bad for my students. I'd be failing them. I've found that weekends are great for reading the publisher's lecture notes, reviewing the publisher's slides, and imagining how I would want to present this information.

I picture each lecture before I give it. I have the roadmap in mind and I leave myself little breadcrumbs so I stay on track. These might be penciled notes on paper or an agenda in PowerPoint. My challenge now is predicting how long it will take to go through a topic. I'm definitely getting better at that, but it's the biggest variable in my preparation. How long will it take to talk about this? I have no idea.

I often find myself rushing at the end of the lecture. Maybe it's good that time seems to fly at the front of the lecture hall? I figure if I felt it going slow, my students would feel it even more so. Better that the 80 minutes goes quickly.

My preparation thus far has been sufficient. I'm sure I could do more, but I'm glad I haven't done any less.

Teaching live takes stamina

Teaching is a workout. I get the same high as an eight-mile run, but here it's all in my head. The feeling also reminds me of playing with the Rolling Sloans band after a really good show. I'd still be pumped up on adrenaline, glad that's over but happy with how the performance went. I get that buzz every Tuesday and Thursday after two back-to-back lectures.

I'm not sure what about it is so tiring. I do feel like I'm performing. I'm very deliberately shoving my introversions aside and my mind is running in overdrive, especially when I'm going off the cuff on one of my business news tangents. But like these workouts I've been doing recently, I've learned to love the exhaustion. I tell myself during my physical workouts that this is where muscle is born. It hurts because I'm giving birth to strength. Lecturing on a subject like microeconomics, international trade, or a new business framework is like that. I'm giving birth to knowledge. It's supposed to feel hard.

I also appreciate that it's getting easier. Like training to do a five minute straight-arm plank, what once felt impossible is now a daily routine. I'm just three weeks in. I don't know what it will feel like after sixteen, but I can't wait to find out.

Conclusion

I've always been told I'd make a good teacher. I've always agreed. I'm grateful to have the chance to explore this now. I'm glad that Diablo Valley College is a close drive (or, more commonly now, a bike ride) away. I'm glad I got a graduate degree -- without it, I would not have been hired.

This whole experience has been a major positive in my life and I expect it will only get better.

My foray into web3

2022-01-16T18:45:00-08:00

I'm writing this in web2. I own this domain (rbucks.com, although someday that might change) but I don't own the server hosting it. I don't have absolute control over the data that I'm saving to it. I can delete it (more accurately, I can request that the host delete it) but it's possible the host could refuse or comply but keep a backup copy that I don't know about. More concerning, the host of this blog, wordpress.com, could accidentally erase this post and everything else I've written and saved on here. Then it would be gone. I don't have a backup (edit: I do now).

But I trust. I've read enough about Matt Mullenweg, the founder of WordPress, to believe that his company will keep my content safe. Why? Because Capitalism. This is the social contract that makes WordPress worth billions of dollars. The software won't spontaneously delete my blog posts, and even if it did, WordPress would keep a backup for me, because of the incentive to remain valuable. (That being said, after sweating the end of my the paragraph, I downloaded a backup of this entire blog and saved it to my Google Drive!)

This is the web2 world: cloud-based platforms. These are clusters of powerful servers strung together across timezones, a patchwork of nodes and entrypoints programmed to distribute traffic so as to not overburden any one cluster. If a server goes down, it's simply removed from the cluster and another one is spun up. If a cluster goes down, traffic gets redirected somewhere else. Databases work the same way with writes synchronized almost instantaneously and reads distributed across a network.

It's a good system. I like it. It works. I don't want to own or maintain my own blogging server anyway.

My friend Jake shared this post by Moxie titled, "My first impressions of web3." It's a unique critique of the false promise of a completely decentralized web. That's what web3 means to me. It's the idea that we can shift those web2 clusters out of private control and into the hands of the public (or, really, the geeks and nerds who will be paid handsomely for hosting them). This way, everyone has a copy (or, really, everyone who wants one can get one) and we don't have to worry about one company going down or acting badly. It's a vision that means well, even if it's currently and always will be reliant on web2 infrastructure to function properly.

Moxie takes aim at non-fungible tokens (NFTs) and gas fees, noting that NFTs simply point to a storage address on a web2 server. He also notes that web3, by being decentralized, is inefficient and upgrades much slower than a centralized organization would. Interestingly, when it comes to speeding up blockchain reads, centralization has emerged organically, with two services copying the Ethereum blockchain onto a developer-friendly web2 system.

Having just read The Evolution of Everything by Matt Ridley, with particular interest on his chapter, "The Evolution of Money," which hails bitcoin as the most important technological development in our lifetimes, I can relate Moxie's critique to Ridley's compliment. What we're witnessing is an evolution. Where Moxie dismisses the "early days" explanation of these hypocritical attributes of web3, Ridley would say the evolution is moving apace. Bitcoin was introduced ten years ago. For half that time it was completely obscure, known only to some fringe cryptology and technologists. As a technology, ten years is a long time, but as a cultural phenomenon, five years is nothing. When considering the promise of bitcoin and blockchain technology in general as a cultural shift, I think five years is too short. It is still very, very early and the impact has a long, long way to go.

I started paying attention to bitcoin when social media caught notice. In other words, I became interested years after the first debates about the origin of Satoshi Nakamoto and years before my mother-in-law created her Coinbase account. Somewhere in the middle, say around 2014 and 2015.

I bought my first Udemy course on Solidity (the programming language for Ethereum) in 2017. I got my first bit of bitcoin a year or two earlier, likely a gift from one of my avant-garde friends. Timing wasn't right for me then to chase the scent. I rode the bull run in 2017 and did some gifting of cryptocurrencies myself, amazed by the free money flowing into my Coinbase account. I tripled and quadrupled my (meager) principal and shrugged when one of my friends told me he was going to quit Dropbox and start a new blockchain. I continued to shrug when my other friends joined and they changed the company name from Loom to Solana investors started taking notice, purchasing the promise of a token distribution for hundreds of thousands and then millions of dollars, even in the depths of "crypto winter" when the then-sky high bitcoin prices fell back down.

I never considered working full-time in crypto then. I got an offer to ({filename}mightysignals-new-leadership.md) and took it. Across the bay from my new house and two young kids, Solana took off, and so did everything else. They couldn't have timed their ICO better, launching the Solana token to the public just as the first drops of crytpo thaw began to emerge and accelerated into the incredible 2021 run that dwarfed the 2017 peaks ten-fold. My friends got rich! I did fine too, but ({filename}above-average-mediocrity.md).

I was engrossed in web2, a hired CEO struggling to get a foothold on the mountain of mobile data, feeling stuck. I managed to work my way to higher ground, selling MightySignal to Airnow in mid-2021. I'm there now, a modest web2 success. But when I'm not thinking about the next mountain to climb for MightySignal, I'm thinking about web3 and climate change. And here's where I get really excited.

I don't give a shit about today's implementation of NFTs. I think it's dumb. When I think about the promise of crypto, I think about public datasets. Which data, if made public, would make the world a better place? I had a weekly conversation with Jude Barry, a political strategist in the Bay Area, and my ideas and thinking evolved with these phone calls. I considered water rights, carbon offsets, energy bills, and philanthropic donations. Eventually I settled on campaign finance, and I couldn't let it go. It seemed like the perfect application of blockchain technology: an immutable ledger of gifts to political entities. Money could be traced from place to place. The public would see it, own it, and be able to hold the donors and recipients accountable. If ever there was a private database that ought to be made completely public, this was it!

We pursued this idea for months. I started thinking about payments and payment processing, and how companies like MightySignal would benefit from not having to pay 3% of revenue in credit card processing fees. On blockchain, these transfers have flat charges. There's no difference between a $10 or $10 million payment. Crypto disruption here makes perfect sense and I know people are working on it already. I turned back to politics.

I thought about building a crypto-based clone of ActBlue, helping political campaigns accept cryptocurrency donations, but instead of stopping there, we'd then track where the money goes and how much each campaign raised. It's a noble idea but is flawed in that campaigns could opt-out. There'd be nothing preventing them from exiting web3, going back into the black box of web2, and taking their web3 money with them. I stuck with it for months, though, discovering a new curiosity in the actual technology itself. I dusted off that Solidity course I purchased in 2017 and actually completed it. Meanwhile, I discovered crypto communities on Twitter and Discord. I lurked and read and talked to Jude and others. I spoke to two political campaigns about their interests in crypto and got lukewarm responses. It wasn't the crypto itself, they said, it's the reporting and regulation around it. If we could solve that operational challenge, we'd have a business. The only problem was I didn't want to build that. So I kept looking.

The year 2021 in California was a rough one. In the midst of a severe drought, with rampant wildfire smoke in the air, I watched my creek dry up. It scared me. My neighbors who lived here their entire lives said they've never seen it happen. Then in the fall, when the smoke cleared and rains returned, the COP 26 UN Climate Conference failed to reach consensus about what to do next. I read How to Avoid a Climate Disaster and did Al Gore's Climate Reality Training. Another idea began to emerge, a way to approach my political fundraising idea from the other side, creating an "activist investor"-type mechanism to influence the outcome, our outcome, in this race against a climate disaster. It was beginning to look a lot like a PAC.

This PAC would be different. It would be distributed, public, on a blockchain. It would collect funds from donors and place them into a smart contract. The contract would move the money if conditions where met, like a vote, an election, or any other trigger. I read about how to do this on blockchains using Chainlink oracles. It was starting to make sense, but then my wife, who used to track legislation for her job, poured a bit of cold water on the idea. Bills evolve, she said. You often can't know exactly what's going to be in the bill until after the votes are counted. Thus, a smart contract trigger might not really work. To trigger the transfer, we'd need a discussion and a vote. In crypto-speak, we'd need to make a distributed autonomous organization, or DAO.

This idea has become the DAOPAC white paper.

Our mission is to provide a counterweight to the dark money rampantly flowing into our political system by publicly pooling money from the people in order to win political fights for the common good.

Our vision is for the laws of the United States of America to accurately reflect the will of the people.

- DAOPAC White Paper

The blockchain comes into the picture by allowing us to create a codified escrow with some creative triggers. A regular escrow allows for the trustless swap of goods (e.g. Person A and Person B want to transact, but neither once to move first, so they rely on a trusted escrow to collect the item from each person and then redistribute.) We used an escrow when we bought our house, putting funds into escrow that would only be released when the seller signed their forms. On a blockchain, this can be done with code, taking money or keys or anything else digital from one party and only releasing them to another party when a condition is met. The difference is the escrow is basically this wide open public computer. Both parties can trust the escrow equally, and, importantly, there's no way that the escrow provider runs off with my down payment.

In political fundraising, the escrow concept gets very interesting. A donor could put money into an escrow account (DAOPAC calls this a campaign) that would be released if:

An elected official votes a certain way- An elected official gets a certain voter rating (e.g. League of Conservation Voters scorecard)- A candidate gets a specific endorsement- A candidate makes a specific statement on an issue- A candidate wins the primary- A candidate raises a certain amount of money

If the conditions aren't met, the money goes back to the donor automatically. This doesn't exist in the political world today. I think it should, because it's better for donors.

I also think it can be better for humanity. Since 67% of Americans perceive a rise in extreme weather, I would like to see money being pooled and guaranteed for specific legislative outcomes. On the one hand, it's bribery, but on the other, it's how politics works. I give to politicians who vote the way I want them to vote. Does the cart push the horse? It's impossible to say, but to the extent that it does, it might as well be put on a blockchain for all to see.

This is, in essence, the promise of web3. Data becomes publicly held. Sensitive private data can still be on a blockchain when it's encrypted using a safely stored private key. It's a really elegant way to think about the Internet.

Why I run

2022-01-02T20:47:00-08:00

I run because I need to. When I don't run, I don't feel great. I need the exercise, I need the exhaustion, but most importantly, I need the time alone. I've found that I don't love running with other people. I'll do it because it makes me better at running and introduces me to new routes and possibilities, but I'm happiest when I run alone.

I run because it feels good. I'm pushing 40 now and my achilles and ankles take a few minutes to warm up. I feel them when I take those first few steps down my driveway. I know that the little aches and pains will go away within 10 minutes. I'll be just over a mile away from my house by then, and happy to have at least another hour ahead of me. A good run for me takes about an hour and a half. That's when the little bits of pain start to return, but in different places. I'll feel it first at the bottom of my feet. My heel will get a dull ache, and then that bony ball below my toes will join the chorus. This is when I know I've reached the outer limits of my running fitness. It usually comes after about two hours.

I run because it's fun to explore. I enjoy not knowing exactly where I'm going. When I discover a new route, I set out in a general direction uphill, figuring that two sides of a ridge must connect to a trail or road somewhere. I'll consult my Strava app's heat maps to make sure I have some hope of finding a loop, but once I'm out there I mostly rely on instinct. I did this a month ago, trying to turn the eight miles back from a park where my family took holiday pictures into a twelve-mile mostly trail run. I set on Bollinger Canyon Road, noting that after a few miles it appeared to dead-end into a trailhead. However, a neighbor told me there's a bunch of No Trespassing signs and some folks who aren't used to having visitors.

Deciding to trust Google and Strava more than my neighbor, I turned up that road and sweated my way to the end of it. I ran past dirt driveways and gurgling streams, through oak forests and grassy fields. Finally the road ended at a gate and a couple of dirt driveways. I met two guys there who looked at me inquisitively.

"You ran all the way up this road?"

"Yessir. I'm looking for a trail."

"Well, there ain't no trail past here."

I didn't believe him but I didn't push it. I ran back down the road, knowing that just on the other side of the ridge to the north I would find the network of trails on my map. When those guys were out of sight, I headed up a dirt driveway and followed it as far up the hill as I could before it turned into a much more private road close to someone's house. Seeing no semblance of a hiking trail anywhere, I turned around once more and headed back to the main road.

About a quarter of a mile down, I decided to try again. This time it was a fire road that went straight up a steep grassy hillside in exactly the direction I needed to head. I set out, hopped a railing and climbed up to another cattle gate. Beyond it was the ridge, and on the ridge, I saw another trail heading toward the neighborhood of my daughter's elementary school. I figured I would be able to get back on a road over there.

At the ridge I looked to the north and west. It's another world. A small ranch and pond, another ridge with a few houses overlooking the valley. Clusters of oak trees and waves of green, flowing grass. I smiled on the inside.

This is why I run.

How we did our home addition and remodel

2021-11-14T19:47:00-08:00

This was the last and final remodel. There were earlier projects.

Between March and September 2021 we more than doubled the size of our house here in Contra Costa County, going from 1,500 square feet to just over 3,900. It took more than a year to go from our first drawings to the finished product, with permits and construction each taking about six months.

In my telling, it all started with the walls.

"I wish we could get new walls," my wife said.

And she went on to say how new walls would make our old house feel new. That despite numerous small and large home projects, including two coats of paint when we first bought it, the old house still felt and looked old.

"Well, if we do the walls, we might as well do the floors," I replied.

And I went on to say how much I despise having to tiptoe around the squeaky spots in the small hallway between our room and the girls' rooms when we wake up in the morning. Step in the wrong spot and POP! The doors would open and out would jump our little princesses, dispelling our plans for a quiet early morning.

At some point doing the floors became moving some walls around, because we'd have to get all the furniture out of the house anyway. And if we're moving walls then we should just do a little addition too, get the master suite we always wanted. And if we're adding on there, let's just expand the kitchen into the garage, and that would mean adding a new garage. And if we're doing all that, then we should get the guest room and bath we need so family won't have to stay at hotels when they come visit.

In product development, we call this scope creep. It's the domino effect, the snowball rolling downhill, gathering mass, collecting ideas, until you've knocked down every wall and are basically building a brand new house from scratch.

That's exactly what happened here. We scope-creep-snowballed our way into a complete rebuild of our old house... And I couldn't be happier that we did it.

The designer

I called Jill sometime in May 2020 on a recommendation from our neighbors down the street. She did their remodel and they gave a roaring endorsement. They suggested, when the time came, that we go with their general contractor too. I'll come back to that later.

I dialed her number and Jill picked up right away. She sounded pleasant and said she would be happy to meet. Although she lived out in the Sierra Nevada foothills, she was in our area frequently to visit family.

I remember that she arrived at our first meeting with a small ruler, a pencil, and some sheets of drafting paper. She brainstormed with her hands and I sat mesmerized. We talked through some ideas and she said she would get back to us with some more thorough sketches, but before she could do that, she needed to take some exact measurements of our house.

We never bothered to interview anyone else. I wanted Jill to figure this out for us. These are some of the first sketches of the downstairs addition layout after our meetings in late June 2020.

We received this clean set of drawings just a couple of weeks later. The left is the downstairs and the right is the upstairs. With tiny modifications, this would be the final layout of our new house.

Later, she modified the drawings to show which walls are new (dark filled) and which are existing (no fill).

This was my first foray into architecture and it continued to amaze and surprise me because my mind doesn't work like this. I'm artistic with sound but not with shapes. Witnessing the work of a professional, an artist, really, was very satisfying. Jill seemed to be able to picture our house and walk through it in her mind.

The placement of the laundry room, for example, was her idea. She put it in the middle of the house, close to the girls' rooms, knowing that's where it would be most useful. She encouraged the extra wide hallway in front of the new master suite. The position of the pantry and powder room was also her vision. I couldn't see it. And the layout of the kitchen was influenced by both my wife and Jill, as I recall, since there was a lot of discussion around those specifics.

As with nearly everything home-related before and after this big project, I mostly just listened.

Finally, we settled on the completed plans. I loved seeing these elevation drawings, which Jill also drew by hand.

The final, complete plans included a site survey, electrical drawings, engineering drawings, Title 24 (energy efficiency stuff), and roof drawings. It looked very impressive.

I still can't believe Jill drew this. It looks like a computer drawing. It's unbelievable.

So there it is. The final final. Jill dropped off our completed plans at the county sanitary department for initial approval on September 14. They approved on September 24 and we were off to the building department to begin their much, much longer process.

The journey had begun! Started on May 20 and ended almost exactly four months later. And now we needed a contractor.

The contractor

I didn't know this when we started, but drawing the plans for the house and building the house itself are two very separate disciplines.

Builders (aka "contractors") like to work from designs. They don't like to make decisions. Designers (aka "architects") like to start from scratch, the blank pieces of paper that Jill brought to our living room, and figure everything out.

Designers make plans. Contractors use plans. The better your plans, the faster and easier the process. Good contractors know this, so they want as many decisions made for them up front as possible:

What kind of siding do you want?- Where are you going to order your windows from?- What kind of doors?- What type of roof? - Floors, cabinets, vanities, tiles, trims, paints, pulls, handles... everything?

When it comes to working with a contractor, there is no, "Gee, what do you think?" If you give off that vibe, they'll run away from you... fast.

On the other hand, if you have good, completed plans, a solid vision for all the little details that aren't in the plans, and are willing to start spending some money ASAP ("Buy the windows NOW!"), then you're ready to talk to contractors.

We asked Jill for her recommendations and I asked my neighbors, the same ones who gave us Jill, for their contractor's email address. They told me his name was Byron and that they loved working with him, too.

We contacted Byron and all four of Jill's recommendations, and we wound up with four bids. We put them into a spreadsheet and tried to compare them. It was difficult because the line items wouldn't line up. Some bids included countertops, for example, and others didn't. Some had a flooring or HVAC allowance and others left it out. It made the comparison tricky, but I eventually figured it out.

One bidder was really high, almost 50% higher than the rest. He came off very professional and clearly wanted our business, but it scared us off. I couldn't understand why his bid would be so far off, so I didn't trust it. We turned him down. Another bid was in range but we didn't like the contractor as much. He seemed a little distracted and we didn't want delays. We let him go too.

That left Byron and Jim. Their bids were similar. They both were very nice. The difference was Jim had a crew of full-time employees and Byron worked with sub-contractors; he had no staff. On first blush, having a crew might seem like an advantage -- they work for Jim! But on the other hand, they're not incentivized to work fast. The length of our project has no bearing on their steady paychecks.

Byron claimed he could get our job done in about 5 months. Jim quoted 8 months. We obviously liked five months better, and with the cost of our rental, that was at least a $12,000 cash difference. And although Byron came off very casual (he admitted to not reviewing our plans when we first met), I believed that he could do it. I remembered how quickly my neighbor's job was completed, and they just gushed over Byron and his crew.

We took a deep breath and agreed to go with Byron on October 29, 2020. We wouldn't actually sign Byron's contract until February 25, 2021, but we gave him a verbal commitment then. He told us to go and get our permits.

This took far longer than we expected.

The county

We live in unincorporated Walnut Creek. It's a weird designation which basically means we don't belong to any particular city. For all the normal things you might need, like police services and building permits, we just go directly to the county. No city hall or special city rules. We call 9-1-1, and we get the county sheriff. We want to build something, and we go straight to Martinez, the capitol of Contra Costa County.

I will not mince words: the permitting process was a PAIN. You would think the county would be incentivized to push us through this process and collect on the higher property taxes. I get that it needs to be done right, but the delays here were unreal. Maybe it was COVID, maybe it was the holiday season. Who knows?

All I do know is this timeline was crazy.

September 14, 2020: Dropped off the building plans at sanitation department- September 24, 2020: Began working with an arborist on required tree removal plans- September 25, 2020: Picked up approved building plans at sanitation department- October 9, 2020: Planning department entered us into the online ePermit system- October 20, 2020: Received the arborist report- October 26, 2020: County told us that the building permit approval process will pause until we get the tree permits (!!!!)- November 6, 2020: Assigned to a tree permit person- ..... crickets ......- December 22, 2020: ePermit updated with tree permit requirement- December 29, 2020: Reached out to tree permit guy's boss

I was getting desperate.

January 5, 2021: Notice sent out to neighbors about our building and tree removal plans- January 19, 2021: Public comment period ended- January 28, 2020: Received the tree permit- ..... crickets ......- March 5, 2021: BUILDING PERMIT ISSUED!

Rejoice!

We discovered, to our dismay, that even despite bypassing city regulations, permits are not cheap.

Tree permits: $6,500- Building permits: $17,500- Total permits: $24,000

Five months, 19 days, and twenty-four thousand dollars. Just for the privilege to build in Contra Costa County.

The preparations

In the time between when we first got Byron's numbers in October 2020 and when we signed his contract in February 2021, a lot happened. We worked with his suppliers and subs to refine our bid. We made a bunch of decisions on windows and doors and exterior trim.

We ordered all the big new appliances, like the Sub-Zero panel-ready side-by-side refrigerator and freezer, the wine refrigerator, and the dishwasher (we hand-washed dishes for six years with two kids at our old house!)

We went to Golden State Lumber and ordered our windows and doors. We checked out their trim options too and started talking about paint colors. We got swatches, lots and lots of swatches. And then we got samples to test out the swatches.

My wife bought a bunch of discounted tile from Heath Ceramics and some custom fresh tile from them too. We talked endlessly about floors and carpets. We visited every kitchen appliance and countertop store in a 20 mile radius. We were starting to get all that figured out too.

We also needed to find a place to live! In order for Byron to work his five-month-magic, we needed to get out of his way. I found an option in San Francisco. Melissa found one elsewhere in our neighborhood.

Then I got an idea. There was a rental house getting remodeled just down the street from us. It was going really slowly, but timing just might work. The landlady lived around the corner from us. I called her and explained our situation. Would she be interested in a short-term tenant?

YES! I asked her for the lease and we locked it in. We'd live four doors down from our remodel. I was nervous about the arrangement since it could go either way: agonizing slow or fantastically fast. Fortunately, we witnessed the latter.

Here's a glimpse of what we saw between March and September 2021.

The expansion

Because of our creek setback and the forest of oak and bay trees in our yard, the only area we could expand was right along our neighbor's fence. The problem was we had a bunch of trees in the way here too, hence the extended tree permitting process.

In all, we had to cut down eight trees, some much larger than others, and at the last minute we added a ninth. I'm not proud of this, but we really had no choice, and if we didn't do it then I'm sure the next owners would. I still remember the last tree going down, its massive trunk hauled by crane over our house, dripping water like tears onto our roof.

Anyway, here's the time lapse of the work done on this part of project. First, the deck was removed to get at the big cluster of bays and oaks. The large oak closest to our house was tricky because its massive root system went right up to our existing foundation and since the footing needed to pass through it, we had to grind really deep, and the stump grinders aren't built to go more than 18 inches into the soil cover.

We eventually managed, though, and the foundation crew was able to set up the wooden forms to pour the footings. When the footings dried, the framing crew went to work, setting up the joists that criss-cross to support the subfloor. These guys worked fast. As soon as the footings were dry, they went to work, making huge progress every day. Subfloors went down and walls went up in no time, it seemed. Before we knew it, they were nailing on the external plywood, then the cement board exterior, and then the paint!

The final step, which was not part of the original contract (scope creep... again), was to wrap our deck around from the new extension to the new door in our new kitchen. The crew figured out that since they leveled off the house, raising it up to six inches in some places, the old deck framing was too low. They decided to completely strip the old deck and start over.

The upstairs

High on my must-have list was a bedroom and full bath for our guests. I always felt bad sending our family off to a hotel when they came to visit. It just didn't feel right. We could have put the master suite upstairs but that also didn't feel right. We wanted to be on the same level as our kids. So guest room up there just made sense.

The other half of the vaulted room would become an open media and play room. One thing my wife need to have, and I didn't disagree, was a TV-free downstairs. She's bothered by extraneous sounds -- much more than I am -- and Spongebob Squarepants sounds very extraneous. The TV common area was going to be upstairs.

I was worried at first that splitting the space in half was going to make both rooms feel too small. Upstairs before the walls went up actually felt pretty small. I didn't believe Byron when he told me that the space will feel bigger and bigger as they progress through framing, drywall, and paint. He was right. Again.

When the walls were up we measured out a space for a couch and discovered that normal-sized couches were not going to cut it. This was a long wall and we were going to need a big couch. We settled on a 150"x100" Ethan Allen sectional. We sat on a million couches and liked the look and feel of Ethan Allen best.

We also weren't sure how big of a TV to get. We penciled it out on the wall but it was still hard to picture without the couch being there too. We bought a Samsung 75" Frame TV and it's perfect for the space. I really think we nailed this whole setup.

I'm also quite proud of my audio selection. You'll see in the final picture a Sonos home theater system system. It includes two wall-mounted Sonos One speakers, a sound bar, and a sub woofer. I love that the eArc HDMI allows the TV to automatically chooses the Sonos speakers when it's on. I never have to set the external audio. When the TV isn't on, I can play music through the home theater system simply by choosing it from my Spotify controls or by talking to Alexa. It's amazing.

Plus, the sub woofer is LOUD. It gives you the deep warm bass sound that you really want on some songs. And somehow the Sonos software routes certain sounds between the sound bar and the mounted speakers to make an amazing surround sound. It's a remarkable system and there's no extra hardware. No rack in the back, no special receiver. It's just Sonos.

Another thing we got right about the TV room is getting all the cables routed through the wall so the TV can mount flush. The whole point of The Frame is for it to be totally flush. Its hardware and ports are in a box in the corner of the room which is connected to the TV by a special cable. The HDMI cable for the Sonos sound bar also runs from the middle of the wall to the corner of the room. All of that was taken care of before the walls were closed up.

I just love this room. I'm sitting here now as I type this.

Here's the progression of how the upstairs came to be.

The Saranap kitchen

The kitchen was my wife's domain. So many decisions. So. Many. Decisions.

We knew we wanted it to be big, and we knew it made sense to have it basically take over the entirety of the old garage. We wanted a massive island, a prep sink in addition to the main sink, and we needed a pantry. My wife was also certain that we should add a "powder room" -- basically a bathroom dedicated to our downstairs guests.

Her inspiration was this Emily Henderson kitchen remodel. I couldn't complain -- it's beautiful -- and since visualizing colors and tiles and cabinet locations is not my thing, I mostly just nodded as she described her vision.

Here are a few bullet points about kitchen remodels that I learned:

Cabinet boxes and drawers are constructed before the doors. The doors are a specialty service ordered to spec based on the box dimensions. We used Igor, one of Byron's guys, for the boxes and Dutchman Doors for the doors. - It really helps to have a 3D rendering. We commissioned one on Upwork for about $2,500 and ended up changing the design as a result. our 3D kitchen rendering. - There are a million types of countertop and you can't really go wrong (unless you pick marble, which stains easily). I'm really glad we landed on quartzite (Victoria Falls, to be exact) after almost going with a Cambria quartz. - The pantry is clutch. It's just so nice to have all the dry food stored on open shelves instead of having to rummage through low cabinets to find that can of beans.

Stacked ovens are the way to go. Our lower oven is a standard convection and our upper is a "speed oven" which basically is a combination toaster oven microwave. This setup will come in handy on Thanksgiving. - Induction cooktops are amazing. I've written about electrification before.- Our kitchen is big. I mean BIG. Byron approved, though. He said in most houses, even fancy ones, the kitchens are too small and the master bedrooms are too big. He said we got it right.- We tiled to the ceiling and didn't put any cabinet uppers where traditionally they'd go above the cooktop. It's a nice clean look, but we had the luxury of not needing the additional storage.- We put two speakers in the ceiling and connected them to a Sonos amp so we can ask Alexa to play music there or select it from our Spotify app. Wired speakers in the kitchen are awesome.- We got Brizo SmartTouch faucets. I didn't care when my wife brought this up, figuring I didn't have to use it if I didn't want to. Now I can't imagine life without it. It's nice to be able to turn the sink on and off by touching the back of my hand to it when they're dirty or full. - We added an insta-hot faucet. I love to have water on tap that's hot enough to brew tea or coffee on the fly. I also use it to clean stubborn greasy dishes.

We got this Franke sink with a tray that has two levels. This feature works because the sides are square. Seems like a subtle, shrug-worthy feature but it's actually quite nice to have the raised sink tray for prepping vegetables and the lower one for washing out bowls.

We splurged on panel-ready Sub-Zero side-by-side refrigerator freezer. That's the cabinet to the right in the picture below. It's not at all necessary but I'm glad we stretched the budget and did it. Super clean look. - We also wanted an "appliance garage" for the coffee maker and toaster. This essentially means putting a 4-plug jack in the back of a cabinet. We put that to the left of the Sub-Zero with a little decorative space between them. We could have put an upper cabinet here but we opted not to.

I also got my booze cabinet. Here we have a dual-zone beverage refrigerator (properly chilled red wine is divine), wine rack, and hard liquor sliding drawer. - The smaller drawers are holding junk mail and coloring materials for the kiddos for now. The way we use this area will evolve over time.

Finally, I really wanted drawer inserts. These are all Rev-A-Shelf pre-fabricated inserts that we cut down to size to fit into our drawers. It really makes a difference in look and feel and they're each just around $50 each.

The kitchen is gorgeous. There's no other way to describe it. It's a show-stopper when people walk into our house. It's welcoming, functional, clean, and BIG. It's where we eat breakfast, where I read the newspaper, and catch up with my wife halfway through the day. I love it. There's nothing I would change.

Finally, here are a few before-and-after shots of the kitchen construction.

Emily Henderson called hers the "Portland kitchen." So we'll call this one the "Saranap."

The big vaulted bedroom

This is the room that my wife is probably most proud of. Even prouder than the kitchen, which is saying a lot.

I love this room too because, if you'll recall from the beginning of this novella, having a real grownup bedroom was the main thrust of this whole endeavor. We didn't remodel the whole house to get a nice kitchen. We did it for the bedroom.

Before I go on, you have to understand that our bedroom before was small. It could fit a king bed and a dresser and that's it. There was a big window but no fan, and we had a closet with two sliding doors. We stepped out onto a squeaky hallway that inevitably woke our daughters up when we were just trying to sneak into the kitchen to brew a quiet cup of coffee. So having a big bedroom with a sitting area, our own bathroom with a carpeted walk-in closet, and an enclosed toilet room so it doesn't monopolize the bathroom is... amazing.

Our vanity was custom-built by the same guy who did our kitchen. The wood was stained by the same guy who painted our kitchen cabinets. The vanity countertop is also the same quartzite that we used in the kitchen. It helps to have the same guys knock out all the upgrades in all the rooms!

Rather than dual sinks, we opted for one. We just don't brush our teeth at exactly the same time and don't run into bathroom faucet conflicts. A single sink has been just fine and makes the vanity look even bigger (and at 10 feet long, it's already big!)

The shower is tiled top-to-bottom with more Heath. There's not a lot to say about it. It's beautiful, of course, and we knew it would be because we love Heath. It's big but not absurdly big. I don't know why some houses have showers bigger than the master closet. Or two shower heads, for that matter. (Do most couples take showers together all the time? Are we the odd ones out?) The glass door finishes the look so we can always see that lovely tile.

We carpeted the walk-in closet and added two sets of built-in drawers. The top drawer is slightly shorter than the rest. Igor did a beautiful job with these too. It's a treat to have solid, custom built-ins like this.

The closet is simple, just 6' by 10'. It's big enough for us both to stand in there but with the drawers and clothes in the way, we wouldn't both get dressed at the same time. It's plenty for one, though. Since neither of us have a ton of clothes, and our bulky jackets are in the new coat closet by the entrance, it's been totally fine.

The wide hallway

The hallways in our addition are about six feet wide. It's a subtle touch on paper, but it's a luxurious vibe to walk through them. It's the horizontal equivalent of a high ceiling. If you have the space, I definitely recommend it. It feels really, really nice.

The garage

We got a finished garage because the crews were here and it was one of those things we figured we'd regret if we didn't do it. I'm glad we tacked it on.

The shape of the garage is odd along the perimeter because of our creek setback and other constraints. We wanted at least a 20' x 20' garage and wound up with one a bit over 520 square feet in size. It has a bunch of plugs along the walls, and an ethernet port just for good measure.

One thing I was adamant about, and very glad we included, was a utility sink. Our last garage had one and I used it all the time. Painting supplies, shoes with dog poop, and anything else gross got washed in it. I definitely did not want to use our kitchen sinks for that mess, so the garage utility sink got brought into the fold. I bought the floating cast iron sink on Wayfair and it has held up well so far.

A few more thoughts about construction

Construction is insane. It's chaotic, it's expensive, it takes a long time, and it stresses you out. Looking back, I can't believe my family moved out of our house for six months while this happened. I can't believe we were able to save and borrow (Figure.com home equity line of credit for the win!) enough to do a project like this.

I also can't believe how well it turned out. Everyone seemed to be on the same page. They shared the vision. I credit our designer and contractor tremendously for that. I also give a tremendous amount of credit and respect to my wife for making 99% of the decisions that make this house so beautiful.

I remember taking these pictures below, eager with anticipation, scared at how un-finished it looked, and really having no idea what I would be looking at standing in the same place just a few months later. And this is the magic and beauty of construction. Plans get drawn, a framework goes up, and then it gets polished off. The same series of steps that happens in every project: digging foundations, pouring concrete into forms, framing walls and pushing them up, trusses on the roof, siding on the outside, paint. The same process for each build yields a different result.

The guys that do this must get great satisfaction in seeing a building go up. I hope they do.

Above-average mediocrity

2021-10-10T20:17:00-07:00

*I started writing this a while ago and am publishing it now even though I don't feel this anymore. Nonetheless, I edited and finished it because I think the vibe is interesting and might be helpful to another fellow "bottom of the top 1%"-er. *

So here we go.

I'm going to chip off a piece of the feeling I described in my previous posts, ({filename}its-been-a-long-long-time.md) and ({filename}my-unannounced-and-inconsequential-break-from-social-media.md), and dissect it a bit more, just for fun.

Delusions of grandeur

Oh, I had big plans, big ambitions. "Three million by 30," is what I used to tell myself in my mid-to-late 20s when my ({filename}the-bitter-taste-of-failure.md) was starting up in San Francisco. I figured three million dollars at six percent interest (conservative investments) would yield $180,000 per year. I could retire with that annuity if I wanted to (but of course I wouldn't).

I believed I was destined for greatness, that all I had to do was put one foot in front of the other and I'd walk my way, chest puffed and bent arms swinging, to the top of the heap.

I recalled a mentor at UC Berkeley meeting my girlfriend at the time at a fancy banquet. When I introduced him to her he smiled and pointed at me. "He's going to be rich," he said to her. I never forgot that.

When I was leading some environmental programs at UC Berkeley I remember one of the campus facilities leaders introduced me to her peers as the future governor of California. I don't remember what I was there to talk about, but I remember she said that.

When I was in high school, I sat in the right rear seat of a car while my friend's mom drove. My friend sat in front of me, on the passenger side. Out of the blue, his mom turned around at a red light and told me she'll vote for me when I run for governor. Another friend, someone I volunteered with at a community organization in high school, also reminds people we meet that I'll be governor someday.

Governor. Someday. Sigh.

The older I get, the harder it is to live up to these lofty expectations. It's as if my first two decades were a dream where everyone I knew seemed to anticipate my gilded future. Now I'm awake, two decades later, and those things I was told were supposed to happen haven't happened.

I've worked hard. I've put one foot in front of the other. But the fortune and fame have not materialized. I'm not at the top of the heap.

Instead, I find myself at the bottom of the top 1-ish percent, a no man's land of far more than most but far, far, far away from the best.

Pride and punishment

I know I shouldn't care. Sometimes I really truly honestly don't, and those days are wonderful. Sometimes that feeling of freedom from expectation and comparison lasts for a week. In that time I'm at peace. I don't want, I don't need. I'm content with my work, my assets, and my friends and family. My lot is just fine.

And then I get a LinkedIn or Twitter alert. A guy I know from graduate school is listing his company on the NASDAQ. A friend from college has a top position in the Biden administration. Another one sold his company for $30 million, has $500 million in cryptocurrency tokens, or a hundred thousand Twitter followers.

I think about the companies I've started and sold for barely a fraction of those amounts. I look at my bank account, Twitter likes, blog visits, and crypto portfolio. I ask myself what I've been doing, why I missed those opportunities, started the wrong companies, bought the wrong stocks.

Sometimes it comes on a phone call. Just a regular check in with an old friend.

"Oh, you're still doing that?"

"You're going to sell for what?"

"You can't join the syndicate? It's just $30,000."

And suddenly I'm inadequate. It corkscrews my intestines. It impacts my mood. I get off the call and just think. I cross my arms across my chest and stare at the wall, lost in thought, feeling bad about myself for feeling bad about myself.

I tell myself to let the feelings cycle through. I chew them up, like I'm digesting them, and explore the colors and textures, shapes and smells. I've mulled over these so much in the last few months, and I'm finally, finally able to get them out. A long-awaited defecation of self-destructive emotional waste.

I'm a proud person. I want for myself what many people along the way have also wanted for me: above average success. I went to Berkeley, Harvard, and MIT. I started companies, sold them, got married, started a family, bought a house. I'm a good leader and a great husband and father. I know these things and I'm proud of them.

I also recognize that it's the same forces that got me this far that keep me from settling down. I haven't lost the lust to have a "great" career.

But what's a "great" career and how is it measured? I'm still figuring that out.

Personal greatness

The opinions that matter most to me are my wife's and kids'. It's been that way since I became a husband and a dad and I know that I'm doing A+ work there.

I don't compare myself to other dads. How can I? I don't know what happens when their front doors close. I don't know if they fight or yell or ignore their kids all evening while staring at the TV or their phones. But I really truly doubt it. Either way, it has no bearing on me (but I'm glad, for my neighborhood's sake, that my fellow fathers all seem to be very good at this parenting thing.)

So I have no father FOMO. When I see a happy family walking through my neighborhood with beautiful, happy children, it warms my insides. I want to meet them, let some of their good vibes rub off on me, and make a new friend. I want them to come over for dinner, to invite the dad to a creek campfire, to celebrate each other's good fortune to be raising a family right here, right now.

There's no jealousy at all, so I have what I might call a "dad swagger." I'm confident, happy, and friendly with every dad I meet.

Professional greatness

It's not the same for me professionally. I compare myself to everyone and feign a smile through the bitter taste of jealousy when someone has achieved something that I want. This is the punishment for my pride, the thing I'm improving upon but still dealing with. It's the shit I need to extricate after chewing on it for years but really being aware of it for the last few months.

I can't cap off my corporate career until I've maxed out my earning potential. I have another company or two left to build, run, and sell. I think about it all the time. I mean all the time.

On the one hand, it's good. I'm ambitious. But on the other, it impacts my appreciation of right now. My professional aspirations are future-facing. My personal ones are right now. I'm happy with right now, but I lust for the future. It beckons me, like a siren song, to be smarter, get luckier, try harder, work longer, and get the big break I've been craving since we first started Scripted.

I know I'll regret not giving myself the opportunity to be a founder or super early employee of a unicorn (that's a company with a $1 billion valuation, for you non-tech people). Odds are not in my favor that it happens, and I'm okay with that, but I need to try. This is my next Harvard.

So, I'm preparing. ({filename}welcome-letter-to-my-search-marketing-class.md) is one way of prepping myself. Taking classes on Solidity and anything else I find interesting is another. I also find that exercise does wonders for my energy and creativity, so I'm working out a lot and treating my body well. This process is taking time, but I'm enjoying it.

When the next big break opportunity comes, I'll jump on it.

Political opportunities

Someday I will retire as a politician and get back into teaching and writing. I know this for sure. What happens between now and then is still up in the air.

I'm 39 now, going on 40. That's still pretty young but also pretty damn old. I once believed I needed to be running for something or already in office by my 40th birthday. I've given myself another decade.

I met a MIT Media Lab guy who ran for congress in Southern California. He's very impressive and working on fundraising software and blockchain technology now. He told me that his 30s were about "me" and his 40s will be about "we." He's going to do one company only and focus on his family for the next decade.

I feel like my 30s were "we" (especially since my first kid was born when I was 32) and my 40s will be a little bit more "me" but still mostly "we" and my 50s will be downright selfish as I'll definitely be in politics by then, fully immersed in the whole scene. All of it. The dinners, the ceremonies, the late-night dinners and networking. I'll be all over it once my kids have moved out of the house when I'm in my early 50s.

I'll be a good politician. I might even be a great one. Time will tell.

Until then

One day at a time. That's it.

The importance of electrification

2021-08-26T14:55:00-07:00

This is a long post. And to make my long post even longer, I begin with a preamble.

I visited my mom recently and spent a lot of time in her house. She entertained my kids and my wife talked for a while with my stepdad. I stumbled upon a pamphlet I recognized while rummaging through magazines on the side table by her couch. It was for an awards banquet at UC Berkeley in 2005. I was a recipient of the UC Berkeley Foundation Award, a special recognition for anyone doing interesting stuff with alumni. I had organized an alumni association for the College of Natural Resources, and that got the attention of the award committee.

I remember that night. I invited my parents, my grandfather, and Lisa Bauer, my mentor from the Campus Recycling and Refuse Services office where I worked as a student. I was really happy and tickled to continue receiving awards from Cal. Plus, I knew it would look good on my graduate school application.

Back at my mom's house, I read through my bio for the Young Bear Award and smiled. I handed to my wife and she read it. "You sure were into environmental stuff," she said.

I was indeed. Two hundred words of every conceivable environmental activity were packed into that description. It sounded like I never took a regular class. I did take classes, but I took them because I had to. And since I was an environmental sciences major, I took them because they were interesting. But I had a sense of urgency then. Global warming was coming and I needed my peers to become good environmental stewards, even if it just meant taking shorter showers and separating trash from recyclables.

In time, that passion faded. Al Gore produced An Inconvenient Truth, Leonard DiCaprio rode a Prius to the Oscars, and all of a sudden the whole world was talking about global warming. I figured the job was done. The former Vice President beat me to it. I quit the environmental organizing job I took right after college and looked to the private sector. I moved to LA and joined Navigant Consulting. I stopped thinking about environmental activism.

Fast-forward 15 years and boy... Could I have been more wrong? Al Gore didn't save us. Neither did Leo. And all I did in the meantime was get a couple of graduate degrees and start some B2B web companies. If I'd stuck with environmental work, I know what I would do right now.

I would focus on building electrification. Maybe it's not too late.

