I’m a general partner at MetaStable Capital, a cryptocurrency hedge fund.
I’m also a programmer, a writer, a teacher, a public speaker, and an Effective Altruist.
I teach a class on cryptocurrencies at the Bradfield School of Computer Science. I was formerly a software engineer at Airbnb. Before that I was Director of Product at App Academy. Before that I was a mental coach and wrote a book called The Philosophy of Poker. And before that I was a world-class professional poker player, sponsored by Full Tilt Poker.
That’s me in a nutshell. It’s a pretty strange path, from professional poker player to software engineer to investor. But if you want to get the full picture, you’ll need to know my origin story. It’s good, I promise.
I’ve never been much of a gambler. So when at the age of 16 I played my first hand of Texas Hold’em, naturally, I had no idea what I was doing.
A couple of friends had invited me to play a small home game. I’d never played any kind of poker before. I didn’t know what checking was, how betting rounds worked, or what beat what. I immediately lost all my chips.
Annoyed and feeling stupid, I decided to research how poker worked. In learning more about the game, I kept coming across discussions on poker strategy, and they captured my imagination. The more I read, the more it seemed there was a universe of complexity—mathematics, psychology, probability, game theory—nestled within this little card game. I was hooked. I wanted to try my hand at it.
I started with $50 that I got for free from an online promotion (being 16, I had no money of my own to deposit), and I painstakingly grinded my way up from the 5c-10c games. I was relentlessly cautious with my bankroll. Before long I turned $50 into $200, then into $2,000, and by the end of a year, into $100,000.
A couple years later, I was a millionaire, considered at the age of 19 to be among the top 10 strongest No-limit Heads-up Texas Hold’em players in the world. I got a sponsorship from Full Tilt Poker, produced instructional videos, wrote articles for magazines, traveled to tournaments, and coached poker pros from all over the world.
But despite my success, I slowly grew ambivalent toward my new career.
I’d withdrawn from university to focus on poker full-time, but I knew I didn’t want to play poker forever. In many ways, my relationship with poker was more happenstance than choice. There was much more I wanted to do with my life. I came close to quitting a few times, but my friends always talked me out of it—after all, when I was ever going to be able to make money like that again?
Despite my anxiety, I kept playing on and off until 2011, when I turned 21 years old. Then a series of events would change my life forever.
My entanglement with the Girah Scandal began when, in 2010, I was contacted by a young Portuguese boy named José Macedo, who went by the name of “Girah.” He was a fan of mine, had learned a lot from my teachings, and wanted advice on his career. He was only 17, but was already very successful. José was uncommonly forthright. I liked him. He soon befriended me, and before long, I became his mentor.
He continually sought my advice and I supplied it. Eventually he asked me to become his manager and to back and coach him, alongside my friend Daniel Cates. I’d never done anything of the sort before, but José’s career was growing rapidly. People had started calling him the “Portuguese Poker Prodigy”. I had seen the poker world chew up and spit out many young superstars, and I didn’t want to see the same happen to José. I agreed, and set to helping him establish his career. I wanted him to succeed.
Then, one night in the August of 2011, everything changed. I learned that José had cheated his friends out of large sums of money. When I confronted him, he fled. I contacted the victims, explained to them what happened, and then tried to protect José as best I could. I hoped that José could pay them back along with reparations and that they’d refrain from telling the public about it and destroying his career. I thought I could protect him. But my plea backfired.
When news of the cheating came out, the poker community exploded with anger. And when the victims revealed that I had tried to protect José, that wrath turned on me. More and more information started to come out about just how much José had been deceiving everyone, including me and Daniel. Not wanting the extent of our relationship public, I lied to the community about my history with José. But those lies quickly dissolved, and the truth was discovered. Before long, I was reviled in the poker world—even more so than José himself.
I was dropped from my sponsorships. Former friends denounced me. My career and reputation, which I had painstakingly built over the last five years of my life, was now in shambles.
Although I could still make money, there seemed to be little else for me in the world of poker. Heavy with disgrace, I decided to leave the game for good. I settled my affairs, made amends to those I could, said goodbye to my friends, and left my old life behind.
It was one of the darkest episodes of my life.
I wandered from country to country. I wrote. I reflected on what I’d done with my life. The months that followed were scattered and bleak. I interrogated myself, blamed myself, forgave myself, and played out different histories in my mind.
What was I now? No longer a poker player. I was just a 21 year-old college dropout. I was lost.
In the year that followed, I searched desperately for what to do with myself. I lived and worked on a farm, took a ten-day vow of silence, trained myself in meditation, taught English to refugees, went back to university finish my English/philosophy degree, and worked writing on a book.
In December 2013, I finally published that book, How to Be a Poker Player: The Philosophy of Poker. It was the book that long ago I promised myself I’d someday write, and the the culmination of everything I’d learned in my career. It became the #1 Amazon best-seller for poker for almost half a year.
With that now behind me, I knew that I was done with poker. I needed to close that chapter of my life.
