I’ve talked to Sam once a long time ago which gives me a rudimentary answer to your curiosity. PG’s notes on Sam in that 2009 essay ring true to me (http://www.paulgraham.com/5founders.html).
> there are a few people with such force of will that they're going to get whatever they want.
We discussed nuclear power which was an industry I left but dreamed of building a successful startup in. Sam asked me why I wasn’t building a startup in nuclear power if I thought the technology was so powerful. What I realized in what he was conveying was that if he had the same conviction he would have no doubt about the ability to drive it to success. The more experienced I get the more I value that type of conviction and determination. The more I also see that behavior being rewarded with results.
I imagine what I’m missing most is how he handles those huge obstacles. We all can turn on sheer force of will for a set amount of time but keeping it buoyant in the face of huge obstacles is another matter entirely.
His company failed, selling for a bit over the amount of cash they burned. So he didn't handle huge obstacles. And at YC, it's the startups that have obstacles that need to be surmounted, not YC itself. YC has perpetuated the cult of the startup (and the cult of "you need YC for your startup to be successful") so well that they can take equity in a number of the world's tech startups very, very cheaply at the nascent, "fruit fly" stage, ensuring that YC has enough lottery tickets that some will pay off. It's the "startup factory" play, all the founders triumphs and tragedies are just so much grist for the mill.
YC is like a doctor which takes a 10% cut of the lifetime earnings of every baby they deliver. Adding some value, yes, and some kids won't earn very much, but the wealth earned by the new human would have almost certainly been earned regardless of the doctor's skill. And this doctor happens to deliver half the babies of the entire state of California.
The cult part was thanks to PaulG. As long as that continues, YC will be successful.
OpenAI was the result of a fear that big tech. was going to monopolize all the fruits from recent deep learning advances, because they had all the data and the money. That was the obvious new hotness to get into. Proprietary AI was an existential risk to VC livelihoods.
I don’t know much about Sam Altman, but the OP listed a bunch of external signals which are just that.
My guess is the Sam has a solid combination of vision, determination, intelligence, realism and connections. Strong determination with all those other positive supports can take you a long way.
Sam also got the timing right: doubling down on AI just as the technology was ripe for it to flourish.
> there are a few people with such force of will that they're going to get whatever they want.
We discussed nuclear power which was an industry I left but dreamed of building a successful startup in. Sam asked me why I wasn’t building a startup in nuclear power if I thought the technology was so powerful. What I realized in what he was conveying was that if he had the same conviction he would have no doubt about the ability to drive it to success. The more experienced I get the more I value that type of conviction and determination. The more I also see that behavior being rewarded with results.