Why should everyone electrify their home?

Humanity produces 51 billion tons of greenhouse gas (GHG) emissions each year. We need to get that number to zero (or reasonably close) as quickly as possible.

Of that 51 billion, about 29% of GHGs come from buildings.

Of that 29%, more than 85% of the emissions come from on-site fossil-fuel combustion (natural gas -- the remainder is leaky refrigerants).

When you multiply 29% by 85% you get about 25%. This makes it easy to remember: we can knock out 25% of our GHG missions if our buildings get electrified and the electricity comes from non-carbon sources.

To do that, we need mass adoption of electric building technology, and to do that, we need both political willpower and community activism. Then we need to green the grid, but that's inevitable at this point and easier to do because there are far fewer power plants (~1,500) than homes (~14,000,000) in California (and I assume the ratio holds nationally). So we need to tackle the home problem ASAP.

Fortunately, the technology is already here. It's available and it works great. The problem essentially boils down to economics: how do we incentivize people to do the right thing, even if it costs a bit more?

What's an all-electronic home?

Here are the main electrical components of a fossil fuel-free home. In most homes today these appliances run on natural gas.

Electric central heating and cooling- Electric water heater- Electric cooktop- Electric clothes dryer

Fortunately the non-gas appliance options all kick ass. I'll describe each of them and what we decided to do here with our own major remodel.

Heating air without burning gas

I admit that I didn't think about this one at all when my wife and I launched our remodel and expansion in early 2021. I didn't ask to switch out our gas appliances and our contractor didn't suggest to me that we do. It wasn't until I read the Bill Gates How to Avoid a Climate Disaster book that I realized I had an opportunity to be part of the solution. I decided that our remodel was gonna go green.

So, how do you efficiently heat air without burning fossil fuels? You purchase a magical device called heat pump.

Our Fujitsu heat pump

A heat pump is a refrigerator in reverse. It uses the thermodynamic properties of refrigerant to capture heat and transfer it somewhere else. It can heat your home when the outside temperature is very cold, even below freezing, by dropping the temperature of the refrigerant fluid far enough below the ambient temperature to create a heat differential. The energy from that difference in heat warms your house. It's magic.

When it's hot outside, the system runs in reverse, using the same principles as your refrigerator and freezer to cool you off. Heat from the inside of your house gets absorbed by the refrigerant and again using thermodynamic magic, that fluid gets cooled and produces cool air. The heat pump unit does both the heating and the cooling and can toggle back and forth (but can't do both simultaneously).

I asked my friend Wei-Tai Kwok about his decarbonization project and he referred me to a blog post about his electrification project about his project. I asked him how well the heat pump units heat and cool his home; he said they work great and they're really quiet. He had no regrets.

I wanted to learn more about this technology, and I found this:

In a study by the city and county of San Francisco of ways to reduce emissions 80 percent by 2050, researchers found widespread adoption of electric heat pumps to be the “single most important lever considered.” Heat pumps are currently the most efficient available technology for space heating in the commercial and residential sectors. Although heat pumps have high initial capital costs, high efficiency and minimal maintenance make air source heat pumps a positive financial investment over 20 years.

Center for Climate and Energy Solutions report by Jessica Leung

I asked my general contractor about switching out our furnace system and putting in a heat pump. We were still pouring foundations at the time, so it wasn't too late to make the change, but he was skeptical about the power draw.

We have a 120 amp system (standard in our area) so that's the limit on how much current we can consume at once. An electric furnace uses 60 to 80 amps. If we had that on and were cooking and our water heater was firing up too, we might hit capacity. He advised me against it. When I pressed him on heat pumps, he confessed to not knowing about their power needs. He promised to ask Bill, his HVAC guy.

Bill responded with good news the following day. It turned out the heat pump would use less than half the amps that a purely electric furnace would use. It was essentially the same electricity profile as the original system, so we were good.

My contractor relented. I could get the heat pumps!

I spoke more with Bill and I learned that he'd been pushing heat pumps on my contractor for a while. He was happy to get a large residential system installed. He said half of his jobs involve heat pumps now and they last a really long time with far less maintenance.

Furthermore, with a typical mini-split system we could have temperature-controlled zones throughout the house. My kids could adjust their own temperatures in their rooms and we could turn it off completely in the common rooms overnight. Our last system was a single zone, so in the winter we were heating an empty living room, hallways, and kitchen all night. I loved the idea of having all these zones so we only heat and cool small parts of our house at any given time. I told him let's do it.

I got the quote a week later and we needed to pay $20,000 extra for the system we talked about. I don't know how much of that was my desire for five zones or the complexity of wiring the system upstairs where there's no attic or crawl space, but I didn't protest. I wanted the better system that would use less energy and no fossil fuels. Since it was still early in our renovation process I could stomach the difference. It would have been much harder to do towards the end. We agreed to the extra cost.

Lest you think that having a heat pump means putting one of these appendages up on the wall, rest assured that standard ducting works too. We have these upstairs because there's no attic or subfloor to run ducts. The only solution was the wall-mounted air handler which, by the way, is super quiet and works great. After a while you don't even see it. The rest of the vents look like this.

They're all very low-profile, normal vents and the ceiling air handler is especially slick. It's actually the equivalent of the boxy thing we have upstairs but we couldn't use it there because of the slant in the ceiling. The sleeker square air handler only works on flat ceilings.

So the way our heating and cooling system works is this:

Kid Bedroom 1: Separate zone with square air handler in ceiling- Kid Bedroom 2: Separate zone with square air handler in ceiling- Guest Bedroom: Separate zone with boxy air handler in wall- TV room: Separate zone with boxy air handler in wall- Office and master bedroom and bathroom: Separate zone with floor vents (I forget why these needed to be combined, but they did. They share a wall in our new addition)- Open spaces: The kitchen, living room, entryway, and hallways share a zone

What this ultimately means is my kids can set their own room temperatures. They can go really cold or really hot at night. I don't care because it only impacts their room. At night we schedule our vent control system to "unoccupied" status so the heating and cooling is effectively shut off between 9pm and 6am. Then we can control our temp in the bedroom separately too.

We also put fans in every room to distribute the heating and cooling better and to take advantage of the the four to five months a year when we can enjoy mid-70s all day with the windows open. On those days, all we need is air circulation with the ceiling fans.

Our system does two great things: it uses no gas, and it heats and cools with precision. I'm really happy with it so far.

Heating water without burning gas

Heating water with a heat pump is a much easier proposition. We originally had a typical gas-fired 80-gallon water heater and after some quick research, I found a Rheem heat pump water heater that I liked at Home Depot and had it delivered.

Traditional gas

Heat pump

The cost difference here was about $1,300. However, the energy efficiency saves several hundred dollars per year, paying this extra cost off in just 3-4 years. Since the lifespan is at least 10 years, this one's a no-brainer.

Because the water heater system only runs in one direction (transfer heat from the air to the water), the appliance constantly exhausts cool air. Therefore, in the summer months our water heater will cool down the garage. We didn't put any AC vents to the garage so this will be a really nice perk when it's 100 degrees outside. I don't like hot, stuffy garages.

As for performance, my friend Wei-Tai had no qualms. The water heater can keep up with his family just fine, and since my family doesn't take long showers, I suspect we'll be fine too -- the customer reviews are very positive.

Cooking without burning gas

I grew up using an electric stove, the kind with the metal coils that glowed orange as they heated. I had no problem with it. Boiling water took a while and the filaments were hard to clean, but it worked. My grandparents remodeled their kitchen and bought a different kind of electric stove. It had a glass top and glowed red from underneath. It was easier to clean but also took a while to boil water.

I got my first gas stove in college. I loved it. I liked seeing the flame, adjusting the burners, and feeling like I could control the heat better directly. Later, in grad school, I bought a small set of Cuisinart cookware to use on my gas stove in Cambridge. I use that same set of cookware today.

I couldn't imagine swapping out my gas range for an electric one. This was a bridge too far. But then I read about induction cooktops and I changed my mind. Yes, our entire kitchen was going to be electric, too.

Here's what we got:

Bosch induction cooktop- Bosch wall oven- Bosch speed oven

Yes, we went Bosch all the way. That's because we didn't buy anything new! All of our appliance purchases came through Craigslist from people who changed their minds or somehow wound up with two appliances. Their misfortune was our gain -- especially since supply chain backups were going to cause major delays. It was nice to drive to someone's house and pick up a box with our appliance and take it home. (And if you're wondering -- all purchases turned out to be legit.)

Our ovens do not use heat pumps. These are regular old electric ovens with heating elements and fans that do the heating work. I think this is because heat pumps don't get that hot. Shower water is going to be 110 degrees or less. Anything above 140 will burn your skin within five seconds! A heat pump can get you there, but it can't reach the 350 or 500 degrees needed for a convection oven. This technology is back to basics, but that's fine. It's still electric, and we pay a premium to get our energy from renewable sources.

Our cooktop doesn't use heat pumps either. Instead, it uses magnets. But like a heat pump, it feels like magic. Behind the scenes, induction cooktops leverage the reaction of a ferrous material in the presence of a magnetic field to produce heat. Basically, iron molecules become really active and produce electronic friction which makes the pan heat up. The induction cooktop itself doesn't get hot -- it makes the pan get hot. This is what makes it super efficient.

When you use a gas stove, a ton of the heat from the flame escapes into the room. The sides of the pan get hot, the air around the pan gets hot... if you cook for long enough, the entire kitchen gets hot. This is a huge waste. You pay for all that heat. Electric stoves are wasteful in a different way. Electricity heats the resistance element, which (usually) heats some sort of glass or ceramic cooktop, which heats the pan, which then heats your food. Each layer of heat transfer creates energy loss. It's not as bad as gas, but not nearly as good as induction.

Remember: induction cooktops cause the pan to heat up, which directly heats the food. The air around the pan remains cool. The cooktop itself remains relatively cool -- it's the pan that heats the cooktop, not the other way around. So there still could be some residual heat, but it's not going to blister your hand.

Here's a really good video I found from a chef who has adopted induction cooking.

Watch this

Drying clothes without using gas

This one is aspirational. For now, we're sticking with our gas dryer because we recently bought it and I couldn't find a heat pump dryer that would match our washer dimensions. Call me vain, but I didn't want our washer and dryer to have different heights.

However, when the time comes, I will absolutely positively replace our gas dryer with -- you guessed it -- a heat pump dryer. I've seen this Samsung heat pump dryer and it looks amazing. No vents needed, just a standard outlet. The dry times take a bit longer, presumably because of the lower heat temperature, but that's fine by me. We're usually not in a rush when we run our dryer anyway.

This decision was a toss up between throwing or giving away a 2-year-old gas dryer to replace it with a new heat pump dryer, and that decision triggering the need (vain, again) to get a matching washer. That seemed a bit indulgent. We already have gas pipes in our home and we could build the exhaust vent into our laundry room. At this point I had already eaten the extra cost of our heat pump air system and I had buyer's fatigue. We didn't spring for the matching new washer / heat pump dryer combo. Instead, I'll look forward to adding this appliance to our gas-free family when our current ones wear out.

My closing argument for going gas-free

It's pretty simple, really. In the long-run, it costs less to build, it costs less to run, and it saves us from destroying civilization.

It costs less to build

E3 report "E3 Residential Building Electrification in California", Apr. 2019, indicates that new all-electric residential construction will be less expensive as compared to homes with gas heating systems. - San Jose's new building electrification policy includes the following statement: "In most cases, all-electric buildings are less costly to build. The service and piping for natural gas is an expense that is often ignored when comparing the cost of gas and electric equipment. An all-electric building starts without that expense, so even when electric equipment might be more expensive in some cases than its natural gas counterparts, that cost is offset by the gas infrastructure savings."

It costs less to run

Frontier Energy's Electrification Cost Story infographic showed that electric heating systems for single-family homes cost less to construct, and less to operate, as compared to gas heating systems.- Sacramento's new New Building Electrification FAQ includes the following statement: "Cost Savings: All-electric new buildings do not require the installation of gas infrastructure, reducing capital costs. New, and existing all-electric buildings can benefit from reduced operating costs. Studies have shown that cost savings for all electric construction can range, with potential savings upwards of tens of thousands of dollars, depending on the type of construction". - Wei-Tai Kwok's gas-free renovation resulted in lower overall cost. He recorded his energy costs and split between gas and electric before and after the conversion in a very detailed cost analysis.

It's less dangerous

Electricity is dangerous. It causes wildfires and burns down homes. But it's here to stay... we're not going to live without it ever again.

Natural gas is also dangerous, but it's optional. We can live -- and I'd argue we can thrive -- without it. As I was completing this blog post, I saw a news alert about a natural gas leak in Alameda, just 20 miles from me. Some residents were ordered to evacuate, others to shelter.

If that weren't enough, I've also seen my kids accidentally turn my gas stove on. They were building a fort in the kitched, pushed a chair into the stove, and managed to turn the knob in just the right position to light flame at full blast. I was in the other room and heard the clicking of the lighter before I noticed the flame. If I hadn't been home, if the blanket they used as the roof of the fort had caught fire... it would have been an absolute disaster. It would have also been bad if they turned the nob without lighting the flame, releasing gas into our kitchen. I can't think about it without getting chills.

But this is what families allow into their homes. Any kid can light a gas stove on accident, and they can certainly do it on purpose. There's no way for me to turn the stove off without unplugging it. If my kid turned on the induction cooktop, nothing would happen. It's so much better.

When my county put an all-electric new building ordinance up for a vote, my county supervisor voted against it. She argued that during rolling blackouts, natural gas helps residents survive without electricity. She's wrong. Without power, most gas appliances won't work. You might get hot water, but my gas stove still needs an outlet. Plus, most hot water heaters hold at least 60 gallons. With rationing, that hot water can go a long way when the power's not on. And in the summer, when these rolling blackouts happen, it's the air conditioning that people miss most. The gas line won't fix it.

So what's holding us back? Why won't we plug the gas lines? My own experience will tell us something about that.

My new house will still have four gas appliances: the clothes dryer (for now), an indoor fireplace, an outdoor fire pit, and an outdoor grill. I've already described what's going on with the dryer. The rest are remaining with the house simply because they're already there, and without the gas versions, I would use wood-burning alternatives.

From what I've read, natural gas is better for public and environmental health. I figured it would be more hypocritical for me to replace a gas appliance with a wood-burning one rather than just keeping the gas appliance we already have.

I don't feel great about continuing to burn gas, but I feel better about this approach than loading up my fireplace or fire pit whenever we want the benefit of fire.

I'd be fine without gas, but since we already have it... why not?

This is going to be the same question everyone will ask when confronted with the reality that sacrifices need to be made by existing homeowners. Their answer may be similar to mine... at least while utilities continue to feed our homes with natural gas.

My unannounced and inconsequential break from social media

2021-07-19T11:08:00-07:00

I took about four months off of regularly reading and somewhat regularly posting to social media. I took Facebook off my phone entirely and removed all Facebook email notifications a while ago. LinkedIn followed. Then Twitter. With each step away from the incessant drone of snippets and soundbites my overall well-being improved. It felt like exercising: hard at first, then easier, and totally worth it.

I stopped consuming, but I also stopped creating, and not creating bothered me. Then my grandfather passed away and I needed to write about that. I shared it on Twitter. Then I sold MightySignal and that seemed Twitter-worthy, so I shared that too. Now I'm easing back into social media, a bite at a time, still unsure if it's adding to my life or taking away.

I recognize that this problem is of my own making. These are my own insecurities, my own weaknesses, my own inability to focus or perhaps more critically and to the point, my allergic reaction to the uber-success of my peers. I don't blame Twitter or Facebook or any of my beautiful and wealthy friends who post their many fabulous accomplishments for the world to see and applaud.

To be completely open and honest about my social media FOMO issues, I had to take a hard look at myself.

The 98th percentile

A few months ago, back in October and November of 2020, I was feeling bad. I had nothing to complain about, really, and that was the problem. My non-issues filled the space. I had the luxury of moping about silly things like the fact that I'm not in the top 1% of 1% of earners. Every time another friend got rich, I'd feel a little bit worse. It kept happening, too. Random friends from high school, close friends from San Francisco, distant friends from business school. A new IPO, a nine-figure acquisition, a viral cryptocurrency -- I watched it all happen on my social media feeds.

And from the comfort of my phone I didn't feel happy for my friends. I felt bad. I felt inadequate, sorry for myself, bummed that my many business at-bats didn't make me fabulously rich. The family members who invested in my creations lost all their money. The friends and family who invested in my friends must be so proud. It hurt to think this way but I kept doing it, spinning in mental circles, making myself feel worse.

I spoke to one friend in late 2020 who sold his company for $3 million a year or so earlier. He made some money off of that sale, but most of the acquisition was stock. He figured already that his $3 million was worth closer to $30 million. The company that bought him was blowing up, a unicorn ready to IPO. He started his own fund, expecting that I might invest.

My answer was easy: I couldn't. The double-whammy of feeling jealous of his success and ashamed that not only was I not in his same income bracket and definitely not starting a fund, I also didn't have $50,000 laying around to invest in high-risk sales tech startups. It was just more than I could handle. I ended that call feeling like shit.

A couple of weeks later, a friend who got rich in crypto texted for advice about where to park his cash. He asked if I knew anyone running a fund. I made the referral to my $30 million friend. My crypto friend thanked me and invested $50,000. I felt shitty all over again. I'd find out a few months later that my crypto friend's tokens were worth well over $100 million.

I get The Information newsletter. It's great and the stories are unique. Someday I'll pay for it, but for now I just read the headlines when they enter my inbox. In the space of one week there was a headline about a friend's successful IPO who I went to the Harvard Kennedy School with, and another about the crazy stock growth of another friend from MIT Sloan who went public back in 2017. I felt small.

This is what it's like in the bottom of the 98th percentile. It's the no-man's land of having more than plenty, far more than my share of resources and savings, but simultaneously far less than everyone above me. It'd be one thing if those above me were famous names on a Forbes list. It's different when they're my friends, people I know well, guys who started out ten years ago with the same bank balance that I did. Guys who once looked up to me for having it all figured out.

The even stupider part of this pity party is I know now and knew then how ridiculous it sounds. However, self-awareness did not solve anything. I can't say why I couldn't talk myself out of this rut. I had moments of clarity, sure, but the fog of jealousy would roll over me again. So I learned to sit with it, shuddering at times, just waiting for it to pass.

Uncertainty of transition

In the meantime, life happened. Transition was all around me. The world was coming out of COVID. My girls were finally able to return to kindergarten and preschool. My family moved into a rental house so we could begin a home remodel. I started teaching part-time at DVC and was in the throes of negotiating an exit for MightySignal.

This was all great and the time passed quickly. I started to think about what I would do after MightySignal and asked some friends for advice. A couple of them gave me job offers. One was a Head of Growth role at a rapidly growing crypto company. Another was a CEO job at a residential proxy startup. I turned them both down.

One thing I learned from my wealthy friends is that the real money, the major, big money usually comes late. You have to see something all the way through in order to get crazy rich. Thinking this way got me excited about continuing my work on MightySignal. Plus, I didn't want to abandon my team. After a couple of months of uncertainty, I whole-heartedly agreed to stay on the same path. And with that decision came a huge sense of relief.

It turned out that a lot of what I was feeling, which I attributed to jealousy and self-pity, was really just uncertainty of transition. I was going through something, for sure, but the core of the problem wasn't the success of my friends. It was not knowing what's around the corner for myself. Knowing that I would stay with Airnow, the new owners of MightySignal, for at least a year and likely longer, was a load off of my shoulders. I felt a lot better as soon as I committed to the decision.

Some other certainties unfolded as well. The remodel project started and I found a great rental for my family just down the street from our old house. This was a big relief, and as the remodel progressed and moved at the pace we'd hoped, that remodel uncertainty and risk decreased a lot. My class at DVC was awesome. I was prepared, the online format worked, and my first two months as an associate professor went really smoothly. In Spring 2021 I also joined two community boards: Sustainable Contra Costa and the DVC Foundation. I felt good about having a strong leadership foothold in my community and no longer needed to seek out new things to do. I have them. I'm where I need to be. I just need to execute.

Focusing on myself, being happy with my work, and being excited to upgrade my family's house made a big difference in the way that I felt. My friend's crypto assets swelled up to $200 million in the early 2021 crypto bull run. I felt nothing, which felt great. I stumbled upon more news stories about my grad school friends' IPOs. I actually felt happy for them. Things were looking up.

The freedom from caring

By feeling good about what I was doing I cared a lot less about what other people were doing. It sounds obvious in retrospect, but I needed to work my way there.

I'd like to think that I can be like Thoreau, content to simply watch the passing of the seasons, but I'm probably not built for that. In my respite from social media I was able to tune out what my friends were doing and instead focus on my family, my neighbors, and the volunteers and students that I work with. It's more than enough; in fact, it's all I need. I just need to remind myself of this and be insulated by it as I dip my toes back into the feeds.

The freedom from caring what others think and do is the ultimate freedom. I'm not there yet, but I understand that this is the promised land. The people who find that freedom have the most fun. They also might be the most successful at their trade. But more importantly, they're able to focus on what makes them happy, whether it's family, work, arts, or just being alone. I envy those who found this, but unlike becoming a multi-gazillionaire, contentment is completely attainable by anyone. There's no luck or timing needed. It's just a mindset.

Going forward

For six months, that's where I was: sorry for myself about not being richer than my crazy rich friends while simultaneously spending gobs of money on a new house, paying a mortgage and Bay Area rent, still saving money and not caring what the Whole Foods receipt added up to. That one definition of success -- to live without financial stress -- and I've done that in the country's most expensive region.

That should be enough, and it is. I'm happy again. I text with my rich crypto friend about normal stuff. We'll hang out again soon. I like the LinkedIn posts about my friends' successful fundraises. I read my friends' newsletters with sincere interest. It's like I passed a kidney stone of insecurity and it just took a painful while. I'm better now, more resilient to the symptoms described above, and able to think again for myself.

A couple of nights ago I was at my neighbor's house with four other dads. We're all in our mid-late 30s with young kids. We met after 8pm so we could help put the children to bed. As I sat there, cocktail in hand, Settlers of Catan laid out on the table in front of me, I thought, This is my Walden Pond. These are my trees, ants, and leaves. I'll watch these guys grow old as I age along with them. I'll know their kids almost as well as I know my own. This, right here, is what life is about for me right now. It's enjoying this stage of life, being a parent, growing a career, building a family and a home.

These are years I'll never get back. I'm spending them the way I want to spend them.

In memory of Irving Katuna

2021-05-08T12:17:00-07:00

Edit: I've turned this blog post into a eulogy that I'll give at Rossmoor for my grandpa's funeral. He passed away early in the morning on Tuesday, April 27, 2021.

My grandpa, Irving Katuna, was born on January 12, 1929 in Wilkes-Barre, Pennsylvania. It was a Saturday, and it was cold. A light dusting of snow passed through Pennsylvania the previous night and the temperature stayed just above freezing the day he was born. I'm not sure how many of his dozen older siblings were still living in the house then, but I picture my infant grandfather passed around to plenty of happy hands when he arrived home from the hospital.

Wilkes-Barre is a coal mining town about 120 miles west of New York City. Its population swelled to a peak of 80,000 around 1930 and declined through the depression and the aftermath of World War II. My grandpa was 11 when the draft was instituted in 1940 and was still too young to serve when the draft ended in 1946. Only about 30,000 people live in Wilkes-Barre today. Industry left, and so did my grandpa.

He matriculated to UCLA but graduated from UC Berkeley and settled in San Francisco. He was the first of his siblings to go to college, a unique opportunity that did not go unnoticed by his older brothers. But in addition to being the youngest, he also was born with a stunted right arm, a midwife's mishap made during delivery at the hospital that cold Saturday in Wilkes-Barre, which prevented him from helping at the feed store his family owned.

He met my grandma, Berna Mendell, at a dance at the Hillel in San Francisco while he was studying history at Cal. They quickly married and had four children: Linda (my mom), Judy, Bruce, and Brad. Along the way, he earned a Master's degree from San Francisco State and attempted a Ph.D. but did not submit a thesis. He began his career as a teacher and became a vice principal at Benjamin Franklin Junior High School in the Fillmore District before returning once again to the classroom.

My grandpa's Jewish faith, along with his many years teaching Black students, brought him to Selma, Alabama in 1964. He accompanied five rabbis to support the Montgomery bus boycott and show solidarity of the Jewish community with a popular Christian pastor named Martin Luther King, Jr. My grandpa and these rabbis marched and were imprisoned with Dr. King. He spent less than a week in Selma but it would leave an impression on him and his family for the rest of his life. We celebrated his trip to Selma for his 80th birthday, and at 92 he had just completed writing a book about it with support from my mom and cousin Lisa.

My grandpa was opinionated and curious. He was a docent at the San Francisco Academy of Sciences and loved to buy books at thrift shops, a few of which he actually read. He liked pastries for breakfast and would go out of his way to pick up a scone or a bear claw from his favorite bakery. Breakfast at home usually involved cereal, which he kept in neat airtight plastic bins, and he preferred to eat it with fruit salad on top. On special occasions, like when his grandson stayed over, he made french toast in the morning. He enjoyed jogging and playing tennis, and when age forced him to hang up his running shoes, he returned to his lifelong love of swimming. He was a natural leader, someone who tended to reside over the organizations he volunteered for. He loved to join elder hostels, especially in Ashland, Oregon, where he attended the Shakespeare Festival with his wife Thelma for many years.

My grandpa eventually left San Francisco and settled here in Rossmoor where he and Thelma became members of local Democratic and Jewish organizations and discovered the best local Chinese restaurants. Lucid and curious until the end, Irving loved to read and talk to his family.

My house is only a couple of miles away from his apartment here and over the last few years we settled into a routine of bringing Chinese food over and eating dinner together: sweet and sour fish filets for Thelma, tomato beef chow mein for Irv, and vegetable chow mein for me and my girls. When COVID hit, I'd drop the food off and leave, aware that I wouldn't know which of these dinners would be our last.

Grandpa Irv was immensely proud of all of us. And we were proud of him too.

Farewell, Grandpa Irv. We will miss you.

It's been a long, long time

2021-03-24T20:53:00-07:00

A year or so before the pandemic, which would be about two years before today, I took singing lessons in the "piano room" at our house. We called it the piano room because it's where we put my grandmother's piano. This was a behemoth of a piano -- a beautiful black seven-foot long Baldwin parlor grand -- and it weighed a metric ton. It hardly fit, so a few years later, we swapped it for a Yamaha Clavinova. Now my piano has a volume control and stands against the wall.

Too much piano for a small house

One of the songs I decided to learn to sing is this one, "It's Been A Long, Long Time," by Bing Crosby and Les Paul. I first heard it on Spotify, and it touched me. The guitar is beautiful, the lyrics are haunting, and the purity of just Bing's voice and Les's guitar is magical. I've been on a WW1 and WW2 movie-watching kick for a while and I figured that this song was about the war. A quick google search confirmed my hunch. (Another one that would be obvious, if you listened closely, is "I'll Be Home For Christmas.")

So I learned the chords and the lovely guitar solo and took it to my piano and vocal teacher and asked her to work with me on it. We spent a few weeks improving my tone and breathing through the high notes and then moved on to other songs, but this one still has a special place in my heart. And that sentiment has only deepened over the last two momentous years.

As I write this, my dog is five and a half years old. He's middle-aged, just like me, and he's sore after our long jogs. My oldest daughter is six, and she's lanky and has a big gap-toothed smile. I still remember her smiling to herself, asleep in a crib in San Francisco, her arm stretched out in that baby sleeping pose. I knew then that she'd be a happy kid, and she is.

A smiling baby Lily

My youngest is now four years old. She's sassy, strong, and increasingly independent. Before the pandemic, we followed her around everywhere, protecting her fall. She was barely three years old then. Within weeks of the lockdowns we let her out of sight, playing with our neighbors at the end of our cul-de-sac. Now she's even more mobile, on a bike, a scooter, a skateboard, or rollerblades. I couldn't keep up if I tried, so I don't.

Indeed, it's been a long, long time since I've changed a diaper. I'm grateful for that, and also sad.

I sold our BOB jogging stroller last weekend. I can't count how many miles I pushed that thing. It would be in the hundreds. We went all over the northern flats and hills of San Francisco, along Crissy Field and up into the Presidio. My runs got longer when we moved to the suburbs. I jogged that stroller to preschool, daycare, and elementary school. Countless trips to Noah's Bagels with plain reduced fat smears stuffed into the pockets on our way home.

I'm now a dad without a stroller. It took six years, but it happened fast.

- - -

When my neighborhood dad friends get together and drink beers by a fire in one of our backyards, I'm reminded that I'm the old guy now. Most of my neighbors are still having kids, planning on having more. They're in their early to mid-30s. I'm at the end of that decade. I moved into this neighborhood before them. Now I'm the one who knows the history, who lived in what house and has since moved away. That's crazy to me. When I first moved here there were other guys who knew the lore. Now I'm one of them. The old guard.

I've been running MightySignal longer than I was at the Harvard Kennedy School. I've been living in Saranap longer than I was at UC Berkeley. All of these experiences are stacking on top of each other like loaded bricks and sometimes they weigh down on me. What does it all mean? What's it supposed to mean? Does it mean anything? I don't know.

Recently I've been going through a transition. I have too much on the line right now to say exactly what it's about, but it has involved months of debate with myself and friends who will listen. There's a longer post to be written about this, and I will get to it (I look forward to multiple sittings on this one), but it all boils down to this same refrain: "It's Been A Long, Long Time."

I've been alive for a long, long time. I've been an adult for a long, long time. I've been out of grad school for a long, long time. My kids are older, I'm older, and in many ways, I'm able to do whatever I want.

So now what?

Welcome letter to my search marketing class

2021-01-08T05:42:00-08:00

I'm teaching my ({filename}im-now-an-adjunct.md) in a couple of months. It's exciting. It's intimidating. It's an incredible amount of prep work, since it's completely online, so it's tiring too. However, I'm already feeling proud of this course despite being nowhere close to ready.

The online course I took at DVC about teaching an online course (how's that for meta?) emphasized how important it is to be authentic and let your personality through. In the online format, you almost have to go overboard with it. They say it helps students connect not only with you, the professor, but also with the course material.

To that end, I wrote this welcome letter to my students. I'm proud of this too.

Hello!

How's it going? Nice to meet you! This is the speech I'd normally give to you in person, except for two not-so-minor things:

As of this writing, at least, times are (still) not normal, and- This course was always going to be online.

So we wouldn't actually meet face-to-face anyway. Therefore, this was always going to be done in writing or on video. Oh well.

I write this on a cold December night in 2020. There's a fire in the gas fireplace, my dog is snoring next to me, and my family is in bed. I'm sipping on Angel's Envy bourbon whiskey. Why? Because it's been a long, long day. I was up at 4am and couldn't go back to sleep, so I read Sam Walton's Made In America until about 4:45am. Then I tried to go back to sleep, failed, and five minutes later was in my living room. I turned on the fireplace. My dog was snoring next to me then, too. I did my daily ten-minute core exercise routine, drank some coffee, and felt grateful that my kids didn't come out of their rooms until after 7am. My day began and is ending on the same couch, with the same fireplace and same dog, but with a different beverage in my hand.

By day I am a professional entrepreneur. I build and run and sell businesses for a living. Just last month I sold three more businesses to a data company in Santa Barbara. Two years before that, I sold a website to a team in Texas. Next month, in January 2021, I hope to sell another business to a company in London right before they list their stock on the London Stock Exchange.

It all sounds glamorous, and maybe it is, but what it really is is very technical. And I don't just mean bytes and code snippets. The marketing is technical. The negotiations are technical. The people I work with and work for are all very technical. And I suppose, by technical, what I really mean is data-driven. You can't be a tech entrepreneur without at least an appreciation of and at best a deep understanding of... data.

This is especially true for digital marketing (a.k.a. search marketing.) The best marketers live and breathe data. Data all day, every day. They're comfortable with spreadsheets, graphs, and statistics. They can ask the right questions and when they don't know the answers, they at least know how to find them (hint: it usually involves collecting more data.) This is what it means to be a search marketer.

But if data is not your thing, fear not! There's an art behind this science, too. And when you start to see the art in the data, the numbers begin to look far more friendly. I think you'll find that "data analysis" is far less intimidating when you're talking about clicks and views and what things cost. Put dots on a graph, draw a line through them, and that's it. You can tell the story because you understand that there's a story to be told.

And this is why, tonight, I'm tired, I'm cold, and I'm ready for bed. But I'm also really excited to be teaching this class and exploring search marketing with you at DVC. We're going to learn a lot together this spring and I'm glad to have you in my class!

We're going to cover a lot of ground together over just a couple of months. We'll learn about the Internet, about with HTML and CSS code, and then we'll dive into the guts of SEO and PPC and finally conclude with a real, honest-to-goodness search marketing project that you can put on your resume.

If you want to get good at search marketing for yourself or for people that pay you, this is the course for you.

Cheers,

Prof. Buckley

Read Write Play: 2020

2020-12-31T22:48:00-08:00

In a normal year I would have posted my quarterly Read Write Play posts every quarter, as I've done since launching this blog in its current form in 2018. However, this is no ordinary year and my reading, writing, and playing schedule got tossed about as one might expect amidst a global pandemic and prolonged school shutdowns.

Thus, I didn't keep up with this blog nearly as much as I did in past years. However, there was plenty of writing. A ton of it, in fact. A healthy amount of reading, and yes, some playing too. This post, in annual form this time, recaps my 2020 "me-time" -- the hours of the day that don't revolve around family and work.

Read

I didn't hit my reading groove until later in the year. I read all of these since August. Before that... I don't know! I guess I wasn't feeling it. I did (and still do) read the newspaper every day and some of The Economist on my Kindle most weeks. Since my wife subscribed us to the New Yorker (paper edition) that has become a welcome addition to my weekly routine. I try to read the whole thing on my Sundays.

Here's a quick rundown on each of these books, why I read them, and what I thought.

Russell Rules

A great book about leadership and business. I read it because it's on the reading list suggested in The Art of Profitability. I learned that focus is important. Bill Russell was one of the greatest basketball players of all time because he worked harder and played smarter than everyone else. However, he also recognized that he doesn't play every position. He needs to have a great team, one that adapts to the competition. He needs them all to play at his level and he was able to do that, winning the NBA Finals a record-breaking 11 seasons.

The Art of Profitability

This book came by recommendation from Josh Siegel, the brains and brawn behind Xenon, where I currently work. This book summarizes several profit models presented by a fictional mentor coaching a business executive. It's clever, poignant, and was helpful to me in thinking about other profitable business models. For example, MightySignal relies on Specialist Profit: paying a premium for specific knowledge. In my side-hustle life, I use the Profit-Multiplier Model: running multiple small SaaS businesses in parallel using the same tech stack (make money off the same good or skill in different markets).

On Writing

My neighbor gave me this book (my first non-Kindle book of the year!) when she heard I was writing a novel. She said it was good; she was right. I thought Lisa Cron's Wired for Story was the formula for writing a good novel. In fact, Steven King gave it away 16 years earlier, in 2000. A few things resonated with me. First, he describes writing as "dreaming while awake," a state of mind I can relate to. It's why I need writing retreats to make giant leaps in my books. He also confessed to not having a complete outline for his books when he writes them. Instead, he find some inspiration for a situation. That spark comes a bit randomly, and then he noodles on it, maybe writes down the scenario, and comes back to it when he's ready. At that point, he sets the characters up "in medias res" (in the midst of the thing) and lets them tell him what happens. The story is already there; like an archaeologist, he just has to uncover it.

The Shining

Since I loved his memoir so much, I decided to take up a Stephen King book. I'm not sure I've ever read one cover to cover. I'm sure I tried to tackle It at some point and didn't make it through. I know my mom used to read his books. I picked the one he felt most proud of at the time of his memoir and verified that it was on the top of some his fan clubs' lists. My impression, ultimately, was meh. I didn't love it. I noticed that he didn't stick to some of own rules ("never put an adjective after 'said' -- e.g. 'he said slyly' -- King did this a few times in The Shining). I also didn't fall for the ghosts (or were they hallucinations? I wasn't sure, since I don't think his wife and boy could see them.) And the coming-to-life of the hedges was odd to me. Why were they the only inanimate objects to come alive? The setup, though, was great. Man goes crazy with his wife and boy in a huge, empty, isolated mountain hotel. Who wouldn't want to read that story?

Becoming a Digital Marketer

Since I'm teaching a search marketing class at DVC this spring, I figured I should start reading some search marketing books. If I liked one well enough, I might assign it. This one didn't fit the bill. It was mostly trite, and the good parts they offered were few and far between. If they'd peppered in more case studies and anecdotes I would have enjoyed it. Instead, I made it about halfway through. It just wasn't that good.

Everything We Keep

This was the last Kindle Unlimited book I read. I canceled my membership soon afterwards. Since I've been working on a novel (see the Writing section below), I figured I should read more novels. I picked this one because the plot, like mine, involves cancer. I didn't care about the main character enough. I made it all the way through, because I wanted to understand what exactly it was that I didn't like. I determined that the main character (and narrator) were trying to be too cute. There was a triteness to the descriptions and dialogue that felt juvenile. It lacked depth. I related to the author in that I felt her struggle to bring about the full spectrum of emotion in her characters but in the end it was still shallow. I just didn't like it.

Mr. Penumbra's 24-Hour Bookstore

I also didn't like this book. I picked it because I saw it at a Barnes & Nobles and it involves a secret society, like my novel. This one was better than Everything We Keep. I liked that it takes place in San Francisco and New York and incorporated some tech startup references and characters. That part felt real, but the plot itself didn't capture me. I didn't care about Mr. Penumbra or his bookstore. I could tell the main character cared, and his love interest also eventually cared, but the whole plot was just a bit too geeky. I didn't believe that the main character would get so wrapped up in it. He had his own life too, and I suppose that's where it lost me. I took mental notes about what not to do with my own plot.

Writing

If you were keeping score on my Rbucks blog, you'd be correct to say I fell off on blog writing this year. It is true. The numbers don't lie.

2019: 35 posts for 44,188 words (1,263 words per post)- 2020: 12 posts for 15,784 words (1,315 words per post)

I wrote 1/3 the blog posts in 2020 that I did in 2019. This wasn't intentional. It's just what happened as my routine got chewed up and spit out. Where I used to enjoy writing at night and doing other "me time" activities, I had to spend that time working. I used to eschew computering after the kids go to sleep. Now I embrace it. But this is what happens with no childcare, no school, two kids and a wife at home ALL. THE. TIME.

So I adapted. And sacrificed. Apparently writing blog posts fell to the wayside.

However, I did make huge progress on my book. I'm up to over 70,000 words now. About half was written in 2019 (the latter half) and the rest was written in spring and summer 2020. I'm stuck on the ending but I have an idea and I'm one writing retreat away from capping this sucker off. It'll feel really good when it's done. I already have a book cover.

*Just looking at this cover makes me want to finish writing the damn book. *

My top post of 2020 wasn't even written in 2020. I published How chess and entrepreneurship are the same about a year ago and for some reason it started to pop in traffic this past summer. Nothing else I wrote this year even comes close. So it goes.

I also blogged on MightySignal. My top post on my company blog was Data Products vs Data Solutions. I do feel good about this one. It was a labor love and I felt like I had something important to say. For the next person redoing their B2B website, I think this will be a useful post and I'm glad it's on the Internet for anyone to see.

As I wrote before, content marketing and social media marketing are about giving. The best posts I've written are also the best gifts. This year I've come to appreciate other writers, particularly Alex Danco and Investor Amnesia. These two guys produce tremendous value every week and they give it away for free. I'm sure they feel good about it. I'm sure there's value in the followerships they're gathering and the personal brands they're builidng, but when they click "Publish," there's no immediate "ca-ching" sound. It's a long game they're playing. My game is likely much longer.

Playing

In May of this year I did something unusual. I tweeted a video of myself playing piano and singing.

Don't let the sun go down on me

It's not the first time I've performed publicly. It is the first time I've done it while playing piano, though, and that's a milestone for me. Although the pandemic canceled my singing lessons, I continued to play, working on Christmas carols throughout the summer and getting decent at "Jingle Bells", "Rudolph the Red-Nosed Reindeer," and "I'll Be Home For Christmas."

The last one, "I'll Be Home For Christmas," is my favorite. The voicings and flourishes that Dan Coates, the arranger, added are exactly what I need to take my playing to the next level. Where my Elton John playing has me doing octaves on my left hand, this Christmas Carol book has introduced me to the magic of the dominant seventh on my left hand, giving everything a more complex, jazzy feel. I love it. I'm not singing as much but I play piano just about every day.

On the guitar front, I've been dabbling in Grateful Dead. I can't get over "Fire on the Mountain" and "Eyes of the World". I put them both in the top 10 songs I've ever heard. I play half-assed versions on my Taylor 214 while hanging out with my kids and neighbors in the front yard. When our house is remodeled and I'm under the same roof as my Telecaster I will begin to really tackle these songs, giving them the focus and dedication they require.

Until then, I make slow but steady progress on piano, and I fully expect to be able to throw down some Christmas carols next year, full voice, for all to hear.

Here's to you, 2021.

A new routine

2020-12-10T22:41:00-08:00

By Day

It starts at about 5:30am. My wife gets out of bed first, her iPhone flashlight leading her way down the hallway. I stretch and look out the window, a soft gray backdrop against the silhouettes of large oak and bay trunks. The sun won't rise for another hour.

I lie awake for ten minutes, anticipating the day. I remind myself what work lies ahead, what the kids' schedule will be (Is the tutor coming today? It's not "wacky Wednesday" on Zoom Kindergarten again, is it?) and whether or not my call schedule will allow for a morning jog. After ten minutes of this, I'm up.

I take my thyroid medication with a swig of water, a routine I've had now for three years, and follow my wife's footsteps into the hallway, through the sitting room with our Clavinova, and into the galley kitchen that connects our living room to the rest of the house. It's winter now, so our Malm fireplace is on. I walk over and kiss my wife, pat Blue, and then return to the kitchen to grind the Peet's and make a fresh pot of coffee.

While the coffee maker hisses and gargles, I roll out the yoga mat and perform what has become a critical part of my day: a ten-minute body-weight core routine. I start with a straight-arm plank. The Peloton series with this workout topped out at 90 seconds. I hold it now for four minutes. I then do a sequence of moves from the "Crush Your Core" workout with Emma Lovewell and go back to a one to two-minute plank with some added moves (knee to elbow, rolling push ups, etc.) and finish, as Peloton has taught me to do, with about 30 seconds of bicycle crunches.

Sweat is still on my brow as I pour that cup of coffee at about 6:15am. With coffee in one hand and my MacBook in the other, I head to my favorite chair and turn on whatever segments of Morning Joe that the Roku app has queued for me. My wife and I watch together for 15 minutes, and then she'll usually head to our office cottage in the backyard to begin her work day (her calls are primarily east coast hours) and I clear out my inbox as much as possible before our two daughters pitter patter into the room just before 7am and settle in for about an hour of cartoons.

Around 7:15am they will ask for breakfast. After I pour their cereal, I'll walk down the driveway in my plaid pajamas and pick up the East Bay Times. I'll eat breakfast while reading the paper until about 8am, when it's time to get the kids dressed, teeth brushed, and in front of our respective screens by 8:30am: one daughter doing online Kindergarten, the other doing online cartoons, and me doing online work.

This is my morning, a clockwork set of routines we've adopted due to the pandemic. I don't mind waking up early. I'm grateful for the ten-minute core. This daily morning structure sets me up for what has become an unpredictable period between 8:30am and 5pm. The children of our cul de sac, the neighbors we've come to rely more than ever in this pandemic, come out around 1pm. If the weather is good, our kids will play until dusk. If one of them is not feeling well, or if it's raining, then the indoor activity saps my work focus. I try to make up for it after bed.

I can't count on the late mornings and afternoons, but I have the early morning trained well, and it is good. I've come to accept and appreciate both the structured and unstructured parts of my day. Most of all, I've learned not to fight them.