At the end of 2013, I gave away all the money I made as a poker player. I donated $75,000 of cash to charity and deeded my other assets to my family, in total about $500,000. I wanted a clean slate.
My relationship with poker was always rocky. But it was only then that I could appreciate how much poker had nurtured me. I needed to prove to myself that I was truly better off for having been a poker player—not for the money I made, but for the wisdom it imbued in me.
Not knowing what else to do with myself, I worked for a year as a mind coach, training professional poker players, entrepreneurs, and daytraders on the mental and psychological skills I’d learned from mastering the highest levels of poker. I wanted to help others. Slowly and steadily, I was forging a path forward.
The course of my life again changed when in 2014, I came across the writings of a little movement known as Effective Altruism.
The basic premise of Effective Altruism is this: altruism is not as straightforward as most of us like to pretend it is. Most people turn their brains off when they think about doing good. But Effective Altruism demands a rigorous approach to changing the world. It asks you to be willing to accept counterintuitive conclusions if the evidence is strong enough. This is exactly what happened to me.
When I read the original argument posed by William MacAskill on why you should earn-to-give—that is, why you should take a high-paying career so you can donate the money to charity—I could not refute it. Uncomfortable and weird as it was, it seemed correct. Indeed, as a smart and healthy beneficiary of a first-world economy, if someone like me wouldn’t do this, who would? I decided then that this is what I should do with my life.
I made up my mind to earn-to-give, to devote my life to earning money so I could donate it to the most impactful charities in the world. The only question left was how?
Heavily influenced by 80000 Hours, I decided that the best fit for my skillset would be to go into tech entrepreneurship. Given my comfort with risk and uncertainty, and my love of technology, it seemed like a natural fit. But as a former poker player with a liberal arts degree, having graduated college at the age of 23, my resume looked like a bad joke. I needed to find some way to break into the industry.
When I stumbled upon the world of coding bootcamps, I knew I’d found that way in. People with no background had taken these bootcamps, learned how to code, and gotten hired at the top tech companies in the world. I’d get to build things, work directly with technology, and earn-to-give almost immediately. I was in.
I applied in a flurry to every single bootcamp in San Francisco. My top choice was App Academy, one of the most selective coding schools in the world with a less than 5% acceptance rate. For two ecstatic weeks I did nothing but study the Ruby programming language, barely eating or leaving my room, desperate to pass my interviews.
My preparation paid off. I was accepted to App Academy. In April of 2015, I moved to San Francisco and matriculated into a coding bootcamp. That’s how I began my second career, this time as a technologist.
At App Academy, I worked my ass off to learn programming. I was routinely the last person to leave, working from 9AM to midnight or later, 7 days a week. I was voracious, and from my career in poker, I had already learned how to learn. My work paid off: despite my unconventional background, I quickly rose to the top of my class.
At the end of the first 8 weeks of the 12-week course, the founders whisked me into a room and asked me to join the instructional team. I accepted the offer.
I quickly rose up as an instructor. After gaining the confidence of the two founders, I was promoted three months later to Director of Product.
But despite my love of teaching, I couldn’t shake the itch to dive deeper into technology and build things. In 2016 I decided to join the tech industry as a software engineer.
Having such a weird background, I had a tough job search, getting rejected from 40+ companies before I ever got an interview. But I pressed on, and eventually landing amazing offers from top tech companies including Google, Airbnb, and Uber. I wrote a blog post about what happened, which went viral, being featured on Business Insider, Buzzfeed, and Yahoo News.
I ended up accepting the offer at Airbnb, joining their anti-fraud team where I worked on mitigating payments fraud. I learned a lot about security, distributed systems, and machine learning in adversarial environments. It was fascinating work, and going deep in the payments space, I got to know the cogs deep in the traditional financial system.
Working in payments fraud, you get an appreciation for the weaknesses of our financial infrastructure. Really, it’s kind of a mess. As an engineer, when you see a system full of technical debt and bad design choices, there’s only one conclusion you can reach: this thing is due for a rewrite.
That, in large part, is what made me catch the crypto bug.
In June 2017, I decided the blockchain space was too interesting to sit on the sidelines. I said goodbye to Airbnb so I could pursue crypto full-time. Since then I’ve worked on some security research, consulted to a company called 21 (now Earn.com), did a lot of writing and speaking, and taught a course on cryptocurrencies at the Bradfield School of Computer Science. I’m now working at MetaStable Capital as a general partner, investing in promising blockchain projects that will lead to the future of money. I also donate 33% of my pre-tax income to charity.
So that’s what I’m about.
Outside of the aforementioned, I can be found reading, writing, audiobooking/podcasting, meditating, training kickboxing, watching standup comedy, and picking up heavy things and putting them down. I eat a paleo diet, which I think is mostly arbitrary, but I follow it anyway. I plan to become a vegetarian someday, but I don’t have the moral fortitude yet. I generally fast one full day a week. Oh, and I only drink water—but don’t worry, I’m not weird about it.
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