Hi, I’m Haseeb.

I’m a managing partner at Dragonfly, a crypto fund.

I’m also a programmer, a writer, a teacher, a public speaker, and an Effective Altruist.

I’ve taught a class on web3 Entrepreneurship at UC Berkeley. I used to teach a class on cryptocurrencies for programmers at the Bradfield School of Computer Science. I was formerly a software engineer at Earn.com (acquired by Coinbase), and before that 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 top-ranked high stakes 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 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I’d withdrawn from university to focus on poker full-time, but I knew I didn’t want to play poker forever. There was much more I wanted to do with my life. My relationship with poker was more happenstance than choice.

I came close to quitting, 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. 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 asked them to refrain from telling the public about it, since it would destroy 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. Before long, I was reviled in the poker world—just as much as 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, were 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 the book behind me, I knew that I was done with poker. It closed 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 understood how much poker had shielded 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.

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 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 already knew how to direct myself toward learning something new. 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 become an instructor. I accepted the offer.

I quickly rose up as an instructor. After gaining the confidence of the 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 Airbnb, Google, and Uber. I wrote a blog post about my job search, 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 battling 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 learned more about the plumbing 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: this thing is due for a rewrite.

That, in large part, is what made me catch the crypto bug.

In June 2017, I became convinced that blockchains were going to change the world. I said goodbye to Airbnb so I could pursue crypto full-time.

I began my career in crypto by publishing a security vulnerability in one of the first DeFi protocols on Ethereum, Bancor. That built me a bit of street cred. After that I worked for Balaji Srinivasan at Earn.com, which got acquired by Coinbase.

I then cofounded a startup building a centralized stablecoin. Several exchanges wanted to acquire us to build out their internal stablecoins (this was before USDC, PAX, and BUSD). It was while navigating these acquisition offers that I met Naval Ravikant, the legendary angel investor and cofounder of Meta Stable Capital, one of the oldest funds in crypto.

I asked him for advice on these acquisitions. Instead of giving advice, he gave me an invitation to become a partner at Meta Stable Capital. I didn’t know a damn thing about investing—I always saw myself as a builder. But the way Naval put it: being an entrepreneur is like being a single grain of sand in the ocean, fighting to make it to shore. But an investor gets to pull up a chair and watch the whole beach, making bets on which waves he thinks will make it to shore. If you think crypto will change the world, then intellectually, being an investor is the best seat in the house.

He convinced me to shelve my startup and join Meta Stable as a GP. That’s how I got my start as an investor. Although I understood the technological aspects of crypto, I knew very little about investing (in my first week, my reading list included Mastering Ethereum: Building Smart Contracts and Dapps, Handbook of Applied Cryptography, and Hedge Funds for Dummies).

But as Naval put it to me: in investing, the terminology, reading term sheets, how to price deals, that’s all easy to learn. It’s not easy, but it’s easy to learn. It’s judgment that’s the hard part, and nobody can teach you judgment.

We made many early investments in my time at Meta Stable, including Avalanche, NEAR Protocol, Starkware, and Filecoin. But Meta Stable was a quintessential Silicon Valley VC firm, with all of us based out of San Francisco. I had little awareness of what was happening outside of the SF crypto bubble.

While I was at Meta Stable, I met Bo Feng, a legendary venture capitalist from China and a big investor in the fund. He and I built a relationship, and our conversations revealed to me how little I understood the global impact of crypto. As an American, I lived on Crypto Twitter and understood the anglophone crypto universe. But most of the users, the exchanges, the miners, and the trading volume of crypto was outside of the US, mostly in Asia. I knew little about it. But the more we talked, the more we realized how limited my vantage point was.

Bo and I decided to strike out together to build Dragonfly, a global crypto investment firm, combining our perspectives and strengths. (A few years later, we would end up acquiring Meta Stable.)

Today, I’m a managing partner at Dragonfly, investing in promising blockchain projects that will lead to the future of money and online ownership. If you’re working on something cool in this space, I’d love to talk to you.

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 focus yet. I try to fast one full day a week.

I also donate 33% of my income to charity as part of my commitment to Effective Altruism. I’ve done this yearly since 2015 (though as a fund manager, this has gotten a lot more complicated, since more of my compensation is non-salary and requires re-investment; but the end result will remain the same).

Oh, and I only drink water—but don’t worry, I’m not weird about it.