By Week

Over a decade ago my wife and I did the Israel Outdoors Birthright trip. We spent nine days in Israel and had an incredible time. I enjoyed every moment of that adventure. Because of the timing, we were able to have two Shabbat celebrations with our Birthright group.

I knew of Shabbat but I never practiced it, certainly not religiously. However, in Israel, in that setting, with those people, I embraced it. I sang the songs and lit the candles and appreciated the emphasis on personal and community well-being. For a few weeks, maybe even a few months after we returned, my wife and I tried to keep the Friday sundown to Saturday sundown schedule of intentional reflection and rest. We even lit the candles, but it didn't last long. A few months later, it was forgotten.

The pandemic brought Shabbat back to my routine. For months now, I've been enjoying a Saturday free of work. When we're not under lockdown restriction, I find something to do with my girls. I take them to see my mom. We go on bike rides with neighbors, or if the neighborhood kids just want to play on the court, then I pull up a guitar or a New Yorker magazine and do that. My phone is gone, powered off. My laptop is too. Saturdays are my time to read, play music, be with my kids, and not care at all what the Internet is doing or what my Google Calendar is alerting. For one day each week, I'm free.

I've extended this Shabbat concept to my diet as well. This area has not been as rigorous, but the rules I'm trying to follow are:

Outside of Shabbat

No red meat - No special dessert-like treats- No seconds; be slightly hungry as much as possible- No full servings of alcohol (okay to split a beer with wife or have a small glass of red wine)- Order the healthiest thing on the menu when dining out

On Shabbat

Eat as much of whatever I want- Day drinking is acceptable behavior- Expensive wine permitted- Sleep in and skip the core workout

The more strict I am during the week, the more I feel entitled to be a glutton on Saturdays. I've noticed, though, that the allure of the 16oz rib-eye steak has faded on Friday nights. I'll drink that 3pm Saturday beer but it's not as satisfying as it once was. I see this as a good thing.

The healthier I feel during the week, the less I want to go crazy and spoil it. That doesn't mean I don't. I mean, having a second cocktail on Friday night, engrossed in a Netflix series (no computer, remember?) is quite a treat. I look forward to it every time. It makes the weeks go by fast.

And perhaps the biggest Shabbat routine of them all is sourdough bake. I make three rounds every Saturday and give away one or two of them, depending on how generous we feel. The process begins Thursday night when I take my sourdough starter out of the refrigerator and feed it. I make the rounds on Friday morning and let them prove in the refrigerator until Saturday morning, when I bake.

Having fresh sourdough on Saturday mornings has become a bit of a family tradition. My girls love it. I like having an excuse to eat copious amounts of it. My wife looks forward to it too. This is my Shabbat, my cheat day, after all. And my neighbors get to be surprised with a text every few weeks as I roll through the rolodex, asking myself who I should deliver to next.

Whatever this is, whatever you call it, it's working for me. Bedtime routines help children sleep, and these daily and weekly routines help parents cope and survive. It's my new routine, and I think at least my core workouts and sourdough bakes will stand the test of time.

On community

2020-10-25T08:49:00-07:00

This post has been in draft form for a long time. On this Sunday morning, I'm reminded that I have a natural park in my backyard, a resort-like setting, and a 16-inch 2019 MacBook Pro to warm my lap as I type. What could be better than to spoil this moment by writing about politics?

Thus I set about to finish this post.

There’s a pretty basic difference in priorities between the left and the right and you see it play out in everything from immigration to fuel economy policies. It goes something like this:

Right: protect what’s mine- Left: share what’s ours

I identify more with the left side of this spectrum but I understand the impulse behind the right side. My left lean here stems from the simple belief that a lot of what I have came out of just plain luck. That's not to say I didn't earn any of it. I certainly worked hard. But even being in the position to study as much as I needed to in high school puts me at a certain advantage. I didn't have any debt when I graduated with my four-year undergrad degree because my parents covered what I didn't earn from work and scholarships. That was another huge advantage going into graduate school. To be able to consider taking two or three years off from my professional career with no income in my mid-20s was another huge luxury, a gift I was given largely by my parents.

That's why I believe people with the means should, within reason, share what they have. They should be generous, pay taxes, volunteer, and tip extra. I want to enjoy what I have but by no means do I feel entitled to be greedy about it.

The theme from the right, particularly now that Trump has been the namesake of the Republican party, is that everything held should be kept. Even if it was given to you, unearned, by luck of the lottery or birth into a wealthy family it's yours and you don't have to share it, certainly not by government mandate. It's a pretty simple way to think about community: be happy with what you got. If someone else has more, find a way to get it yourself. If you're down on your luck, toughen up and figure it out. Even though I'm opposed to the philosophy, I see the elegance in it.

Ultimately, I ask myself this: what kind of community do I want to live in? If I'm baking and see that I'm down an egg, do I want to know my neighbor would gladly share their egg with me? Or do I want to be frustrated that my texts won't get returned and I'll have to shuttle myself down to 7-11 because my neighbor won't share?

The answer is obvious. I want neighbors who will help me out. That's community. The funny thing is, I know even the most brash conservative would say the same thing. Within their tight circles, the community is actually very strong. It's church, it's neighbors, it's softball teams and bowling parties. People help themselves out because they know each other.

Maybe the big question is this: what happens when someone you don't know asks for a favor? Does your community extend outward to them? Or does it stay within the confines of your church, your league, your street?

Here we see another difference in definition:

Right: keep your circle small- Left: all are welcome

I started writing this post from the expansive sun deck at my family’s cabin on the north shore of Pinecrest Lake. It is beautiful. As night fell I'd hear crickets and the faint hum of a motorboat puttering along the south side of the lake. I'd watch as other cabin owners as lucky as me would turn on their lights, the glow reflecting off the lake like little fuzzy stars.

I say I'm lucky because I didn’t earn this cabin. I was born into it. My great grandpa got the lease, built the cabin, and handed it down two generations. I’m the third generation and with any more luck, my cousins and I will be the custodians of this magical piece of property someday too.

Back in August, while at Pinecrest, I listened to a podcast featuring stories of farmers from Guatemala who, fearing for their lives, sought asylum in my country. They brought their children with them, some no older than mine, on a perilous journey across dirt roads and trails, through land infested by drug cartels and robbers. Luckily they made it the border, crossed, and exercised their constitutional right as immigrants on American soil to seek asylum. Then my government separated the kids from their parents, coerced them to sign legal documents they couldn’t read, and sent them back to Guatemala without their kids.

We're now a week from the 2020 election and immigration is still a huge issue. We learned this week that over 500 kids who were separated, like the Guatemalans I learned about in August, have lost their parents. They simply can't be found. These are kids like mine.

But why? Why do I care? My kids are fine. What do these stories have to do with me?

Well, it goes back to this difference in priority. I could, justifiably, say it’s not my problem. I’m here and they’re there. But I don’t see it like that.

Flipping my Pinecrest story around, I could have just as easily been born to a Guatemalan farmer family. Sounds silly to say, but I didn’t choose to be born to white middle class parents in California. It was just plain luck and I’m not comfortable with that. Getting something I didn’t earn makes me uneasy, especially when I see how terrible things could have been. I could have worked just as hard, been the same good, patient, curious person, and lived a tragic life where I too could have chosen to take my pre-school aged kids on that same dangerous journey across the southern border of the United States.

I think about them because it could have been me. I didn’t earn my American citizenship. It was given to me by birth.

So that why I want to share what’s ours. That’s why I’m tolerant of immigrants. Because I would do the same thing and if I were them then I would hope that the American sitting in his picturesque cabin in the Sierra Nevada mountains would take a moment and think about me.

And that maybe someday he would do something about it.

I'm now an adjunct!

2020-10-24T21:17:00-07:00

Last October, a professor in the business department at Diablo Valley College (DVC) asked me if I would apply to teach part-time in a new digital marketing certificate program.

It was an easy decision; ({filename}why-im-applying-to-be-an-instructor-at-dvc.md).

I'd been volunteering at DVC since late 2018, speaking in classes and helping with pitch competitions. I met faculty and staff and got involved officially as an advisor to the business department and I also joined the newly-formed DVTI. I was enamored with DVC. I liked everything about it.

My history with this community college goes back further than 2018, actually. Much further. DVC to me was "DVC," the place where my grandpa had his choir practice. It was the place where I would sit next to my aunt in the performing arts theater and watch my grandpa walk on stage with about thirty other septuagenarians and sing songs in languages I'd never heard before. I remember we always went at night, so my memories of DVC back then are dark. Not in a bad way, just in a late evening, not very bright way.

I wouldn't see DVC in the broad daylight until I was in my mid-30s and living just over the hill from campus. One of my neighbors, a teenager, was performing in a community theater and his parents invited us to go with them. My daughter Lily was into dressing up and singing Disney songs at the time, so I knew she'd love to see some "real princesses" on stage. We parked in the same lot where my grandpa would pull up in his white Toyota pickup. We walked up the stairs to the same auditorium where he used to perform. We sat in the same seats.

It was deja vu, lifetimes apart. Here I was, all grown up with a daughter in hand, another napping at home, in the same place where I watched my grandpa perform decades earlier. He was ({filename}remembering-meredith.md), a victim of old age, and I couldn't help but think of him as the teens and pre-teens on stage acted out scenes from Peter Pan. Indeed, life moves in circles.

I would get to know DVC much better, largely thanks to Professor Charlie Shi, who responded to a cold introduction of myself and the book I'd my book The Parallel Entrepreneur. I detailed the rest in my ({filename}why-im-applying-to-be-an-instructor-at-dvc.md) about this position, so I'll fast-forward to this latest news.

Yes, I got the job! It took a while for DVC to move on my application, but they verified my transcripts, spoke to my references, and interviewed me in May amidst the pandemic shutdowns. I learned a couple of weeks later that I was going to be permitted to teach, but also that nothing would be official until I was assigned a class. The summer passed and I learned just this month that I will be teaching Digital Marketing course (BUSMK-264) for two months between March and May 2021. I'm stoked!

The class was always going to be entirely online; it's designed to accommodate both students and working professionals. I'll give live lectures but they will be optional and I'll record them. We'll run the class using Canvas, a surprisingly intuitive LMS, or learning management system. I recently completed a course for DVC instructors to get familiar with Canvas and build out a couple of course modules. It was great; I actually feel very prepared now.

I was nervous about taking this on at first. I had to give DVC my current employer's contact info as a reference, and I wanted to assure them that this wouldn't conflict with my day job. I believed then, and am even more certain now, that teaching this course will make me better at my job. It will force me to look at search marketing (SEO, PPC / SEM) in a fresh way. I'm excited to force myself to become an expert in all aspects of this subject and infuse my course materials with my day-to-day work. It's all very relevant and I can give "this is what I was actually working on today" types of real-world examples in my lessons. Rather than distract from my day job, this work will enhance it.

I'm an adjunct business professor at a community college! I'm really looking forward to it.

A one-hour brain dump

2020-09-27T21:31:00-07:00

It's almost 9:30pm on a Sunday night. I haven't posted here in about a month. Tonight, for the first time in a while, I feel like blogging. So I'm going to write for an hour, straight through with very minimal editing, and wrap up at about 10:30pm.

It's now the end of September. The statewide "shelter-in-place" order came in mid-March. That means the world has been upside-down for about 6.5 months. The impact on me personally has not been severe. My family is safe. My wife and I have job stability. The waves of anxiety I feel are not for myself but rather for my neighbors, the strangers I read about, and the state of California.

Last night I invited two neighbors over. We sat down by the creek in Adirondack chairs facing each other, a wood fire pit in the middle of us. Normally I put out a little cocktail station with some tumblers and a bowl of ice. Not this time. We had cans of beer, a couple of cigars, and lots of relief to have a few hours of normalcy. Hosting these nights several times a year has become a tradition. In the past, we'd chat about family, sports, business, real estate (did you SEE how much that house got listed for??). The last one I hosted, sometime back May, I think, when the BLM protests really gained steam, was my first intentionally political creek night. With fair warning, I invited some neighbors who I thought would have opinions to share. It was a good discussion.

Last night I didn't put that asterisk out on my invite. Frankly, I just wanted to sit by a real fire, smoke a cigar, and drink beer. If they wanted to join me, they would be welcomed. And indeed, they did. We talked a lot about the state of things around us. One of my neighbors lost his job but received a really generous severance. He's been spending his time reading progressive philosophy and watching Netflix documentaries about racial politics. The other neighbor works in medicine and reads The Economist every week. The tone this time was more subdued. We're all worried. We're all nervous. More concerning, we've all flirted with the idea of moving out of state. Only one of us was actually taking it seriously.

The problem with California is it is segregated (a.k.a. "gentrified") and dastardly expensive to live. You're lucky to find a house in a desirable neighborhood for less than a million dollars. You can still buy in the $500s or $600s, but you're definitely not getting good schools at that price and you might not be able to go out after dark. That's the housing market in the Bay Area. Half a million dollars is the first rung on the ladder. It's aggravating.

Once you get into the nice neighborhood, you look around and it's mostly White with a smattering of Asians. In Contra Costa County, San Ramon is probably the most wealthy non-White suburb, with with majority Asian, Hispanic, and Black. I'm glad to have neighbors who think about this and care about it, but the irony of course is the three of us are... White. Three White guys each living in homes worth a million bucks or more bemoaning the lack of diversity in our neighborhood. I know how this sounds.

We also rehashed bits of American history. Starting from the Revolutionary War, which I've had to dive back into since my almost-six-year-old adores the Hamilton soundtrack, through to the Civil War and Reconstruction. I made the point, from my reading of The Conservative Sensibility by George Will, that Thomas Jefferson and the framers were intentional in the phrase "life, liberty, and the pursuit of happiness." Why not just write, "life, liberty, and happiness"? What is so important about "the pursuit of" as it pertains to "happiness"?

Well, George Will makes the point that the state should not dictate what happiness is. Life and liberty can be universally defined. Happiness, however, is subjective. Therefore, the role of the state is to formulate the conditions by which most people can find happiness. Happiness itself is not a natural right, but the ability to find it is.

So although I would be pretty bummed out if any of my neighborhood dad friends decided to bail on the Bay Area, I would be happy that they chose to find happiness. Moving, especially with school-aged children, is a big deal. If anyone I knew had the guts to make that move, I would be in full support. It's a hard thing to do.

I remember thinking one of my neighbors said something important last night. I've just spent a few minutes trying to remember what it was, but I've lost it. I'll ask the next time I see him.

Politics has been front and center the last few months. I've been plotting my way into the system and making some headway. I found that economic development is the perfect combination of my political and business interests. I'm now chairing the Diablo Valley Technology Initiative and intend to do a great job as Chair, both because the work is important, but also because it's the clearest path for me into a public career. As I've written before, I've intended to ditch tech for public office for a long time. It's just been a matter of figuring out how to get there. I'm closer now than ever.

The other major theme since I last wrote one month ago is my sudden and deep fall into the colorful abyss of the Grateful Dead. The last time I remember hearing of anyone being a fan of the Dead was when two Scripted colleagues, JD Petersen and Nico Canova, discovered they both were into it. I overheard the conversation and had no idea what they were talking about. The Grateful Dead? That old fat guy who looked like Santa Claus? The Grateful Dead seemed like a gimmick to me back then, something you liked in order to say that you liked it.

Welp, I was wrong. A few weeks ago, I randomly started listening listening to the This is Grateful Dead playlist on Spotify. I'm not sure why I chose it that one fateful day. I was curious and clicked the button. Two things struck me right away: 1) The Grateful Dead has some terrific lyrics, and 2) Jerry Garcia is a phenomenal guitar player and I love his tone. I can break these observations down further.

My favorite line from their songs come from "Brown-Eyed Women." Part of the chorus goes, "The bottle was dusty but the liquor was clean." It's a short phrase but for me it pulls on so many strings. I've always loved the old sepia pictures of the West, farmers and vigilantes in overalls. The lyric speaks to that. It also summons what old age means to me. You become a dusty bottle, but if your mind is intact, the liquor is clean. I can also picture the cowboy drinking that dusty bottle of liquor. That man might be the same age as me. The whole song tells a story, but that chorus lyric stands out.

The other sorrowful song that sticks with me is "Morning Dew." The lyrics are short and sweet:

Walk me out in the mornin' dew my honey Walk me out in the mornin' dew today I can't walk you out in the mornin' dew my honey I can't walk you out in the mornin' dew today

I thought I heard a baby cry this mornin' I thought I heard a baby cry today You didn't hear no baby cry this mornin' You didn't hear no baby cry today

Where have all the people gone my honey? Where have all the people gone today? Well there's no need for you to be worryin' about all those people You never see those people anyway

I thought I heard a young man moan this mornin' I thought I heard a young man moan today I thought I heard a young man moan this mornin' I can't walk you out in the morning dew today

Walk me out in the mornin' dew my honey Walk me out in the mornin' dew today I'll walk you out in the mornin' dew my honey I guess it doesn't matter anyway Well I guess it doesn't matter anyway, no no I guess it doesn't matter anyway

Grateful Dead

There are plenty of versions of this song on Spotify, but my favorite is this one.

I think this song has it all: the melancholy Jerry, haunting lyrics, fat guitar tone, and an epic guitar solo. It's everything I love, all at once. The other thing that probably draws me to it is Jerry is not a great singer. He can hit the notes, which matters, but what you really get is authenticity. That's what's so important, and I respect him and the band even more for it.

My hour is up. I covered a lot of ground. I admit to spending some of the past hour looking up LinkedIn profiles for the Scripted people I mentioned. I wanted to say exactly when I first started listening to the Dead and discovered I needed a Last.fm account for that. So I went there and lost some more time. But for the most part this was a straight up writing session.

Three early observations about writing a novel

2020-08-23T20:38:00-07:00

I'll state the obvious first: it actually is as hard as you think.

When I ({filename}a-few-days-of-radioactive-seclusion.md) around around this time last year, I told myself not to overthink it. I was going to write a novel, simple as that. I wasn't going to agonize over plot lines and details. I wasn't going to do any reader panels. I wasn't writing for fame, after all, but rather to try something new. Prior to diving into this project I hadn't done any creative writing. None. In a long time, at least a decade.

I had the spark of an idea. I'd been thinking about it a lot. I knew the premise: *Man gets sick and is certain to die. Man hears about a faraway adventure hospice and decides to go, leaving his family behind. Man regrets. Man dies. *

I thought about the characters, the setting, and how agonizing this decision would be for everyone involved. It felt like there was a lot of meat on this bone and when I shared that much of the story with family and friends, their eyebrows raised. They were immediately intrigued and it spurred all kinds of questions, and even some disgust.

"I can't believe anyone would do that! Would you do that to your wife and family?" Probably not, actually, but I loved that my plot elicited that type of reaction. It meant readership and book groups once it was published. And it meant it would be fun, even easy, to write.

I was right and wrong. It has been fun. It has not been easy.

Observation #1: It's the main character, stupid

Story Genius by Lisa Cron

When I was about 40,000 words into it, I read Story Genius by Lisa Cron and loved it. Around the time I started the novel I also read Save the Cat! on the recommendation of a neighbor. Both touch on the same theme: character, character, character. Plots are just things that happen. Characters are what we remember. Characters are what we care about. Characters are what actually drives the story and makes the plot matter.

When we read a great novel, we emote as the main character struggles with a misguided belief that drives him against the roiling ocean that is the plot. We feel him as he makes decisions and rejoice as he evolves, becoming a new person at the end. This is the formula that the most commercially successful novels and screenplays use to sell copies and move people. You want your reader immersed in your story, rooting for or enamored with your character. You want them invested through to the last page, and you want your story to be a real gift to them. For those five or six hours the reader spent with you, they got a real glimpse into another world, a new universe, a sidecar's view into something extraordinary.

Humans seem to be uniquely able to get wrapped up fiction. The story is a device unlike any other. It takes us away from one reality and places us into another one. It's science fiction, but it's just words on paper.

Observation #2: Writing fiction is dreaming while awake

Getting "in the zone" on a piece of fiction is much different than feeling the same effect while writing non-fiction, as I typically do on this blog. When I get in the mood to write, as I did tonight, I can flow for a good 45 minutes, finishing a post in one sitting. During that time I'm focused. I feel good. Basically, I just feel like writing, and the ideas come and I jot them down and the sentences just write themselves with very little editing. But I'm very much awake.

The flow of creative writing is much different. At peak flow, I'm barely there. I'm fully engaged with the story. For those moments, the characters are real and I'm in it, watching them talk and make decisions, trying to take notes as fast and as best I can. I've cried while writing, which is actually an incredible experience. Two people who read early drafts of this novel told me they cried too. I wonder if we cried at the same part.

The best analogy I can offer is it's like a dream, except you're awake. You're aware that you're awake, because you're working hard, furiously trying to record it in writing, which is maybe the thing that makes it most distinct from a real dream. But during those moments you're a voyeur, a spy, a fly on the wall and your mind is working in two dimensions at once but it's just buzzing on a creative writing high. That feeling is addictive. I wish I could say that it happens every time I sit down and write. It does not, but now that I know it's there, I keep holding out for it to show up again.

This insight is one reason that I keep chipping away at this novel. It also helps me to justify my writing retreats. I know that getting there requires open mental space, the long runway of an open afternoon where my only obligation is to use that time to write.

Observation #3: Decision fatigue is real

The other big difference about non-fiction and fiction writing is the exponentially greater number of decisions that must be made in a fiction story.

Whatever the topic is of my non-fiction piece (business, usually), I have a framework to follow. There's a set of facts and my decision-making is simply around how I describe my observations, what references to make, and how deep I want to go. (By the way, for some of the best non-fiction writing I've found, check out Alex Danco's blog.)

Great non-fiction writing is academic but accessible. It might also weave a storyline through it, using some of the character techniques described in Observation #1. For the epitome of that technique, look no further than Alexander Hamilton's biography or the musical inspired by it. Laden with facts, it had to decide what to keep and what to ignore, what to expand upon and what to merely mention in passing. These are big decisions, no doubt, but not as many as would have been made if Alexander Hamilton were a purely fiction character.

Dealing with decision fatigue is actually what originally led me to the second observation. In the flow state, decisions feel like they're being made for me. Even though I'm writing a fiction, in the "dream" I have as I write, the story just happens and I simply record it, like a biographer reviewing source material for his subject.

I can manufacture it in some ways by basing a character on someone I know, much the way an artist uses a living model for a painting or sculpture. I can make fewer decisions this way, letting my memory of that person take the reins. It helps me save energy for the scenes when I don't have an experience to run them against. These take real work, a bit of googling, and progress the slowest.

Conclusion

I'm 72,000 words into what should be an 80,000-word novel. The last 10 percent has been the hardest. I'm stuck on the ending. I thought I had it, but now I'm not so sure, and I'm aware that if I deviate too far, I'll either end up having to rewrite a good portion before this ending or extend the novel out another 20-30,000 words. Neither outcome is appealing.

So this is what I think about when I go to bed, when I swim laps, and when I'm mindlessly throwing the ball from my ({filename}the-ascent-of-blue.md). Because ultimately that's what writing a novel is. It's getting absorbed in it, thinking about it, and knocking out some of the thousand hours it takes to write a book that will get consumed 200x faster.

That's the glory in writing a novel. "It's the journey, not the destination" has never felt more true.

Origin story of my protagonist's wife

2020-07-02T08:02:00-07:00

Here's the result of another exercise. My protagonist's wife, Jo, will play a big role in the novel and I needed to figure out what she stands for.

The first thing she noticed was the smell. It was dusty and sweet, like a rotting peach. She yawned as the staff ushered her to the front of the line and through the doors at the front of the building. She walked down a flight of stairs to the kitchen and took off her coat. Winter mornings in South Central Los Angeles were cold before the sun came up.

Jo signed in, put on the disposable gloves and hairnet, and asked Rita, the manager of the food kitchen, what shift she wanted Jo to take today.

“Apples,” Rita said, and motioned her to a food prep table where a box of apples was waiting to be washed and cored. “We makin’ applesauce today, girl.”

Jo’s grandma approached Jo and Rita. “Where you want me?” She asked.

“At the line with me, of course, “ Rita said with a smile. “Peoples is sad today. They need you to cheer ‘em up.”

Jo watched in admiration as her grandma and Rita stood behind the counter, filling trays up with hot oatmeal and banana halves. The homeless, the poor, the needy would smile at them, thank them, and turn to take a table. They would eat with their heads hung low, not making eye contact with anyone. Jo was always surprised to see how little the food kitchen customers would speak to each other.

Later in life, Jo would recall the faces of people lined up for food. She saw looks of pain, of hope, of despair and despondence. Those faces stuck with her. She was barely nine years old when she entered this routine with her grandma.

An hour later, Jo bussed any trays left on the tables, cleaned up the spills, and put the dining area back in order. Her grandma joined her.

“They’s somebody’s child, somebody mama. You lookin’ at somebody’s uncle or auntie. They’s your brothers and sisters.” Her grandma looked up and through the wall, along a dusty trail, decades long, back to her childhood home in southeastern Georgia.

“Our folks was poor too, you know. We lucky we made it out. Thems that’s still back there, they’s not doing so good. Most of them need help. That’s why we here. That’s why I brung you.”

Jo and her grandma moved in silence as they wiped down the seats and mopped the floor. The scent of old peaches mixed with bleach, making Jo’s stomach turn. She wanted to leave but her grandma’s mind was still lost in thought, somewhere between South LA and Georgia.

“We have to take care of them, Jo. It’s our duty. We jus’ have to.”

This left a lasting impression on Jo.

My first protagonist's origin story

2020-06-30T09:29:00-07:00

In case you weren't aware, about a year ago I started writing a novel. It's bound to be a tragedy. In the end, my protagonist will die a lonely death. Readers will know this upfront; the opening scene is his terminal cancer diagnosis.

There's a lot more to it, of course, and I've read Story Genius by Lisa Cron to help me think through the "third rail" of my novel, the essence of the story, the reason why it matters. My initial draft had two-dimensional characters, driven by plot, without the depth that would really make this story shine. I'm now trying to fix that.

A critical exercise that Lisa Cron requires is to write up an origin story that sets up the a core belief held by the protagonist. This is his third rail, the core code that he lives by and gets tested throughout the story.

For several months before his seventh birthday, getting new Air Jordans was all Ben could think about.

Chester, his best friend, had a pair. Chester’s parents would drop them off at the local mall, where Ben and Chester would sprint up the escalator steps, dodging by irate elderly couples, to Footlocker. Ben could smell the inside of those shoes from three storefronts away.

They would arrive at the entrance to the store shoulder to shoulder, and walk slowly to the Air Jordan display as if they were in line for communion. Ben held the red and black shoe, embraced it, flipped it upside down and stared at the sole, mesmerized by the design of the concentric circles and shooting star. It was like looking into another world.

The price was other-worldly too. At $135, he knew it was more than his parents could afford. His mom was a photographer, his dad a writer, and they met at an anti-war protest. Neither of his parents came from money or cared much about it. Although the Bay Area was getting more expensive to live in the 1980s and 90s, his parents rented small apartment in San Rafael, a small city in Marin County, and could get by.

“We’ll see what we can do about those shoes, Ben,” his mom told him when he asked again after returning from Footlocker. “I know you want them.”

A little twinkle in her eye told Ben she was keeping a secret. His insides burst with happiness and anticipation. He was sure his parents were going to find a way to get his Air Jordans for his birthday.

As the day drew closer, he kept looking to his mom for a sign. She would give him none. He pressed his dad, who knew nothing of sports and only knew the name Michael Jordan because it was plastered all over the sports pages in the newspapers he wrote for. But he probably never read the articles. His dad simply shrugged. Clearly he had no understanding of what the shoes meant to Ben.

Ben kept his hopes, sure that his parents would find a way. He’d never asked for anything else, not like this, and he was clear to his parents that the shoes were all he wanted. No party, no money, not even a cake. He just wanted the shoes.

On the morning of his birthday, Ben woke up early in anticipation. He could hear his parents in the kitchen talking in hushed tones. He smelled the coffee. Quickly Ben pulled on his Nike shorts and a tank top. He stuffed his favorite pair socks in his pocket, hoping he’d be wearing his own pair of Air Jordans in just a few minutes.

When he opened the door to his room and stepped into the hallway his parents stopped talking. A knot formed in his throat. The air felt thick. He walked into the kitchen and the look on his parents’ faces told him what he’d already sensed was true. There would be no Air Jordans today.

“I’m so sorry, Ben,” his mom said, tears welling in her eyes.

“Your mom lost her job yesterday, son,” his dad said. “We were going to surprise you with those Nikes you wanted, but right now, we just can’t.”

Ben turned and ran back to his room before his parents could see him cry. He threw the socks against the wall. They bounced hard off a Michael Jordan poster, causing it to rip and hang at an angle. Ben buried his face into his pillow.

“When I grow up,” Ben thought to himself. “I will never lose my job. I’ll never be poor. I’ll always have control, and that will make me happy.”

Ten years of marriage

2020-06-12T00:01:00-07:00

March 14, 2008. Kennebunkport, ME.

It was hot in June 2010, but not too hot. I remember being worried that the flowers at the estate where we had our wine country wedding might wilt in the Windsor, California heat.

We picked Madrona Manor after touring a few other venues earlier in the year. It was stately, quiet, peaceful, and absolutely stunning in the evening. There's a Michelin-rated restaurant, elegant rooms with no televisions, and a view over the Anderson Valley. Inside it smelled like a rustic mansion, because that's what it was.

I was happy to have a small wedding. There were 64 guests in total, and since my wife's family is neat and compact, my side of the equation ended up with a majority of the seats. Not that anyone was counting.

We hired a local string quartet to play Pachelbel's "Canon in D" for the procession and Eric Clapton's "Wonderful Tonight" for our first dance. My wife's uncle officiated and we each had two people join our wedding party. My two guys went on to start a business together. Her two ladies were her sisters.

I recall forgetting my vows. Something about the moment got the better of me, but fortunately I gave our officiant a copy so he could assist. I might have had a line in there about always putting our children first. Or maybe it was her. Whatever it was, I recognize it now as unadulterated twenty-something naiveté. How could I know back then what being married actually means? Was I really trying to give myself marriage advice ten years ago?

I'm glad I've forgotten whatever I said at the Madrona altar. I hope everyone else did too.

What I remember most is how beautiful she was. Like the day we met, when I locked eyes on the prettiest girl in the room, I was there again, with the prettiest girl, on love's most celebrated day, in the most romantic setting. I was overcome, to be sure. I was proud, nervous, and excited. But most of all, I was relieved.

I could have titled my wedding toast, "I'm so glad this was so easy." That was the theme of my speech and also of our relationship. It was easy. We made it easy. From the time we settled into our relationship, there was very little stress. Our greatest concern early on was how long we'd have to wait until our next rendezvous in the broader New England area. She was living and working in Sacramento. I was studying at Harvard and MIT (yes, that had a nice ring to it.) Every month or so we'd find a reason to meet. It was in San Diego, Maine, Cape Cod, or, of course, Cambridge.

My friends loved her. "Ryan's girlfriend is sooo hooooooot," one of my now-successful politicos used to say aloud, a big grin on his face, whenever she was referenced in conversation. I didn't mind. She was hot. She is hot. I was just glad they liked her, and more importantly, that she liked them and felt comfortable around them. She was not intimidated to hang around my group of friends, a motley mix of Ivy League frat boys and social activists. I think she was just happy to be near me.

She was the first girl I lived with. I remember when it came up. I hesitated.

It was my fall of 2008, going into my last winter in Boston. My Harvard friends had already graduated and moved away. I was staying on for another year to complete a MBA at MIT Sloan. I lived in a room off of Central Square, midway between the two campuses. There was a small park behind the flat and one night I called a friend to help me parse out my feelings. I told him I knew that if she moved out east and in with me, that was it. I was certain this next step would lead to us getting engaged and married. I knew the transition would come easily and that was, ironically, making me nervous.

My friend quelled that anxiety. "Choosing to lose control," he said, "is the essence of freedom."

So I took a deep breath and let go. We moved into a small furnished apartment together on Joy Street in the quaint Beacon Hill neighborhood just off the Charles River in Boston. Eight months later we were engaged, and less than a year after that, we were married, on June 12, 2010, in the gardens of the Madrona Manor.

It's hard to describe the proximity you have to someone you love, with whom you've done everything major in your life, like buying a house, starting a family, and putting together a living trust. There's no one I trust more. How could I? I can't imagine it.

I know not all marriages last forever and I can't take ours for granted. I would be foolish to assume that because the last thirteen years of loving each other and living together, ten of which we've spent married, has been so easy that the next thirteen will be too. All relationships take work and I feel grateful, still so incredibly grateful, that the work I'm putting into this every day still doesn't feel like work.

Our days these days revolve around our children, a rambunctious 3-and-a-half-year-old and a 5-going-on-fifteen-year-old. Both girls, they have vastly different tastes in clothes. Our youngest is sporty, obsessed with Nike workout gear. Her favorite shirts are the ones I bought in the boys section at Gap. Our oldest is also athletic but very comfortable in a nightgown or dress. When our oldest was the age that our youngest is now, she was wearing Moana and Elsa outfits. Our youngest today would refuse to wear anything like that.

Fortunately, they're both sweet girls who love their mommy and give their daddy some much appreciated affection every once in a while. I knew their mommy would be a supermom right away.

She was 22 going on 23 when we met. I was 24 going on 25. I was interning for the Lieutenant Governor in Sacramento. She held a policy job at healthcare company. She accompanied a family friend to a food and wine expo. I took advantage of a free ticket that Lt. Gov. Garamendi's wife, Patti, offered to the office that fateful evening in July. At the event, I waited until the last minute to go up to her and say hi. She seemed to be expecting me.

"Hi, I'm Ryan," I said. I had her phone number by the time the conversation ended. I needed to see her again. We met the next morning at a briefing at the capitol. I sat next her. "Lunch?" I scribbled on a newspaper, and handed it to her. She told me she was heading out of town to see family, but we met up at a bar in Sacramento the following week. My roommate, who also had an internship in Sacramento that summer, came with me. He came to our wedding, too.

A few months later, in October 2007, I hesitated once again. I didn't mean to fall into a relationship like this so soon. I knew if we stayed together we would wind up married. When I stared down that prospect, I blinked. Over the phone, I think it was, I broke up with her. I don't remember what I said or how I said it. I do remember a couple of months later, sometime in December that year, I reached back out. I missed her. I missed the simplicity of being with someone who I could see myself being with forever. She responded. She was in New York with her family, and she was moving to San Francisco. As luck would have it, I would be there too.

She met my mom over lunch in Burlingame in early January 2008, a few days after we'd reconnected. I don't remember those details. I only remember feeling relaxed, and when my mom and I had a moment to ourselves at the end of the visit, she told me what I already knew, that I could wind up married to this girl.

I wasn't planning to call my mom before I proposed to her, but she caught me walking between the florist on Union Street and our apartment off of Chestnut Street in the Marina District of San Francisco. I had a bag full of pink, white, and red rose petals and plans to propose. I told my mom what I was about to do and she became giddy with excitement. I ended the call quickly, feeling a little odd that my mom, who always waited for me to call her, would call me right at that moment. Something was in the air.

I felt the ring in my pocket. I had stuffed it in my guitar case, figuring that would be the last thing I would lose and the last thing she would open, when we moved up to San Francisco after our temporary stay with her family in Los Angeles. The center diamond belonged to her grandmother, and I purchased the side stones and ring itself from her mother's jeweler.

I was in a chocolate shop in San Antonio, Texas, with her mom when I suggested that we figure out what her ring size was. Her mom pulled me aside, eyes wide, nodding with approval. A few weeks later, I had both the ring size and the ring.

I discovered after being married that living together while dating and being engaged was all the same flavor of existence. The mechanical benefits of marriage would come later, when we applied for a mortgage and when we filed our taxes. We settled into our lives as urban twenty-somethings. She worked downtown, and later from home. I worked at a startup, and I started a startup with a friend at my wedding, and that became my career for the next long while. We'd have a house, a dog, and a kid before I gave that job up.

The biggest decision we made together, besides starting a family, was buying a house in Walnut Creek. We were able to save up the money by ourselves, and I was eager to move onto the next stage of adulthood. We agreed to focus our search on the far side of the east bay, in the suburbs where my grandparents lived. She and I would go visit my grandpa pretty often, and he was delighted when our daughter started showing up on those visits. When he fell ill, I coupled my visits to see him with open houses. For a short while we considered buying his house from my family. Eventually, after several false starts, we found our house. We liquidated every dollar we'd saved together to get it, and it was worth every penny. To our surprise, a new group of friends emerged who have helped us expand our sense of home throughout the neighborhood.

A neighborhood community is a unique and powerful thing, and I think we're so embedded in ours because she values it too. It's never been more important to us than it is now, in the midst of a crisis, where everyone is impacted and no one has childcare, so we quarantine together in our oak-lined bubble.

I imagine myself an old man. I'm still with the girl I married ten years ago. I'm not sure what else I could ask for.

Personal, Perceptible, Practical

2020-03-28T06:52:00-07:00

Some time ago I learned about Susan Solomon, the atmospheric chemist who discovered that chlorofluorocarbons (a.k.a. CFCs) caused the huge hole in the ozone layer. Remember all that noise about this from the 90s? It went away because of Dr. Solomon. She received her PhD from UC Berkeley and she is currently still teaching and still doing atmospheric research at MIT.

I've been thinking about something she said about the tactics she used to get the world to care and do something about the problem. I was struck that she thought as much about the "marketing" of the ozone layer problem as the science behind it.

Susan Solomon at MIT. Credit: PBS

Solomon said that effective environmental problem solving requires that the solution be personal, perceptible, and practical. I'd argue that this framework works for any problem, public or private, economic or environmental. It's relevant even when rallying the globe around fending off a global pandemic, too. I keep coming back to this when I read about the response to coronavirus, so let's apply Dr. Solomon's framework to our current global crisis.

Personal

Make people relate. Help individuals understand how the problem relates to them personally. Not the world, or the rainforests, or the spotted owls. Biologically, we are wired to care about #1 (ourselves) and although we can all point to examples of selfless behavior, on average, we're selfish. Rather than fight that tendency, make it work for the cause.

The harrowing stories of frontline health workers ring louder than the pleas of politicians. Doctors and nurses have an effective way of making things personal. Shelter in place to protect your family, your community, your own health. It also helps that nurses consistently rank among the most trusted professions.

Perceptible

Help people understand the units of measurement. In the case of coronavirus, it's the number of tests, cases, and deaths. Charts fly around Twitter comparing rates of infection by country, often on logarithmic scales.

The early challenge with coronavirus is that people who don't study math or economics don't have an appreciation for exponential growth. We all probably think we know what it means, but early dismissal of the risks show that most of us don't appreciate its gravity.

The reason coronavirus spread so quickly is the same reason why you can't fold a paper in half more than eight times. It doesn't matter if you're folding a playing card or a football field. The reason is the thickness of the folds increases exponentially. After that eighth fold, no matter how thin it is to begin with (I mean, you need to be able to feel it), the material you'd need to fold is simply too thick.

To apply this principal to the spread of a virus, the number of initial vectors is like the thickness of the flat piece of paper. The more vectors, the thicker your piece of paper, so as you fold it and the vectors go out and infect, your thickness grows faster. The analogy of a really thin piece of paper is having just a few vectors, maybe just one, in a rural area, so he can't infect very many people very quickly.

You're starting with smaller numbers, so you might get more folds in. But exponential growth eventually looks the same, no matter how small the base. This is the perceptibility challenge we faced with coronavirus. Fortunately, it has helped that testing kit production is ramped up and we can see the exponential activity clearer now.

Circling back to the environmental application, when scientists were able to measure the rate of growth of the ozone hole and capture icebergs collapsing into the Arctic Ocean, people started to care. When the ban on CFCs went into effect and measurements showed the hole closing up, it reinforced the global community's behavior. Now it's no longer a problem.

Fortunately, the feedback cycles on the coronavirus are even shorter than they are with the ozone hole. Effects of social distancing and lockdowns will be measured within two weeks.

Personally, this is the most important of the three. I believe the business adage that you can't fix what you can't measure.

Practical

Make the solution easy to understand. People don't want to think too hard. And if you're asking for a lot, then problem should be very personal and very perceptible.

Indeed, this is where we really succumb to the human condition. Unlike many environmentalists I know, I don't think it's practical for everyone to give up meat and dairy products. Being 100% off fossil fuels is also not practical. But switching out the chemical in an aerosol can or using a product with a different applicator, as the ask was during the ozone crisis, is definitely practical.

Today the asks are huge. One billion people are restricted from congregating. Schools are closed. Small businesses are shut down. Public transportation ridership dropped by 90% in the Bay Area as employees were forced to work from home. The scale of this impact is mind-numbing.

I do believe this is the right solution, though, and my neighbors agree. These measures are practical in that they're easy to comprehend and it's easy to understand how they will help. With daily reports coming out about the spread of the virus, we're able to follow along as community by community we "flatten the curve" on the epidemic.

So to sum it up, for me to get behind an action, I have to relate to it, be able to track progress, and have a well-defined way to contribute. When I first heard of this framework I thought it was a brilliant tool for activists to use. I never imagined that I'd experience a global pandemic, and it's interesting to see how this framework applies in this most extreme of circumstances too.

How I could be Republican

2020-02-24T06:55:00-08:00

A year and a half ago I published a piece here describing why I'm a Democrat. It was a bit of a diatribe, really, and it railed against the California Republican Party's platform. I titled it "Why I'm not a Republican."

A friend recently challenged me to take a different spin on this topic. Even if merely as an exercise, could I find the silver lining in the Republican party today? Or could I at least seek out the bits of wisdom that originally formed the party of Lincoln and describe how they fit with my current values?

I took it as a challenge, figuring it was worthwhile given the overwhelming partisanship in America today. This is an exercise that anyone who has sworn at their Twitter feed or cable news show should try. I assigned myself the task

Here's my submission.

Conservation is conservative

Preservation of our environment is not a liberal or conservative challenge, it's common sense.

President Ronald Reagan, State of the Union address, 1984

Nothing says austerity like keeping your bank accounts full. The conservative approach to the environment looks at natural resources this way.

Traditional conservatives don't feel cash burning a hole in their pocket. If there's money in their wallet, they don't peel off and run to the nearest mall. Instead, they stick it in a bank account or invest in stocks. And indeed, my paternal grandpa, the conservative thinker I knew best, was a saver rather than a spender. There was nothing extravagant about his lifestyle, which probably was how he was able to live comfortably in one of the most expensive neighborhoods in the Bay Area on two teachers' salaries.

Our natural resources, the great American environment, are just like a bank account. We spend ore when we build factories, we withdraw clean water when we irrigate our crops, and we draw against a stable climate when we warm our homes and drive our cars using fossil fuels. This is just the normal, everyday spending we do on our natural resources account.

Unfortunately, this essential spending is done on top of flagrant, unnecessary, over-the-top spending we also do on sloppy mining operations, dirty coal plants, and ozone-depleting chemical bi-products.

This extra spending is like buying $500 flip-flop sandals just to wear around the house. My grandpa would never do that. Having cash doesn't mean spending cash.

These are our natural resources. Natural resources should be nurtured, enjoyed, and used when needed. They should be shared with our children. They should never be abused, and certainly never wasted.

Furthermore, a truly conservative approach to the balance in our natural resource bank account would consider a rate of return. Instead of spending the principal, we should be thinking, "How can we compound these assets over time?" When we consider spending, we should be asking, "What's going to be the cost to replace these assets after they're spent?" If we thought about forests and clean water and clean air this way, we would make different decisions.

Conservatism takes a long view. The conservative approach to spending is to reduce the amount we spend today in order to allow for greater spending tomorrow. Conservatives save their pennies, clip their coupons, don't take more than they need. These values are very aligned with Native American culture and the philosophies of Thoreau and Muir, all of which resonate with me. The common thread is to move cautiously, thoughtfully, and to not need so much.

