Sam was already a billionaire years ago. He is one of SV most prolific investors, with equity in hundreds of startups. He writes big checks as well from time to time, Helion for instance he gave 375 million.
To be clear, Altman invested $375 million in Helion Energy's 2021 funding round. Helion Energy a for-profit fusion energy company of which he is the chairman.
How? He did not have a large exit to give him a bankroll to invest. Unless you mean from whatever YC shares he received as President, which seems unlikely. Even if he was paid ~25 million in equity per year, did YC shares increase 10x in that time?
Didn't he own like 10% of Reddit. Here what pg had to say about the guy.
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Sam Altman has it. You could parachute him into an island full of cannibals and come back in 5 years and he'd be the king. If you're Sam Altman, you don't have to be profitable to convey to investors that you'll succeed with or without them. (He wasn't, and he did.) Not everyone has Sam's deal-making ability. I myself don't. But if you don't, you can let the numbers speak for you.
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https://paulgraham.com/fundraising.html
My understanding is Altman joined the Three Comma Club only this year not years ago.
Yes, he has made lots of investments over the years as head of YC but not every investment was successful. This was discussed on BBC's podcast 'Good Billionaire Bad Billionaire' recently.