My next 10 years

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.

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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 day job now 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 a marketing instructor (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 Scripped 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 building Toofr.com 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 College of Natural Resources 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 a dog and a grill
• Stopped playing squash and road biking
• Sentiment: all grown up

2016

• First round of Scripted layoffs
• Second daughter born
• Toofr began paying me more than Scripted
• Became the CEO of Scripted
• Launched Thinbox
• Launched eNPS
• Sentiment: business can be unpredictable

2017

• Found out I had thyroid cancer
• Second round of Scripted layoffs
• Sold Scripted to Xenon Partners
• Bought my first car, a Hyundai Santa Fe
• Launched TrackJobChanges
• Launched Voxloca
• Launched Glistio
• 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
• 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.