Apparently a smart guy, but it's always hard to distinguish "smart at selling himself" from "smart at building good things."
And even though Loopt failed, it failed in the right way. This is America: failure is not a negative.
What he has done with OpenAI is only the second time true disruption has happened in the last decade after SpaceX.
I am not sure I get the "failed in the right way", though. From one point of view, I think it's a great story here that, given how much of a role is played by luck and external factors, someone who might have proven himself to have great instincts and intelligence can get ahead even if, due to external factors, his particular startup failed.
But from another point of view, Sam is just an example of "those who can, do; those who can't...", only in this case it's "become hugely successful VCs and CEOs."
Which is weird! But maybe the wrong interpretation. I don't know.
Everyone who has ever slept with a YC founder has known this for more than 10 years, and there are still going to be holdouts?
It’s over folks. It was fun while it lasted. Not.
He's one of those guys like Kevin Rose who seems to be able to fail upward again and again. Like every venture is a failure but the person responsible ends up being given even more responsibility and even more money. They're very common in silicon valley for some reason.
As in, his rep seems (from my distant POV) to be about his acumen as a mentor, not investor. Maybe that's bullshit! Maybe he's just great at picking the right horses! And that's totally a talent on its own, and one deserving of a lot of respect.
But it seems like his star was really made on the perception that he knows how to give good advice, which as I said above has a bit of a weird "those who can, do..." vibe to it.