He dropped out of Stanford in 2005, at 19, to co-found Loopt. Yeah, it ultimately failed, but over 7 years they got 5 million users, raised $30 mil in funding, and were acquihired for $43.4 mil.
He was a YC partner at ~25, YC’s president at ~28, and seemed to do a good job leading it for ~5 years. He’s also been pretty personally successful as an Angel investor.
He was an early investor in OpenAI, left YC a few years ago to become their CEO, and they’ve done extremely well under him.
No, he’s not Steve Jobs, Bill Gates, Zuck, etc., but his accomplishments at 37 are pretty damn good. I’m not really seeing how this is failing upwards?
And FWIW, Loopt sold for $43m, but $10m of that went on employee retention. The investors made $3m on their $30m investment. That's an annualized return of 1.3%. It was worse than a zero risk savings account.
Sure, there are other ways of measuring success. Clearly from Altman's view, life has worked out pretty well, presumably in part because of experiences he had and people he met while spending seven years making his investors 1.3%. But doing worse than a savings account is not on it's own a sign that you are a great leader, and clearly Loopt was a failure for its investors.