Unschooling

Life is Education

Update 2016: 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 some ‘crappy jobs’ helps you relate to people at many levels of an organization. You respect people at the ‘bottom’ of the ladder 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, which convinced me that many people don’t realize what a luxury it is to focus only on your studies for several years.

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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.

I graduated in the highest academic bracket with studies in Philosophy, Politics, and Economics. My undergraduate thesis was an economic history of a weird period in the early New Deal era when the U.S. government tried to join millions of local businesses into cartels.

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

For my senior panel I argued for a transpartisan update to how we pursue positive social causes like: rights for oppressed groups, increased capacities for the poor, free expression, tolerance, and economic growth that doesn’t destroy the planet.

My argument was that progress in these complex domains will require a shift away from top-down tools of traditional governance. Governance organizations can’t generate enough complexity and enough trial and error on their own.

They’ll have to support and structure environments where trial-and-error experiments can occur.

Forward-looking corporations and governance organizations will need to become supportive partners to entrepreneurs and problem-solvers.

I believe this decentralized, bottom-up approach is 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 for various groups towards the end of college, including 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.

Right 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.

I’ve always loved technology, but I’ve always been on the business side of things. In 2016 I became determined to get technical and trained as a software engineer. I built video games because I figured they would keep my attention during the difficult early-phases of learning a new discipline. Then I spent 30 days in a cabin on a llama farm to learn Python so that I could apply to a coding bootcamp. In 2017, I graduated from Fullstack Academy in New York City with a solid grounding in full stack Javascript.

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

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