Sam's startup didn't fail miserably, it sold for $40 million, on $30 million raised. You can do worse, but by VC standards, it's not a real success story, let alone what you'd expect from a guy you describe him as one of your top 5 founders.
This doesn't imply an overall assessment of Altman (most startups fail, and so on...). My outsider opinion is Altman's public persona seems ok, it seems like YC did well under his stewardship, etc. But it sure looks like he was annointed. Paul Graham and folks like to talk about how in school, you just try to make the teacher happy. Well, sometimes making Paul Graham happy is really important too.
I've been investing since 2007. One of the things I've seen is a founder that managed to sell a company that by rights should have folded, made a bunch of money for himself and for the investors and ended up starting another one which was a much bigger success. I would bet on that guy any day. The assumption when starting a company is that it will fail. A founder that manages to make it to any kind of exit is already exceptional, and depending on the circumstances their performance may inspire further trust or a reduction of that trust. In this case, apparently even though the business did not see the returns originally envisioned Sam came through in ways that inspired those that invested to increase their trust factor.
And having seen a similar case I don't think that is something strange at all. Maybe another CEO would have caused that $30M to evaporate.
I would disagree. Seems more prescient to me than ever. Gmail became far more important to the free world which I didn't see coming, and SamA lived up to the hype with OpenAI (before OpenAI he was quite accomplished, but OpenAI put him in the history books).
I haven't started a company nor done angel or VC investing, so I obviously down played that part of things.