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?
Also, from the outside, he seems to have been an impactful/successful leader at YC and now OpenAI. People who know him personally seem to thing he’s an extremely bright and driven person, and his results at YC and OpenAI indicate they’re probably on to something.