Indeed, true conservatives don't like change. And guess what? Neither do forests.

Thus, climate change should make conservatives bristle in their britches. True conservatives don't like change. This is why conservation is a conservative value.

Small is good

I'm not a big company entrepreneur. I like lean. I prefer small teams. I like efficient. I don't like bureaucracy. The fewer people I have to work with and manage, the better.

Operationally, I like to break up and outsource products and services that aren't core to my business. I think the best metric to run my businesses on is revenue per employee. The higher that number, the better. I’d rather own a $5 million business with five remote employees than a $10 million business with twenty staffers in a fancy downtown office. It’s just how I’m wired.

Translated to a government context, this would mean I like privatization. Government should get out of "businesses" that are not core to its mission and capabilities. This could mean privatized energy distribution, social services, health care, and even prisons. I’m a student of environmental economics, though, and understand that capitalism maximizes profits, not social welfare. Thus, in certain markets, the goal posts should be modified.

To make this point clear, let’s take the example of private prisons. They’re controversial, and rightly so. I don’t think prisons should be profit maximizing. Their goal should not be to fill every bed and collect money from the government on a per-capita basis. Instead, prisons should receive bonuses for keeping repeat offenders out. Put the other way, they should be penalized when prisoners leave and get sent back. This would indicate the prison system failed. I’m simplifying for the sake of brevity but the broader point is this: for critical social services, the profit motivation should be replaced or enhanced by goals that maximize social welfare. We should not make a blanket assumption that government should run everything.

Simply put, I believe that government should privatize as much as possible and should preserve the ability to influence the bottom line of its vendors. I call this Reaganism 2.0.

Profitability is ideal

Traditionally, conservatism was fiscal. Conservatives promoted cuts in taxes and spending, yielding a smaller government that met its current obligations without increasing its deficit. Recently that brand of conservatism has faded away, as Trumpian economics have yielded tax cuts that served to increase our deficit despite an expanding economy.

However, there’s nothing inherently wrong with debt. Debt is merely an instrument for growth. But like any tool, overuse can wear it out. In good times, we should allow cash to pile up and spend it on the backlog of funding priorities: infrastructure, education, pensions, and health care. When times are bad, we should run in the red and borrow and pull from the rainy day fund, whichever has the lower cost of capital.

Although government is not a business, it can still be run like one, and take queues from the private sector that have shown over and over again that Ponzi schemes don’t last forever. Governments today are using a Madoff-like scheme, paying existing loans by borrowing evermore money. It’s not sustainable and old school Republicans would shake their heads in disgust with what happened under a Republican president and a Republican Congress in recent years.

Today’s Republicans do not represent the values this party once held, but this idea of profitability is still traditionally a more Republican value than a Democratic one. If the Republicans led with this platform, I'd be a more likely convert.

Freedom is fundamental

I like freedom. You do too. Freedom is fundamental to Americanism. Both parties wrap themselves in freedom's banner.

It's interesting how it cuts across the parties in different ways. Republicans hold up the second amendment, the right to carry arms and defend yourself, as the embodiment of freedom. Democrats apply the same principle to marriage, the freedom to marry a consenting adult regardless of gender pairing, and freedom to abort an unwanted pregnancy.

If you read headlines about these three examples: guns, gay marriage, and abortion, you'll find that freedom is controversial. It shouldn’t be. A small government, concerned only about the health and safety of its people, the security of its borders, and the stability of its neighbors, would not care about who wants to marry who. It wouldn’t have an opinion on what a woman decides with the guidance of her doctor and in the best interest of herself and her family. It wouldn’t care whether or not people want to own guns for hunting, protection, or hobby.

The barometer for when a government should restrict freedom is when it materially impacts the health and safety of its citizens. I have the freedom to move my fist through the air until it comes in contact with your jaw. I have the freedom to say whatever I want until my yelling "Fire!" in a crowded theater injures you in the stampede toward the exits. I have the freedom to bear arms until the prevalence of semi-automatic rifles makes it easy for criminals to acquire one and inflict mass casualties before police can respond. We have the freedom to abort a pregnancy until permanent mental and physical damage is done to mothers who decide too late.

Republicans and Democrats today talk a big game about freedom but do so selectively, applying it only to the freedoms they care about most. I believe freedom is universal, fundamental, and applies whether you like it or not, whether your Bible likes it or not, and whether it makes you uncomfortable or not. Unless that discomfort stems from a legitimate concern of social health and safety, the principal of small government and fundamental freedoms should supersede it.

Labor markets are efficient

The main issue that I would have running for office as a Democrat is that I am not inherently pro-Union. I'm very much pro-labor, pro-worker, pro-jobs and economy. But I'm probably closer to the Chambers of Commerce than the union halls when it comes to labor law. I should explain.

My experience dealing with union rules goes back to my first company, Scripped, which tried to make it easier for amateur screenwriters to sell scripts to Hollywood studios. There was one catch, though, and it was a big one. Studios had to buy scripts from the screenwriters' guild (a powerful union in Hollywood). So if you wanted to make it as a screenwriter, you had to join the guild and pony up.

The union, in other words, had a monopoly on screenwriters' access to studios. The history goes back to the early days of Hollywood when the large studios bullied writers around, agreeing in cartel-like fashion to blacklist writers. To combat this, the writers formed a union to increase their bargaining power and fight back against the wage reduction. This skirmish in the 1920s and 30s caused a wave that is still rocking Hollywood a century later.

My concern about unions is that while they are no longer as relevant, they hold onto the power and influence they have simply because they're so used to having it. We don't have one-company towns anymore. Labor is mobile, educated, and able to make noise with the drop of a tweet. The days of companies being able to bully workers around are, in most cases, long-gone.

The one exception I can think of is agriculture. We have a problem where seasonal workers, in search of jobs and willing to do hard labor in hot temperatures, end up living for months at a time on huge farms in Central California. The farms have all the power. I wouldn't be surprised if they took advantage of it, and those workers would benefit from union rights. Absolutely.

But let's look at blue collar workers here in the Bay Area for a moment. Most of them are union members. They are pipe fitters, longshoremen, carpenters, and plumbers. These are highly-skilled people doing technical work that’s in very high demand right now. May can charge upwards of $100 per hour for their residential services. California currently is in a crazy housing deficit and construction costs are sky high.

What is the union doing to help? Not much, from what I can tell. I’m not expecting anyone to volunteer a lower salary, but I would expect wages in a competitive labor market to plateau. The stories I read in Contra Costa County, where I live, tell of unions forcing developers to guarantee a certain amount of work for unions. If a developer wants to use non-union labor, they’re publicly shunned.

The economist side of me calls this anti-competitive and wrong. If I’m a steelworker and I’m bidding for a contract, I’ll justify my higher cost by touting my history of meeting deadlines, staying on budget, and producing great results. I’d tell the developer not to go with the cheaper guys, not to source from other areas, not to take a lower bid at the risk of paying more due to delays. I’ll lose some deals, but I’ll get some too, especially in a booming construction market. Furthermore, if I really care about blue collar workers, I’d be happy so many people are getting work, union or not.

This is how a free market economy would work. I’m fully aware that markets aren’t perfect. There certainly are confounding factors, but I’d put unions in that bucket.

This puts me out of favor with my local Democratic party establishment. The central committee and regional club leadership would not endorse me unless I fully back the unions. As a Democrat hoping run for office some day, this juncture is something I have to come to grips with.

Faith is important

I'm not a traditional God-fearing kind of guy, but I believe in higher powers. Birth is magical. Nature is incredible. Look into a blooming camellia flower and tell me that's not divinity staring back at you.

Since I wasn't raised going to church or synagogue, I had the freedom to learn and explore and develop my own relationship with religion. Because I wasn't told that I had to believe the Bible or the Torah or any particular Western god, I was able to go to church with one grandpa and synagogue with other and decide what I liked and didn't like about each. In high school and college I learned about Buddhism and Taoism and studied geography of religion. I went to Unitarian Universalist services in Berkeley with my friends. I thought about god and talked about god. It was fun.

Through all four years of high school choir I sang Negro spirituals, Catholic hymns, Jewish choir songs, and loads and loads of Christmas carols. I sang Ave Marias in Latin in Notre Dame and beautiful, sorrowful Jewish prayers in Anne Frank's house in Amsterdam. I was moved by it. The music and architecture that history's most talented artists have produced in the name of religion is awe-inspiring. Secular art simply doesn't pack the same punch.

Today my faith is closer to home. I believe in my family, that family is important and worthwhile and a source of inspiration. I want to be a good person not because of a commandment in a religious text, but because I want to raise good, happy kids. My church is my community, the neighborhood I live in, and the people I meet volunteering. I have faith that people want to feel safe, welcomed, and among those closest to them, loved. This faith forms the fabric of society, both the the macro and the micro. The same faith that binds the 10 homes nearest mine together also binds together the 100 million homes beyond it.

It’s faith, in a way, that makes me feel safe when I use a crosswalk in front of oncoming traffic or even when I’m just jogging along a residential street. I trust that the driver won’t run me or my kids over because they also want to live in a world where you can have that kind of trust in strangers. I put my life in the hands of other people several times a day. Most of the time I don’t even recognize it. But yes, that’s faith too.

So when I think of faith, I don't think merely of biblical texts and trinities. I think of the desires of an entire nation, and I believe that what everyone wants is good.

Indeed, faith is important. Without it we are less than human.

Conclusion

To really describe why I could be a Republican, I’d have to also describe why I could not be a Democrat. The fact is, I could go either way. It’s almost like deciding what to wear on a given day.

If I wear a tuxedo on Tuesday and a tank top on Wednesday, does it change who I am beneath the fabric? No, it doesn’t. But I’m looked at differently. That’s what the (D) and (R) do to voters. It’s just a label, but unfortunately party affiliation is not just a t-shirt you can take off and throw in the laundry. Instead, it's treated like a window to your soul, but it’s not that at all.

I’ve been around long enough to know that like the spectrum of visible light, people fill every shade of every color of the rainbow. It’s simply not possible to apply red or blue hue to every American. We’re not built like that. I’m not the only one.

So I leave open the possibility that I could one day switch parties. It won’t be because I’m suddenly all-in on Trump or Sanders. It will be because I’m not feeling this one shirt anymore and I want to try a different one. And if you interpret that one way or the other, well, that’s on you.

But I’ll try my best to explain.

Read Write Play: Q4 2019

2020-01-16T08:26:00-08:00

Last quarter I maintained a good mix of all three hobbies. My writing was the big focus, though, although you wouldn't notice it from my blog activity. I'll get to that.

On the play front, although I continue to progress on piano, the real story was that my wife and daughter started playing too. I'll recall the end of 2019 as the time when the rest of my family became musical. It makes me happy.

And reading, yes, I read some books about trees.

Read

I read a novel about trees and a non-fiction book about trees that was mentioned in the novel. The novel is The Overstory by Richard Powers and I really liked it. It follows a half dozen people and very cleverly incorporates different species of trees into each of their stories. It's written beautifully and parts of the story reminded me of my youthful environmental activism. Mostly, I learned a lot about trees and the people who study them.

In fact, on of the characters referenced a book, The Hidden Life of Trees, and since it sounded like a real book, I had to look it up. Indeed it was, and it was as described by the character, so I bought it. This one is essentially the diary of an arborist / naturalist / ecologist / forester type person who clearly loves and admires trees. The author, Peter Wohlleben, has convinced me that trees are sentient creatures, not unlike us, but live on a timeline that makes them seem inert.

Most trees live to be several hundred years old, so the stages of their lives last 3-4X longer than ours. The same applies to the growth and spread of forests. It all happens very slowly. The study of trees is the study of patience. I can see why the author had a zen-like aura about his work.

This quarter I expect to finish reading hardbacks of Daily Rituals and The Art of Profitability, both recommended by friends.

Finally, I've been reading East Bay Times. I signed up for the delivery and man oh man, what a treat to have real paper. I feel like a middle-aged suburban dad every time I walk down the driveway in my pajamas, stretch, and pick up the paper. But whatever, I am one.

Write

I must have written about 30,000 words in Q4 2019. Most of that work went into the novel I'm writing.

It's really exciting and has been a really fun project. I'm calling it The Jupiter Society. I've written it mainly in two sittings. The first was during my ({filename}a-few-days-of-radioactive-seclusion.md). The second was a couple of days in early December, back at the Sonoma Fairmont Mission Inn, where I wrote The Parallel Entrepreneur. That first retreat, back in December 2017, I was able to write about ({filename}how-i-wrote-17k-words-in-just-two-days.md). This time I beat that, clocking in about 18,000 over the same amount of time.

It's hard to describe how good it feels to sit and write for two days straight. It's such a treat, and I'm grateful my wife lets me do it (it was essentially her holiday gift to me) given the obligations I have at home. When I'm able to do nothing but write, I feel fulfilled, content, happy, and productive. I get some of that in my normal career and the entrepreneurial stuff I do that pays the bills, but there's something different about writing. I can't quite put my finger on what it is. Maybe it's authenticity? I feel like I'm most myself when I write words, rather than emails and code, which is most of my professional writing.

I've discovered also that fiction writing is a lot different than non-fiction writing. There are so many more decisions to make when writing a novel. With non-fiction the boundaries are pretty clear. I'm working within the confines of the real world, describing things that actually happened or actually could happen.

With a novel, I'm completely making it up. Every little detail is new. I can "cheat" and base characters around people I know and use places I'm familiar with when describing scenes, but those are just foundations. The details get created on the fly. From an infinite palette of colors, I have to choose one. It can be daunting, but I get used to making the choice and moving on. This is what makes writing exhilarating.

I hope to finish my novel in Q1 2020. Then I'll write to some publishers and see what happens.

Play

I'm playing, but I'm playing the same stuff I played all year. I've got "Don't Let The Sun Go Down On Me" down now, and I can also play Piano Man pretty well. I'm still singing along as much as I can, getting more comfortable with the high F's and G's.

I'm playing a lot more Beatles music because my daughters demand it and it's fun. Right now "Lady Madonna" is my go-to Beatles song. It's fun to play both fast and slow, drawing out chorus line, "Friiiiday niiiight arrives without a suuuuitcase." You could almost imagine Bing Crosby singing it.

As I put in my stated ({filename}my-next-10-years.md), I want to be as comfortable on piano as I am on guitar. It's already starting to happen and I'm very, very pleased about that. Every quarter I'm getting noticeably better at playing and singing.

The case for decentralized workforces

2020-01-16T06:12:00-08:00

Spoiler alert!

At the end of Season 5 of HBO's Silicon Valley, Richard Hendrix, the CEO of Pied Piper whose company built the world’s first “decentralized Internet,” steps into his massive new headquarters and pukes. It’s a running theme in the season: Richard is deathly afraid of public speaking. When the CFO-type executive on his team tells him they need to plan to hire 500 engineers, his stomach turns and he vomits.

The irony here is this: Richard loves decentralization, the complete distribution of assets and information, and proselytizes the virtues of not putting everything of value under the same roof. And yet he allows this to happen with his own people. All Pied Piper employees must work, literally, under the same roof. Perhaps his stomach is so upset because he’s aware of this irony: his employees should be decentralized, too.

This version of Pied Piper wouldn’t make for such great television, of course. We wouldn’t get the awkward dynamic between Gilfoyle, the long-haired bearded chief engineer and the pretty young CFO. There wouldn’t be the hilarious exchanges between eager-to-please COO Jared and the aloof CEO Richard. It would all play out differently in real-life scenarios too. I’ll get to that.

The costs of remote working are real, but so are the benefits. I’m a firm believer that the benefits outweigh the costs and I’ll do my darnedest here to prove it out.

What is a remote or distributed workforce?

In short, a distributed team is one that doesn’t have an office. It’s decentralized. It means that the company can hire workers in any location in the world. By leveraging the Internet, managers can assign tasks, monitor performance, communicate in real-time, and submit paychecks to anyone, anywhere. There are literally hundreds of products available to move every esoteric piece of the office machinery puzzle into the cloud. Here are just a few of them:

Communication

The number one concern I hear from my executive friends who worry about the impact of ditching their office revolves around performance management. They worry that people will slack off, become less engaged, and that managers won’t see the telltale signs of an employee who’s about to quit. I’ll explain how each of the tools here can be used to mitigate that concern.

Google GSuite: email, calendar, documents, and file storage

Google GSuite includes a bunch of other office tools like shared documents, shared drives, and calendars which frankly are essential now whether or not your team is distributed. Every startup I know uses them, remote or otherwise.

Email is still the dominant communication medium in business, and it can be used as a proxy for engagement. Since usage of email will vary greatly across employees, what managers need to be aware of is a decrease in engagement, which means taking longer to respond and not sending as many emails. GSuite has ways of measuring this or your can build your own monitoring tool. There’s similar monitoring that can be done for GSuite’s calendar feature.

For the most part, though, GSuite is not a tool for monitoring productivity. It’s a suite of office communication tools that are awesome whether you’re in an office or remote. When you’re remote, you probably end up sending more emails, so you should have the best email tooling to support that communication. Google is it.

Slack: chat, group chat, video call, screenshare

Slack, in case you’re new to tech office culture in the late 2010’s, is an office chat tool that swiftly replaced Yammer as the de facto go-between for phone calls and emails. It's essentially a virtual water cooler and productivity suite rolled up in one.

Slack activity cuts both ways. Employees who are constantly on Slack may actually be unproductive, socializing rather than working. A lot has been written about how being constantly tethered to a chat app can negatively impact office culture. There are options available to Slack admins to monitor engagement here too.

Zoom: video conference and screenshare

Regular team video chats are a very effective tool. A Zoom video call with the team goes a long way toward getting everyone on the same page and remaining connected to the company.

I do a daily 15 minute “stand up” video call where each of my remote teammates checks in and says what they did the previous day and what they plan to do today. As a manager, it’s very efficient, and it helps me feel connected to my team.

Trello, Asana: project management

These are tools that are equally effective for centralized and decentralized teams. Even if we had an office, we’d still want to stay organized by using Trello, which is essentially an online shared post-it board (with some very clever enhancements.)

These simple yet powerful tools provide the equivalent of a white board. Combined with a video conference that allows you to share your screen, it’s about as effective a brainstorming tool as it gets. They make for a fully functional virtual conference room.

Off-sites and retreats

Proponents of distributed workforces aren’t hermits who never like to meet in person. On the contrary, remote teams make a point of scheduling a company meeting at least once a year. They take the money they’ve saved by not paying office rent and deploy a fraction of it on a nice resort.

The fully-remote companies in the Xenon Partners private equity portfolio that I’m involved with have team meetups all over the world, most recently in Hawaii, Las Vegas, Tokyo, and Sydney. The distributed team behind Hunter.io chooses a new location in Europe every year. Zapier meets in Hawaii. Customer.io and Baremetrics fly employees out to exotic locales too.

When you don’t see your teammates face-to-face every day, these company retreats hold a deeper purpose. You feel more motivated to attend, engage, and make the most of that time together. I do this twice a year with my team. We’ve met in Las Vegas, where one of my employees lives, and in Walnut Creek, where I live. I think our next one will be in Arizona or New Mexico, just because.

Payments

Most of this operational technology is used by traditional companies as well. Remote or local, the days of printing out paychecks and handing them out on Fridays are long gone. Salaries for employees and contractors alike are paid electronically and it’s easier than ever to make those payments, administer benefits, and account for taxes.

Bill.com: invoicing and accounting

I’ve used Bill.com at every large startup I’ve been involved with. It’s simply the best way to handle vendors, customers, and the related (and seemingly endless) accounting tasks involved with doing it right. Bill.com is not perfect but it’s about as good as it reasonably gets.

Justworks, Gusto, Zenefits: payroll and insurance

HR tech is a fascinating segment of the startup market, and these three are the market leaders in payroll (primarily for W2 employees) and health benefits. If you’re going to have employees, you need one of these tools. Doesn’t matter if you’re remote or not.

Engineering

Engineering is usually the first department to let go remote. Monitoring performance is the same no matter what your office situation is. How many issues did the engineer solve? Is he or she submitting or reviewing pull requests on time? Did the code have bugs?

The benefit of having engineers in office are largely social. Killer ideas can be conjured in hallway discussions, over lunches and happy hours, and yes, sometimes it will even happen in conference rooms. But do you need these employees to move themselves from one location to another twice a day, sometimes in hours of traffic, just for a daily opportunity to bump into each other? I say no, and I’ll explain why in the summary.

AWS, Digital Ocean: hosting, database management, etc, etc.

There’s no longer a need for in-house servers. Even if you wanted to manage your own hardware, it’s better to go through a colocation facility where you can install your own rack in an air-conditioned building with backup power. Or borrow Amazon’s hardware instead. My point is, you no longer need to keep servers in the office closet. Don't kid yourself; it’s pointless.

GitHub, Bitbucket: code repository

A code repository is like the main file cabinet for all of your engineering output. GitHub is the most well-known of them but there are others.

This system allows teams of pretty much any size to collaborate on libraries of code without stepping on each other’s toes. It’s a brilliant system that allows anyone to create, merge, and revert copies of the code. The entire history is logically recorded. Git, as the versioning system is called, is actually pretty magical. GitHub and others add a pleasant web interface to git and a bunch of complimentary features for tracking, commenting, and approving code changes.

Summary

The tools are readily available to help those who manage people who are on computers all day do their jobs remotely. The only rationale for making people work on computers in an office when they could do the exact same work at home is this:

I dunno. It's how we've always done it and I just think people should work in an office.

- Too many executives

And that, I suppose, is a fair point. If there's no desire to change then it won't happen. Employees have to make noise, try to get management to move an inch, and build a case for what's in it for the company. Those benefits in bulleted form are (each could be a separate blog post):

Higher productivity. I'm convinced people who work from home get more done. - Lower turnover. Contrary to management's fears, people who work from home are happier with their employers and less likely to leave.- Better candidates. When you can hire someone anywhere in the world, you get the best of the best.- Lower wages, sometimes. The best people know what they're worth, but there's still a fair cost of living adjustment that can be bargained. - Lower operational overhead, always. Think about this. No office, no snacks, no team lunches, no receptionist, no paper towel and toilet paper restocking. You can still offer perks like gym memberships, and maybe be more generous with bonuses because of these operational savings, but the cost cutting here is huge.

I think this tweet sums it up well.

My next 10 years

2019-12-31T12:05:00-08:00

I started writing this post back in July 2019. Since 2020 is almost up, I figured now would be a good time to finish it.

These past ten years have been all about myself: My education, my companies, my career, my health, and my family.

The ten years before my 25th birthday I was more worldly, interested in large-scale environmental problems. It’s what I cared about in high school and what I studied and focused on in college.

Ten years from now I hope that’s what I’m into again. To get there, I have to solve a few things locally first.

I live in one of the most expensive areas in the country. I love Lamorinda (Lafayette, Walnut Creek, Moraga) but leaving here with two kids means I need a lot of money. About 12 years ago I decided not to pursue a career in environmental non-profits and instead have taken a decade-long detour through the private sector. I figured it’d be an education and also an opportunity to find financial freedom.

My first bet on a huge windfall didn't work out, but I’ve been placing smaller bets over the last few years, and a few of them have paid off. My new CEO job at MightySignal pays well, has some decent upside if it really works out, and is a lot of fun. I still have side projects, being the parallel entrepreneur I've written about and all, and these require just a few hours a week to maintain. If I can keep growing my side income without putting more time into it (so I can keep doing a good job at MightySignal), then financial freedom will come. And once I have that, I can focus my attention elsewhere.

There’s a lot that's been happening in the world today while I’ve had my head down, saving money and raising a family (very much in partnership with my wife, on both fronts.) I pay attention to the news. Sometimes I write and tweet about it, but most of the time I feel overwhelmed. What's a suburban dad like myself supposed to do to fix our climate chaos? What am I supposed to do about homelessness and the real estate crisis in California?

I don't really know, so I've been trying out a few different things. I joined a new regional environmental organization, the Contra Costa Climate Action Network, which is an umbrella group of sorts for all the eco groups in my area. We coordinate on actions, talk about the county general plan, and collectively try to figure out how "think globally, act locally" applies to us. I also got placed on the county sustainability commission which has provided even more insights into how Contra Costa operates. It's eye-opening and I could see myself running for my county supervisor office in a few years.

On the economic development side, I've very happily been active with Diablo Valley College this year. I applied to be an instructor at DVC (as of this writing, still haven't heard back) and managed to be among the founding group of the Diablo Valley Tech Initiative. At its best, DVTI will help bring tech jobs into the county, thereby reducing commute times (and GHG emissions), and help local residents get access to higher paying tech jobs.

Although my neighborhood is very homogenous (I'll just say it -- "white" -- the one knock I have on where I live), I believe there's opportunity to bring more diversity into the nicer neighborhoods like mine by giving the less-white neighborhoods in the Diablo Valley the access to education they need to get these jobs and the paychecks that come with them. DVC is the vector for that change, so I'm optimistic that the hours I've been putting into DVC are time well-spent.

But for the most part, I've opted to solve my own problems first. Here's the year-by-year of what I did in the 2010's and a checklist for what I hope to accomplish in the 2020's.

2010

First Scripped co-founder breakup (3 down to 2)- Got married- Started a sales job at Rapleaf- Sold my stake in B2G Media, a gov tech consultancy- Started playing squash and road biking- Sentiment: broke but happy

2011

Pivoted from B2G Media to Scripted- Launched Scripted.com- Left Rapleaf to go back on Scripted full-time- Learned to scrape websites with Python- Raised $1M for Scripted from Crosslink Capital- Moved into our first Scripted office- Hired our first Scripted employees- Sentiment: the world is my oyster

2012

Started Toofr, my side hustle in PHP CodeIgniter- Started re-building Scripted.com- Registered Toofr LLC and started consulting for Rapleaf- Sentiment: programming is fun

2013

Launched Toofr.com- Sold Scripped.com - Raised $4M for Scripted from Redpoint Ventures- Sentiment: multiple revenue streams is better than one

2014

First daughter born- Raised another $9M for Scripted from Storm Ventures- Toofr started to make some real income- Got a house down payment from Scripted secondary stock sale- Became President of the UC Berkeley UC Berkeley Nature Alumni Association- Sentiment: look at the bigger picture

2015

Second founder breakup at Scripted (2 down to 1)- Started to learn Ruby on Rails and re-wrote Toofr in Rails- Toofr paid me more than my Scripted salary- Bought a house and moved to the suburbs- Got our dog Blue and a Weber grill- Stopped playing squash and road biking- Sentiment: all grown up

2016

First round of layoffs at Scripted- Second daughter born- Toofr began paying me more than Scripted- Became the third CEO of Scripted- Launched Thinbox.com- Launched eNPS.co- Sentiment: business can be unpredictable

2017

Found out I had thyroid cancer- Second round of layoffs at Scripted- Sold Scripted to Xenon Partners- Bought my first car, a Hyundai Santa Fe- Launched TrackJobChanges.com- Launched VoxLoca.com- Launched GList.io- Sentiment: life can be unpredictable too so make and take as much money as you can

2018

Published my first book, The Parallel Entrepreneur- Happily ran my portfolio of small businesses from home- Sold Toofr and paved our side yard- Got hired to be CEO of MightySignal, a Xenon Partners portfolio company- Didn't launch anything(!)- Sentiment: learn from the best to become one of the best

2019

Took voice and piano lessons and began to enjoy performing music again- Started writing a novel- Paid off the Hyundai- Swallowed some radioactive iodine- Turned my daughters into huge Beatles fans- Paid down the mortgage- Found a partner for my side projects- Remained CEO of MightySignal- Launched MyKidColors.com- Sentiment: teamwork makes the dream work

2020's

And here's what I hope for myself this next decade. Basically, I want to do more of the same, and my definition of success is being able to pay off the mortgage. When my family is completely debt-free I'll be able to retire from tech and start the public career I've been thinking about since high school.

Get a book published by a real publishing house- Pay off the mortgage; be completely debt-free- Start teaching, either in person at DVC or online with my own courses- Launch 10 new companies- Sell at least two of them- Buy at least one (small) company and run it and sell it too- Retire from tech and run for public office- End the 2020's with my weight same as it is now: ~210 lbs- Be as comfortable on piano as I am on guitar

Summary

It was interesting to go back through the many web apps I've built and mark down which year I launched them. I didn't realize I launched three apps in 2017. It's probably no coincidence that this was also a crazy year. My second daughter was just born, the startup I'd pinned my financial dreams on was falling apart, and I was diagnosed with cancer.

That's a lot to deal with separately, but in early 2017 it happened all at once. My reaction was to build even more.

Sometime in the 2020s I hope to retire from tech. It will be weird to not have this as a creative outlet, but I'm confident I'll be able to channel this same entrepreneurial energy into a campaign for office, and once I'm in office, into campaigns for whatever I'm working on.

The world, alas, doesn't need more web apps. What it needs is better politicians.

How chess and entrepreneurship are the same

2019-11-28T21:10:00-08:00

I’ve always been a decent chess player, but recently I’ve started playing a lot more. Like, a lot more. I am happily addicted to the beautiful game once again.

I learned to play when I was really young and have always enjoyed chess despite the fact that I haven’t improved all that much in the past 30 years. Before there was ubiquitous internet, my uncle and I used to play chess by mail. I had a little paper board and we’d mail our chess moves back and forth with little notes.

Then I got an electronic chess board and soon after that I played chess on my Gameboy. Eventually my mom bought a PC for our house and I played chess on that. Then the internet showed up when I was in middle school and I remember playing online chess on Yahoo, amazed that I could be randomly paired up with someone halfway around the world to play a live chess game.

This was the first time I became familiar with chess scoring and I think I peaked in the low 1600s when I was really into playing chess in high school. I joined the chess club and played games during lunch. I remember there was a group of boys who would hang around the classroom where we played and sneer at us. My friends and I dubbed them the “Chess Club Bullies.” We didn’t mind them at all, noting how absurd their focus on us was.

Around this time my uncle introduced me to Chess.com, and I’ve been playing there ever since. I thought I’d get more into it in college at UC Berkeley, but I fell into other interests. My chess playing at Berkeley was primarily with my friend Howard Chong, who was perfectly matched with me. We played some great games. But the most memorable experience I had playing chess at Cal was with Walter.

I never found out what Walter’s deal was. Anybody at Cal in the early 2000s would remember him. He was a funny, friendly Black man with a beret who kept a chess board on display where Telegraph t-bones into Bancroft at one of the major entrances to the Cal campus, just steps from the famous Sather Gate. Walter played speed chess and talked jive. Games cost a dollar and he always won. I still remember his voice.

“Awww here come the pusher man!” he’d exclaim as I sent my pawns down the board.

“You know what they say ‘bout pressure? They say it bust a steel pipe,” he’d tease as he attacked my knights and bishops, plopping his pieces down hard on the board.

“If you not careful Imma take yo bitch,” he’d say whenever he attacked my queen.

We always played with a clock, and as he got to know me he’d set the timer so he had three minutes and I had five, giving me a generous two minute advantage. I’d still often lose on time. And since Walter and his chess board were between my classes and my house, I lost a lot of dollar bills. I gained those memories though, and an appreciation for this style of chess that players call “blitz.” It’s all I’m playing these days: five minutes per side blitz.

When I need to take a quick break from work, instead of going to social media or YouTube, I’ll play a blitz game. Then it’s back to my day job, entrepreneurship, which is a much longer type of game, but there are a lot of similarities.

If you haven't inferred from the title, I’m going to point out a few of them here.

There are three main strategies that any guide to chess will describe. First, you should try to control the center of the board. The most commonly played chess openings are all variations on this strategy. The four squares in the center of the board are the most important and if you play your pieces up the side of the board, you will probably lose the game.

Second, you need to develop all of your pieces. Your opponent will have an advantage if you leave a knight or bishop in its initial position behind the row of pawns. That piece might as well be off the board. Players who develop all of their pieces early in the game have the best chance of winning.

Finally, the other goal is to protect your king. If you’re unfamiliar with chess, the goal of the game is to “checkmate” your opponent’s king, which means to attack the king and prevent his escape. You’re given one opportunity to “castle” during the game, which allows you to move the king from the center of the board to the side and swing a rook around to protect him. It’s the only chance you have to move two pieces in a single turn. So under most circumstances, your third goal basically is to castle.

As I look at this, and since I’ve recently fallen back in love with the game just as I’m hitting my tenth year in entrepreneurship, I see some loud and clear parallels. Chess parallels real life in many ways, but the startup game is a great analogy. Check this out.

Chess rule #1: Control the center

(Startup rule #1: Be the first mover)

I’ve written about this before. The faster you can get to market, establish your brand, get customer feedback, and cement yourself in position, the better your chances of surviving the rest of the game.

Google rewards seniority and it takes time for customers to familiarize themselves with a new brand. Controlling the center of the board means your brand becomes synonymous with the market (i.e. the brand has become a verb, like “to Uber”, or a noun, like “a Kleenex”).

Incumbent positions are very hard to move. There are examples where it has happened (Facebook taking over MySpace and Friendster, Google taking over Yahoo and AltaVista) but those are cases where, to use my next chess analogy, the upstarts developed their pieces faster and essentially castled with a superior product. The other guys didn’t see the threat, so they didn’t castle and didn’t develop all of their pieces.

Chess rule #2: Develop your pieces

(Startup rule #2: Develop multiple channels)

The single most important thing I’ve learned as entrepreneur recently is the importance of developing multiple channels of customer acquisition. The best way to remain competitive in a dynamic market is to have SEO, PPC, sales, and customer referrals all working simultaneously for your business. If the PPC industry changes, it’s okay, you don’t need it. If Google changes its algorithm again and your organic traffic drops, it’s okay, you’re not depending on it. You have multiple products, multiple approaches to your customers. You’re resilient.

Building a chess attack is the same way. If you see a vulnerability in your opponent’s pawn structure, don’t just put your queen right in front of it. Point your bishop at it, get a knight or two close by. Start pushing pawns in that direction. The combined impact will be greater than the sum of its parts. Even if you don’t know exactly how these pieces will work in unison, it doesn’t matter. Their presence will change the dynamic of the game.

Your business funnel works the same way. Reach out to customers via sales reps and cold email marketing. Make them see you on social media using pay-per-click (PPC) ads. When they search for a solution like yours, make them see you in the search results. Be relentless in this strategy and you will see results.

Chess rule #3: Castle early

(Startup rule #3: Build a moat)

If you try to sell all or part of your business (selling a part = fundraising) then you will inevitably be asked how “defensible” your business is. A defensible business is one that is difficult to replicate. It’s the billion active users that Facebook has. It’s the billions of dollars that Google invested in perfecting its search algorithm. It’s the secret formula that makes Coke. It’s the Nike swoosh and their athlete endorsements.

Moats come a lot of different forms, but the common thread is that they are difficult, if not impossible, to replicate. The moat makes your core product impenetrable. No one else can have the Nike swoosh logo. No one else can have Tiger Woods and Michael Jordan endorsements. For Facebook it’s users, for Google it’s algorithms. These are trade secrets, company assets, specific R&D that an upstart will need to climb mountains to overcome.

The castle in chess is similar. It’s a unique opportunity to protect your most valuable asset: the king. It’s what makes your opponent have to work harder, smarter, and be more clever to gain the upper hand. If you don’t castle, your king remains in the center of the board. He’s protected by a line of pawns, but he’s vulnerable. Leave him exposed at your peril. Your opponent will thank you. The best chess players will castle except in the rare circumstances where an attack is so timely that it cannot afford the loss of tempo to protect the king. These games are highly unusual and result from an opponent failing to adhere to the previous two rules.

Beyond these three chess rules and their startup analogies, which mostly apply to openings, I have a few more general parallels that are most analogous to middle and end games in both chess and entrepreneurship.

Chess strategy: Study openings

(Startup strategy: Use a playbook)

Chess openings and marketing playbooks are very similar. They prescribe a set of moves that are designed and tested to maximize the likelihood of a win. There are countless variations of chess openings (go ahead and search YouTube for Kings Pawn, Queen’s Pawn, Queen’s Gambit, Sicilian Defense). Likewise, there are many variations of startup launch and funnel optimization playbooks.

Startup playbooks will contain things like tools to use, analytics to track, pages to create, and experiments to run. They usually start with a single landing page and go through the development of multiple channels (see the second rule above) and suggestions about when to make hires and fundraise. Playbooks are just like chess openings: they suggest a route forward and give you variations to try, depending on how your opponent (or the market) reacts.

Even if you don’t follow a playbook to its letter, they’re still good study, because your competitors will likely use the same techniques. I don’t see a downside to being prepared and understanding the cultural zeitgeist. You may dismiss the playbooks, but it’s better to make that decision consciously.

Chess strategy: Wait for mistakes

(Startup strategy: Look for market openings)

At my current chess level (a bit above average), my opponents still make mistakes. Chess.com actually does a great job of analyzing games that I’ve completed and coaching me through my own mistakes. It scores my every move! This is one of the reasons why I’m so addicted.

Some games I’ve played have been simply to avoid making a mistake like dropping a piece or leaving a vulnerable pawn. Playing a tough defense can force my opponents to make brash moves, leaving open an opportunity to fork a valuable piece. If I’m patient, I can capitalize on my opponent’s mistakes.

The same can be said for startups, except it’s usually not a single competitor that opens a line of attack. Sometimes it’s an entire market or industry that moves its aggregate demand towards your product. In the span of just a few months, like a flock of sheep, customers can suddenly start knocking down your door, asking for demos and pricing sheets. Sometimes this takes years. You have to be patient.

The most successful businesses in the world sometimes just have to wait for their time to come. Salesforce in its movement away from box software and onto online “software-as-a-service” business modeling comes to mind. Amazon started selling books before all of America realized it wanted to have the world’s largest retailer offer free two-day shipping. The business world swung toward Salesforce. The consumer market swung toward Netflix and Amazon. It happened over many years.

Chess strategy: Balance attacks and defense

(Startup strategy: Don’t over-invest in sales or engineering)

Building out a sales team is an offensive strategy. Building out product is a defensive one. The best companies are able to do both, but most companies don’t have the resources or time to do that effectively.

Chess is the same way. If you go all-in on offense, you inevitably leave your king vulnerable to attack. If you go all-in on defense, you fail to develop your pieces and in the long-run are likely to succumb to your opponent’s offensive attack. In chess, as in startups, a balanced approach is best.

The common tendency in tech startups is to over-invest in product and under-invest in marketing. Usually this happens because the founding team is rarely made up of marketers; rather, the founders tend to be engineers. Engineers typically don’t enjoy sales and marketing, so those bits get less focus early on. There’s a sense that the product should market and sell itself. While this is true in some lightning-in-a-bottle cases, it’s not true most of the time. Even a brilliant product needs help to see daylight, and in today’s saturated business environment, that’s a difficult feat.

The perspective I’ve gained recently as a general manager at a private equity firm shows that many companies stall in their growth, despite raising millions of dollars in venture financing. If all that money is spent on product development, when the investors pull back and ask for profitability, the company is suddenly extremely vulnerable. In those cases, they sell for far less than what they raised.

When private equity firms purchase these companies, they take the opposite approach: invest much more into sales and marketing than product and engineering. Even though we all feel the magnetic pull of boosting our engineering budget, we’re intentionally constrained. Hiring an engineer requires extensive justification from my board; hiring a marketer basically gets rubber stamped. The thinking is basically, “If over-investing in engineering got the company into this position, why would be continue doing the same thing?”

I say, like a good chess player, you should balance offense and defense. Make offensive moves (sales and marketing) when there’s an opening to capture pieces. Make defensive moves (product and engineering) when the marketing needs aren’t so clear.

Chess strategy: Watch the clock

(Startup strategy: Don’t agonize over decisions)

This is how Walter was so good and why I gave him so much of my lunch money. He moved fast.

These days, I continue to lose and win a lot of games on the clock. If I take too long to make moves early on, I’m likely to lose on time later in the game. On the other hand, if I can see that my opponent is taking a long time on each move, it gives me confidence. I know he’s going to feel the pressure and I can play my game differently and take fewer risks because the clock becomes my weapon.

Similarly, I’ve been in many business situations where I’ve watched my colleagues agonize over decisions. Sometimes we’d make a decision and re-litigate it a week later. It was demoralizing; it felt like we could never move forward because decisions were never final.

In business, as in chess, you need to have a strategy (for example, to balance marketing and product investments) and stick to it long enough to gather data and then adjust the approach. There’s no benefit to circuitously rehashing old ideas. Pick a tact and go for it. If it turns out to be the wrong approach, then adjust.

Adjustments happen in chess all the time. You may assume your opponent has a sequence of moves in mind and set your strategy accordingly, only to discover that he had a completely line of attack. With this new info, your original idea was flawed, so you change it. If you spend too much time thinking through every possible outcome you’ll lose. The clock will run out.

In business, the clock is cash. Whether you move left, right, or straight, the cash clock keeps running. Use that time to learn something.

Make a move.

Read Write Play: Q3 2019

2019-11-18T22:11:00-08:00

In just a couple of months I will have been tracking my RWP for two years. Not bad for a silly little trope that nobody (except me) cares about. I try to be consistent in what I do, though, and being conscious of the RWP is just as important to me as the RWP itself.

To put it another way, when there's so much noise, so much to care about and be stressed out about and want to care about, it's nice to be able to shove it all aside because I've already distilled it all down to three things that actually matter. Indeed, these three things that are always going to be alone-time well-spent: Reading, writing, and playing (music).

Read

Well, I basically failed my design curriculum. I really meant to get into it, but I got distracted. I'm not sure if or when I'll pick it back up. I want to learn to draw better, but that kind of itch is getting scratched by my piano playing, which I'll describe below. I feel like that's my physical art, and when my kids are drawing, I can be in the same room with them playing piano. It's what I want to do and it makes me happy, so I'm not going to fight it.

Instead, I started reading Save the Cat!, a book about screenwriting that could be applied to any kind of writing. It was recommended to me by a neighbor and I thought it prudent since I am working on my first novel and am about halfway through writing it. Save The Cat has good ideas about character and story development. I think about it as I edit my half-written novel. I'm also about halfway through Save The Cat. Someday I will finish it.

One night I didn't feel like working or watching television or playing chess. I pulled up the Kindle Store and quickly settled in on The Overstory by Richard Powers. It's a long book. It took me about three weeks of reading at night to get through it, and I thought the ending dragged on a ways, but I thoroughly enjoyed it. It's a book about people and the environment. More specifically, it's about different peoples' interactions with trees. Many parts of the book are moving and beautiful. The writing reminds me of Paulo Coelho or Gabriel García Márquez.

As soon as I finished The Overstory, I started reading a book, The Hidden Life of Trees by Peter Wohlleben, that Richard Powers referenced. I'll write more about this book next time.

So, true to form, I read one long book in Q3. The march continues.

Write

I'm happy to report that there was a lot of writing happening in Q3 2019! I started a novel and gave a 5,000 word speech at Diablo Valley College. If I include the smattering of blog posts I bet I wrote more than 40,000 words last quarter. That's a hefty amount.

I mentioned my novel in this blog post about the radioactive seclusion I had to endure in August 2019. This wasn't a physical hardship. There was some mental stress, I suppose, but fortunately everything worked out fine, and I got to take advantage of a "doctor's orders" excuse to be secluded with my dad at my family's cabin at my happy place. I had four nights and five days up there, able to set my own schedule, unbound by the family routine back home.

I used this reprieve to start a novel that had been banging around in my head for months. I wrote a short outline and gave myself at least five hours each day to sit and write. In all I cranked out over 25,000 words and I managed to write another 7,000 after I got home. Progress has slowed down significantly since then, but I'm not too worried about it. I'll pick it back up at a writing retreat or something similar this winter. I really want to get the first draft done.

Part of the reason it stalled is I had another writing project, a big speech at Diablo Valley College. I gave a talk about four simple truths about entrepreneurship. I had over an hour to stand in front of a bunch of people and talk. I did the math and figured if I had no slides, I would need a speech of about 5,000 words to fill that time. So, I wrote it. I felt pretty good about how it all went.

