Managing Partner at Dragonfly. Effective Altruist. Airbnb, Earn.com (acquired by Coinbase) alum. Writer. Former poker pro. Donate 33% of my income to charity.
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I started shaving my head in my early 20s. I was way too young to be balding that early, and it terrified me. So I decided, fuck it, just go all the way to the finish line.
The first time I shaved my head, I thought I looked like a ghoul. In my dreams, I still had hair. It didn’t feel like the real me. It was really distressing. But I came to appreciate that to everyone else, I was just a bald dude. Nobody who met me ever thought twice about it.
I think over my life, being a bald man has actually helped in subtle ways. There’s something about being bald that subtly exudes competence. It makes you seem strong and self-assured. It makes random people less likely to mess with you. I think there are some real advantages in life to being bald that nobody ever told me before I started shaving my head.
You also look older than you are, less boyish. This can be an advantage. Not all women like it, but those who do find it very masculine.
But largely what I’ve found is people care less than you think they do. Also saves time and money on haircuts, which is a real thing. So if you’re thinking about taking the leap, give it a try. You can always grow it back. (Or if you can’t, then welcome to the club.)
Originally published on X, September 2025.
Here’s what I would do if I was a young person trying to break into VC: Write. Short writeups, on Twitter. Not generic market philosophical thinkpieces, because those will be assumed to be AI slop or regurgitated research. No one will read it unless you’re brilliant, which you’re probably not. Original research, on a specific company or sub-sector. If you want to write about robotics, even that is too broad....
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I passed on @solana’s seed round in early 2018 at $0.04. At current prices, that’s a 3,250x. Solana was one of my first ever pitches as a junior VC, and back then I wrote memos for every deal I passed on (adorably naive and overconfident). Re-reading this memo now is peak junior VC cringe. At the time we were obsessed with “Ethereum killers,” consensus protocols, and what was going to...
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