Life is Education

2017: My education is featured in a chapter on grit, self-directed learning, and the power of rule-breaking for the 2017 book Mindshift by Barbara Oakley. Dr. Oakley is the creator of Coursera’s Learning How to Learn, a practical and valuable course.

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Things don’t always work out the way you expect.

I was raised in rural Maryland, where my parents were caretakers of a trailer park. I was a Boy Scout and spent a lot of time outside, in worlds of my own creation.

I had great grades but was bored and miserable in school. I love learning new things and, as any geek knows, sometimes school is the worst place for those hungry to learn.

So I left school in 9th grade to start working.

This was a tough time, because many people suggested that my life was over. My parents needed to work and couldn’t teach me. We went to visit private schools but couldn’t afford them. So they left me at home with simple rules: “You must work. And you must show progress that you’re learning something new.”

I have grown to appreciate the power of simple rules.

To learn, I took courses on the internet and read from the local library. It wasn’t prestigious, but it was scrappy, affordable, and I learned a lot. Sometimes my Dad would leave a question written on a napkin on the kitchen table. I would have to research and give him the answer when he got home from work.

I still love books and donated several hundred to the MPC, an education project in Guatemala that I worked on. You can tell so much about a person by their bookshelf.

My first job was cleaning bathrooms and offices. I also worked as a street performer, playing music on the beach. (The beach paid way better!) I’ve also worked as a cashier, novelty photo salesman, and a computer repairman.

I used to feel ashamed of talking about these jobs with successful people. But the experience has been valuable. Working jobs like these helps you relate to people at many levels of an organization. You respect people more, because you never know what phase of life they’re in, where they’re going, or what they do outside of work.

Getting Entrepreneurial

I had an entrepreneurial streak early in life. I started dumpster diving to find rare items and broken electronics to repair and sell on eBay. You wouldn’t believe what people throw away! I started tutoring music and grew my little business to dozens of students – I even had to rent a space. I used this money to get myself to college.

I learned early how to make my own luck and how to spot opportunities and say ‘Yes!’ when they appear.

When I couldn’t afford music lessons, I offered to work as an assistant to a classical composer in exchange for learning. I entered music school in my mid-teens, where I studied jazz, classical guitar, and music theory.

I still think that if early-stage entrepreneurship were a musical form, it would be a jazz quartet. I left music school and went to NYU. I worked full-time in college in an IT role.

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Around this time I discovered the work of Karl Popper, whose philosophy of science has become something like a mantra in my life.

I began to see entrepreneurship not only as a life discipline and path to wealth, but as a solution to serious problems in the world. Partisan politics fails. But entrepreneurship is a practical way to pursue positive social causes like: increased capacities for the poor, better opportunities for oppressed groups, free expression, tolerance, and economic growth that doesn’t destroy the planet.

From Karl Popper I learned that trial-and-error is how learning and progress occurs. Since startups are like miniature experiments in solving problems sustainably (i.e. at a profit), I see entrepreneurship as the most effective way to generate enough new ideas to solve humanity’s hardest problems.

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I also learned a lot while researching entrepreneurship at the end of college, including for a Harvard economist studying online labor markets, a historian studying New York City’s bankruptcy in the 1970’s, and a political scientist looking for why terrorist groups build schools and clinics for the poor.

After graduating, I co-founded and edited a startup media outlet and magazine which focused on positive, entrepreneurial solutions to world problems.

I went to Chihuahua, Mexico to learn about immigration and the War on Drugs. Wanting to see how entrepreneurship can thrive in difficult places, I went to Kenya to study street markets and the entrepreneurs that run them with the Kenya National Alliance of Street Vendors and Informal Traders.

I lived in slums across the country and interviewed smugglers, disabled traders, and vigilantes about market structure and informal dispute resolution. These experiences equipped me well to later work in difficult environments.

The magazine startup eventually failed, which was an education in itself. Since then, I’ve had some successes and many more failures. If you want, you can read about some here.

Eventually, I became determined to get the hard skills necessary to become a software engineer.

My self-education in programming was a series of big bets to force myself to learn:

First, I hired a programmer to build a video game with me. I knew a game would hold my interest during the difficult early days of the discipline. I ran out of money during the development of this game. It was never released but was accepted to the Google/Improbable games innovation program because of our wild ideas and compelling prototype.

After that, I rented an AirBnB for 30 days on a llama farm in rural Virginia, the cheapest one I could find within driving distance. I spent the month there, alone, learning as much Python as I could.

Finally, I realized that web development was the most useful technical skillset that someone like me could have today. I learned Javascript and rounded myself out with the latest frameworks by attending Fullstack Academy in New York City.

My programmer’s trial-by-fire was with the engineering team at AskLorem. I led the development of their two-sided conversational commerce marketplace, embedded inside DIY tools like Squarespace and Wordpress. The product included a marketplace, real-time chat and collaboration, numerous third party service integrations, a custom marketing and analytics pipeline – all delivered within the constraints of a Chrome extension.

It was a hugely challenging job and I’m proud of the product that we built. Since them I’ve built more apps, won a few hackathons, contributed to open source, and published some Chrome extensions, which you can check out on my GitHub.

In 2018, I got the entrepreneurial itch again and transitioned to software consulting. Since then, I’ve helped multiple teams and founders make their visions a reality. I’m grateful that by 2019 my consulting practice blossomed into more-than-full-time work and I occasionally need to manage other contractors.

Things don’t always work out how you expect. But I can’t get enough of the adventure.

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