That speech and my follow-up post about dealing with public speaking panic attacks performed relatively well on my blog. My personal favorite, though, is the post I wrote about becoming a better public singer with my neighbors on one sunny day at the end of summer. I really enjoyed it. The blog post has some videos.

Play

In September I bid farewell to the Baldwin 7 foot parlor grand piano that I inherited from my grandparents. It just wasn't practical to have a piano this size in our small home. And although we kept it for nearly four years, it was time to let it go and let the room where we kept it turn into something else.

I still needed a piano, of course, and looked all around for good uprights. I played some at the Music Exchange in Walnut Creek but since the grand was all I knew, these pianos just didn't sound right. They were tinny and shrill compared to the broad, warm tones of my Baldwin. It was really disappointing to make the step down. Then, one day at Music Exchange, I sat down at one of the Yamaha Clavinova digital pianos in the showroom. I loved it. I loved everything about it. The weighted keys, the tone, the look, the sound. Best of all, they were priced the same as a used upright piano. I had to convince my wife that this wasn't some dinky synthesizer, that it was basically the same thing as an upright piano, except a lot better.

She agreed to trust me and I was able to find a family in Alamo who had the space and the desire for our piano. I sold it and with money to spare I bought the Clavinova. I'd like to say I miss my grandparents' piano, but I don't. I love the Clav, and since I can adjust the volume and play piano in the same room where my girls are drawing, I play a lot more. Like, a LOT more. This is all that would have mattered to my grandparents. They just want to know that music is being played. I know it.

![Piano before and after]({static}/images/2019/11/75e3344b-d2e8-4b2a-8273-e971326eb94a.jpg) ![Piano before and after]({static}/images/2019/11/a20c1926-f200-425c-8159-bf7fd7634aa9.jpg) *After and before.*

So, I paused my piano lessons while this transition took place. When I contacted my piano teacher again, I was happy to introduce her to two new pupils: my wife and my oldest daughter. All of my piano practicing has finally paid off: two more people are learning to play.

In the meantime, I'm going over the same songs I've been playing since the first RWP, but doing a lot better. I've been wanting to play Bennie and The Jets for years. Just this past month I settled in and focused on it, and I had it down within a week. I'm now able to play multiple inversions of common chords by sight. Crazy chords like F#m7 will trip me up, but I'm seeing now how relative minors factor in. That F#m7 chord has the same notes as an A chord. So I play an A, which I already know, and put an F# octave on the base. Boom: F#m7.

I also continue to sing along with the Elton John tunes, even though they're out of my range. I keep hoping one day I'll wake up and be able to sing a high G as well as Billy Joel, but that day hasn't come yet.

I'm still playing guitar too, mostly because my oldest daughter has become obsessed with The Beatles. It's the cutest thing, and a proud dad moment for me. I bought a book of Beatles songs on a whim at a music shop near my house that was closing. I figured it'd be nice to have on hand. What I couldn't have known then, and what I still can't believe, is that my daughter would use this book to teach herself to read by listening to Beatles songs and following the lyrics. Often, instead of asking Alexa, I'll play along on guitar and sing with her.

Tonight, when I put her to bed, we sang "You Like Me Too Much" and "Here Comes The Sun."

The girl loves George Harrison.

Becoming a better public singer

2019-10-17T10:36:00-07:00

Public speaking is for wimps. Try public singing.

This past Sunday I invited a dozen of my neighbors and their families to our house. They started to arrive around 3pm, just as a few select neighbors pulled up with their guitars and bass amps. I’d spent the preceding several weeks acquiring some new equipment:

Two Shure SM58 mics- A Mackie 6-track mixer- Four power strips- Four XLR cables- Two music stands- Two mic stands with booms- Two FetHead mic preamps

I already had the small PA speaker we used to use for Scripted panels. It packed a punch and had two 1/4 and XLR plugs in the back. The Mackie mixer I got also included some nice vocal effects, including a digital delay commonly used on vocal track recordings. When everything was plugged in, it sounded pretty good.

Total cost was about $400. Benefit was priceless. ROI was infinite.

This was the second time I organized one of these backyard concerts. The first was back in May, prior to the show I did with the Rolling Sloans for my 10th graduate school reunion. I wanted to practice singing in front of an audience, so my neighbor and I did an all-acoustic set. No mics, although I did play my electric guitar through an amp and used a couple of effects pedals. My neighbors loved it, but the kids reacted the best. They were amazed, somewhat in awe, and it seemed to relax everyone. We had maybe a dozen kids and literally there was not a single meltdown. Everyone stayed late.

This time we were louder and although the kids did love it, I can’t say there were no tears. The first event must have been a miraculous fluke of nature. The feedback, still, was overwhelmingly positive. They said we sounded great. My wife, who would not be subtle about critiquing the performance, said it sounded like this is something I normally do. She said if she walked in and didn’t know me, she’d hear the music and singing and think, “That’s nice. He must do this a lot.” That’s all I was hoping for.

I wrote recently about dealing with public speaking panic attacks. Here’s a summary of what I’ve learned in the last year about public singing.

It takes repetition

I started taking voice and piano lessons last year, about ten months ago now. We’d meet every other week and spend about 45 minutes, half on piano and half on voice. As my Rolling Sloans concert got closer, we focused mainly on voice.

I remember being nervous at our first lesson. I wasn’t used to singing in front of anyone, not even my wife. But the thing is, I love music, and I want to be able to perform. I want to have a repertoire I can bust out whenever the moment calls for it. I told my teacher that’s my goal: to have a set of songs I can sing any time, two drinks deep or stone cold sober.

It turned out I was drawn to songs just out of my upper range. Even though I can sing high, I can’t match Elton John's or Paul Simon's or Paul McCartney’s high G’s. It’s not going to sound good, and I shouldn’t be shy about changing the key.

Figuring this out, getting comfortable with it, and learning about the strengths and weaknesses of my voice simply takes time. I’m ten months in and still getting started, but I’m a heck of a lot better than I was in January.

It takes courage

The fear of public singing doesn’t diminish with age. I’d assumed when I was younger, struggling to sing in front my family over campfires, that at some point I’d suddenly find my voice, enjoy singing in public, and everything would fall into place.

It turns out that’s not the way it works. Public singing doesn’t get easier simply by getting older. It takes repetition, as I just said, but it also takes courage. My singing teacher told me the worst thing you can do when performing is feel insecure. The audience will feel your discomfort and that will make them uncomfortable. Nobody wants to watch some squirm in the spotlight. On the contrary, people are drawn to those who are extremely comfortable and confident when all eyes are on them. This is an aside, but I think this explains the great draw (and, arguably, the great success) of Donald Trump.

I think the best way to become courageous is to attempt to be courageous and succeed. It’s a muscle that needs to be exercised. These performances are my way of flexing the muscle, pushing its limits, and building its fiber. I don’t think there’s any other way to do it.

It’s incredibly fun

When everything is clicking, performance is a drug. I can only imagine what it’s like to stand on stage in front of a stadium full of people. My experience this weekend, that weekend in May, and at the Boston bar during reunion weekend with my cover band, is only a sliver of that experience, but it’s potent nonetheless. Two days removed from my last performance, I’m ready to do it again.

I got a taste of what it’s like at the Bohemian Grove where my neighbor took me for the public picnic weekend. He’s part of the artist community there where incredible musicians perform for members and their guests. They do covers and originals and feed off the eager audience. Outside of the main concerts, there are dozens of side shows in the camps scattered around the grove.

I wanted to jump behind the piano and sing “Don’t Let The Sun Go Down On Me.” I wanted to grab someone’s guitar and noodle out “Kathy’s Song,” but I’m not quite ready yet. I don’t have the lyrics memorized. These songs are not in my ideal keys. If I’m invited again next year, I’ll be ready then. I’ll have my repertoire and I’ll be able to participate as a performer and an audience member. It’s a major box on my bucket list and I'm working towards putting a big bold check in it.

Why I’m applying to be an instructor at DVC

2019-10-17T09:38:00-07:00

Here’s the cover letter for my application to be a part-time adjunct marketing instructor at Diablo Valley College (DVC). In essence, I’m doing this because I’ve really enjoyed every opportunity I’ve had to speak, volunteer, and recruit at DVC. Prior to reaching out to a professor there just over a year ago, I didn’t know what community colleges were all about. I didn’t know what types of students went there, what classes they took, and what gap in the education market these schools filled.

Now that I have a better understanding, I’m all about it. DVC is both a vocational school and a feeder to four-year colleges. They serve veterans, adults, and underprivileged high schoolers. They are firmly rooted in the communities where they teach. Since I’m committed to living in the Diablo Valley (that’s Walnut Creek, Concord, Martinez, and surrounding cities) long-term, getting involved with my local community college makes sense. It also happens that DVC has some really good programs already brewing.

The role I’m applying for is part of a new digital marketing certificate program. Its objective is to help people in the Diablo area take advantage of the tech sector jobs that will inevitably move this way. It’s smart, and it took the faculty and staff here just under two years (lightning fast, by most standards!) to get the program approved and funded. I think this is exactly what a community college 20 miles from San Francisco should be doing.

In addition, I’d like to see DVC start to offer these courses too:

Technology sales: basics of CRM, contracts, sales writing, commissions, account-based marketing.- Ruby on Rails bootcamp: basics of web app development, relational databases, web hosting, front-end frameworks, HTML and CSS- Advanced Excel: pivot tables, VLOOKUP, table cleansing, table summaries

These are all practical skills that are highly desirable in this geographical area. If tech companies knew that there were relatively inexpensive (livable wage, but not crazy SF salaries) employees, hungry for jobs, eager to please, no sense of entitlement (the opposite, in fact) then the employers and the jobs would come running.

That’s my thesis, but it’s a long way from getting proven out. The next step for me is to get further involved by becoming a DVC instructor.

To Whom It May Concern:

A little over one year ago I reached out to Professor Charlie Shi about my interest in speaking with DVC students about entrepreneurship. We met in his office and then over lunch. I brought with me a copy of my recent book, The Parallel Entrepreneur, and we talked about the decade I’ve spent as a founder, CEO, and General Manager within a private equity firm.

He invited me to speak in one class, and then another, and then he introduced me to other professors at DVC who also invited me to speak, and then Charlie invited me to join the Business Administration Department Advisory Board. From there I became involved with the DVTI led by Professor Jim Blair. Delightfully, one opportunity has led to another, and I’m very pleased that this sequence of events has led here, to my application to be an adjunct instructor at the college.

I believe digital marketing is the underpinning of success for entrepreneurship today. Product is rapidly being commoditized; it has never been cheaper to create a web application. What sets companies and employees apart is their understanding of marketing fundamentals. The best founders think about their marketing strategy from day one; the most marketable employees approach their job interviews and daily tasks with the same marketing-oriented perspective.

For the DVC community to be prepared to take advantage of the Bay Area’s tech sector, it must teach a deep understanding of digital marketing and, I’d argue, its down-funnel partner, sales. It all starts with the top of the funnel, though. Email, social, search engine, content marketing, must be taught. I strongly believe that if the technology sector sees well-trained marketing students graduating from DVC, they will enthusiastically hire them and open local offices, bringing more jobs to the Diablo Valley. Every tech startup hiring manager I know is looking for talented marketers.

So that’s my rationale for being interested in this position. Here’s how I can help.

Experience

I have been working in technology since I graduated with my MBA from MIT Sloan in 2009. The first company I started was Scripted, a content marketing marketplace. I was immersed in everything about content marketing, even becoming friends with Joe Pulizzi, the founder of the Content Marketing Institute. Having seen it from all sides, working with hundreds of clients and producing (literally) hundreds of thousands of content marketing documents, I know this field well.

Along the way, we had to run our own digital marketing campaigns of various kinds. We did huge email campaigns. We spent over a hundred thousand dollars on Google, Facebook, and LinkedIn ads. We learned a lot about how to do this right. We also learned how to do it wrong.

Over the course of ten years at Scripted, I helped raise $18 million dollars, had a staff of over 35 employees, and grew to just over $2 million in annual revenue. It was quite a journey.

When I sold Scripted to a private equity firm, I continued working on a B2B email marketing tool that I built myself in Ruby on Rails, a popular web programming language. I grew this business up to over $200,000 in annual revenue before selling it to another private equity firm. My customers for this product were small and large tech and brick-and-mortar companies, and all of the customer acquisition was done organically through search engine optimization.

Today I am running a company in a private equity portfolio. Everything we talk about is marketing-related. We are encouraged to focus a majority of our time and budget on digital marketing campaigns: SEO, PPC, social, email. We measure everything, and I continue to learn best practices and enhance my understanding of how digital marketing works in the real world.

Importantly, I also know exactly what my peers and I look for in marketing hires.

Ability to teach

Many Business Administration professors at DVC have seen me speak. I was honored to be invited to keynote the first entrepreneur lecture series this year, where I spoke about my experience getting into a top college and grad schools, and the things I’ve learned about entrepreneurship since then.

I really enjoy speaking and teaching, and I put time into making sure my content is accessible and interesting. This is a skill I would also like to improve, and that is what draws me to this instructor opportunity.

I wrote a book, The Parallel Entrepreneur, that did very well when I launched it on Amazon in April 2018. It became the #1 New Release in the Small Business category and it continues to sell. The consistent feedback I get on the book is that is very easy to read. People like my writing style, and I try to bring that writing style to my teaching style as well.

Focus on community

Finally, I want to add that I am passionate about supporting the greater Diablo Valley in bringing new jobs into the area and helping the current residents access high-paying tech jobs. It would be extremely rewarding to play a hands-on role in educating our diverse community to prepare people to succeed in this competitive but very exciting market.

My dad's family lived in Lafayette for over 50 years. My grandfather actually sang in the DVC choir. My dad and his siblings went to Acalanes High School. I spent nearly every summer of my childhood in Lafayette with my grandparents (and at Emil Villa’s Hick’ry Pit in Walnut Creek) and I was grateful to be able to buy a home in Saranap, just over the 24 freeway from my late grandparents’ home.

My family is committed to this area; we already call our house our “forever home.” We love it here and want to make living in the Diablo Valley accessible to everyone. It starts with the right education.

Thank you for your consideration.

Sincerely,

Ryan Buckley Walnut Creek, CA

A few days of radioactive seclusion

2019-09-19T12:53:00-07:00

Part 1: My thyroid got cancer Part 2: My thyroid got cancer: one year later Part 3: The thing that won't go away Part 4: Here I go again Part 5: And now, a bit of certainty

The pill is smaller than you’d think. It’s oblong with red and white caps. It comes in a cylindrical container, tapered at the top like a perfume bottle.

“We call it the rabbit,” the radiologist joked to me, stepping back as the nurse opened it and took out the pill. She placed it carefully in a small plastic pill cup and handed me a larger cup filled with water. They watched me as I swallowed the pill and drank the water. Then she asked me to take a couple of steps back and held a geiger counter towards me, her arm straight and stiff. She nodded with approval.

I was officially radioactive.

The days leading up to my "therapy dose" of iodine 131, a radioactive isotope with an eight-day half-life designed to kill the thyroid cancer remaining in my lymph nodes, were a blitz of scans, meetings, and blood labs. They warned me it would be like this.

It started on a Monday. I took a shot of thyrogen, a synthetic hormone that mimics what my pituitary gland produces when it doesn’t see enough thyroid hormone. It’s meant to send my thyroid cells into overdrive, looking for the iodine required to produce the thyroid hormone. To make them even more thirsty, I spent the preceding two weeks on an iodine fast. Essentially, this meant no seafood, no dairy, and no sea salt (but really, to be safe, no processed food with any salt — because it might be iodized — which essentially meant no processed food at all.)

The waiting room.

On Tuesday I took a “test dose” of iodine 131, just enough to show up on scans but not enough to be dangerous. I went immediately from the nuclear medicine department to the LabCorp office for another quick blood draw. Then I was home for the rest of the day, catching up on work and preparing to disappear for a few days after the therapy dose made me officially, dangerously radioactive.

On Wednesday I got up early, before my kids were awake, and skirted back to the hospital to get scanned. They wanted to confirm that the iodine was taken up by the thyroid cancer cells on the lymph node they had already biopsied. This would confirm that everything was working as expected: the thyrogen activated the thyroid cancer cells and my low-iodine diet successfully starved them. As soon as the radioactive iodine entered my blood stream, it should have been picked up by those cells.

The scan took a long time. The room was cold, and I must have looked pretty odd walking in there with my solid green swimming trunks, t-shirt, and sandals. I went there already dressed for my mountain seclusion. I should have worn socks, though; my feet got cold during the scan and I had to stay completely still. With my arms strapped to my side, a large flat white plate, maybe two feet square, lowered within an inch of my nose. It stayed there and then ever so slowly, a centimeter at a time, inched toward my torso. To force myself to ignore the urge to itch my nose, my cheek, my ear (of course as soon as my arms are strapped down, everything itches), I thought about the novel I wanted to write. I thought about what meats I wanted to grill at Pinecrest. I thought about anything other than being flat on my back with a big square plate slowly traversing my body.

The scan took 45 minutes and I was escorted to another machine that did 3D scans. For another 22 minutes I sat with my face sandwiched between two more square white plates. This time they rotated around my head. I closed my eyes again and waited.

Finally, I was done, and the radiologist man with the short brown mustache sat in front of me with a look of approval.

"We saw two focii in your neck but we didn't see any others, which is good." He turned the computer screen toward me and I saw the outline of my neck with two white clouds right in the middle of it. This doctor warned me before the micro dose that it was possible they'd find thyroid cancer cells where they don't want to see them: on my lungs, liver, or stomach. He said he's seen it spread like this before, and since two years had gone by since my surgery, it was possible that my mild cancer could have turned into an aggressive one.

This was not something fun to think about. Great, more scanxiety, I thought. As I'd done during the many ultrasounds and MRIs I'd taken in the past, I listened and watched for clues. Even while my eyes were closed, even while I tried to think about something else, I'd pick up on the technician's taps and clicks, the way her weight would shift, whether her breathing would change. I thought these might be tells as to whether she was seeing cloudy blobs where they weren't supposed to be.

I could tell as soon as the radiologist walked in that there were no surprises. I was okay. He came in chipper, perhaps as relieved as I was that we could proceed as planned. If they found it elsewhere, there would probably be more tests and scans, my treatment might need to be delayed, or they would need to opt for surgery to take out a bunch of lymph nodes.

Instead of just one lymph node with cancer, I had two, and for the second time this doctor told me this was not a huge deal. "If I can see it, I can kill it," he repeated. I liked this guy.

He told me come back a few hours later for the real deal, after which I would need to follow some precise rules to keep my fellow humans safe while in seclusion up at my happy place.

It was still pretty early when I headed back home. My wife had already taken my girls to school. I'd already done the grocery shopping I needed for five days at the cabin. So, I went home and waited.

The pill, the very radioactive one, didn't taste like anything. I read on Reddit that some people experienced a metallic taste. I didn't. I had no nausea, no headaches, no symptoms at all. I walked back to my car, conscious of the fact that for the next couple of days I would not be able to throw anything away that I put my mouth on.

"The dumps have dirty bomb detectors," my radiologist explained. "They'll detect radioactivity on that beer bottle or Coke can and trace it back to me and you. Then we'll both be in trouble."

Blue was in my car, patiently waiting for me. Since I was not supposed to spend more than 2 hours in close quarters with anybody, even pets, I drove him about 40 minutes to Dublin, where I met my dad. Blue would drive up to the mountains with him and I would go the rest of the way alone with my radioactive isotopes.

I stopped in Oakdale because I was hungry. There was a taco truck outside a fruit stand, so I quickly confirmed with the cook that they don't use sea salt and ordered a carnitas burrito, no sour cream, no cheese. I had to stay on my low-iodine diet for two more days. That burrito was awesome. Since I ate it all and was careful not to put my mouth anywhere on the foil, I threw the packaging away.

Such a weird thing to need to be careful of, I thought.

Up at the lake I was able to carry my bags and groceries to our boat in the marina in one trip. The engine started and I sped to the north shore, content that I didn't put anyone in harms way and kept any stray bits of radioactive iodine safely inside my beige Toyota Camry.

My dad arrived about an hour later. I'd already unpacked all of my groceries, began to thaw the frozen meat, and popped open a beer. It was hot that day, and I smiled as I recalled the advice my radiologist gave: "Drink as much as you can," he said. "Beer, wine, water, whatever. I want you to drink so much you have to wake up in the middle of the night to urinate."

Cheers to that, I thought as I popped the cap off my Lagunitas IPA.

My dad texted when he arrived. I pulled our little boat up to the loading dock on the south shore of the lake, grabbed my dad's bags and groceries, helped him into the boat and turned back around to the north shore.

It was about four in the afternoon on a Wednesday. My radioactive seclusion had officially begun.

The following days were wonderful. I'd been up to Pinecrest several times already this summer, but being up for five days with just my dad was a treat. It was the unexpected benefit of having radioactive iodine therapy. Seclusion is not something I get much of anymore as a husband and parent, and most certainly not for five days in a row.

The days were split in two. We'd exercise in the morning with a long hike, make lunch when we returned to the cabin a few hours later, and then I'd get the next 4 to 5 hours to focus on writing a novel, something I'd always wanted to do. I decided to take this opportunity to give it a running start. When I was done writing around 5 in the afternoon, I'd start the fire and get the coals ready for grilling dinner.

Thursday we woke up to oatmeal and coffee and decided to hike up to Herring Creek, a beautiful waterway through dense forest that merges into the Stanislaus just south of Pinecrest lake.

It had been years since I hiked this trail and decades since my dad and I had hiked this trail just the two of us. The huge fallen ponderosa log leading up to the first big climb had nearly decomposed. When I was younger, 20 or so years ago, I could walk along that log. The bark was still on it back then. Now the whole thing was practically dust.

At the top of this first incline there used to stand an old ghost of a cedar. Its leaves and branches had long since fallen away, and it leaned nearly twenty degrees off center, toward the lake and away from the trail. When I was much younger my dad and I would throw rocks at that tree, trying to see if we coould tip it over. As I got older and stopped hiking that trail, my dad would send me updates. Finally, this past spring when he hiked up there with my aunt, he told me it had fallen and sent this picture.

Where the old leaning tree used to lean

It was bittersweet to see it myself, halfway up to Herring Creek. It was an odd reminder of my own mortality: I was at Pinecrest to recover from cancer treatment, keenly aware of the aging world all around me.

At the top of the ridge, the trail flattens out into a pine forest with several small ponds filled with reeds and lily pads as it winds its way to the creek. A long the trail there's a fork that angles back up a steeper ridge. It's known as the Lookout Trail, and connects at the very top to a network of trails that traverse the entire Sierra Nevada mountains.

I was feeling good and didn't want to turn around just yet.

"Are you up for going to the Outlook?" I asked my dad. The outlook is a spot along the Lookout Trail that leads to a large granite shoulder overlooking the lake and the south fork of the Stanislaus River that feeds it.

He agreed and we took that turn back up the mountain.

We talked for most of the hike up the hill, which is a bit unusual for us because neither of us particularly enjoy starting conversations, so our phone calls are always short. My dad is a quiet, thoughtful person, happy to go along with whatever the situation calls for. He'll talk if I want to talk and will stay quiet if I don't. Since I knew this time together was a rare opportunity, I kept the conversation going, asking him about his relationship with my grandparents, with my aunt and uncle, and his childhood. We talked about work and politics and I lost track of our time on the trail. Before I knew it, we would be back at the cabin eating lunch.

Lunch is familiar ground for us. For the last ten years or so, our visiting routine was for him to meet me for lunch every month or so. He travels and I pay, a trade I'm happy to make. When I worked in San Francisco, my dad would catch the BART in Fremont, take it into the city, and meet me at the Scripted office. I remember him coming for lunch at each of the offices we had back then. We'd go to a restaurant and catch up about the normal things you catch up on: work, health, relationships. Since I don't talk to my half-sister very often, I'd hear about her through my dad.

After my wife and I moved to the suburbs and I was able to work from home, he would drive to our house and since my kids don't have pre-school on Fridays, he'd get to visit with them too. I'd usually have take-out delivered or order sandwiches and we'd inevitably wind up at the creek where he loves to throw rocks for Blue as much as I do. It's funny how little things like that, the satisfaction of throwing rocks in a creek, demonstrate to me that I like this guy and yes, he's my dad.

We don't talk on the phone or email much. He sends me articles from the San Jose Mercury News that I'll always read and usually comment on. And then roughly every four weeks I'll get a text from him to set up a lunch. I really enjoy this routine and the rest of my family appreciates it too. I thought about all of this on the days my dad and I shared up there.

On Friday we hiked up to Cleo's bath, a section of the Stanislaus where it runs almost entirely over granite rock, emptying into deep pools with small and large waterfalls. It had also been years since I hiked it, and I recall that last hike was depressing. It was during the nasty drought California faced between 2011-2016. I hiked with a couple of friends and discovered the baths were dry. There was hardly a trickle and the water that was there was stagnant.

I figured this year, with the long winter and late thaw, would be good. I was not disappointed.

It was refreshing to see Cleo's bath replenished and beautiful, the way I remembered it from summers past when we'd hike up several times and go further up the canyon into what my grandpa called the first and second forests. My dad and I didn't talk as much on this hike. I was content to soak it all in. The weather was perfect and the water felt great, crisp and cool, snow melt warmed by the summer sun. I jumped into the small waterfall pool and my dad, not having a swim suit, stripped down to his underwear and joined me. It was something I would also do if the situation called for it. However, this trip, the only shorts I packed were swimming trunks. I was prepared to be in the water several times a day.

On Saturday, instead of hiking, we swam from our boat dock to the swimming cove, about 15 minutes each way. Since this was a lighter workout, we supplemented it with a Peloton core workout routine I had downloaded to my phone. My dad went along for all of it, keeping up with me on both the swim and the floor exercises. For a guy pushing 70, it was remarkable. I hope I can do the same when I'm his age.

I was okay with the truncated morning routine, though. I had writing to do, and I wanted to break 20,000 words on the trip. As it turned out, I got up to 28,000 words before I drove back home. In the weeks since I've had to focus my writing in other areas, but I'm now over 32,000 words and figure I'm a bit less than halfway through the novel. It's a labor, but calling it a labor of love would be an understatement. I think about it all the time and can't wait to dive back in.

Is there anything better than writing a novel lakeside at sunset?

Our evening grilling was on point. I don't have a picture of every meal, but I did snap a pic of the wood fire BBQ'd salmon since it was perfect. I got the coals just right and this filet flipped over without sticking anywhere.

A perfectly grilled Atlantic salmon

This particular dinner was symbolic because it meant my radioactive iodine treatment was over. I could go back to seafood and dairy, which meant I could eat salmon, cheese, and chocolate, the three foods I missed most in the preceding two-and-a-half weeks. I did not have to skimp on alcohol, at least, and got to enjoy this bottle of whiskey that one of my doctor neighbors generously gave me before I left.

A perfect place to sip Basil Hayden's

The long weekend at Pinecrest was as uneventful as it was eventful. Although I was radioactive, I had no symptoms, and the treatment and scans had no complications. This was the best that I could have hoped for. On the other hand, the five days I spent with my dad were some of the most memorable we've had together. It had been at least twenty years since I spent time like this alone with my dad and I'm very grateful that we had this opportunity and took it. I'm glad my wife encouraged me to do it and that my dad was willing to disrupt his routine for a few days, risk some exposure to his radioactive son, and take advantage of this special time together.

Dealing with public speaking panic attacks

2019-09-18T12:48:00-07:00

There are people who can talk and talk and talk. You know who I’m talking about. They have opinions on pretty much everything and can relay facts and anecdotes on any topic. And they like to share it all.

Then there are people who write prolifically. It’s their main medium of communication. Ask them to talk and they clam up. If they haven’t written it yet, they don’t know what to say. I’m kind of like that.

On the other end of the writing spectrum, there are people who tweet. The best at this medium are witty and smart, able to distill paragraphs down to 280 characters. The worst of them are mean and controversial. Oddly, there's not much intersection between these two groups of writers: bloggers don’t tweet (is Tim Ferriss even on Twitter?) and tweeters don’t blog (can you imagine if Donald Trump blogged?)

Public speaking is one area where these forms of communication all converge. That's why it's so hard; great public speakers and speech writers are rare. I think a good speech is written as a series of tweets. It’s a special form of blog writing that is snappy, clever, and packs a big punch on a small page. I think public speaking is not so much about the delivery — yes, that’s important — but a really truly great speech can deliver itself. If it’s written to be spoken, written for the audience, then the person giving the speech simply needs to get out of the way.

In other words, let the speech do the talking. Spend all the time and energy on getting the speech right and the rest will fall into place.

Yesterday I gave a talk about entrepreneurship at Diablo Valley College. I don’t claim that it held up to the ideal I just described. It’s long. It’s not very “tweet-able.” Parts of it are pretty dense. However, it did do a good job of telling stories, stopping to reiterate the notable points, and providing a few light moments to laugh at.

I got laughs. I got stares. I also got snores. But I got through it, and I think I for the most part got out of the speech’s way.

This event had one particular challenge that I wasn’t prepared for: there was no podium.

I arrived 30 minutes early and chatted with the organizers a bit. There were already people in their seats, and I learned that an entire class from a local high school was required to attend my talk. It was going to be a full house.

I printed the speech on double-spaced pages. It was 17 sheets long, double-sided, so a hefty stack to have to hold in my hand while speaking. During a lull in the conversation, I turned around to google “how to give speech with no podium.” The top results were a bit alarming: effectively they said, “Don’t do it.”

They said the tendency will be look down, straight down, and lose your connection with your audience. With a podium, at least you can look slightly down. The other concern was the involuntary shaking a lot of people get when they speak publicly. A small tremor in your hand will get amplified by a sheet of paper, distracting everyone.

I wasn’t sure what to do about this, so I decided to do nothing. I went up, stack of sheets in hand, and started talking. I knew most of the content without needing to read it and instead used the pages as a guide, looking down only a couple of times per page. For the most part, the speech did the talking. I tried to talk loud and slowly, letting the speech rest sometimes, and keeping eye contact with my audience, which I’d estimate was around 50 people.

Public speaking has definitely not been my forte. Often in the seconds leading up to a speaking event, I get small panic attacks. My mouth dries up, the lump in my throat starts as a seed and quickly grows into a grapefruit. My jaw locks shut. I begin to regret. I want to turn around, give up, not speak. It’s a terrible way to go into a public speaking opportunity. I know that it's going to happen and I dread it.

Other times I’ve started out fine and I’ll get to a point in the speech where my brain goes numb. The panic then sets in. I feel the audience’s stares like daggers at my gut. I know this feeling well. My breathing gets fast and short, my mouth dries out, and I feel scared, vulnerable, and desperate. This happened one time at a pitch competition at MIT and I walked off the stage. I didn’t even finish. I went outside and cried. It happened another time at a content marketing conference. I spoke at a session with slides behind me and midway through I felt that I’d lost the audience. I thought they hated me and my talk and then the panic set in. I pushed through it but I still remember my desperation up on that stage. I’m sure the audience noticed.

So going back to yesterday, I felt fine leading up to the talk. I was confident. In the seconds leading up to my grand entrance, as the DVC business professor read my bio, saying what an “honor and a privilege” it was to have me there, I wanted to run up and talk. I was excited to do it. I’m not sure what the difference was about yesterday, but I was pretty pumped up.

I got up there and broke the ice (and referenced the Harvard degree they mentioned in my bio) with a joke about how my in-laws probably reacted to their daughter quitting her job and moving across the country to be with her boyfriend (punchline: they shrugged it off since he went to Harvard.) And then I dove into the speech. I felt vulnerable but I didn’t feel any daggers. A majority of the audience stayed engaged. When I looked at them, they looked back.

I played the other speech-giving game of choosing one person in the back row to speak to. I picked a kind-looking young girl with a black and white striped shirt to be the focus of my performance. At one point she got up and left. I panicked for a second and went on. Fortunately she came back. It must have been a bathroom break.

At the end of the speech I had a line of students, young and adult, wanting to engage and ask questions. I’m not used to that — it was very welcomed. I stayed and talked to all of them and then went home, tired and happy, ready to put my girls to bed and drink a glass of wine. Which I did.

Four simple truths about entrepreneurship

2019-09-11T15:54:00-07:00

I'm going to give a solo speech this week at Diablo Valley College. I'm the headliner of the event. It's going to be an hour and a half (!) and is part of a "Business Beyond the Classroom" series that the business department has been doing annually for three years.

I'm excited about it. Scared too. It's a lot of time to stand in front of a group and talk and I'm going to do it without slides. I want to force myself to be a bit more engaging with my speaking. It's a challenge.

The topic is of my choosing, and I'm going to take bits of my book and combine it with bits of other experience I've had since then. I'll run through five topics and try to dive into them for a bit over 10 minutes each. That means this whole thing has to be at least 5,000 words.

That also means this is one realllly long blog post.

Let's do this.

Prologue

As you just heard in the introduction, I have academic degrees from Berkeley, Harvard, and MIT.

Yes, that's great and all, but I have developed an anxiety in the ten years since my last graduation: holding degrees from these three schools might be it. It might be my claim to fame. I may have to retire my jersey because I'm just not ever going to top it.

At least I have a girl to show for it. Actually three. It probably helped my wife-to-be move out to Boston when we were dating, which probably helped us get married. Then we had two baby girls. That's the three.

But back to the story. I imagine her conversation with her parents that fateful summer in 2008 went something like this.

"Mom, Dad, I'm going to quit my job and move across the country to be with my boyfriend."

They gasped. "WHAT?"

"By the way he's going to Harvard and MIT -- at the same time."

"Okay honey, have a great trip."

That's what it's like, in a nutshell, to go to Harvard.

Now back to my anxiety. Did I hit my peak at age 26? Maybe. Fortunately I still have a good 50 more years ahead of me to find out.

So I want to start by going into this part of my story a bit because it all ties back to entrepreneurship. Yes, the secret to getting into these types of schools is to be an entrepreneur -- not necessarily to start a business, but to get a little bit drunk on a big shot glass full of the entrepreneurial spirit.

The first organization I ever started from scratch was a group of guys (we were all dudes) who picked up trash on Wednesdays after high school. It was a volunteer campus cleanup crew. I don't quite remember what triggered this project, but I do remember that the janitors gave us our own rolling trash can.

I found the old "Mission: Trash Pickup" trash can at my high school years after I graduated

They loved us, and some of the teachers did too. I managed to leverage this notoriety as the trash pickup guy to become head of the environmental club and then, somewhat miraculously, Senior Class President. As class president, I had access to the display case in the quad. I filled it trash and told people to stop littering. I also was responsible for organizing prom. Instead of having it at a lame expensive hotel, I chose the Exploratorium, a science museum.

I also organized an Earth Week, retired a ton of CO2 on the cap-and-trade market and got to meet the founder of Earth Day, a man up in Seattle named Denis Hayes.

My grades were good, my SATs were okay, but it was this stuff, what I now call entrepreneurial stuff, that got me into UC Berkeley. It wasn't my test scores, it was the stories I told in my essays, and probably the letter of recommendation I got from one of the Vice Principals, that got me over the line.

That's my advice for any of you who are contemplating an application to UC Berkeley. Test scores and grades all look the same. They're the same five crayon colors. But stories, stories can express every color in the rainbow.

Focus on the stories.

Few things can rival the story arc of an entrepreneur: getting an idea, building that idea, and measuring the results.

Through various means I got 100 fellow students to pick up trash after school. The janitors in my high school spent ten fewer hours each week on trash collection. My prom had over 400 in attendance; there were only 340 seniors in my class.

These are measurable results. I'll get into why these are important in a business setting later on in this talk, but my point here is that these are important in any setting. And admissions officers eat them up.

High school administrators do too. It's because I had these good stories to tell that I got called up to the podium three times at my high school graduation: I'd won the competition to give the senior class commencement speech, I had a quick role as senior class president to present the senior class gift, and then I won the Eagle Award, a sort of top prize at graduation.

So that was getting into Berkeley.

At Berkeley, I did more of the same. My freshman year, I was hired by the Campus Recycling and Refuse Services office and found an incredible mentor in a woman named Lisa Bauer. She ran that office and gave me the wings I needed to broaden my reach across campus.

I started more programs, a reusable art project, a dorm recycling ambassador program, a sustainability awards program and finally, the Chancellor's Advisory Committee on Sustainability. This committee, called "CACS" for short, was my swan song. I wrote a proposal, pitched it myself to the chancellor, got his approval, and together Lisa and I assembled the crew that would meet bi-monthly during the school year to get this environmental stuff organized.

Nearly 20 years later, CACS still exists at UC Berkeley. In fact, it's been replicated in some form at all the other UC campuses.

Now, most students don't just get a meeting with the chancellor. I was able to get that meeting through an odd chain of events. But it starts with doing environmental (a.k.a. entrepreneurial) stuff. For the sake of hammering this point home, I'll cover this in some detail.

In order to do my environmental projects, I needed to go through the student government office. In that office I met and became friends with a staff person named Millicent Morris-Cheney. She helped me navigate that part of the campus administration, and I must have impressed her, because she got me selected into a secret society on the UC Berkeley campus.

That secret society is called the Order of the Golden Bear. It happens to be the oldest student group in the entire UC system. And it's not that secret (there is a website), it's just not that well-known, on purpose, so it can do its business, which is to connect leaders in the student body, the faculty, and the staff, to make the campus a better place.

One of the more influential members of the order is the chancellor, and the student-elected leader of the Order of the Golden Bear gets to meet twice a year with the chancellor. These are kind of standing, expected meetings.

You might see where this is going now. My senior year at UC Berkeley, the members of the Order of the Golden Bear elected me to be its leader. And I used that position to do what I did best: launch more environmental stuff. That's how I got audience with the chancellor to convince him to allow the creation of the Chancellor's Advisory Committee on Sustainability.

With all that as preface, here's how you get into Harvard. Over a few nights, you pour a few glasses of wine, and write concise stories that point toward a common theme. Mine, it should be painfully obvious by now, was that of an environmental leader, someone passionate about making the communities I'm in a little bit greener.

It also helped, of course, to get a letter from the chancellor of UC Berkeley to reinforce that theme. I never read his letter, but I'm pretty sure it was good.

Another brief aside, because this is important. Be nice to everyone. Especially the staff in the chancellor's office.

I needed this letter from Chancellor Berdahl two years after I graduated. The chancellor "graduated" the same year I did; he wasn't on campus anymore. Hmm... how the heck do you get in touch with a retired chancellor?

Fortunately, I'd befriended someone in his office named Sean Ireland, and Sean was my on-campus conduit to the now-previous chancellor, and I believe Sean ghostwrote most if not all of my recommendation letter. Without Sean I wouldn't have that letter of recommendation and without that letter I might not have been accepted to the Master in Public Policy program at the Harvard Kennedy School of Government.

To be clear, my GPA was a 3.7, an A- average, which was maybe 90th percentile at Cal. My GRE was also in the 90th percentile range. I got a handful of scholarships and won one of the campus-wide awards at UC Berkeley (for doing my environmental stuff!) but I am certain what got me noticed and over the line were the stories I wrote and the supporting evidence I provided in the chancellor's letter of recommendation.

So that is how I got into Harvard. The takeaways for you, if you want to go this route, are variations on the same theme:

Be consistent in your stories. Paint a picture. Use lots of different colors, but the picture should be coherent and make sense. - But first, take risks. Go out and start things. You won't have good stories if you don't go and put yourself on the line. - Get the best grades and test scores you can, but I'm pretty sure the weight they hold is dropping.- Finally, understand who your audience is (policy school admissions officers) and who your competition is (other people with impressive backgrounds) and be conscious about how you can stand out. In other words, use bright colors.

Finally, and very briefly, my MIT opportunity came about the fall after I started at the Harvard Kennedy School. I heard that the registrars at the Kennedy School and a handful of business schools will each knock off a semester's worth of credits required to graduate, so you get two 2-year degrees in three years if you can get accepted to both schools.

That seemed like a deal, so I went for it.

My story this time was about the business I started with some friends in Los Angeles, called Scripted.com, and how I wanted to explore all things business-related at MIT and correlate and compare it with my policy studies at Harvard. I argued that I'd be a better public policy person if I had a strong private sector background, and that as a Kennedy School-type student I'd add a new perspective to my MIT classmates.

In retrospect, this story was not as tight or coherent as it could have been. But whatever, I got in. And then in June 2009, just a couple of days apart, I graduated from Harvard and MIT.

So with this overtly long and detailed intro about applying to college and grad school now behind us, I want to dive into four lessons I've learned about entrepreneurship in the ten years since then.

It's all about the market

Nothing else matters... well, almost. Yes, it is all about the market, but I don't mean to imply that if you start a business in a hot market you'll be catapulted into success.

Chances are you won't, but that's simply the market telling you you've arrived too late.

Most venture capitalists believe there's room for two or three decent exits in a given market. After that first three, it's rapidly diminishing returns. The first one to IPO and the first one to get acquired for over $500 million are huge financial events. Most observers believe those events will suck all the air out of that market. All the exits after that will be smaller, so the big institutional money won't be interested.

Think of it this way. Car sharing is a huge market. I just googled it -- it will be north of $12 billion in 2019 and it's probably only going to keep growing. That's a lot of wind to catch!

But let me say something obvious: don't go out and start a ride hailing app. You won't be able to raise any money. You won't get support from partners, cities, and the more logistical business requirements like supply and demand will be extremely difficult to acquire.

Just because the pool's big doesn't mean you should dive in. The ride hailing market, in case you had your head under a rock this year, already had two huge IPOs. The wind has been sucked out. If this was your calling, well, your timing is off as a founder. But you can always send Uber and Lyft your resume.

We can look at this from the other direction too. Let's say you're a piano player and a carpenter, a tinkerer. Let's say you love to work with your hands and restore pieces of furniture.

I'm happy for you, even a little bit jealous. Piano playing and woodworking are both on my skills-to-learn bucket list.

But let me say something obvious again: don't start a business restoring old pianos.

Why, you might ask? Have there been IPOs in the used piano market too?

Well, no, but instead of there being huge swales and a couple of massive billion dollar yachts choking the wind on your little sloop, this market simply has no wind at all. You could set sail in Oracle's championship America's Cup yacht and still go nowhere.

If you search Craigslist for used pianos, you'll see a sad and sorry picture. Owners of used pianos struggle even to give them away. So forget selling pianos, it looks like there's actually better market for destroying them. Seriously, people would probably pay you just to pick their piano up, move it into a dump truck, and turn it into match sticks and chicken wire.

But even that business won't make you rich.

In fact, you could put Travis Kalinick, Mark Zuckerberg, Steve Jobs, and Elon Musk all in a room and tell them to start a used piano company and it would still flop. Their startup might deliver your used piano in a self-driving Tesla via an iPhone app and post it to your Facebook feed, but this company will fail.

Even the best entrepreneurs can't make a mountain of a mole hill... when there's no sand.

So here's where we're at so far: you can get into a great market too late and most likely lose. You can get into a bad market at any time and definitely lose. But what happens if you get into a good market at a good time?

Well, let's look at that for a minute. I'll let the cat out and say my answer is "it depends," and what it depends on is what your expectations are.

If you're trying to hit a home run on this one at-bat, then you'll need to do your research. To fully utilize this analogy, I'd say that the good market means you're already ahead of the count. For non-baseball fans, this translates to a situation where the pitcher is more likely to throw a ball you can hit.

So you're at bat. You know the pitcher's going to give you something good, because market conditions are in your favor, like I just said. If you're in a big market, the analogy would say you have runners on every base. So if you execute well, it's not just a home run, it's a grand slam.

A typical bootstrapped entrepreneur would just get one swing. One and done. If you miss, then you're out. Investors like venture capitalists might look at you, evaluate your batting stance, see that the market has given you a favorable count, see that you have runners in scoring position, so the upside is huge, and buy you an extra swing or two.

