Managing Partner at Dragonfly Capital. Effective Altruist. Airbnb, Earn.com (acquired by Coinbase) alum. Instructor @ Bradfield. Writer. Former poker pro. Donate 33% of my income to charity.
I recently turned 30. When the decade began in 2010, I was still 20, a professional poker player, a college dropout, and deeply unhappy. What did I believe I’d be doing a decade later? I don’t think I knew, only that I definitely wouldn’t be playing poker anymore. I’d be doing something much more valuable to the world, I thought. But I had no idea what it might be.
I now manage a cryptocurrency venture capital fund. I can imagine in 2010, I’d be very confused reading that about my future self.
The skills demanded of me have changed a lot along the way, from poker player, to mental coach, to programmer, to entrepreneur, to now investor. It also has also meant that since I first came to Silicon Valley (almost 6 years ago), the skills I’m actively cultivating are very different.
One thing that hasn’t changed is that I’m constantly learning new things. The areas that I’m learning about these days are:
And I’m actively working to improve different skills:
And then of course, getting better at investing itself. But that’s hard—it’s difficult to pinpoint what improving at investing even looks like on a day-to-day basis. But that’s what makes it so fun and intellectually demanding.
Looking back over the last decade, I don’t think I have too much to complain about. It was a wild ten years, full of changes and reorientations. If I had to guess, I’d expect the next decade to be slower, full of harder work, but less anxiety and turmoil. I’ve been through a couple careers already, and something tells me this won’t be the last. But probably the only one for this decade, assuming quantum computers don’t annihilate the crypto industry before then. (Kidding. Mostly.)
Over this last decade, I’ve felt my politics and worldview shifting underneath me. I thought this was worth examining.
When I first came to Silicon Valley, my politics was pretty left of center, but overall I was not particularly opinionated about politics. I felt very little personal connection to it in my life.
Since I’ve moved out here, I’ve noticed myself become more libertarian, more in favor of free markets, and much more technocratic in my worldview (basically that direct democratic institutions are fraught with issues that must be mitigated by scientific, well-designed policies). I have lower confidence in the efficacy of most government interventions, and I notice more often when they fail at their policy objectives. I am increasingly suspect of politically motivated rhetoric. I also basically believe that incentives explain almost everything in politics, and that it’s disqualifyingly naive to believe otherwise. Trump’s absurd parade of presidential realpolitik has served as a stark confirmation of this.
It’s hard to know how much of my changed beliefs is due to my environment and incentives. I believe a lot of these changes are due to becoming much more informed about economics, history, and game theory—but of course I’d believe that.
I’ve been thrust into a higher social echelon in the last few years (not myself personally, but the company I keep). I’ve noticed myself become more sympathetic to industrious wealth, which I distinguish from rent-seeking wealth or dynastic wealth. And still, I give away 33% of my pretax income, and it wasn’t that long ago that I was living off very little. I still have a fundamental affinity for the poor, and I’m deeply attracted to minimalism, frugality, and living in service to others.
At the same time, I’ve learned to ruthlessly trade off money for time whenever I can. I believe this has been essential to me maintaining a high degree of productivity, especially when living in a big city.
What else has changed? Ah, probably this too: my relationship with the Internet has changed.
I grew up on the Internet. As a nerdy kid growing up in Texas, it was my home away from home, my community and my intellectual sanctuary. I wanted the Internet to validate me, to assure me that I was smart and worthy. (Of course, by today the “Internet” just means the wider world.)
At some point in the last decade, that changed. I no longer want or need that. And as such, I’ve mostly distanced myself from networks like Twitter, Reddit, and Facebook. I still write and produce content of course. I want to help people, and the most scalable way to do that is through the Internet. I still love teaching, and I’ll always be a teacher at heart. But I don’t really care about winning any Internet status games. At this point, my principal motivation is lifting up those who are behind me.
But most of my values, I think, haven’t changed in the last ten years. I still believe in self-sufficiency. I still believe in shortcuts, though only when those shortcuts are harder than the straight path. I still believe in taking intelligent risks. I still believe in optimizing for the upside. I still believe the well-lived life is one full of challenge and responsibility.
Let’s see what this decade has to offer. Finally, as always, I’ll discuss my year-end donations.
I wasn’t working for a significant chunk of the year since I left Metastable and joined Dragonfly Capital. So while I’m still donating 33% of my pre-tax income, my donations are actually smaller than they were last year. Next year hopefully will see an uptick.
This year I’ve donated entirely through EA Funds. I’d strongly advocate for anyone else in a similar situation do the same. EA Funds are small 501(c)(3) charities managed by top (EA-aligned) analysts and researchers who are tasked with finding the most compelling underserved opportunities within a particular cause area.
Now that I’m a fund manager myself, the specialization really resonates. My time has become so scarce, it’s silly to believe that I could do a better job allocating capital than experts who are working on this full-time. Seeing the enormous delta between an expert and an amateur in my own field, I’d expect it to be no different in philanthropy.
This year I’ve split my donations into three buckets:
Since last year, my donations to the far future have decreased. This is for three reasons: first, I’ve lowered my confidence in AI risk interventions (so far, AI risk organizations haven’t put out that promising of work), second, most AI risk organizations are no longer funding constrained, and third, I’ve become marginally less convinced that runaway superintelligence is all that likely (due in part to David Chalmer’s paper on the subject).
I want to always be giving to global health and development for the obvious reason that visible, low-risk, high-impact giving is an extremely powerful thing to amplify.
I’m working more and traveling more than I’ve ever done in my life. It’s been challenging, but immensely motivating. Actually, I’ve always wondered whether I could handle work of this intensity. Having done it for several months now, I can safely say: yes, yes I can. It’s kind of a relief to know that.
I’ve got a big project in the works that is going to be launching soon after the publication of this blog post. My guess that between that, other projects, and the demands of managing a fund, most of my time this year will be accounted for. But my goal is to keep being prolific, keep helping others, and inspire people along the way.
Here’s to another decade. (Also, crypto, if you could keep going up in this one, that’d be great.)
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