Four simple truths about entrepreneurship

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 The Parallel Entrepreneur 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.

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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.

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:

• 11 Years to Overnight Success: From Beach Towels to A Successful Exit
• 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!