In essence, this is the difference between bootstrapping and having investors. Investors give you a longer at-bat. They do this because they see huge returns if you hit a home run. And by huge I mean 100X. They want to put money in when you're valued at less that $10 million and take money out when your company is worth over $1 billion. They know it's unlikely, but they need to believe that it could happen.

For most of us, that kind of return is entirely unnecessary. For most of us, if we sold a company for $100,000 that would be huge. It would be life-changing. So let's talk more about that.

You don't need runners in scoring position to net a six-figure outcome. You should be ahead of the count (have a good market) and be able to swing the bat (have discipline and creativity) and ideally know something about the pitcher (have done your research). If you have these things, and most anybody can get them (that may be why you're at DVC and coming to my talk), then it's worth the risk of time and money to be on the field swinging at pitches.

In a good market, you will have the following conditions:

Lots of customers willing to pay at least twice what it costs to produce your product- Some customers willing to pay at least twice what the cheapest customer pays (e.g. a 2X premium version) - A product that requires multiple purchases for optimal use - A product that you can prototype with minimal time or money

That's it! You need to see high margins, tiered customer strata, and repeat buyers. And you also need to be able to test it. If you see these things, you should definitely give it a go. Build that prototype and see if you can get your first dollar of revenue. A good market will support your journey to that first dollar.

Just understand that if the air is sucked out of the room, investors won't back you. If investors see that the major IPO or acquisition has happened to someone else, they won't believe it will happen to you, and they will probably be right. That alone doesn't mean it's a bad market, though.

Feeling the market out is entirely up to you and your desires. It's about your willingness to risk your time and maybe your money to get something off the ground.

Know that as you step up to home plate and stare that pitcher down, you need to believe he's going to throw a strike (because the market is good and you're ahead of the count) and that you know how to swing a bat with good form.

In fact, that's the topic of our next point. Keep it simple.

Keep it simple

Complexity killed the cat.

There's a ton of jargon out there about how to start a business.

"Build a MVP -- minimum viable product."

"Find PMF -- product market fit."

"Identify your ICP -- ideal customer profile."

After ten years of living and breathing this stuff, my distillation is simply this: whatever. Just keep it simple.

The best political speechwriters pick a single person -- a suburban middle-class mom in Kentucky -- and write the speech for them. The best songwriters choose an inspiration -- usually a long-lost love interest -- and write their song for them. The best performers pick one person in the audience, and ignoring everyone else, perform just for them.

Starting a business can be like that too. Choose one person, a friend, a family member, even yourself, and build the product for that one person. Don't build a product for every person. You can do that later if investors start throwing gobs of money at you. When you launch, pick one person and build the product for him.

You may ask, "What if I pick the wrong person and build the wrong features?" I say, so be it. It's still better than building for too many people. If you build too much, you may never launch. Furthermore, your product will be a bit, shall we say, undefined.

In short, if you try to build for everybody, you're going to build for nobody.

If you're doing it right then it should be very easy to describe what your company does.

"I restore used pianos and sell them online." (Again, don't do this.)

"People pay me to turn their used pianos into match sticks and chicken wire." (Might actually work.)

"My app connects people looking for rides with the people available to drive them."

"I built a web app that figures out anyone's current employment information."

"I started an organization that promotes a litter-free high school campus."

"I started a pour-over coffee cafe with a bunch of bespoke coffee bean blends. Also, my name is Phil."

That's what you do want to do. What you don't want to do is something like this.

"I built a marketing tool that identifies who your best customers are, uses artificial intelligence to write them an email, utilizes an email address pattern recognizer to figure out their email address, and then sends them a sequence of email messages that uses machine learning to optimize the time between sends."

I mean, that could have been distilled down to, "I built a fully-featured marketing automation app to automate customer acquisition," but even this more succinct version is too much.

Who is that for? Every business on the planet?

Get real, I'm not going to believe you and even if you did actually try to do all that, you would either need a ton of money or the ability to write computer code for 6 months straight with no sleep.

Either way, it's crazy. I don't mean to burst anyone's bubble, but building complex products is no way to start an enterprise. Unless you're Elon Musk, that is, but let's focus on human entrepreneurs, not the cyborgs sent back in time from the future.

So I say, instead, take a small bite. Chew. Enjoy. Swallow. When you can handle more, take bigger bites. But it should always start small.

There is a small but mighty group of business builders out there called "solopreneurs" or "indiehackers." These are entrepreneurs who opted out of the traditional path of getting investors to fund them. Instead, they use "customer financing." It's the ancient notion that you should grow with your customers rather than trade slices of your company on the promises of rapid future growth to investors. I'll tell you how I met them later in this talk.

This solopreneur movement says that you should build your business toward getting your first customer as soon as possible. This means launching early and iterating often. This means definitely, absolutely, not going in "stealth mode." Stealth mode reeks of fear and insecurity. Put it all out there. Be confident both in your idea and your ability to execute. The faster you get customer feedback, the faster you'll make your first revenue.

Once you get that first customer, you can grow at a healthy 30-40% per year rather than the 300-400% per year that your board will expect in return for the honor of accepting their money.

To tie these concepts together, it's a lot easier to get that first customer when you're building your app for that one singular customer. This is the reason you should keep it simple. Save the complexity for later iterations when you have more time, more money, and more customers or investors to support you.

Reporting discipline is crucial

Okay, here's a hard segue into my next topic about reporting discipline.

Day in, day out, report the same numbers every month.

You know that saying about how you should dance as if nobody's watching?

Well, do the same for your business metrics. Report them even if no one's watching. Do it because you want to hold yourself accountable. Or do it because you've taken the altruistic route of holding public board meetings.

Some people do that, by the way. It’s an odd thing, but seems to be taking hold of some entrepreneurs who really want to hold themselves individually accountable.

Or do it because it'll mean the difference between a win and a loss. Do it because the risk of not doing any reporting at all is you can lose the trees for the forest.

Yes, that’s backwards on purpose because that’s exactly what it is.

If you don’t pay attention to the critical metrics (the trees), you’ll keep doing stuff that you want to do (the forest). It's like driving along Highway 5 and losing track of your speed, or worse yet, veering onto the shoulder. You're too busy singing along to the radio, lost in thought, or enthralled with the monotonous drone of the Central Valley mountains, that you don't notice the critical metrics. Are you in the right lane? Are you driving the speed limit?

Sometimes when you lose focus on driving you'll be fine. But then the next time can be fatal.

It's true for business too.

I didn’t describe my entrepreneurial experience that much. About ten years ago I started Scripted.com. We ultimately raised about $18 million and built up a staff of 35 employees. We had a nice big office in San Francisco and some top-tier investors. We were set up to make it big!

The problem, which I now see in retrospect, was that we didn’t have reporting discipline. Every time we had a board meeting we picked different numbers to share, and our board let us do it. Our dashboard changed every three months so there was no continuity. We reported cash but our losses, which could be as high as $400,000 per month, would get explained away by some vanity metric we’d share which was meant to justify the expense.

Instead, we should have determined the set of metrics that really truly mattered to the business. Since we were a marketplace for freelance writers, we should have regularly reported things like the number of active buyers each month, the number of job requests per buyer each month, and the average number of months that a customer remained active.

We had a cancellation and activation problem at Scripted. This was the wound that got infected and never healed. It's all that mattered, and we didn't diagnose or treat it properly.

So we should have presented those critical numbers rain or shine, good or bad, embarrassing or not. We also should have been held accountable to those numbers by our board and our investors.

The truth is, we were scared. If we shared the bad news, our investors might have been spooked. We could have lost our jobs, future funding, or been forced into layoffs.

The other truth, which I see now, is that facing those facts early on would have been the best thing for our business. Sadly, as it would turn out, we had to do those layoffs anyway. All we did was prolong the inevitable and had we right-sized the business sooner, made decisions based on the facts that mattered sooner, we would have had a much better outcome for ourselves and our investors.

And here's where the rubber meets the road. My stepmom put $10,000 into the business. My uncle put $15,000 in. My co-founders' parents invested similar amounts. Other angels invested even more. Our VCs put millions of dollars into this business. Everyone got hosed, including the three of us founders who lost $10,000 each. That was my student loan money.

My point with all of this is that numbers can lie. You can put lipstick on a pig if you’re clever enough. For a couple of years before grad school, before Scripted, I did this professionally for a consulting firm. I know how this works. I did it back then and then I did it at Scripted.

You should not do it. Don't play with your numbers. Choose real metrics to report and you won’t find yourself holding onto nothing.

It's always better to have a bag of pennies than a bag of rocks.

Today I'm the CEO of MightySignal, a company that tracks the various technologies that mobile apps use. It's owned by a private equity company. They hired me to run it. They're all great with numbers, and you'd better believe I'm reporting the same dozen or so metrics to them every month. I report about six metrics to them every week.

Same ones, week over week, month over month. This whole section was inspired by them.

People are strange

You'll meet all kinds of people as an entrepreneur. Each one will be unique.

You’ll meet super rich guys who got lucky. You’ll meet brilliant engineers who can’t get customers. You’ll meet quiet CEOs who are forces of nature that see opportunities better than anyone else.

Personally, that quiet, thoughtful CEO is who I want to be. I’m not a loud, charismatic kind of guy. I’m not going to get on stage at an all-hands meeting and wax philosophical and get everyone fired up to save the world. I’m the kind of guy who tries to put his head down and lead by example, trying to stay a few moves ahead, and being honest and authentic about my strengths and weaknesses.

It took me a while to figure that out. I felt pressured to be like the other founders I've met. The "founder bro" types who talked about venture capitalists like they were pin ups or sorority girls. They memorized all the venture capital firms like they were football teams. Many of those guys are very wealthy now, far richer than I'll ever be. I'm now perfectly okay with that.

But I wish I’d known that it was okay to be authentically me sooner, but that’s life. Everyone is on their own timeline as they navigate their careers. You just have to roll with it and do the best you can. There are rules that you can live by to figure it out sooner, but sometimes you have to learn the hard way. So it goes.

Here are some things I've learned about dealing with people in entrepreneurship.

When you start a business, try to do it alone. You don't actually need a co-founder.

Getting married to a co-founder too early in the process can cause problems down to road. Unlike an actual marriage, it doesn't need to be an equal partnership. It’ll work out better if your “co-founder” is actually your first employee.

The faster you can get your business to support you and you alone, the faster you can start to be generous, pulling more people into your enterprise to spreading the wealth around. You’ll grow organically as a leader and make stronger decisions when you do it alone. You can pull people into the fold later, but wait as long as you can. Try not to give away equity until you can truly afford to do it.

Sometimes you may need that co-founder. That’s fine. But don’t go into entrepreneurship assuming you need one. Remember: most of the time you actually don’t need them when you start.

You also don’t need investors. Most investors will cause you to make bad decisions. The best investors, the ones that cause you to make good decisions, are actually called something else: customers. They’re harder to get. They invest in smaller amounts, but they’re the healthiest thing for you and your business.

Around here we glamorize fundraising. We shouldn’t. We glamorize big offices and payrolls. We shouldn’t. The entrepreneurs I’m most impressed by right now are those who started small and built a team as profit allowed them to. There are a lot more of these than you’d think. They’re just not in the news. No books or movies get written about them. They may not walk away with hundreds of millions of dollars, but many of them will be millionaires.

I bet if you plotted out the probability of a life-changing outcome between investor-backed entrepreneurs and bootstrapped entrepreneurs, the chances of making good money are higher for bootstrapped set. The chances of taking a company public or exiting for gobs of money are much lower, but the chances of exiting at all and making anything at all are much higher.

I wish I had the stats to prove this, but I don't. It's purely anecdotal.

Finally, and most importantly, you do need founder friends. The more the better! They will help you get through the muck that you’ll inevitably face.

So find a network of them. Out where I live, in Walnut Creek, there's a group called Lamorinda Entrepreneurs. They're photographers, bakery and furniture store owners, consultants and real estate agents. It's a really interesting group of people because none of them are software entrepreneurs with $50,000 per month office leases and Sand Hill Road investors. It's really refreshing, even though we're just 20 miles from the heart of all of that stuff.

There's a conference called MicroConf that I've attended for the last two years in Las Vegas. Two brilliant entrepreneurs started it and their sessions have titles like:

Rob Walling's talk- I'm a Terrible CEO and- Growing Your Userbase with Better Onboarding

I've met some of my best founder friends from this conference and I've continued to stay in touch with them primarily on Twitter.

Having your support network is critical. They just don’t need to have a piece of your business.

Your founder friends will help you for free. Like me. Start a company and maybe I'll be one of them.

Good luck!

Four lessons to learn about selling a business

2019-08-24T06:30:00-07:00

For entrepreneurs, especially the bootstrapped variety, the moment of exit is a mix of nostalgia and jubilation. You can't help but wonder what might have been if you'd only held on, but you also experience that wondrous relief of having a windfall of hundreds of thousands (or, more rarely, millions) of dollars suddenly hit your bank account.

Sometimes businesses fail, but you usually know it's coming well in advance. You're already piloting the plane, the engines are already on fire, you're already losing altitude fast, and the control tower (a.k.a. your board) tells you to figure it out your damn self. You've given your passengers (a.k.a. employees) all of your parachutes and although it was uncomfortable and awkward, you pushed them off the plane before impact (a.k.a. laid them off.) Now it's just you and your co-pilot (a.k.a. co-founder) and maybe a flight attendant or two (a.k.a. senior staff) still with you as the forest canopy starts scraping the bottom of your plane. And sometimes you don't quit.

But I'm not talking about those kinds of exits. Here's a different kind, one I didn't even know existed.

I wasn't planning to sell my email finding business, but when Xenon Partners asked me to head up MightySignal in October 2018, I couldn't help exploring the option.

I interviewed Jonathan Siegel, Xenon's founder, in my book, The Parallel Entrepreneur, so he knew about my penchant for side projects. He'd also offered to purchase this company in 2016, which was how we first met. That initial connection led to our first meeting in 2017. Nearly two years later, I was back in conversations with him about MightySignal, another acquisition he was making.

Jonathan and I were in my car in San Francisco after a long day doing technical diligence on MightySignal when he offered me the CEO job. "What about my email business?" I asked. "I assume you don't want me to keep running it."

He confirmed that I should focus on MightySignal and suggested that MightySignal could buy my business, and a few minutes later and we agreed to terms that we both thought were fair based on its current monthly revenue. A few days later I agreed to take the CEO job and part ways with my side business, and we immediately dove into MightySignal, transitioning the technology, sales and marketing processes, and all the HR and other logistics you deal with while taking over a live business.

Time moved quickly, and one night a few weeks later, my wife and I were talking about my compensation incentives at MightySignal and it occurred to us that it would be significantly better for me if I sold my business to a third party rather than to MightySignal. Since I'm incentivized to accumulate MightySignal's cash, if I could avoid spending it on acquiring my side business, I'd be able to reach my incentive bonus faster. I hadn't considered that option -- again, a lot was going on -- so the following day I sent a few emails around to people who had shown interest in buying it previously.

Within a few days I'd opened up a diligence process with three potential acquirers. One of them was more serious and moved faster than the others. We quickly started drafting a letter of intent (LOI).

When I started having these conversations a year ago, the business was not in pristine condition. There was high revenue concentration; one customer made up between 50 and 70% of revenue monthly revenue, depending on how much usage I billed for. I also discovered that my switch to metered billing was a mistake: while it worked fine for me, acquirers were confused by the lower subscription fees. That was an unintended side effect of the billing change. Finally, to cap things off, revenue was flat.

This all added up to a low multiple. I was expecting to land on a valuation somewhere between 1-2X annual revenue, and since Jonathan agreed to that range, I made that same ask upfront to my acquirers. The acquirer I went with offered the valuation I wanted with a few caveats:

Some compensation would be upfront and the rest would be paid out in monthly installments so long as these conditions were met:

Specified major customer paid > $X, OR - All other customers paid > $Y

I agreed to this because I thought it was fair. If my whale customer went belly up, we'd have to rely on the other customers to compensate. This incentivized me to be on the acquirer's team, helping them meet this revenue target because I'd get paid and they'd get a more valuable asset.

Our goals were aligned, so I was fine with it. If they win, I win. If the major customer churned (and I didn't think they would) and I'd kept the business myself (or with MightySignal) then I'd be either screwed or in an awkward position with Xenon. I didn't want that outcome, so the LOI terms seemed fair. The risks -- and rewards -- were shared.

In retrospect, this turned out to be big learning #1: Always keep your business in a great position to sell.

Lesson 1: Be ready to sell your business at any time

I wish I'd learned this lesson sooner. My revenue was flat leading up to the sale and of course during diligence this would be easy to see. The buyers knew this as well as I did; they had full access to all payment histories and this revenue concentration issue was discussed at great length, to the point where the deal almost fell apart. However, we eventually found common ground and executed the LOI and Asset Purchase Agreement (APA). It was a done deal. Or so I thought.

Acquirers of business-to-business (B2B) software-as-a-service (SaaS) businesses have certain expectations. Generally speaking, these are:

The business has high (> 80%) gross margins (net profit divided by revenue). This was true for my business. Like a typical online software product, my server and data costs were less than 20% of revenues.
The business is growing every month (> 2% month-over-month growth). At this point in its revenue trajectory (as I documented), my business's new revenue acquisition (new subscriptions) was entirely offset by its churn (cancellations). When the new revenue ($1-2K per month) equals the churn ($1-2K per month) then growth stalls. Sometimes it might drop if a big customer leaves. Unfortunately, this was the case with my business at the time of sale.
The business has a lot of customers which distribute the revenue impact of any single churn. As stated, at the time of sale, I had one customer that made up a majority of revenue. This is not a healthy situation, and if I had more time to prepare to sell, I would have worked harder to get at least one more major customer like the one we ended up calling out in the deal terms.
Average sale price (ASP) is increasing over time. Increasing ASP indicates that value is being added to the product. If new customers are paying more than older customers, then there's good product-market fit, positive market conditions, or both. In my case, ASP was also flat. I wasn't able to find a way to get new customers to pay more, either by raising prices or by adding new paid features.

But these were known, fully transparent faults. It's why the valuation was what it was, just slightly over its trailing 12 month revenue. If everything about the business was attractive, the market valuation would have been a multiple (usually 2-4X) of trailing 12 month revenue. Better metrics would have provided hundreds of thousands of dollars of more value to me. But they weren't there, so I didn't get that valuation.

The business issues were also why I couldn't get full payment upfront. There was risk to the acquirer, and I was forced to share it by agreeing to the lower upfront payment and contingent future payments. If my business were healthy then the buyer would not have required these conditions.

Nonetheless, we closed the deal. We signed the APA and I handed over the keys to my little kingdom: full access to my Heroku app, Stripe keys, and domain. I joined a Slack channel to help their developers take over the (minimal) day-to-day maintenance of the app. I wrote a bunch of documentation and answered all of their questions. Since our incentives were aligned, I was as helpful as I could possibly be. I thought I had a good relationship with their developers and the principals I worked with. I responded to every email and Slack message within 24 hours. I was the ideal acquiree.

Looking back, I don't see how I could have done any better. When they migrated the entire app off of Heroku and onto Elastic Beanstalk, a competitive service by Amazon Web Services, a critical service silently went down. I noticed and told them, even though at this point, per our APA, my job was done. They told me they appreciated the heads up. I was happy to do it, again, because our incentives were aligned.

I was surprised, therefore, when I received an email from them less than two months after our deal closed. They wanted to talk on the phone, and when we got on the phone, they asked to change the payment terms.

This is not supposed to happen. Payment terms are not supposed to be up for negotiation after a deal is signed. It's bad form, shows poor etiquette, bad faith, and in the community of B2B buyers and sellers, it's just straight up unheard of. You don't put a business partner in that position, and if that partner pushes back, you don't keep pressing. Or so I thought.

I declined. I told them that since I was no longer running the business, it was not fair of them to ask me to take on a new level of risk. They could accidentally take the site down, or intentionally raise prices or introduce some other change that could drive this customer away. I would have no say in the matter, and that change could strip me of my future payouts. A rationale actor would not take this deal. If the tables were turned, they wouldn't take this deal. That's what I told them, and that's when things began to really turn south.

Lesson 2: Nothing is final until the money's in the bank.

I thought a signed Asset Purchase Agreement, with all of its legalese, references to courthouses, and carefully negotiated commitments, was cast in stone. I thought once you sign a big multi-page business agreement, you're stuck with it. Apparently not, because these guys kept trying to get me to change it.

When I said no a second time, they respond with the nuclear option: *they "terminated" our agreement and referred me to their lawyer. *

It was written formally, as if drafted by a lawyer, and they followed up by sending a written version via certified postal mail a few days later. Except there was a problem. They'd referenced the wrong clause, and even though I should have been able to work this out with their lawyer, they refused and offered a ridiculously low settlement. I turned it down and asked her if they wanted me to hire a lawyer and sue them. She didn't reply. So, despite my best efforts to avoid it, I hired a lawyer.

I met JP Schnapper-Casteras at the Harvard Kennedy School sometime in late 2006. He was a bright young Stanford guy and I liked him right away. He was in the group of friends I went to Puerto Rico with during our graduate school spring break in 2007, successfully re-living our college years at a beachside rental in Rincón. All of my friends at Harvard were smart, but JP had a special wit and warmth about him that I always admired.

We stayed in touch over the decade between then and now. I was happy for him when he told me he started his own law firm after clerking and working at a big fancy private firm. When I was negotiating the Asset Purchase Agreement for this acquisition, I asked him to take a look. And when I needed a lawyer to protect myself from these jackals, JP was the first person I called. He took the case.

Oddly enough, I've always liked lawyers. I enjoyed talking to them over the years at Scripted, working through the process of incorporating the business, raising money, and hiring and firing employees. The lawyers I knew were smart, articulate, and most of all, disciplined. They were on time, on point, prepared. It must be a state of mind in the lawyer community, because I've never known a lawyer to not be on it. I always appreciated that.

So working with JP was, dare I say it, fun. We brainstormed strategy, talked business and family, and managed to thread that needle between old friends and new business associates. I told him what I cared about in this dispute, what I ultimately wanted, and why it was important to me. He took the lead in communicating with their lawyer and for a while ran into the same walls that I did. It wasn't until we drafted a complete, official complaint and threatened to file it that these jokers finally came around.

The content of the complaint was nothing new. These were all points that we'd made on the phone and in writing previously. They just needed me to spend the time and money to write it up before they'd take my position seriously. It was, in short, a dick move. If they'd offered the amount we ultimately settled on from the beginning, I would have taken it. I shouldn't have needed to hire a lawyer, but this was their game, their tactic, and they forced me to do it, because they're assholes.

It led me to the next lesson of this blog post: you can't know what's going on in anybody's head; anybody can be an asshole.

Lesson 3: Don't assume that your counterparts are normal.

While all this crap was happening, I was gearing up for my (hopefully) final cancer treatment. Unless they were regular readers of this blog, they couldn't have known that, and I don't mention this for pity points. It's just a fact.

Conversely, I don't know what was going on with them. Maybe they also had cancer. Maybe a loved one was sick or their marriages were falling apart. Maybe something else was causing financial distress. I don't know. I can't know. And that's my point. You can't assume that your opposition has it all together, that everything's fine, and they'll make decisions as if they're in a perfect world kind of scenario. Chances are that's not the case.

Going into and throughout this negotiation, I assumed they were rational. I assumed that they wouldn't want to take on the reputation risk. Although I'm not outing their firm in this post, they have to assume that close friends and advisors of mine, many of whom are influential, will know the full details. It's within my legal rights to share these details with lawyers and financial advisors, and word gets around. The private equity community, especially for small SaaS businesses, is small. Bad actors get outed fast.

Private equity influencers like the partners at Xenon (it should be obvious by now, but Xenon is not the firm in the dispute I've described here) told me they can't believe the firm in question here would put their reputation at risk over a sum of this amount. They told me this is completely irrational. If word of my experience keeps them out of just one deal, it's not worth it for them. The rational thing for them to do would have been to shrug off their buyer's remorse, pay me out, and move on.

I agree, of course, but that doesn't matter. They didn't act rationally and I couldn't will them to do so. This leads to me the fourth and final lesson I learned: always keep a plan B.

Lesson 4: Keep your options open.

There's an important corollary here too: keep a cool head. You need a cool head to see the cracks in your opponent's plan. Use their hot-headedness against them. Let them make a mistake or two.

In fact, these guys made plenty of mistakes along the way. I had more information than they knew I did. I knew the monthly revenue and the size of the payments from the whale customer. All I had to do was ask that client; I'm still friends with those guys, and they remain happy (albeit smaller) customers of my old business. I also had good reason to believe that the revenue from other customers was below the payment trigger threshold.

Thus, per the letter of the contract, they didn't owe me anything. The business, due to some technicalities in the agreement (using only subscription revenue instead of total billings), didn't trigger the payout criteria and wouldn't get me there any time soon.

They could have just ridden it out, but they didn't. A rational actor would have said cool, the agreement is doing its job, protecting us from downside risk. We don't need to pay Ryan right now because the payout triggers aren't met. Sucks for Ryan. Poor guy! Oh well, he'll survive.

No, instead they sent that stupid letter, made me hire a lawyer, and settled for more than I'm due right now.

That's ultimately why I took the deal.

So I'm not bitter about where this whole thing landed. I'll never sell a business this way again, but this entrepreneurship thing a is a living, learning process. I hope this blog post is useful for those who want to sell and those who want to buy small businesses. There are tons of lessons here for both sides of the deal.

If I'd had the opportunity to read a post like this earlier, I might not have signed the deal. That's why I published this.

As for the principals at the private equity firm I sold my business to, I hope they learned some valuable lessons too.

(I also hope they drive to the beach and realize they forgot their sunscreen. I hope they get pulled over for a broken tail light. I hope they sit in front of a crying baby on a five-hour red eye flight. I hope they have to sleep outside with a bunch of mosquitos.)

Outside of that, I don't harbor any real ill will. It's just business. I get it. They tried to do what's best for their fledgling private equity firm. They made mistakes. They're paying for those mistakes, even now. I am too. But we're both learning.

What else is there, really?

Back to the office and back again

2019-08-07T20:35:00-07:00

I'm just going to say it. Offices should be optional. They are a tool to be used when you need them, not a mandate, not an expectation, not an assumption that the tool is always needed.

I'm not saying that offices are useless and face-to-face interactions are not worthwhile. I want to be clear -- I'm not saying that at all. Rather, I'm saying that assuming that offices are needed every day is just... wrong. They’re not. The more I see and hear and experience the benefits of remote and semi-remote working, the more of a champion I'm becoming for the cause of simply working from home more often than not.

Note: this obviously does not apply to doctors, janitors, teachers, airplane pilots, and others who don't work a typical office job. My discussion here is about office work.

At some point this past spring I got a jolt of an idea: I should hire some interns.

I had projects piling up and I was busy at MightySignal. With our small team, we're pulling in north of $250,000 per employee per year in revenue. I'm happy with that ratio, but it means we're pretty strapped for time. I had one daunting project in particular that I wanted to knock out this summer and I didn't want to do it alone. It would be the perfect project for an intern. Or two. Or heck, even four.

I got to work and had a really easy time finding qualified candidates. I was shocked, actually, at how well we were able to attract exactly the kind of students I hoped to work with. I settled on two engineering interns to knock out some lingering R&D on our app scanning technology, and two marketing interns to finally, once and for all, pound out a big SEO project I'd been wanting to do.

However, recruiting interns from all over the country meant putting them somewhere. I didn't think a remote internship was a good idea. It felt too risky. My full-time staff are all remote, but I didn't want to assume a student would want that experience. Internships, I think, are about the experience of learning face-to-face. This is one area where I'm totally on board with office time.

So, since I was working from home at the time, I needed an office. With the blessing of my board, I signed a three-month lease for a small office in downtown Walnut Creek this summer. It was furnished with good internet and cell phone reception, and sat across the street from my gym. It took about six minutes to ride my bike to work, coasting a slight grade downhill the whole time.

The first intern started in late May and three more piled on in June. I ultimately lost an intern to an unexpected research opportunity that she couldn't pass up. I chocked that one up to good hiring. So my intern class settled in at three: Rohan, Siddhant, and Zach. I'm happy with how it went, and yes, the office had something to do with it.

Benefits

Offices provide structure and routine. It's positive peer pressure to show up, work hard, and put in your eight hours. When you're first starting a new position (or an internship) I think this is good habit-forming practice

It also expedites the time it takes to get to know each other. I like to eat, and lunch is one of my three favorite meals. Each week we went out to eat, re-creating one of my favorite perks at Scripted, the weekly catered lunches we provided to everyone. There's something nice about breaking bread together. You can't do that on Slack.

Parts of the MightySignal tech stack are very hands-on. Some of what we do involves physical devices, actual iPhones, and Mac minis that power them. I needed my engineering interns to be in the same room with this stuff. It's not conducive to remote work.

On the SEO and marketing side, I tried to write out a comprehensive project plan, but inevitably as we dove into the details and started to work on it, things would change. Assumptions would be proven wrong and on-the-fly shifts would be needed. Working in the same room with the interns helped to streamline those changes. When a particularly vexing issue arose, I'd suggest we hash it out at Philz, a welcome new addition to the Walnut Creek café scene and a short walk from the office.

I enjoyed being in the vicinity of my team. It feels good to share a room with people who are working towards a common goal. It also felt good to revisit my in-person management approach, something I haven't needed to do since my staff are fully remote.

I ultimately settled on a schedule compromise, which I think my interns also appreciated. We would work Monday through Thursday at the office. Fridays could be from home (or anywhere, really.) I needed this because my kids aren't in pre-school on Fridays and my wife also works, so Fridays can be a bit of a hot potato day, with us taking turns entertaining the kids while the other one shoots out emails or gets on a conference call.

At Rapleaf, the job I had in the lull between Scripped and Scripted, I fell into the habit of not coming into the office on Fridays. I was on the sales team, and we were having a really, really hard time getting sales. The company was going through a steep transition and being commission-heavy sales reps, we were barely treading water. The office felt stifling to me. It zapped my energy. I'd play ping-pong with Grant Lee, the guy who would propel me most during my time there. When I stopped showing up on Fridays, he came up with a term for it: "Buck Friday."

"Having a Buck Friday, ol' buddy?" he'd ping me when I didn't show up.

"Yep!" I'd write back.

Since I'm the boss now, I gave my interns that option. They could have a Buck Friday every week if they wanted to, because I was going to take one for sure. Two of them took me up on it, and one of them went into the office anyway, saying he liked it there. Perhaps coincidence, perhaps not, but I invited that guy to stay on with us part-time after classes start back up. I appreciated his dedication.

To sum it up, I put these in the plus column for having an office and going to it regularly:

Faster onboarding- Easier communication- Team lunches- Technical project management- Camaraderie - More management practice (for me)

Costs

It's now about two-and-a-half months into my summer office experience and I'm very much looking forward to returning to life as it was: taking calls from my creek, responding to emails from my patio, and doing demos in the cottage in my backyard. I miss it.

In fact, I miss being alone during the day. At the office I have to be on. I feel pressured to be accommodating, proactively checking to see if anyone needs help. I wasn't sure how social I should be. Sometimes I just wanted to put on headphones and work; my part of the SEO project involved a few days of coding, and I needed to get my development environment re-configured. It took some time and I didn't want to be distracted. Those days I wished I could have just worked from home.

There's also the literal cost of the office. The rent isn't bad but it isn't free. I happened to have scouted out a great deal on Craigslist; the tenant was motivated to find someone to fill in the office during the exact months that I needed the space. This worked out perfectly, but at Scripted it was the opposite. We paid an exorbitant rent and signed a three year lease which was painful to get out of when we sold the business. Plus the snacks and furniture and lunches, which in my case were minimal, but at scale can be very pricey.

Commute time is a huge one. The interns managed to find housing nearby and one already lived in the area. Nobody mentioned a negative commute experience, but it's time out their day that could decrease productivity. When I was still working on Scripted and commuting to San Francisco every day from Walnut Creek, I would spend exactly two hours roundtrip on bike and BART, door to door. That's two more hours I could have been working rather than thumbing through news articles and crossword puzzles.

For those who don't have public transportation options, the commute impact is even worse. There's traffic, wear and tear on the car, the chance, albeit small, of getting in an accident. The cost to park in San Francisco is tremendously high, and if there's construction or a lane closure, it can double or triple your commute time, taking precious time away from your family at the end of the day.

Commute impact on the environment is huge too. Just under half of all greenhouse gas emissions in Contra Costa County (where I live) come from road transportation. If half of the commuters where I live could work from home, that would not only unclog the roads during rush hour, it would also dramatically reduce the carbon footprint in my community. This is important.

Finally, offices are a distraction. For all the benefits you get in building friendships in the office, those same friendships can also reduce productivity. It's not always helpful to get lost in idle conversation, or pulled into a ping-pong game, or stuck out in a long lunch with co-workers. It's often hard to work in an office.

In summary, here are the negatives:

Distractions from co-workers- Productivity lost commuting- Cost to employees- Cost to employers- Cost to environment

Conclusion

I know I got a lot more work done at home, but I also recognize that the four of us in the intern office combined got a lot more work done than I did alone. I'm glad I hired my interns and that we all spent the summer in an office in Walnut Creek.

However, if these were full-time staff rather than short-term interns, I would have done it differently. I would have signed us up for access to a co-working space and suggested that we meet there every Thursday. We'd get there early, work together all day, have lunch together, and say farewell until the following week.

I believe it's possible to have the benefits and avoid the costs of having an office. The answer is simply to treat the office like a tool. It's there when you need it and you can ignore it when you don't. I think most teams would benefit from meeting together about once a week if they're in the same city. If my remote workers were all in the same country, I'd schedule meetings about once a quarter. Since half my staff are international, we meet together twice a year.

Every team is different. Every company need is different. However, I think it's healthy to challenge the assumption that everyone needs an office and should go to one every day. It's just not the case if you really think about it.

Read Write Play: Q2 2019

2019-08-07T13:02:00-07:00

This quarter there was not a tremendous amount of reading or writing. But playing was good. Very good. Here's the usual summary of last quarter's progress.

Read

I tried to start on my design curriculum. I really did. I purchased Drawing on the Right Side of the Brain, a drawing book at the local Amazon store (how incredible that the company that killed Borders and Barnes has set up its own local bookstores) and read a short ebook on web design, Hello Web Design. I also got halfway through Don't Make Me Think by Steve Krug. Then I got distracted, spending my evening time working on existing side projects and starting new ones.

My goal this quarter was to improve my side projects by addressing a known gap in my entrepreneurial tool belt. I'm a terrible designer. I can use an existing design framework (like Bootstrap) pretty well, and I can modify templates, but I can't draw and I can't build a page from scratch.

I did crack open the drawing book and reminded myself to sit with my daughters and draw whenever they drew. I did that -- sometimes. It helped. I can see lines differently and I have a new perspective on drawing. I understand how to get better and my practice is much more structured than it ever was before. I can look at a picture of Elsa and Anna from my daughters' Frozen coloring book, for example, and sketch out a passable depiction. You could tell who is Anna and who is Elsa, and that's a big win for me.

It might just take me two quarters, even the rest of the year, to get through this course. I'll finish Don't Make Me Think. I'll find another one to read and force myself to sit down and draw a couple of times a week. It will be slow progress, but it will be progress.

Write

I wrote seven blog posts in Q2 and the top performer by far was "On nine whole years of marriage," a short post inspired by my ninth wedding anniversary which we celebrated in the middle of June. It was easy to write, and I think I got a lot more views on this one because it's one of the few that I promoted on Facebook.

Next up was "What my grad school experience meant to me," a nostalgic look back on what it felt like to get accepted to Harvard and MIT and graduate from these elite schools a few years later. All that was ten years ago now, a crazy span of time in which I started some companies and also started a family. I'm the same guy I was ten years ago, but stronger (chin up, everybody) and without much gray hair at all. Plus, I got to jam with my old band again at our 10-year reunion. (More on that in the Play section.)

"The game I'm playing" was my most introspective piece, which actually was good mental prep for my big grad school reunion. I had to remind myself that success is relative. There's no hard definition; it can mean whatever I want it to mean. Am I trying to be the richest guy in my class? The most famous? Or the most interesting? No thanks. As it turns out, I'm doing just fine.

Seven posts that I feel pretty proud of is no small feat. I worked a lot last quarter, moving the ball downfield with MightySignal and a small handful of much smaller projects. I spent some good quality time with my kids too, passing the afternoons in front of my house, in our lovely little cut-de-sac, with the whole neighborhood stopping by to chat and play.

Play

Speaking of which. Play I did.

Together with the Class of 2009 Rolling Sloans I racked up a good 12 hours of studio rehearsal time, and dozens more before that in my little backyard cottage at home. I was more prepared, more comfortable, and more excited to perform than at any of our previous gigs. There were a number of solos that I'd never quite nailed, like The Sweater Song solo and especially the second half of Sweet Child O' Mine.

Importantly, I also became more comfortable singing. As the big reunion gig drew closer, my music teacher and I focused increasingly on vocals rather than piano. I had a list of the songs I was slated to sign at the show and we went through them together. She'd stop me when I pinched a high note and gave me pointers, reminding me to drop my shoulders, lower my jaw, and breath into my stomach rather than my chest.

I'm not sure how much of that I actually did at the show. I recorded our cover of My Hero and feel pretty good about how it sounded. The chorus has some high notes. I couldn't hit them back in January when my lessons started. By the time June came around I was knocking them down easily, smiling my way through the song. That's what mattered most to me. Singing those songs for my classmates was fun. It was not something I enjoyed doing previously and it frustrated me that I didn't enjoy singing in front of people. I wanted to enjoy it. I could sense how fun it would be to sing comfortably in public, to be happy with the music I was making with my guitar and my voice. That show was the closest I'd ever been to finding that comfort.

I'm still working on it. This quarter I'm trying to sing and play Don't Let The Sun Go Down On Me by Elton John on piano. It's a challenge for me but I'm making progress. More on this next time.

The things we all want

2019-07-06T07:08:00-07:00

Yesterday was July 4, and on this day for the last four decades my neighborhood has held a day-long celebration of community and country, in that particular order. I was reminded how much this neighborhood is cherished by an older woman I sat next to. Her son-in-law was raised on the street where we spoke, and his mom still owns that house. He raised his family across the street and helped his daughter buy and remodel the house right behind us.

Some neighborhoods chew you up and spit you out, never wanting to look back. Some are like a cradle that you never want to leave. This neighborhood is that kind of neighborhood. The preferred method of leaving is being carried out feet first. The daughter of the original owner of our house told me that was her mom's plan. And her mom got her wish.

So on this day, long after the bicycle and scooter parade, sometime between the water balloon toss and bubble gum blowing contest, I stood with a dad I recognized from a few streets over. He worked in finance in London and, since I just happened to a read an Economist article detailing the importance of London as a financial trading center, particularly in derivatives (which it turned out he traded), we got to talking about Brexit.

He believed the whole thing was ridiculous, that clearly the Leavers hadn't thought through the impacts of breaking close financial ties with Europe and the devastating impact it would have on the economy, supply chains, and the financial markets he traded in. He want on to qualify his disgust, though, by saying that the underlying problems are real. Much like the populist wave here in the United States, Londoners and Brits are also feeling a sense of urgency to protect their own assets: jobs, property, and culture.

Completely pulling the UK out of the European Union is the wrong answer, but that doesn't mean the question is wrong. How do we make sure as many people are safe, secure, and healthy as possible?

I believe that should be the role of the government, but I definitely understand that government doesn't always live up to that promise.

We talked about all of this, but maybe due to the heat, it being my 3rd red Solo cup of Racer 5 IPA, and having woken up early with two very excited little girls who couldn't stop asking when the parade was going to start, I was not as articulate as I intended to be. When we discussed what the things are that people need most, I had opinions but they didn't come out clearly. I woke up today rehashing parts of that conversation and am writing this now to take a virtual do-over.

Here's a much better articulation of what all people want, Republican and Democrat, neo-liberal and neo-nazi.

Life

Everyone wants the good life, the American dream, a house and a job and savings for retirement all while being able to afford a family vacation every year and meal or two out at a restaurant every week. This is the picture of "middle-class" America: parents with a kid or three, a house in the suburbs, and enough money to be comfortable now and well into the future.

Most people assume that the middle-class is the bell in the bell curve with a relatively small number of poor at the bottom and rich at the top. It's not. **There's nothing "middle" about the middle-class. **

If you are middle-class in California, you're well into the top 10% of earners. There are twice as many households making less than $100K per year as there are making more than $100K. And sadly families with $100K of household income would be considered low income (unable to comfortably afford food, shelter, and fun) in most parts of California.

Here's an interesting exercise. Let's break down the expenses for a family with two kids in the Bay Area on a $200,000 household income. Note that $200K yields about $140K after tax, or $12K per month.

Monthly expenses for a middle class family of four in the Bay Area:

Mortgage + property tax + maintenance on a $1M "starter home": $5K- Childcare (nanny or preschool) for 2 kids: $3K- Loan payments (car, student loans, etc): $1K- Food (groceries and restaurants): $1K- Healthcare (usually taken from paycheck): $1K- Savings or other: $1K

On a household income of $200,000, which is a princely sum by any stretch, you are just getting by in the Bay Area. Move-in ready homes in desirable neighborhoods with good schools run about $1 million. Everywhere you look, that's the rate. You might find a house with some maintenance requirements that will sell for $800-900K but even that will be competitive. Everyone's looking for deals like that.

Childcare is expensive too. I didn't know it when I had kids, but for the first five years of their lives I'd basically be responsible for a second mortgage. Unless you have family or some other resource to help out every day (or a stay-at-home parent) you will need to spend at least $2,500 per month on childcare. And then there's everything else which just adds up.

So if you're really just getting by at $200K, and by that I mean your boxes are checked but you're without much cushion, imagine what it means to make less than that. Think about the sacrifices you make to live on $100K with a family here in California. Then look at this chart.

Most people don't make enough money to be middle class in California. Source: Statistical Atlas

It's crazy. About 9 million households in California make less than $100K. About 4 million make more than $100K. And $100K is not even breaking even if you really want to live the middle class American dream. It's not even close. You need to be in the $200K+ bracket, which is only 8.6% of the population.

In other words, the middle and upper classes are less than 10% of Californians. The rest are barely getting by or not getting by at all. This is the reality we face not only here, but elsewhere in the country as well. It's hard to live the life we thought we were promised in grade school, where we were taught to get a job, wake up in the morning and go to work, collect a paycheck and come home to support your family.

This was supposed to be achievable simply by going to school and working hard. It wasn't supposed to be a top 10% proposition. It was supposed to be for everybody. It is not.

This is what led to Trump, to Brexit, and to a host of other populist movements (France, Poland, Italy) gripping the world right now. It's not an irrational zeal for border protections and trade barriers. It's perfectly rational. It's just not the right answer.

The problem isn't "them." It's us.

Liberty

Our country was founded to avoid religious persecution (and British taxes) but clearly the principal that our founding fathers cared most about was liberty. Freedom to choose your destiny, where you live and work, who you pray to, and how you raise your family. Government was supposed to be primarily invisible, making things work in the background, appearing only when things needed to be fixed. The rest was to be left up to the people.

Our two parties today differ on what ought to be regulated. Democrats lean toward regulating businesses (stronger environmental, labor, and safety restrictions) while Republicans lean toward regulating people (stronger marriage, abortion, immigration, religious restrictions). Neither party is completely "liberal" and instead they differ on where exactly free will should be granted. It's fascinating when you dig into it.

We all agree, however, in freedom of opportunity. I don't know a single Republican or Democrat who doesn't believe that someone should be able to work hard, take some risks, and be rewarded if it works out. That's the common American ideal, shared by everyone, across party and racial lines. It's very American, but I think it transcends countries too. Everyone loves the entrepreneurial success story. Every country and culture celebrates its business titans. When fame and fortune come from movies or sports, all the better. We all love our heroes.

