While Drew, Chesky and the Collison brothers were busy building billion dollar companies, Altman took the “shortcut” and made a concerted effort to cozy up to the most powerful man in the room — and it payed dividends. Altman did the same thing in the early OpenAI days by doing flaterring video series interviews with Elon Musk, Vinod Khosla and others [0]. Incidentally, The YC interview with Elon Musk was done the year Musk made a donation to OpenAI (2016),
I still remember PG’s essay where he gave Altman the ultimate character reference (2008) [1]:
>When we predict good outcomes for startups, the qualities that come up in the supporting arguments are toughness, adaptability, determination. Which means to the extent we're correct, those are the qualities you need to win…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.
(In retrospect, praising Altman for being the “king of cannibals” has a nice touch of gallows humor to it. Hilariously, even recently pg has a seemingly unintentional tendency to give Altman compliments that appear to be character warnings masquerading as compliments.)
In 2009, pg included Altman in the top 5 in a list of the most interesting startup founders of the last 30 years.[2] If this was an observation made from afar, you could easily say it was “prescient”. But objectively at the time, no one could find any verifiable evidence in the real world to justify such an assessment. It wasn’t prescient because pg had became directly responsibly for Altman’s future success, in a case of self-fulfilling prophesy. Altman was often referenced in the acknowledgments of pg’s essays for reading early drafts and is probably referenced more than any other founder in the essays. Altman’s entire streetcred came from pg and also, once he made Altman head of YC, YC. From afar, it looks like a victory for office poltics, a skill incidentally that sociopaths are known to excel at.
[0] https://www.youtube.com/watch?v=tnBQmEqBCY0