Liberty ultimately means the freedom to set your success. If you want to pull in a blue collar paycheck for forty years and retire with a pension to Florida, go for it, it's yours. If you want to drill for oil and strike it rich and get a library named after you then by all means. Give it a go.

Eat as much or as little of the American pie as you want. That's liberty.

The problem is when other interests get in the way of that freedom. The destruction of liberties can be slow and silent. When our government prioritizes the health of businesses over the health of workers, when budgets and tax cuts are set to favor one class or one party over another, our collective ability to make an American living deteriorates.

This is what I believe people have been feeling for the last several years. Instead of lashing out against our elected officials and pushing for policies that prop up the middle-class, we elected someone (Donald Trump) who spoke to middle-class ailments but successfully framed them as coming from external sources. It's Mexico, it's Islam, it's China, it's everything and everyone attacking our liberties except us.

I couldn't disagree more, but nonetheless that's the state of things today.

Pursuit of Happiness

What do you do with this American dream? Well, you feel happy. As you should, because you're lucky to be here. When you have the freedom to either make more money or less money, you're happy.

Happiness comes in many forms, of course, and not everyone needs the yacht and private jet to be perfectly 100% content with their lot. Merely being able to make your own decisions that impact your own outcome is sufficient to bring happiness. It's knowing that you did it your way. And if you don't like it anymore, it's knowing that you can change your course and fix it.

When any of these elements are taken away or appear to unattainable, the entire system falters. That's what happened in the US and UK in 2016, first with the UK's vote to leave the EU and then the US vote to elect Donald Trump. It happened because people lost faith in their ability to reach their goals. They felt suppressed, anxious, untrusting of the existing norms that once yielded happiness but appeared to no longer do so.

I agreed with my neighbor that the populist reaction is wrong, short sighted, and erroneous in thinking that we'll find strength in cutting off the rest of the world.

I don't have the answer right now, but I know that blaming everyone else is not the right answer. We have to solve it by looking at the world and making ourselves better. There's plenty of opportunity, and a lot of it can be taken while actually improving the outlook for ourselves and the rest of the creatures we share this planet with. I'll dive into this in a future post.

How to bring more businesses to Contra Costa County

2019-07-04T06:32:00-07:00

I recently joined the Business Advisory Board in Diablo Valley College's Business Administration department. I thought it sounded like not only a great way to volunteer, give back, and meet similarly-minded people in my community, but also I was simply impressed that DVC had this.

What better way to prepare business students for the real world than to have businesses from the real world come into DVC and talk about what's going on in the real world. At these meetings we have DVC professors, staff, and representatives from both the public and private sectors. The business side is represented by some execs from Google and Amazon, real estate agents and insurance brokers, and me. We come from all around the county too, which is important.

At one meeting a while ago, perhaps the first meeting I attended, I lamented that even though the early-to-mid-career talent is moving out here in droves to the suburbs, the jobs are being left behind. They move from San Francisco to Walnut Creek and then end up commuting back to the city every day for their job.

Why? Why aren't these employees able to persuade their employers to set up an office closer to where they live? There should be a critical mass now to make that ask, and maybe it's already happening. If so, however, what can we do from a policy standpoint to make it happen faster?

This is why we've created Contra Costa Business Coalition, an offshoot of the DVC Business Advisory Board. When we hear about big companies like LendingClub moving to Utah, we need to ask ourselves, why Utah and not San Ramon or Concord? We need to find the answer.

Figure out what works

Just like when I investigate a business problem, I like to investigate what's working now. What businesses do we have in this county, and where are they located?

I used data from Crunchbase Pro to answer the question and the results are not all that surprising.

Top 3 Contra Costa cities with the most businesses:

San Ramon (236)- Walnut Creek (229)- Concord (79)

To give a sense of scale, Palo Alto has nearly 10X (2,300) and San Francisco has 60X (14,000) the number of businesses in our county. So we're barely on the map but we already knew this.

As far as the types of businesses here, we're a product of the Bay Area:

IT & Software (224)- Consulting (59)- Healthcare (58)

This result is a bit surprising. The names you see on the sides of buildings when driving around this area are mainly finance and real estate companies. There's a little bit of industrial and a lot of hospitals and elderly care. I wouldn't have guessed that IT & Software would be so dominant, but given our geography and how most people around here make enough money to afford a house, it makes sense.

We're also dominated by tech

Our commercial centers are Walnut Creek and San Ramon

Our largest companies are a bit surprising, though. Each of these are making between $500M-1B a year:

USS-POSCO (A mining tech company in Pittsburg)- Keller Williams (A real estate company in Walnut Creek)- Pac-12 Conference (A collegiate athletic conference in Walnut Creek)- Bay Alarm (A building security company in Concord)- Old Republic (A home warranty company in San Ramon)

There's not a typical Bay Area software tech company in our top 10. Coming in at 11 is Seal Software, an AI-based enterprise software company headquartered in Walnut Creek. The top 10, though, are mostly finance-related companies.

Then make it better

So that's what's working. About 700 respectably large companies operating in the Diablo Valley serving both local and distant customers. Getting more of them out here will require a combination of better branding, incentives, and some social proof. Here are a few suggestions about how we might do this.

A big conference center and hotel

We have some small Marriott's boutique hotels that are great for business meetings and weddings, but we don't have a world-class facility to host an industry conference. Salesforce or Oracle couldn't do their annual shows here even if they wanted to. We need a great hotel, Fairmont-like, built to handle conferences with 10,000 attendees. If we can get more executives to come here on work trips, we'll eventually get more execs to move here and open offices.

A business club

We have country clubs for retirees. We need the equivalent for the up-and-coming mid-career executives. This would be a place to meet people, attend events, drink and dine. The closest comparison is The Battery in San Francisco. This area needs some resources to facilitate collisions between business partners, customers, and investors. A hub of sorts would go a long way toward making it happen. And resources like this will attract more ambitious business people into the area.

Arts districts

Our cities are doing a pretty good job of supporting the arts. The Lesher Center in Walnut Creek is a great example, but all across this county there are art and wine festivals and small concerts in the summer. We have the Concord Pavilion which hosts some of the greatest performers in the world. These are all tremendous assets, and part of this equation must be to support a diversity of artistic communities.

A branded commercial corridor

Finally, and perhaps most critically, we need to be known for a particular industry. We don't need to become the next favorite place to launch a startup. It would help, though, if we could be known for housing some of the world's greatest companies in a particular industry, like real estate, finance, or green tech. Businesses tend to cluster around each other, even when in direct competition, and cities can use this to snowball ever more businesses in a particular industry.

Economic development is hard. If this were easy, it'd already be done. I like these problems, though. They're fun to think about and I'm glad to have met a few other people with similar interests. We'll keep working on it.

Building a family culture

2019-06-16T12:34:00-07:00

Today is Father's Day, June 16, 2019. It's my fifth one as a dad and my thirty-sixth as a son.

Last night my girls, exhausted from a day playing in the cul-de-sac and then romping all around UC Berkeley with our neighbors, went to sleep blissfully early. My wife and I watched an hour-long episode in the living room, something we rarely do in the evening. This morning we all slept in (meaning we got out of bed after 7am) and I made waffles. Then the five of us (including ({filename}the-ascent-of-blue.md)) went on a long jog / bicycle ride around the neighborhood.

After that, the cul-de-sac sprang back to life and I was able to continue learning to play Kathy's Song, my new favorite Paul Simon tune. It's in the easy part of my range and has some beautiful fingerpicking. I want to add it to my "Oh, you play guitar? Play something!" repertoire.

With progress made on that tune, and my kids entertained by ({filename}an-ode-to-the-suburbs.md) we've found ourselves in, I took the time to finish up this blog post. This is one I've been thinking about for a while and started writing last year. It's about similarities between office culture and family culture.

I’ve spent most of the last two years at home with my family during the hours when I used to be at an office. It’s been rewarding on ({filename}benefits-of-being-a-work-from-home-dad.md) and it has given me a perspective on something I haven’t considered before: my family’s culture.

Families have cultures just like companies have cultures. A tangible way to think about it are the cultural norms.

In an office these are pretty standard:

Are distractions allowed in meetings?- Do meetings start and end on time? - How are conflicts resolved?- Is it okay to be emotional?- How promptly are requests handled?

I’ve ({filename}my-greatest-hits-at-scripted.md) a lot about company culture. One of my side projects, eNPS.co, is a way to measure it. Now that I'm in an office again, although({filename}back-to-the-office-and-back-again.md), I'm conscious of the cultural norms that I'm creating. I'm trying to be deliberate about it, even the "do as I say, not as I do" norms that I wish I could avoid. Resistance is futile, though. The norm setting is unavoidable.

Culture is always set by the CEO. Every one of the bullet points above stem directly from how the CEO conducts himself.

It used to drive me crazy at a previous job when office meetings scheduled for 30 minutes routinely turned into hour-long meetings. Thirty minutes in, the same question would arise, "Are you guys good to stay longer? We've got a lot more to cover."

Since this meeting often started ten minutes late, we could never predict when we'd get out. Thus, meetings scheduled at the end of the day were especially painful. Since I was so concerned about and distracted by the timing of the meeting, I was not as productive or focused as I could have been.

And guess what? It was the CEO causing it. His previous meeting would inevitably run long, causing his next meetings to run long. It was a death spiral of time mismanagement. As a result, other people in the company conducted meetings the same way. We'd tend to show up a few minutes late, unprepared, without concern for how long the meetings would run.

Indeed, culture happens whether you want it to or not. So the other day I had an intriguing thought: Do families have cultures the same way that offices have cultures?

The answer, I believe, is a resounding YES. Families absolutely have cultures. The parents are like the CEOs (and I'd argue that mom has much more sway than dad, but results may vary) and the kids are like the employees. Everything flows from the top.

Those questions I asked above about office norms translate easily to family norms:

Are distractions allowed during meals (e.g. phones, televisions)?- Is there regular a bedtime, playtime, naptime routine? - What's the ratio of discourse to crying/yelling/hitting when conflicts arise?- Are parents allowed to lose their temper?- Do kids listen right away or are they allowed to ignore requests?

There's no right or wrong answer to any of these questions. They're simply embodiments of the culture that we parents are creating, again, whether we like it or not, in the ways that we conduct our parenting.

I would argue, with a fair bit of certainty, that it's beneficial to be aware of the culture that you're creating. Parents should know that how they resolve conflicts feeds back directly to how their kids resolve conflicts. Parents who are easily frustrated, who raise their voices and grab arms (or even hit) to make a point, are setting that behavior as a norm in their family. Even if they attempt to "do as I say, not as I do," the imprint goes deeper than whether or not their kid yells or hits back. Culture is a mentality, a way of thinking, and while it usually manifests in behavior it can also be there lurking behind the scenes. Culture is what you can't see, too.

The best example I can think of in my own family is our use of iPhones and laptops. My kids probably see me using technology a lot more than I realize. Part of that is working from home, part of that is that these are useful tools (YouTube for home fixes, Ultimate Guitar app for learning songs, WordPress for blog writing...) so to some degree it can't be helped. But it's sending a mental signal, one that will show itself when my kids are old enough to have their own phones and laptops.

To mitigate this I try to always and immediately put my device away when my kids want my attention. They should know that they are always more important to me than my technology. Face-to-face connections are more important than internet connections. When they have their own phones I want them to treat me and our friends and family the same way.

The other common sleeper norm is smoking. If a kid sees his parent smoking throughout his childhood, it's sending a signal. He may spend his first eighteen years without smoking a cigarette but given the opportunity, he'll take it up. No amount of public service announcements will prevent it. He'll do it because that's the culture he knows.

My kids right now are two-and-a-half and four-and-a-half. I notice that around the age of two, our family norms (I might even call them "habits") are pretty well cemented. We eat dinner together with no distractions. We don't watch a lot of television. We're very friendly and generous with our neighbors. We bathe, brush teeth, and read books before bed time. We listen to each other, and when we get upset, we talk it out. We tell each other how we're feeling, both the good and the bad. And when Melissa and I give instructions, our kids have to listen. When our kids don't listen, they're not being a "bad kid," they're just being a "bad listener."

A lot of these norms come from my wife, who has a way of parenting that fortunately fits very well with mine. For the most part, I follow her lead on this stuff. The norms I've contributed to are in eating (carrots and hummus are now a staple, as are dinner salads), playing music (both girls want to play guitar and hopefully also piano), and enjoyment of camping, swimming, and throwing rocks in the creek.

There are countless other signals they've taken up too that I may never directly see. I hope they seek out in a partner a relationship like the one I have with Melissa. I hope they recognize what love feels like and how to show it. I hope they raise their kids in a way and a place similar to their own upbringing. I hope they stay curious, enjoy learning and reading and writing. I don't really care what school they go to but I hope they value the process of formal education.

And finally I hope they also choose a huge lovable dog as their first pet. I'm glad my girls will know how special pets can be, and I hope they'll translate that into a love of all animals and the places where animals live.

Even though I'm writing this on my computer while my kids are riding around in the cul-de-sac in front of me, even though I sometimes thumb through my phone in my kids' beds while they drift to sleep, I'm proud of my family culture and the norms we're setting every day.

One Father's Day many years from now, I hope my kids will read this blog post and agree.

*Smooching Lily on this Father's Day as our neighbor looks on. *

On nine whole years of marriage

2019-06-12T22:16:00-07:00

*Note: my wife did not know I was going to write and publish this. *

I am a lucky man. I think most people in my neighborhood would recognize this.

My wife is friendly, attractive, likes to cook and do laundry, is a wonderful mom to my daughters... and works! She makes a lot of money. If we were really keeping score (and we're not), I'd have her beat by a little bit, but we're basically even contributors to the family budget's bottom line.

Most importantly, she loves me. I've never doubted it, never felt otherwise, never needed to question, and I realize that I probably take this entirely for granted.

Like I said, I am a lucky man.

I forgive myself for that oversight, as most men tend to do, because I think I'm a pretty good husband. If I may say so myself. I cook, I clean, I wash dishes and put them away, I do laundry (when she lets me) and I take the kids to school 99.9% of the time (she picks them up). Until just recently I was home every day because I worked from home (I'll describe my first temporary office in Walnut Creek for summer interns in ({filename}back-to-the-office-and-back-again.md)).

From what I can tell, the things most married couples argue over relate to conflicts between work and family time. I'm no saint, but I think I do a pretty good job of managing that balance. Even with my new office situation, I'm home by 5:30pm and I still take the kids to school.

On the improvement side, I work (or at least am on my computer) more than half the evenings in a given week, including weekends. Despite ({filename}three-life-hacks-i-wish-i-did-more-often.md) it, I'm definitely on my phone too much. I could be more proactive about planning meals, family activities, and time alone with just my wife. I'm aware, and writing this down helps me remind myself that it's important to translate awareness into action.

Okay, okay.

Nine years is a long time. A damn long time. If I think about how much happened between when I was born and my ninth birthday, I think wow, that's a lot. Infant to fourth grade. Twice my older daughter's age.

It's a long time, and yet it has flown by. How can it be?

The answer, I believe, is the same one that I described in my wedding toast nine years ago tonight. In it, I described how I was nervous about getting married. There's a lot of divorce in my family, including my own parents. When I was dating my wife-to-be, I wasn't sure what to make of that. I definitely didn't want to get divorced, but it seemed the odds were against me. I decided to get married anyway because it felt so easy.

In fact, everything about our relationship was easy. We just got along. We didn't argue, we didn't suppress feelings. When we had feelings, we shared them. I remember a few times when I felt that she was upset but not telling me, and called her out on it. She relented and we worked through the issues without either of us getting too upset.

I've cried, she's cried, we've cried together at one time or another in these nine years. Looking back on those times now, I don't have bad feelings. Those were part of our evolution as a couple. Those were real moments when we both learned what the other needed to feel happy, safe, protected, and loved. Those were critical moments that actually strengthened our relationship, like building a muscle.

So since she and I have been on a exercise kick the last few months, that's the thought that I will end with. Nine years of marriage is certainly a workout, but the result is strength. Every passing year I feel a tighter, stronger bond with the woman I have married.

I am a lucky man. And she is lucky too :)

My wife and I on our driveway. Photo taken by our neighbor. Out of scene: lots of kids on bikes and scooters.

What my grad school experience meant to me

2019-06-06T13:04:00-07:00

I write this from Cambridge, MA. I took the red eye last night, flying in from SFO. There used to be a lot more flights out of OAK a decade ago when I did this trip several times a year. Now they are few and far between.

This time I have a house and a family to miss and a dog to get cared for while I'm gone. The last time I was here for a class reunion was five years ago. I was almost a dad then, but not quite.

Much of this stretch between Harvard and MIT has remained the same. And the weather in Boston right now is perfect, just barely humid, a nice cool breeze in the shade. I forgot my sweater and am happy to not miss it.

I received my acceptance email from the admissions office at the Harvard Kennedy School of Government on March 4, 2006, just over 13 years ago.

This was obviously a big deal for me and my parents. I'd be the first in my family to attend a school like Harvard and for my mom it was a dream come true. She'd encouraged me to apply to Harvard when I was in high school. I did and got waitlisted, but in my heart of hearts I wanted to go to Cal. I told Harvard College to bugger off, and I made a mental note to do everything I could to build a competitive application for a Harvard grad school program instead.

The path from August 2000, when I matriculated to Cal, to February 2006, when I submitted my Harvard Kennedy School admission application for the Master in Public Policy program, was a long one. I worked hard at UC Berkeley, both in and out of the classroom, to differentiate myself. My grades were good but not among the best. I knew I'd need something special to catch the eye of admissions officers at Harvard, so I focused on environmental activities and leadership in those circles.

The capstone of my admission packet was probably the letter of recommendation from Chancellor Berdahl. I never read it, but I'm pretty sure it was good. He and I had a lot of mutual respect and I was able to capitalize on it to move my sustainability agenda forward.

Of note, it wasn't Chancellor Berdahl who I worked with to get that letter drafted and delivered. It was one of his staff, a guy named Sean Ireland, who probably wrote the letter and got the Chancellor to sign it. He was my man on the inside and nothing would have happened without him.

I've learned time and time again that you have to be nice to and appreciative of everyone.

The Chancellor of UC Berkeley giving me one of the first Berkeley Sustainability Awards.

So I was good at this campus sustainability politicking and probably the best at doing this at UC Berkeley at the time. My skills met the right opportunity and it catapulted me forward. I made sure that my Harvard grad school application emphasized that point. I got in.

I forwarded that fateful email from Harvard to my mom and went to the bar at a nice restaurant downstairs from the office tower I worked at in San Francisco to celebrate. It was five in the afternoon and I decided to splurge on a shot of Johnny Walker Blue on the rocks. My mom called while it was being prepared. She'd been crying. When the bartender overheard what I was celebrating (not too many 24-year-olds order a $60 shot at five in the afternoon, even in San Francisco), she told me it was on the house.

I was on cloud nine. I soon made plans to quit my job, spend the summer on an epic road trip through the southwest to Colorado and then to Spain and Europe. It was a unique and amazing time in my life. Limitless opportunity, no obligations, and most of all, a sense of pride that I'd worked towards an ambitious goal and achieved it. It was done. Nobody could take it away.

For the rest of my life I'd always have that Harvard acceptance letter. I was in the club. Indeed my life would change forever, but not in the ways I originally expected.

It was through the Kennedy School that I met my wife: Chancellor Berdahl introduced me to the Lieutenant Governor of California, John Garamendi. He offered me a summer internship writing environmental policy papers. His wife Patti gave me a ticket to the event where I met Melissa. We would eventually get married and start a family, raising my two daughters as a work-from-home dad. This is easily the biggest, most important thing I've ever done.

I thought the Kennedy School would set me on a path into government, but instead I caught the entrepreneurship bug. I applied to and got accepted to the MBA program at the MIT Sloan School of Management. The registrars at Harvard and MIT allowed me and three other students to get two Master's degrees in three years. The company I'd go on to co-found with Sunil Rajaraman was a ten-year odyssey through the highs and lows of startup culture in Silicon Valley.

My career to date stems entirely from this startup rather than from my graduate school degrees. I can't say that I regret it. The startup experience I've gained allowed me to move to the suburbs and raise two kids in the Bay Area. I have tons of flexibility to explore my community and work on a lot of community projects. I had no idea 13 years ago that this is what I would be doing now, that I'd skip my 10-year Kennedy School reunion in favor of my MIT Sloan reunion, where the cover band I played in would headline the main happy hour party for my entire class.

But such is life. It's unpredictable. At 36, going on 37, I'm still young. I feel young too, physically in better shape than I was when I was a student. I'm definitely stronger. I can do way more pullups now than I could at 24. Jogging up hills pushing a double stroller has done wonders for my fitness, so I'm probably thinner although my weight is more or less the same.

So I'm taking my time here in Boston this weekend to soak it all in. The Charles River is beautiful, the brick sidewalks and lush vegetation as alluring as it was the first time I stepped foot in Cambridge. This place has the same magnetism that it had for me back then, and it gives me the same curiosity about my place in the world, the potential I still have in front of me. I can't help getting excited about what's next for me.

But first I have a concert to practice for, my first rock and roll performance in five years. It's all going to be awesome. All of it.

What I'm most afraid of

2019-05-24T07:47:00-07:00

I started writing this post at my most recent Sustainability Commission meeting which was aptly held on Earth Day. Since then I've been thinking more about this content, tossing it around in my head. The problems I described, just in the past month, have only gotten worse: historically high temperatures in the Arctic, increasing evidence of mass extinctions, and warnings of irreversible changes to crop seasons.

I'm afraid of this. All of it. Thinking about it makes me sad. Imagining the position this puts my kids and their kids in actually makes me kind of depressed. I feel like there's nothing I can do. The challenges are too large and there's too much momentum moving against the changes required to subvert a disaster.

Yes, our future generations, my own future progeny, are destined to face severe problems related to our global inability to curb the impacts that our own science says that our own industries are creating. It's appalling.

Eventually our kids will look back at me and my generation and say, "What the fuck, guys? Why didn't you do something?"

And I won't know what to say in response. That's what I'm most afraid of.

The end of recycling

This is personal.

I worked in waste reduction and recycling throughout my high school and college years. My first real experience in leadership involved convincing some friends to pick up trash on our high school campus every Wednesday after school. Amazingly, we did it consistently and I was able to keep this group together for several years. The janitors appreciated us so much, they gave us our own rolling trash can.

In college at UC Berkeley I got a job in the Campus Recycling and Refuse Services office initially to expand the residential recycling coordinator program in the freshman dormitories. This was a program originally envisioned by another student named Garth Schultz. When he launched a campus thrift store for reusable items, the recycling coordinator position opened up. I got the gig.

Recycling back then, in the early 2000s, made a lot of sense. The market for aluminum, paper, and glass was strong. Studies showed that it was cheaper for companies to acquire raw materials from recycling streams than from fresh sources. When I sought out students to be dormitory ambassadors to our campus recycling program, I could explain with conviction that this was really important work. Recycling was good for the environment, important for business, and simply the righteous, ethical thing to do. The people I worked with felt the same way. It was easy to recruit, and we expanded these programs and added some new ones. I made lifelong friends in the process.

Today, the benefits of recycling are less clear and it’s driven entirely by the global market for recycled material. Going back to those headlines, as recycling importers like China have grown, their need to import recycling from the United States has waned. As a result, recycling is piling up in sorting facilities all over the United States, and a frightening amount of it is being sent to landfills.

My family sorts recyclable plastics and papers from food-contaminated non-compostables. Our recycling bin is always full and is significantly larger than our solid waste bin. Every week I bring our three bins, garbage, recycling, and compost, to the curb and watch three different trucks haul our refuse away. I now wonder, with a sinking feeling, whether our recycling will also wind up in a landfill with the rest of our garbage somewhere outside of Stockton.

I fear this is the case.

The inefficiency of water efficiency

My college senior thesis was titled, “Water Use Characteristics of College Students.” In it I found that when students paid their water bill directly, their water consumption significantly dropped. When students previously lived in Southern California, a drought-prone region with a lot of water use education, water consumption significantly increased. I hypothesized that the irony of Southern Californian students using more water was due to behavior backlash. Once they relocated to an area with better water access, they splurged on longer showers.

I left my water policy interest there and didn’t pick it back up until I reconnected with one of my high school mentors, an activist and policy leader named Peter Drekmeier.

I love this guy. Peter founded Bay Area Action, a community environmental organization headquartered in Mountain View. I was a member of Bay Area Action's high school group and met some amazing other students in my community with whom I never would have otherwise connected. Together we organized environmental summits, supported other activist organizations, and ran our own local protests. It was fun, interesting, and important work.

Peter is now the Policy Director at Tuolumne River Trust, an organization responsible for educating the public and influencing the development of water use policy in Northern California. I read his editorials and watch his organizations videos. In them, he alerts the public that our water conservation efforts are not leading to less overall water usage. Instead, any conservation achieved by residential consumers simply opens up water to be consumed by various industries.

This is big news. I'd never considered that when I encourage my kids to stop wasting water, to not fill up the bath tab so high or leave the water running while they brush their teeth, the benefits of less water consumed are not trickling up to some water planner deciding to divert less water from a Sierra Nevada watershed. No, instead it's giving opportunity for various industries to grab these gallons.

"See, less water per capita is needed for residential use! We can use that water for cattle, crops, or construction!"

This is what's happening when my neighbors and I conserve water. It's not helping the environment. It's helping business. I'm not saving water, trying to be efficient, so that someone else can be inefficient. This is what economists call a "free rider" problem. It's also a familiar irony in business where if one manager runs a tight ship, and ends the year under budget, the following year he will get less budget while managers who are less efficient get more. There's no benefit, in other words, to being efficient. This is what economists call "adverse incentives."

Combine "free riders" and "adverse incentives" and you have what I would call a "shit show." State legislature needs to resolve this problem. The benefits of good residential water behavior should not flow toward poor stewards of our state's clean water supplies.

The end of cheap energy

I can't believe how cheap energy is right now. Check this out:

Last year, in 2018, the national average cost of a gallon of milk was $2.90.
Last year, in 2018, the national average cost of a gallon of gas was $2.72.

Gas is cheaper than milk! It's cheaper to move your 3,500 pound car 25 miles than it is to drink 16 cups of milk.

When you think about it, this is insane. The work, energy, and value of moving a car 25 miles seems to me, at least, to be 50 or 100 times more valuable than filling up my cereal bowl a couple dozen times.

And yet this is how our world works. I can go to the Veranda Shopping Center in Concord, California and enjoy several large outdoor fires running non-stop on natural gas. They keep those fires running because natural gas is so cheap.

The same with my own home. We built a fire pit because the additional cost of running it is so marginal. Heating our home, running a propane BBQ, and using a gas dryer are all relatively low marginal costs.

How can this be? More importantly, how long can this be? I wonder if future generations will also look back on this profligacy and wonder what the hell we were thinking. Natural gas and oil and its gasoline derivatives are not renewable. There's a finite amount on this Earth and all the science in the world today cannot create a synthetic. Once it's tapped, it's gone.

And yet here we are, burning it into the air simply because it's fun and pretty... and cheap.

A bit of hope: The rise of composting and compostables

Our salvation may come from worms.

Whenever I see companies opt for simple, compostable packaging (e.g. a plain brown paper box instead of vacuum wrapped cellophane) I get a glimmer of hope. I'm glad to see bans on plastic bags and straws being passed by cities in California. These are small steps and perhaps minor inconveniences to people who have become accustomed to them, but we should instill a culture of reuse. If you need a straw, then get a cup with a sturdy reusable one. If you need bags, the cloth ones are far superior to the plastic ones anyway.

The world will always need good compost, and the more people learn to compost and create edible gardens in their own backyards, the less we'll need to haul this stuff from residences to industrial composting facilities. The green utopia (or ecotopia? I'm sure someone has coined that...) is all about composting.

The other obvious and very public trend is the emergence of hybrid and electric vehicles. However, there are roadblocks (pun intended). Our current political leadership is stuck in the fossil fuel stoneage and not helping this latest new technology come down in price. As a result, when my family needed a new car a couple of years ago, we bought a gas guzzling Hyundia Santa Fe. Hybrid SUVs were out of our price range. Next time we need to buy car I hope to make a greener choice. In the meantime, my conscience is mollified by the fact that we don't commute to work and I prefer to jog my kids to school and to the park rather than to drive them.

We have a big ol' SUV but we don't put a lot of miles on it. That gives me hope, too.

Read Write Play: Q1 2019

2019-04-28T14:14:00-07:00

Another quarter, another RWP. I'm glad to report that I've been doing a LOT of reading, writing, and playing.

Read: 3 books on Finance

This quarter I managed to read three books as part of my self-improvement curriculum. In ({filename}my-personal-2018-recap.md), I mentioned how I wanted to focus my media consumption on specific topics. Rather than trying to read and keep up on everything, I'd put blinders up and focus on one (fairly broad) topic. I decided to make finance and accounting the inaugural subject matter, and I initially set out to read two books. However long it took to read two books on finance would be the length of my "class." I ended up reading three.

The Ascent of Money by Nial Ferguson

An awesome overview of the financial history of the world. I listened to the audiobook many years ago and told myself then that this book deserved a second pass. It's so dense, so fascinating, so comprehensive that it warrants real study. I tried to read this book slowly and let it sink in, but giving it the treatment it deserved probably would have meant taking months to read it rather than weeks.

I made 16 Kindle highlight notes in this book, which is a lot for me. Ferguson goes deep into economic theory, noting the structures that make economies actually work. Here are some examples I highlighted.

"Poor countries are poor, in other words, because they lack secure property rights, the ‘hidden architecture’ of a successful economy."

Nial Ferguson

He writes a lot about the role that government plays in laying the groundwork for successful economies. It makes a lot of sense. Government policies can also ruin an economy, as in the example of hyperinflation.

"Inflation is a monetary phenomenon, as Milton Friedman said. But hyperinflation is always and everywhere a political phenomenon, in the sense that it cannot occur without a fundamental malfunction of a country’s political economy."

Nial Ferguson

He also explains how government policies in the future can improve the gap between rich and poor. I've often wondered why poverty has existed throughout history. I've not heard of a society in all of modern humanity, going back to the advent of cities, where there wasn't an upper class and a lower class. Prior to the birth of cities, I think there was a forced egalitarianism. I think (and I admit to needing to study this) that Native American societies didn't have the concept of rich and poor. One's hierarchical ascent in their society came only with age.

"Only when borrowers have access to efficient credit networks can they escape from the clutches of loan sharks, and only when savers can deposit their money in reliable banks can it be channelled from the idle rich to the industrious poor."

Nial Ferguson

Of course this purely free market solution could certainly be argued against. Ferguson addresses externalities throughout the book but clearly has a firm belief that when an economic structure exists with clear rules that allows the free economic transfer of goods and services, people will prosper.

This book is a great read for anyone studying economics.

Financial Intelligence by Karen Berman and Joe Knight

This was the perfect book for what I was looking for: a simple review of financial statements and the common ratios to analyze them. It is well-written, informative, and just the right length.

However, unlike The Ascent of Money, I didn't make a single highlight. It's not a reflection on the quality of the book at all. It's just not the kind of read that makes you want to highlight. It is, however, exactly as advertised. I do have a better understanding of the art behind finance. I'm more financially intelligent. I know now where the subjectivity lies in the income statement, around how revenue and depreciation can be impacted simply by what rule the controller chooses to recognize them.

I also now have greater appreciation for Warren Buffet's view on financial statements. He puts the greatest weight on the Statement of Cash Flows, because for the most part, this statement can't be influenced by the whims of the people running the books. There are ratios, which I recall from my MBA classes but didn't really click until I read about them in this context, that compare numbers from Statement of Cash Flows with the Income Statement or Balance Sheet. Those seem like the best way to evaluate a business.

I'm very glad I read this one.

The Undercover Economist by Tim Harford

The Undercover Economist came up in some podcasts and Google searches. I liked Freakonomics and decided that this would be a good book to read to start my finance "course." It turned out to be my least favorite of the three books I read, but it's not necessarily because it's a bad book.

Harford writes about how both positive and negative externalities can be unexpected and some surprising factors that influence pricing. He also makes a case for expanded health care, something similar to "Medicare for all," saying this:

"The best system would be one that compels patients to pay for many of the costs, thus providing an incentive to inform themselves and to make choices that are both in their interests and reasonably cost-effective, but which leaves the most severe costs to the government or insurance."

Tim Harford

I also thought his arguments in favor of free trade were compelling. He explains why presidents are in favor of free trade (it's good for the nation as a whole, even if some specific communities are impacted negatively), and explains why global free trade ought to save the environment and decrease poverty.

However, as is the case with Financial Intelligence, financial statements and global markets don't work perfectly because whims and emotions get in the way. As Hartford writes, "In the end, economics is about people."

I would add, "and people aren't perfect."

Thus my financial class is complete. I subscribed to the Wall Street Journal and started reading it every day, watched some financial documentaries, read some other articles on finance, and finished these books.

This quarter I am going to read 3 books about design and do something I've been wanting to do for decades. I've started to learn how to draw.

Write: Cancer stuff

I have a book in mind that I intend to write, but I haven't started writing it yet. There's an outline but that's it.

Instead, my writing in Q1 was dominated mostly by some good and bad news I got regarding my papillary thyroid cancer. I think it's summarized pretty well in my most ({filename}and-now-a-bit-of-certainty.md).

The news is mostly good, and I am mostly fine. Writing about it is therapeutic and sharing it kind of sets it off to sea. I share because if I write and don't share then I feel like it's still stuck with me. By publishing it, I can push it into the world and out of my head, away from my psyche. So that's why I write and publish these stories.

Play: The Rolling Sloans

I have been playing a lot of guitar and piano and I've started taking singing lessons too. I found a music teacher who I pay a little bit extra for the convenience of her coming to my house for our lessons. She coaches me through beginner to intermediate-ish pieces by Mozart, Beethoven, and Bach. She gives me scale exercises and guidance on how to make sure my fingering is correct when the sheet music isn't explicit. I've become a much better piano player since the lessons began and it's become more and more fun to play piano. It really started to click for me in the last few months.

At the same time, I've been preparing for the 10 year reunion of my grad school band, The Rolling Sloans. We're playing in Boston on Saturday night, June 8, and I've been preparing for this for months. I have a Spotify playlist of our set, printouts of the music, and have been playing along with the songs as frequently as I can. When my girls are playing in the court with my neighbors, I fire up Spotify, grab my acoustic guitar, and jam along with the tracks. It's the best way I can think of to practice.

First half
Second half

I'm going to sing a few, just like I did for our 3-hour set five years ago. This time we'll have between 1.5-2 hours to play and we're going to jam in as much music as possible. The songs I'm leading for are:

Alone - Heart- My Hero - Foo Fighters- Mayonaise - Smashing Pumpkins- Love Yourself - Justin Bieber- Shine - Collective Soul

I've been working on these with my teacher, who in the course of the last few months has increased my upper range by a minor third (three half-steps). More importantly, I'm more confident, more comfortable, and more excited to sing in front of my classmates than ever. I was nervous five years ago, and spent most of my prep time working on guitar solos. I didn't practice singing. When I was an MBA student, I definitely didn't practice singing. There was no time. I played lead guitar and let our rhythm guitar player and singer do all the vocals. We had a blast playing more shows than I can count. We were in demand because we were really good. Like really good.

Ten years later I want to present myself a bit more polished and matured as a musician. I will have more fun on stage if I'm confident, and I will be more confident if I'm comfortable with how I'm playing and sounding. So I've basically been playing my solo songs non-stop, in front of family and neighbors and of course my piano and voice teacher.

My next RWP will feature highlights from the show! Can't wait.

And now, a bit of certainty

2019-04-27T21:33:00-07:00

If you're new to my cancer saga, here are parts one and two. Part three is coming along in a couple of sittings like this and this. It's the part where after I get diagnosed with papillary thyroid cancer, get it removed, and carry on with a bit of cloud hanging over my head, the cloud comes into focus. Now I know what's next.

In case you hadn't heard, cancer sucks. If it doesn't kill your body, it tries to kill your spirit, your innocence, your optimism that you can fight and handle anything if you just eat healthy, work out, and be nice to people.

No, cancer doesn't give a fucking shit about any of it. I could be a paleo-keto-vegan monk teaching orphans how to meditate. I'd still have this fucking cancer.

For the last two years, my biggest concern about my experience with cancer was not my missing thyroid or the pills I have to take, it was the uncertainty that it might still be there, lurking in the shadows of my neck. My blood tests didn't quite pass muster. My ultrasounds and MRIs were not quite pristine. Something was afoot, and the evidence kept pointing back to this one rogue lymph node. An asymmetric blob that my docs at Kaiser found and my docs at John Muir Medical Center finally biopsied.

That's where I left off last time. The follow-up involved an MRI to thoroughly case my neck, explicitly looking for more funny business. Neck MRI scans, because this area of the body is so complex, take a while. The technician told me that these are the longest scans they do. For forty-five minutes I'm squished in a tube, unable to move my upper body, with earplugs in my ears to muddle out the crazy thumping and bumping sounds that the MRI machine makes. It's the worst. I'm grateful for the technology. I'm glad that I have insurance and can afford the copay. But boy do I wish I didn't have to get MRIs of my neck.

I've been coupling these cancer hospital appointments with swim workouts. The motion of my body and the sound of the water feels cleansing, like a baptism. Hospitals, for all of their sterility, feel dirty to me. It's like I need to wash the hospital air right off of me. Hospitals are for sick people. I'm not sick. At least I don't feel like it, don't think it, don't act like it. And technically I'm not sick, even though at this very moment I have papillary thyroid cancer in a lymph node near my clavicle.

I've made the mistake of reading through the r/cancer subreddit. It is not a place for the faint of heart. These are real tragedies. My saga is a fairy tale compared to many people writing on that forum. I can't complain, but I do because it's only natural to gripe when something's not fair, even when other innocent people have it worse. Far worse.

It was on Reddit that I learned a new word, "scanxiety." It's the fear of finding out your test results, the moment when your doctor's number shows up on your phone and you realize that in mere seconds you will find out if the news you've been waiting for is good or bad. Did the numbers go up or down? Is it better or worse? Am I going to live a long life or die next month? After every scan there's more scanxiety waiting for you.

That was how I felt after the MRI. After the biopsy I was fully prepared for the bad news. It was pretty obvious that Dr. B thought they'd find cancer. What she didn't know is if, given that biopsy, there would be evidence of other cancers in my neck. It's not unusual in papillary thyroid cancer for it to spread in the local lymph nodes. However, for this particular cancer, even with the spread it is technically a Stage 1 cancer. Meaning, even without this positive biopsy, I'd be a Stage 1 papillary thyroid cancer patient. Having the one positive lymph node doesn't change the stage. To be Stage 2 they'd have to find it beyond the lymph nodes in my neck. It was possible the MRI could show this.

So yes indeed, I had scanxiety when the report came back, first via email, and then via a phone call from Dr. B's office. I remember I got the email when I was putting my younger daughter to bed. When she's drifting off, I rub her back with one hand and play chess or crossword puzzles on my phone with my other. The email alert popped up and I saw it was a test result from John Muir Hospital.

Suddenly I have two hands on the phone. My breathing is a bit shorter. My lips tense and contract. I try to calm myself as I open the message, click on the link, and log in. I wait for the screen to load, click on the test, and read the results. I scan for the punchline and find it.

No more bad news.

Yes! Finally, some certainty. My bad news stops with one lymph node, and that can be dealt with using a little bit of radioactive iodine. In my position this is as good as it gets.

Right now I'm waiting for my insurance and the pharmacy to do their dance and tell me how much more savings I have to put into my treatment. For the first time in my life, I will probably hit my out-of-pocket maximum.

I'm grateful for insurance, and also that I can afford it, but man oh man. If cancer wasn't scary enough, the cancer treatment bills make it even scarier.

Life goes on though. You make money, you spend it. We'll see what happens next.

The game I'm playing

2019-04-26T21:11:00-07:00

Here's more mid-30s introspection about life and goals. These are things I've been thinking about as the people around me and I get older.

What game am I playing? How do I know if I'm winning or at least doing above average? And why, for goodness sake, does this even matter?

Like most people with a pulse, I have pride and ego. It would be really nice if I honestly truly didn't care about how successful my friends, neighbors, and schoolmates are, that I don't notice when someone I know buys a Porsche or a Tesla or is an early employee (or founder) of a publicly traded company. I do notice, I do think about it, I do introspect for a moment, sometimes longer, and ask myself if I'm still doing it right.

The answer, I've decided, depends on what game I'm playing. Is it the make as much money as possible game? Have the biggest house and fanciest car game? Is it the have the most social impact game? Travel to the most places game? Have the most fun game? All of these are interesting, valid ways to live a life. But am I playing them? Am I even on the field? If not, what am I doing?

I am writing this post to help myself figure out this fairly existential problem.

Game #1: Make the most money. (Answer: No.)

I'd love to have $20M in my bank account. I would not love what it (most likely) takes to get that $20M. Here are a few scenarios.

Be a founder of a public company.

Too much work. I looked into this, tried it on for size, worked really hard for about five years, and came up short. Sadly, the window I had to start a company that might go public ({filename}im-not-fundable.md) on my poor little fingers. We raised $16M and did all the things that venture-backed companies in early stages do to try to make it, ({filename}scripted-dont-quit.md).

I've seen other friends have much more success, and while I tip my hat to each and every one of them, I also recognize the sacrifices they made to get there. It's a lot of work, stress, and time. This is a lifestyle I don't want right now. It's not my game.

Be a partner or senior executive at a large company.

You don't need to start a company to get rich, of course. Managing directors and C-level executives at top consulting and other private sector firms can make north of $1M per year in salary and bonuses. In fact, this is how a majority of millionaires make their millions.

It's also a lifestyle where you go to the office every day, work late, wake up early, and probably travel an awful lot. I caught a glimpse of this during my two years of management consulting after college. I decided this was not for me. So I went to grad school and did my startups.

I've concluded that I'm not great at making gobs of money. I'm good at making enough money to be comfortable in the Bay Area, which is a feat itself, but beyond a certain point, I get complacent. The itch to earn more fades away pretty fast. Like I said, not my game.

Game #2: Have the most expensive things. (Answer: No.)

You don't need to make tons of money to have a lot of nice things. If you maximize for consumption, then you need merely to minimize your other expenses. For example, if I really wanted to have a bunch of nice things, like fancy cars, income properties, and jewelry, I would not have had kids. Having kids is the worst way to go about having expensive things, and yet I had two of them.

Needless to say, this is not my game either, and if you know me then this should come as no surprise. I like comforts. I like nice cigars, scotches, and hotels, but I'd rather ride my bike or jog than drive my Camry or my Hyundai. I have a Rolex but it was a gift from my parents. Our house is expensive but it's below average for the Bay Area. The expensive things I own are not out of some flamboyant need for show or due to personal preference. They're expensive because they have to be expensive.

I wish I didn't have to spend $24,000 on a car for my family, but I did the research and bought a nice, safe, used car. Same with the patio we put on the side of the house and the deck we added soon after we purchased. Those are necessities, and since we plan to live here forever, it felt like good investments to choose the nicer options of those projects. I want to be able to make decisions like that. Get the more expensive, higher quality housing materials. Do some upgrades! We can afford it because we've opted out of the most expensive options elsewhere in our spending.

So no, I don't want to have the most expensive things. I don't want the biggest house or the best car. In fact, I never did. I just want to be comfortable.

Game #3: Have the most impact. (Answer: Maybe.)

At one point in my life, this was definitely a goal. I really wanted to dedicate myself to environmental sustainability. I was going to be an activist, a networker, mover-and-shaker, someone who could influence policy at the highest levels. This was the person I was in high school and college. It's the person who spoke at his college graduation, got some University-wide and national awards, and ultimately got accepted to the ({filename}what-my-grad-school-experience-meant-to-me.md).

That guy is still here, but he's... chillin'. He got older, fell in love, started a family, and fell into the world of technology and startups and the fascinating leadership, management, and other intellectual challenges surrounding them. This is where I'm at now. I'm immersed in the challenge of building and running startups. It checks all of my boxes:

Interesting work - Interesting people- Good salary with great upside- Autonomy

I like to build things. I like to run them too. It's a lot easier to build and run a technology company than an environmental non-profit. I like to have customers. The flow of money is a simple way to measure the value of what I'm building. Even when I know it's not necessarily making the world better, I know that I'm at least making someone's life better. They wouldn't be paying for my product otherwise.

That simple little thing, knowing that I built or am running something valuable enough to make hundreds of thousands or millions of dollars (haven't reached that "tens of millions" stage yet) , is enough to get me by. I'm content, but I do wish that I could add this bullet to the list I wrote above:

Makes a meaningful positive impact on the world

Scripted had elements of this. We helped people with writing talents make ends meet. Moms bought groceries with the money we helped them earn. Dads bought Christmas presents they would not have otherwise afforded. These are real stories we heard and that felt legitimately good. Nothing I've built since has had impact anywhere close.

So yes, this is a game I want to play. I'm not playing it now, but it's a field I want to be on. Someday I will make it happen.

Game #4: Travel, be independent, have fun. (Answer: No.)

The single bachelors I know are not the most happy people I know. They struggle like everyone else to figure out the game that they're playing too. Even though these are the guys that have the freedom, financially and otherwise, to travel anywhere, attend any event, and date anyone. I have seen that this is not the key to happiness.

Happiness takes time to enroot. During that time, I believe, you have to be relatively still. You can't keep moving all the time, forming new relationships with people and places. You need to settle down long enough for the happiness to grow, and the longer you stay still, the deeper those roots grow.

I'm three years into my ({filename}an-ode-to-the-suburbs.md) and still can't believe my luck. We have incredible neighbors. A wonderful community of like-minded people who are friendly and interesting and easy to talk to. I've happened upon a group of dads in my neighborhood whom I'll host ({filename}the-view-from-35.md) and see much more frequently out on the street. This is a neighborhood where people run into each other in front of their houses all the time. It's amazing. And these relationships take time to develop.

I've found that it takes several random meetings like this to make a new friend. The first time I see a new face in the neighborhood, I'm pretty quick to say hi. We exchange the normal pleasantries and pretty quickly move along. I'm usually walking or jogging my kids when this happens. The next time, the conversation lasts longer. If they have a kid, then our kids will play. I learn more about them, more connections are made. The third time I see them, we're basically friends. There's familiarity and a genuine interest in catching up on the last conversation.

The thing is, this sequence of three meetings takes time. In most cases, it takes several months. If this is a dad who happens to, like me, be out in the hood chasing a kid nearly every day, then it can happen faster. Most of the time it's slow. And this is what I mean about happiness taking time to enroot. Happiness is really about community. The people with a strong community are the happiest. That community can be family, church, neighbors, coworkers, but it's a community. You can't build a community when you're moving all the time.

So although I do sometimes wish I could be 23 backpacking through Europe again, I recognize that that was then and this is now.

I was pretty happy then. I'm even happier now. I choose these roots over that freedom.

Game #5: Comfort and flexibility. (Answer: Yes.)

I rigged it. Is this a game? I don't know. I guess so. I've certainly optimized for it, so it must be something, but I picked this game because I'm doing very well at it.

I'm comfortable. I have a mortgage and two kids in pre-school in the California Bay Area and I can shop at Whole Foods, eat out at restaurants, and still save for the future. This is a huge accomplishment by any measure. Add on top of that the fact that I can work from home whenever I want, have a job that I actually enjoy, and get to choose when I work and who I work with, and yes, I'm crushing the game. I'm like 12 under par at the Master's. I'm the Tiger Woods of finding comfort and flexibility.

I also appreciate that I worked hard to get this. This lifestyle wasn't handed to me, and it was never a given that I'd get it. I set myself up for this, took some risks, and I'm enjoying the rewards. I should allow myself to be proud of the fact that the game I ended up playing is the one I'm most equipped to win. Maybe I've already won it. It's been over two years since I've had to be in an office every day. I don't think I'm ever going back. If I have an office again it'll be the office I use when I'm in the office, not the office I'm expected in every day. That's just not how I roll.

So now what?

I've just determined that I'm winning at something. I have a game, comfort and flexibility, and I'm on top of it. So now what?

I think the answer is pretty clear. I want to keep the baseline the same and add two more elements, in this order:

Make a larger social impact- Earn more money

The two could go hand-in-hand. I've often thought that I would be a very good millionnaire. When I think about having tons of disposable income, I don't think about private jets and oil paintings. I think about writing a huge check to UC Berkeley. I think about hearing about or witnessing a tragedy in my community and having the means to address it. I would love nothing more than to find out a community organization that does important work is shy $25,000 of their financing goal and tap the director on the shoulder and tell them I have it covered. That's what I would do if I had the money. I'd totally be that guy.

But that windfall would come only because I set myself up for luck and I got lucky. I'm not going to earn that kind of money by force of sheer will. It's not my game. So if I don't make millions on a windfall, I'll have to make an impact in other ways. Maybe I'll come up with an amazing idea for a product that people or businesses will pay for that actually makes the world a better place. Maybe I'll invent a better compost bin, a new way to ({filename}what-im-most-afraid-of.md), a website that somehow reduces global warming.

If I had that idea, I'd be building it right now. Alas, I don't. So I will keep playing the game I'm playing until the game I want to play comes into view: Comfort, flexibility, and impact.

Yes, that's the game I want to play. It's just a matter of time.

Here I go again

2019-03-22T21:34:00-07:00

It was 3:55 in the afternoon when I got the call. The area code was local to where I live and I rarely got robodials or spam calls with that prefix so I picked up, even though I had a work call in 5 minutes.

It was a receptionist from my endocrinologist's office. My heart sank a bit. I had a biopsy of a lymph node the morning prior. I knew what this was about.

"Mr. Buckley, I'm calling to inform you that your biopsy did come back positive with papillary thyroid cancer. Dr. B would like to see you to discuss next steps in person."

Despite her busy schedule, we managed to schedule an appointment for the next day. At 3:59 I ended that call and dialed into my next one, a weekly performance review for my day job as ({filename}mightysignals-new-leadership.md). I powered through it, unwilling to reschedule so I could take a beat and reflect. After 45 minutes I was done, my last call of the day was over, and I could take a few minutes to mull the news over.

The thing about this cancer is not whether or not it will kill me -- chances are it will not -- it's the time and money that it's taking away. It doesn't ({filename}the-thing-that-wont-go-away.md) that much anymore, so the psychological effects for me at least seem very minimal. It's an annoyance, a gnat flying around while I keep slapping air. I want it to go away but I'm learning to live with it instead.

The following day was busy. I jogged my girls to preschool. The air was crisp and cool, having rained the night before. These mornings are my favorite times to run. Everything smells so good. The crisp, moist air combined with hints of oak, bay, and grasses is one of the many things I love about ({filename}an-ode-to-the-suburbs.md). I slept fine the night before and woke up itching to jog.

I knocked out the roundtrip with just enough time to shower and get in the car to make it into San Francisco for an 11am meeting. After lunch I had another meeting, and after that I went back to Walnut Creek to see my endocrinologist and discuss the biopsy results in person. On the way I prepared by thinking through the worst thing she could say and how I'd react to it. The worst case wasn't terrible; given that this is papillary thyroid cancer it won't get too extreme unless there's some other indicator that something else is wrong. I figured that was very unlikely.

I arrived to my appointment on time and waited for the doctor to come in. If I knew there would be a 20-minute delay, I could actually do some work. Instead, I noodled on my phone. Reddit, Chess, Crossword Puzzle. All my frequently rotated apps. Finally she arrived and dove right in. It was clear she'd just spent that 20 minutes in her office reviewing my reports.

She apologized, saying she knows this is not the news I wanted, and she asked how I was doing. I smiled and said she did a good job preparing me for this. At our last appointment she showed me where some calcification could be seen on the ultrasound image of the cancerous lymph node. She said back then that it's usually tied to cancer. It had also been two years since my previous doctor at Kaiser raised alarm about this lymph node. And in an odd alignment of stars, it was the Kaiser radiologist next door, my literal next door neighbor, who first spotted it.

Her suggestion was to get an MRI and make sure there's nothing else suspicious in my neck. Assuming it's just this one lymph node, I can then choose to take radioactive iodine, a very targeted form of chemotherapy, to attempt to blast the cancer out of my lymph node. That was the plan we set in motion.

I hopped back into my car and drove to Diablo Valley College where I'm on the advisory board to the business administration department. I mostly forgot about the biopsy, the call telling me there's still cancer in my neck, and the treatments I still have to do. I drove back home and saw my kids outside playing with our neighbors. I told the dad, the radiologist from Kaiser, my new news. He was disappointed but also not surprised.

I'm paying attention to this cancer when I have to, but I'm not stressing about it. I'm frustrated that I have to max out my deductibles now and spend many hours each year and hospitals and blood labs, but I'll handle those experiences when they happen.

I don't need to worry about how much time the MRI will take now, or what will be left on the bill after insurance pays its share.

Those are worries for another day.

Being the other co-founder

2019-03-22T21:01:00-07:00

Reflecting back on Scripted, I think it stopped feeling like my own company pretty early on. I had the luster of a co-founder title but I really was an employee like everyone else. There were some extra freedoms, perhaps, but not real freedom. Not like I have it now.

Part of it was not being CEO until the end. Being the second, internal, “other” founder of a company has its drawbacks. I didn’t have direct contact with the board. In the early days of Scripted, outside of board meetings, all contact went through my co-founder, who was CEO. This meant my co-founder knew everything and I only knew what he told me. Being a co-founder is not the same as being the CEO. Not even close.

I'm coming up on two full years since my Scripted days came to a close. Since then I've run my own ship, sold that ship, and become a hired CEO. I haven't had a co-founder since Scripted and that distance and my most recent CEO experience has brought with it some new insights about those old days at Scripted.

The co-founder or CEO / non-CEO-but-still-important pairing has many obvious examples:

Steve Jobs and Steve Wozniak- Warren Buffet and Charlie Munger- Mark Zuckerberg and Sheryl Sandberg- Bill Hewlett and David Packard

And that's just some big names in tech and finance. There's a reason we like to have Presidents and Vice Presidents, Governors and Lieutenant Governors. Most leaders need a competent partner to achieve their greatest potential. Even the most competent CEO can't do it all. He or she needs a confidant, a second opinion, a voice to call out when they make a mistake.

It's that last piece about trusting the second partner's opinion and hearing their voice that is most critical. The CEO can always overrule. That's the CEO's job. But if they don't listen, don't want to hear it, and consistently see things differently, then the partnership breaks down. It's inevitable, and history is littered with examples of partnership breakups too.

Et tu, Brute?

So when I look back and reflect on the glory and the garbage, I think about what I could have done better as the other co-founder, when I wasn't CEO, and also what I could have done better once the mantle was passed to me. Did I speak up enough? Too much? Did I advocate for my CEO, try to make him better and successful? When it was my turn, did I listen and really absorb the opinions around me? Or did I listen too much?

I'm sure the answer is: all of the above. Had I played my cards perfectly, Scripted would have had a better outcome. But one thing I've learned from reading Warren Buffet's shareholder letters is when you have a business with even mediocre leadership but in a great, growing market, you can get away with making mistakes. You can make more than a few. At Scripted we made some mistakes, and unfortunately we were not forgiven. It was and still is a very tough market.

Still, I feel for the co-founder COO's of the world. It's a tough, nearly impossible position to be in. Charlie Munger, Sheryl Sandberg, my hat is off to you. You haven't made it look easy, but you've definitely made it look possible.

Ode to this set of Cuisinart

2019-03-09T10:31:00-08:00

To note the passage of time it’s easiest to point to a thing, like a grandfather clock or a door frame marked with heights and ages. Time moves. Things stay the same. Even though people are things, we move with time too.

I look at a picture of myself from ten years ago and think, yep, that was ten years ago. Not yesterday, not last year. Ten years. I moved with time and I can see the impact.

I see it in this three-piece set of stainless steel Cuisinart too. The age, the passage of time imprinted all over it. The patina like wrinkles forming on an aging face.

I love this Cuisinart. I try not to love material things, but I can't help it. I love ({filename}the-most-expensive-chair-possible.md), I love the piano I inherited from my grandparents (generously via my dad), I love my house and backyard too, I suppose. But this Cuisinart, which cost about $100 when I bought it 10 years ago and is essentially worthless now, has a particularly valuable place in my heart.

I bought this cookware in New York City when I was visiting an old college friend. I remember we went to a Marshall's somewhere in Manhattan, probably close to where he lived nearby Columbia University. I wasn't planning to buy a heavy stainless steel Cuisinart set on that trip, but I got the urge when we were walking around and Marshall's was the perfect place for a broke grad student to buy some expensive pots and pans.

I remember the box was broken, torn at the corners so I couldn't really carry it. The $100 price tag was exactly what I wanted to pay: enough to feel it, but not enough to break the bank. I wanted something high quality, that would last a long time. A really long time, at least a decade.

I remember joking to this friend that one day I will cook dinner for my children with this Cuisinart. Those one days have become just about every day. Tonight I cooked Trader Joe's wild rice in the saucepan. Last weekend I cooked pancakes in the oversized skillet, which is the only pan we have that can cook three pancakes at once. My wife and kids ate that rice and those pancakes. Countless other meals have been prepared with these pans for them too, and countless more in the half-decade before my kids were born.

One of my favorite people in grad school was a woman named Sonu. We cooked southeast asian food together in my little apartment near Harvard Square. She taught me that the base of most of this cuisine required sauteed onion with various combinations of tumeric and cumin and store-bought curry powders. We broke these pans in together and I remember seeing the colors change almost right away, from the shiny, flawless stainless steel to the weathered yellows and oranges and browns that I couldn't remove despite my best scrubbing.

I gave up on keeping the outsides of these pans clean, as you can see. The stains grew, but so did my cooking partners. When I met my wife-to-be, these were the pans we cooked in together one winter in Boston as I finished my last semester of grad school. They traveled back with us to California, remained in storage in Los Angeles for a few weeks and then headed back up to the San Francisco Bay Area where they've been ever since.

Before I knew it, I had a daughter in the same San Francisco apartment with me and these pans. That funny hypothetical, that one day I'd cook food for my offspring with these pans I bought at Marshall's in New York City and carried back to Boston in a trash bag on the Chinatown bus, ultimately came true.

I'm so happy it did. I'll never get rid of them.

![Cuisinart cookware]({static}/images/2019/03/img_8009.jpg) ![Cuisinart cookware]({static}/images/2019/03/img_8012.jpg) ![Cuisinart cookware]({static}/images/2019/03/img_8013.jpg) ![Cuisinart cookware]({static}/images/2019/03/img_8007.jpg)

I don't use shampoo

2019-03-03T22:00:00-08:00

Many years ago, I stopped putting weird liquid soap in my hair every time I showered. The decision point happened amidst a profound and literal "shower thought." I picked up a bottle of shampoo, looked at it, and thought, “Why am I doing this, again?”

And then I stopped doing it. That was a long time ago and I've never looked back.

Now, I do shower regularly. If I didn’t, I’d start to stink pretty fast. I like a good shower and I always use bar soap. I don’t put that habit in the same category as shampooing every day, which I deem entirely unnecessary. I also do occasionally shampoo my hair with actual shampoo, bar soap, or body wash if it's handy and I think my hair needs it.

But honestly, what makes everyone think hair should be washed with soap every day? And when that shampoo dries out your scalp and hair, what do we do? We put this weird lubricant "conditioner" in it. We're replacing the natural oil we washed out of our hair with fake manufactured stuff. The instructions tell us to swap our natural hair oils for fake hair oils every day.

Why? Well, that answer is obvious. These shampoo companies need to grow! They use every social selling trick in the book:

Urgency: Do this every day, even twice a day, for best results. - Social proof: Everyone else is doing it. Don't be the weirdo who doesn't shampoo (me!)- Escalation of commitment: Start with our shampoo, graduate to our conditioner. Start with once a day, expand to twice per day. - Benefits: Fuller, silkier, shinier hair. (Same as it would be if you just thoroughly rinsed with water.)

I've decided to do some research and look into what exactly is shampoo. And while I'm at it, what the heck is soap?

What is soap?

I remembered learning about phospholipids in high school chemistry. It stuck with me because it was a real-world application of science. These molecules are polar: one end is hyprophilic (attracted to water molecules) and the other is hydrophobic (not so much). This is important because the polar ends of the soap molecule allow it to dissolve water into oils, breaking them up the globs of oil and "cleaning" them out.

If you've ever made brownies (I'm quite a pro) you may remember some recipes that call for a fraction of a cup of both water and oil. You mix them into a bowl (often with an egg) and you can immediately see that the oil and water don't mix. They just gel around each other. This happens because oil is nonpolar while water has a charge on both ends (remember how H20 is positive on one side and negative on the other -- it's ionic!) So since water has nothing to grab a hold of, it doesn't mix into the oil. Soap fixes this by being neutral on one end and polar on the other, acting as a bridge between the oil and the water.

And that's how soap cleans.

What is shampoo?

Shampoo is essentially a soap with some other stuff mixed in, including water. I read that shampoo is actually 60-70% water and the soap component comes in a few different varieties, but the most common form are "sodium laurel ether sulphates." This term describes the chemical structure but the important thing for us to know is they are biodegradable and create a foaming effect when mixing into your hair. Other chemicals are added to thicken the shampoo and prevent bacteria growth (yummy!) and make it all smell like a summer rose garden.

What are the downsides of shampooing?

The main one is indeed the gripe that I described earlier. Shampoo strips hair of its sebum, which is a natural, slightly yellow oily substance that glands in our skin secrete to keep our skin and hair moisturized. In the context of your head, sebum protects your hair shaft from getting brittle, dry, and breaking off. When shampoo strips that sebum away, hair can get in bad shape.

That's why the shampoo industry invented conditioners, which replaces the natural sebum that shampoo removed with fake, manufactured sebum, that you get to buy at Walgreens.

So the chemical industry-inspired cycle we're supposed to follow goes something like this:

Dirt and sweat get in our hair through the process of being alive.- Rather than washing it out with water or a bit of soap, we're supposed to lather our whole head, twice even, and stripe our hair of dirt, sweat, and everything good that our body produces to keep our hair healthy.- Replace the good natural hair oils (sebum) with inferior chemical ones.- Repeat

I, for one, am not buying it, and neither should you. However, I understand it can be a bit jarring to make the change. Instead, I encourage you to try it out. Skip shampooing for a day, then two. Wash thoroughly with water instead. It may take a few days, but eventually, you won't notice a difference.

You'll save money and let your body do what it's supposed to do: keep you healthy.

My happy place

2019-03-03T07:42:00-08:00

It’s a little cabin on a little lake in Pinecrest, California. The road ends on the south shore, so the only way in is by boat or foot. That inconvenience is what makes it so special. The boat ride across the lake is like a space shuttle launching from terra firma to zero gravity. You’re in a different mindset when you pull up to our raggedy old dock. You’re on Pinecrest Time now.

It was built by my great grandpa, who heard about some parcels on a lake in the Sierras built by PG&E, where he worked most of his life. Having been raised on a ranch and working in downtown San Francisco, he jumped at the chance to sign a lease in the Stanislaus National Forest. That was right around 1928.

Jim, my great-grandpa, picked our lot because it holds three huge ponderosa pines. Easily the biggest trees on the north shore, they tower over our cabin so high you have to go into the lake to see the top.

Legend has it he built the main frame of the house in just two weeks, which was all the vacation he had at the time. That first part of the cabin is now the kitchen and dining room. A living room and bedroom with bunks notched into the sides were added perpendicular to the kitchen and dining rooms. Later, when my grandpa started his family, a second bedroom was added with a small covered porch connecting it with the main cabin. Both are painted fire engine red with green shingles on the roof and shutters.

But what's special about this cabin and this place is not the pine walls and trees beyond them; it's what happens inside. Hours of gin rummy, spades, and hearts. Quiet nights reading by the fireplace. Family dinners and Pinecrest waffles. Time spent the way it was spent for hundreds of years before cell phones and the Internet.

Our family history makes this place so priceless. Notched on the entry frame to a bedroom are the heights and dates at various ages of everyone in my family.

In this most special spot on the wall, I can see my dad's handwriting marking my height at 12 months. Just above it is where I marked the height of my first daughter at 20 months. It's almost dizzying to think about the 34 years between those two moments in time. Or that my dad and I were the same age when we made those marks.

That's the strange thing about Pinecrest. It marks the passage of time, but at Pinecrest, time itself stands still. Pinecrest doesn't change. Only we do.

![Pinecrest memories 1]({static}/images/2019/01/unadjustednonraw_thumb_163a.jpg) ![Pinecrest memories 2]({static}/images/2019/01/unadjustednonraw_thumb_1637.jpg) ![Pinecrest memories 3]({static}/images/2019/01/unadjustednonraw_thumb_1631.jpg) ![Pinecrest memories 4]({static}/images/2019/01/unadjustednonraw_thumb_1567.jpg) ![Pinecrest memories 5]({static}/images/2019/01/unadjustednonraw_thumb_656.jpg) ![Pinecrest memories 6]({static}/images/2019/01/unadjustednonraw_thumb_65a.jpg) ![Pinecrest memories 7]({static}/images/2019/01/unadjustednonraw_thumb_637.jpg) ![Pinecrest memories 8]({static}/images/2019/01/unadjustednonraw_thumb_626.jpg) ![Pinecrest memories 9]({static}/images/2019/01/unadjustednonraw_thumb_652.jpg) ![Pinecrest memories 10]({static}/images/2019/01/unadjustednonraw_thumb_62c.jpg) ![Pinecrest memories 11]({static}/images/2019/01/unadjustednonraw_thumb_635.jpg) ![Pinecrest memories 12]({static}/images/2019/01/unadjustednonraw_thumb_630.jpg)

When I was young, all of my Pinecrest time was spent with my grandparents. I'd be at the cabin with them for weeks, even months, at a time. Sometimes the time would go slowly. I'd yearn for home but also would be sad to leave. Every year when summer came around again, I looked forward to Pinecrest most. That morning when my grandpa's ancient analog alarm clock would go off when it was still dark and we'd pack the two old aluminum coolers, his knapsack, and my duffel bag into the back of his truck was my favorite morning of the year. Better than Christmas. My grandma would be wide awake with excitement, too. I'd climb into the back of the Toyota with his dog Bowie and bounce across the central valley and up to Pinecrest.

I was in my early 20s the first time I stayed at Pinecrest alone. My grandma had passed away. My grandpa could no longer be at the cabin by himself. My family trusted me to take care of the cabin without supervision. I'd spent every year for my entire life there, after all. I knew how to safely do everything, from cleaning the outhouse to starting the fragile Johnson outboard motor without breaking it.

For a few years, I invited a group of close friends to join me. One year, I pushed the limits a bit and invited 17 of them. I called it "A Fine Time at Pinecrest" and encouraged everyone to bring their favorite food, to splurge on it, and bring enough to share. These were friends from all parts of my life: my LA crew, my UC Berkeley environmental friends, and buddies from high school. All ages, too. It was a blast.

![Fine Time at Pinecrest 1]({static}/images/2019/03/720399-r1-027-12.jpg) ![Fine Time at Pinecrest 2]({static}/images/2019/03/720399-r1-021-9.jpg) ![Fine Time at Pinecrest 3]({static}/images/2019/03/720399-r1-047-22.jpg) ![Fine Time at Pinecrest 4]({static}/images/2019/03/dsc00060.jpg) ![Fine Time at Pinecrest 5]({static}/images/2019/03/dsc00073.jpg) ![Fine Time at Pinecrest 6]({static}/images/2019/03/img_0904.jpg)

I made singalong books in 2006, 2007, and 2012. I called them "The Pinecrest Hymnal." One tradition I've enjoyed is playing guitar and leading a singalong at night at the cabin, but I'd always forget the words. The Hymnals were my answer.

Pinecrest was harder with a wife and kids. The summer before each of my daughters turned one was the most strenuous. We cut the trips short. I believe we've turned a corner now, though. As of this writing, my daughters are two and four years old. They're no longer crawling all over the dirty linoleum and putting bits of pinecone and pine needles in their mouths. They love to swim, hike, and climb up and jump off rocks. Pinecrest will be the ultimate playground for them this summer. It won't be long before they can start bringing friends up too and sharing this magical place like I did so many times before.

My other happy place is, fortunately, my home. It's a lot like Pinecrest. Tons of trees and a room with a tall, vaulted wooden ceiling. My house is old with its own storied family history. In a way, with this house, we've inherited another family's Pinecrest. I find little bits of that history throughout our yard. Old ladder rungs and notches on the oak trees. A buried pond. Real horseshoes. An old wooden fence door hung on a tree trunk.

Bits of beautiful history are everywhere. You just have to look for them.

Some great advice about how to stand out in local politics

2019-03-02T22:04:00-08:00

I recently drove out to Sacramento to try to see some old friends and public officials I know. The folks on my list were Assemblymembers Phil Ting, Rebecca Bauer-Kahan, and Jesse Gabriel. I tried to track down Jason Elliott, my friend from grad school who is now Governor Newsom's Chief Deputy Cabinet Secretary, but our timing was off, so I called up another grad school friend, Zach Neumann, instead.

It felt good to toggle my attention back over to local and state politics for a while. It'd been years since my last trip to Sacramento and I'd forgotten how busy it gets. Close to the capitol, it's all suits and ties and handshakes and ad hoc discussions between people carrying binders and iPads. It reminded me how much political infrastructure the state has. It also made me feel small. How can I make a dent in something this big?

The biggest takeaway I got from my little field trip answered that question:

It's easy to make a name for yourself. Just do what you say you're going to do and you will stand out.

Since my conversations weren't on the record, I won't attribute it directly. The point this person made was clear: there are tons of people who talk a big game, who want attention and power, but who don't put in the work. Just by doing what you say you're going to do, even if it's as simple as sending an email, will make you stand out.

Most people are not dependable. In politics, I was told, the number is something like 99 to 1. You can be in the top 1% simply by following through with your commitments, no matter how small they are.

So, baby steps make a difference. Another important bit of advice was this:

If you want to be helpful to a public official, learn about what matters to them, and volunteer to support their agenda. Don't try to pull them over to yours.

This point is brutally honest. Public officials are already pulled in multiple directions by community groups, public interest groups, and the media. If you're one person trying to establish a relationship, you'll be best served by beginning the relationship by being supportive.

In other words, I have work to do between now and when I throw my hat in the ring. There's a big wide gap between here and there.

Feast on pain

2019-02-24T22:33:00-08:00

For all of the moping around and support-seeking you see on social media these days about the struggle of starting a business, there’s an underlying truth that these entrepreneurs love the pain. They wouldn’t find time to analyze and write their feelings otherwise.

It’s just like a bodybuilder or a model critiquing himself in a mirror in front his workout buddies. It increases the mental bruising which in turn reinvigorates the entrepreneurial spirit.

I see it as a cycle, and it goes something like this.

Step 1: Push hard to launch a product, complete a financing event, or hit a major milestone.

Step 2: Let the mental and physical exhaustion catch up to you, feel it wash through your body and limbs, and reflect on it.

Step 3: Write about it, exploring the suffering in excruciating detail, which in turn releases a competitive drive to try again, perform better, summit that next peak.

Step 4: Repeat Step 1.

If I had a normal 9–5 job I think I would miss the most is not having a backstop. I can’t say that I enjoy the pain of letting a ball go by and having to go back and fetch it, but I respect its absence. I know it’s not there, and that constant bit of anxiety is what makes the entrepreneurial job unique and fun. Without it, I’d feel too comfortable, like I’m not pushing myself enough.

Similarly, if I don’t have an ache somewhere in my upper body or legs, then I know it’s been too long since I ran and did pull-ups. So I try to do that workout every other day.

A tolerable amount of pain and discomfort is good. It's a sign of growth.

What actually happens when you click 'publish'?

2019-02-17T22:00:00-08:00

I’ve wondered this myself. Where exactly does my content go when I click the publish button? And how does the internet work? Here’s my attempt to answer these fundamental questions.

It starts here.

A Brief History of the Internet

The internet is essentially a network of computers that can communicate with each other by transmitting packets of information. It’s old technology. Computers in the 1950s were capable of sending basic information to each other, but only when connected to a hardwired network. The technology was limited, but it suggested possibilities that led to today’s version of the World Wide Web.

By the 1960s, computer scientists had created several networks, including Telenet, ARPANET, and Merit Network that could transfer small amounts of data. Each of these networks relied on linear architecture that made it difficult to find files without extensive searching. In order to locate a file, users had to follow a series of tiers. If users did not find the information they needed, then they had to go back to a higher level and start over.

Linear architecture seems antiquated today thanks to the development of hypertext by Tim Berners-Lee, a scientist working at the European Organization for Nuclear Research (CERN), and Peter J. Brown, a University of Kent researcher who introduced the concept to personal computers a few years later.

If you’re interested in seeing how linear architecture works, you can see a simulation of the first website by visiting the first website.

Hypertext connects documents through a series of links. When you click on a website’s link, you’re using an advanced form of this technology. The links have become so complex that today’s hypertext documents form the World Wide Web. Without the interlinked documents, you would not have the ability to surf from one web page to another. Instead, you would have to follow a linear architecture similar to the one used in the 1960s.

Interesting Fact:The first message sent over the internet was sent in 1969 by UCLA scientists trying to communicate with a computer at Stanford Research Institute in Menlo Park, California. The programmers wanted to send the word “login” to the computer at Stanford Research Institute, but the transmission crashed after “o.” The full message was completed about an hour later. Finally, researchers had found a reliable way to send small packets of information without using wired networks.

Early Days of Page Linking

The hypertext concept has been around since at least the early 1940s when Jorge Lois Borges published his perplexing short story, “The Garden of Forking Paths.” The term “hyperlink” was first used by [Project Xanadu](http://www.xanadu.net/) founder Ted Nelson in 1965. Project Xanadu fell short of its objectives, but it provided guidance that helped other programmers create early hyperlinks. One of the first successful page linking projects, led by Douglas Engelbart, discovered a way to create hyperlinks within a single document in 1966. A couple of years later, Engelbart’s team used hyperlinks to connect several independent documents. These early pages didn’t look like what you see on the internet today, but the concept began to solidify shortly after a group of University of Maryland graduate students developed highlighted links for a proprietary system used to [create hypertext documents](http://www.cs.umd.edu/hcil/pubs/books/hypertext-hands-on.shtml). With highlighted links, readers could easily find hyperlinks without disrupting a document’s narrative flow. Home computer users gained access to linking technology in 1987 through a database program called HyperCard that had been developed for the Apple Macintosh. Microsoft began using hyperlinks in the Help section of Windows 3.0, which was released in 1990. Personal computer users couldn’t create their own linked pages, but they could use pages provided by their operating systems. In 1991, Gopher became the first protocol that let individuals add links to different internet pages within documents. It was quickly replaced by HTML, which became the standard for linking documents. HTML became the more popular linking options because it let users create documents with text and graphics as well as hyperlinks. ### IPs, URLs and DNS The internet has to use a series of addresses to organize servers and web pages. All devices that communicate with the internet receive an Internet Protocol (IP) address. Your laptop computer has an IP address. So does the server that you connect to when you want to access a website. All IP addresses [use 32-bit addressing](http://searchnetworking.techtarget.com/definition/32-bit-IP-addressing). The addresses usually appear as four groups of numbers separated by periods. A random example would look like “572.6.3.98.” Every device connected to a network receives a unique IP address to distinguish it from other devices. The internet organizes websites by assigning each one a Uniform Resource Locator (URL). URLs consist of numbers and periods, so they often look similar to IP addresses. Each web page receives a unique URL. URLs don’t make much sense to humans. Most people simply are not good at recalling long lines of seemingly random numbers. A Domain Name System (DNS) makes it possible for website developers to give their pages names that humans can remember. When you enter a domain name — [Scripted](https://www.scripted.com/), for example — in your web browser’s address field, the DNS looks up the IP address associated with the domain name. DNS, in other words, acts like a giant phone directory that pairs domain names with IP addresses. Most of the time, these systems work extraordinarily well. As long as the internet’s architecture remains intact, you can find the website you want without trying to recall long strings of numbers. It’s a savvy solution that makes it possible for humans and computers to communicate easily. ### Here’s What Happens When You Publish Something on Your Blog Now that you know more about how the internet works, you can understand what happens when you publish something on your blog. After you type your article and click submit, the content gets sent to a server that stores your work and assigns it a unique URL, which is usually based on the title you provide. You then instruct the blogging platform to publish your content, making it available to anyone with internet access. Assuming that someone wants to view your work (you’ll soon learn about strategies that can make your blog posts more popular), he or she types your website’s name into a web browser’s address field. The browser submits this request and gets sent to your site’s URL. It’s actually more likely that readers will visit a search engine and request directions to your website or a specific blog post, but this just adds a couple of invisible steps to the process. Visitors often use search engines because they don’t want to remember exact website addresses. Searching has also become the default option for most people. Now your visitors can read your article, play audio-visual content and follow hypertext links to other pages. A lot of hard work goes into making the web seem effortless. Once you look at the underlying structures and processes, it becomes clear that even something that feels as simple as publishing a blog post only happens because computer scientists have dedicated themselves to building an impressive system that knows how to locate massive amounts of information.

If I could redo all of my content marketing

2019-02-17T21:56:00-08:00

If I could redo all of my content marketing, from every company I've ever worked on, I would keep this single, simple mantra in mind:

The content you publish should feel like you're giving a gift.

I certainly don't feel that about everything I've published. Perhaps the closest I've gotten to that is the Parallel Entrepreneur book. I spent a lot of time on it and put a lot of planning into it. Outlines, research, conversations with people. That's probably what it takes to feel like I'm really giving something valuable.

This is certainly aspirational. I don't expect to achieve this bar every time I click publish but I should be aware of when I don't reach that threshold. It's a good marker to go after.

To get closer to it more often, I'll try to follow this process for future blog posts:

Write an outline first- Write in multiple sittings- Do a final reading before publishing

If I did this with every blog post, not only would I publish better content, I think over time it would make me a better writer.

This post, perhaps ironically, did not have an outline but did get written over multiple sittings and did get a read-through. The first draft was kind of an outline, though. I can give myself credit for that.

The thing that won't go away

2019-02-13T10:58:00-08:00

This is my third article about thyroid cancer I was diagnosed with. The first two are My thyroid got cancer and My thyroid got cancer: one year later.

Yesterday I got another ultrasound of my neck. Today I got a call from my doctor that the lymph node that the various doctors have been tracking for nearly two years now continues to be a concern. There's going to be more blood work, more appointments, more blah.

I'm grateful for modern medicine but at the same time I wish it would all go away. This isn't an app or a loud TV show that I can just turn off. It's real life and every few months I have to think about it again and deal with it.

Now is one of those times, and I'm frustrated about it.

I think if I were twice as old as I am right now, I wouldn't care as much. Biopsies and doctors appointments are for old people, not for me. I'm 36, which I thought was "old" 20 years ago, but now I realize is still quite young. I'm healthy. I exercise multiple times a week and I eat tons of salads. I don't drink excessively. I'm not stressed.

Why do I have to deal with this cancer stuff?

Yes, the "woe is me" refrain in my head during these moments is, put simply, "it's not fair."

I know how it sounds and I don't like it. But if I'm honest with myself, that's how it feels. I can't deny my self-pity sometimes, and I indulge in it like a chocolate sundae. I know it's no good for me but it's a temporary reprieve from the reality that cancer doesn't care. There is no rhyme or reason or sense of fairness.

Why me? Why not me? I don't know. Nobody does.

I was saddened to read about the Top Chef winner Fatima Ali died on January 25, 2019, from Ewing's sarcoma, a bone and soft tissue cancer. She was 29 years old and achieved incredible success in an extremely difficult field. Being a chef is crazy hard work, and breaking through before the age of 30 is basically impossible. She did it, and then she died.

Now that's not fair. My condition is nowhere near as serious. People don't usually die from papillary thyroid cancer, so I have the data in my favor.

I don't know what it feels like to have a serious, terminal cancer. I can relate only slightly, because each time I get an email or a phone call from my doctor after one of my tests, I get a flash of anxiety that I'm going to be told that my cancer is really serious. A pit forms in my stomach and I tune in really close to any changes in tone or fluctuation on the other end of the phone. I keep preparing to hear the worst but it hasn't happened. It probably won't, but I can't help the reaction. I don't think I'll ever get used to receiving my test results.

The best thing I can do is what I imagine Fatima would tell somebody in my position. Enjoy the life and days I have. Anything could end it; don't take these healthy, happy days for granted. Don't spend time doing things I don't like to do. Invest in my health and the health of people around me.

And yes, feeling sorry for myself with this mild cancer condition is a waste of time. Right now I actually have nothing to worry about. So I should stop worrying.

My personal 2018 recap

2019-02-06T21:04:00-08:00

In 2018 I did plenty of Read Write Play (RWP). I was good about reading books; GoodReads says I knocked down 26 books of them. And in April 2018 I published my book. I improved at both piano and guitar. RWP continues to echo through my head during the day and I take care to spend my "me" time wisely.

I have a few other mantras playing in my head these days too. In addition to RWP, they are:

"Be disciplined" — start and then finish what you start- "Be consistent" — there are compounding effects to eating, sleeping, and exercising well- "Take small bites" — be aware of consumption, both in eating and in learning

Related to these two bullets are a few tactics I successfully implemented at the end of last year and plan to keep going throughout 2019. Maybe even the rest of my life too.

No more working late

I'm done pounding away at my keyboard every night. It's for the birds. I'm committed now to doing things that are personally meaningful at night rather than going down a rabbit hole of work. It will vary from family time to RWP time to just mindlessly watching YouTube videos or social media timelines, although I am certain I'm doing increasingly less of that.

Concentrated consumption

For the last few months, I've been copying something I noticed Auren Hoffman doing in his monthly newsletters. If you're not familiar with Auren, I encourage you to check out his blog, Summation. It's a lot denser than my writing. He takes deep dives and is very thoughtful about his writing. He's equally thoughtful about his reading, and he shares 5 links to his followers every month. I read most of them.

Recently he began to theme those links, telling us he's been studying healthcare, for example, so his links are all about that topic because he's forcing himself to read up on them and put blinders up on unrelated content.

I decided to apply this to my consumption as well. I've written out a curriculum for myself to deep dive into new topics. The first one is finance and accounting. I've found it's a lot easier to choose what to read and watch when I have a theme to use as a filter. I do this at night instead of doing regular work to fill out the "read" part of my RWP. It's informed what books and articles I read, what Netflix and YouTube videos I watch, and which subreddits I subscribe to.

I also subscribed to the Wall Street Journal for the first time. I want to absorb all the finance and accounting content I can. The duration of this "class" is however long it takes for me to read these two books: The Undercover Economist and The Ascent of Money. My class isn't over until those books are read, so I'm keeping my blinders up on consuming anything unrelated. Other topics on my class list are (in priority order):

Design- Water- Healthcare- Management- Housing- WW1- WW2- Education- China- Renaissance- Climate Change- Marketing- Basketball- Football- Baseball- Soccer- African-American Studies

As I complete each topic, I'll post my notes and learnings here! I'll also include a link to the Notion page where I've organized all the content I'm reading.

A lot less coffee

I'm not sure whether I was addicted to coffee or the routine, but it felt really good to shake it up. My wife and I used to brew a big pot in the morning and sip on it all day. Now we brew personal cups or brew tea instead. I've gone days at a time without coffee and it's no big deal. I like having a hot cup of something in the morning but it was annoying to get headaches whenever I didn't drink coffee.

So no more coffee withdrawals for me, thanks. The other benefit of drinking less coffee is I've begun to drink a lot more water. This also has generated a domino effect of wellness benefits.

Learning to swim

Speaking of water, I recently started lap swimming. I joined a gym for the first time in November 2018 . I probably will dabble in weight training at some point but the reason I joined was for the year-round outdoor lap pool.

I'm slowly working through Ruth Kazez's Zero to 1 Mile program and am loving it. The progress is real. So is the ass-kicking workout. Swimming does wonderful things to my body. I'm leaner, stronger, more flexible... It's a superhuman workout and it boosts my confidence to feel myself making progress. I look forward to my swimming workouts and this addition to my workout routine has dropped my weight.

Commitment to RWP

RWP is a reminder to myself to keep personal enrichment top of mind. This is probably what I'm most conscious of. I really want to keep this up and for several reasons it's harder than the other ones. RWP can be really daunting. I fall off for a bit and it's hard to get back on track. It's too much to chew on, so I'm doing what I mentioned earlier: breaking it into smaller bites. I'm focusing on finance right now for my reading. My old grad school band is playing at our 10-year reunion so my playing is focusing on the set list for that gig. I also want to start taking piano and voice lessons.

And writing, well, this is it. rbucks.com is now my forever blog. I want to turn ({filename}mightysignals-new-leadership.md) into a truly premium brand and will work on doing my own premium content marketing too.

We shall see how this goes.

The bitter taste of failure

2019-02-01T21:24:00-08:00

Scripted, my first and largest business venture, was simultaneously a great success and a financial failure.

The business today is thriving without me. We sold to Xenon Ventures, a growth-oriented private equity group that will continue the work my employees and investors dedicated many years and millions of dollars to build.

For my investors, though, it was a failure. Everybody lost their money. I hate having to pay a parking ticket, and many of my investors lost 1,000X as much. Startup investing is a huge risk. Nobody forced them to invest. Nobody lied to them. Nobody meant to lose their money.

Some startup deals yield 100X returns. Others go up in flames. This one did the latter.

Someone close to Scripted told me that this financial outcome was the result of a weak management team and a weak board. When he said that, it stung. I don’t think of myself or anyone I hired as weak. We did, in retrospect, make some mistakes along the way, but we did the best we could at the time.

In thinking more about what he said, though, I can see his point. A stronger company with stronger leadership might have:

Foreseen the endgame sooner and executed deeper layoffs right away even though it was harder because there was more uncertainty at the time about whether that was the right move. - Kept the culture alive even if some popular managers left the company, which was a really big concern. - Stood up to some board members, telling them that the best thing for the employees, early investors, and the company itself would not be the best thing for the later, larger investors. Angels don’t need to risk everything for the IPO dream. VCs are only in it for huge returns. Scripted’s leadership could have chosen a safer path with a lower likely outcome that would have been much better than what ultimately happened.

How do I reconcile building a great business and losing everyone’s money? It’s pretty simple, really. By the time we’d built a profitable business, we’d burned through every dollar of equity and debt that we’d raised. When the principal payments on the debt came due, we didn’t have enough profit to pay it. We tried and failed to work around that problem with our debt and equity holders. The best solution we found was to sell the business in exchange for paying off the debt in full, leaving equity holders with nothing.

In the days after I sent each of our 40-ish investors a personal note asking them to sign off on a deal that would yield zero compensation to them I learned the hardest lesson in my startup education.

I learned there are two kinds of investors: the kind who can lose money and the kind who can’t. I learned that money is sensitive. It’s painful, powerful, hard, even for people with a lot of it. I learned it can make grown men lash out and cast blame as though this outcome was somehow in anybody’s best interest. It was not. We all lost.

This was the dark shadow cast as the sun officially, finally set on my ten years at Scripted.

I appreciate everyone who invested in my business. I really do. Regardless of amount, they put money down when the stakes were high and we needed it most. They believed in me, my co-founder, the vision and the team and product we had yet to build. It was a huge leap of faith and I don’t downplay that even as I share my feelings about this closing process. I can both respect and appreciate their support and acknowledge that some investors are more emotional about losing money than others.

What happened in my final days as CEO, acting on behalf of my board and debtholders, doing what we ultimately needed to do in order to keep the business alive, was the worst of what the startup experience can bring.

Nobody wants to be told their money is gone. Nobody wants to be the one telling someone that either.

If you’re going to start a new venture or invest in one, you’d better have the guts to lose it all.