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Sam Altman says Paul Graham and Peter Thiel taught him a key lesson about investing

OpenAI CEO Sam Altman said Peter Thiel and Paul Graham taught him that the best investment opportunities are rarely the most popular, and that to do spectacularly well, investors must do things that are not what everyone else is doing. Altman recalled that after GPT-4, OpenAI faced skepticism from cloud providers, chip fabs, and energy providers when seeking compute, but secured a few key yeses to start building.

read2 min views1 publishedAug 2, 2026
Sam Altman says Paul Graham and Peter Thiel taught him a key lesson about investing
Image: Businessinsider (auto-discovered)

OpenAI CEO Sam Altman said Silicon Valley luminaries taught him how to be ok with standing out when making investments.

"The thing I really learned from Peter Thiel and Paul Graham, both in two different ways, which is that the very best companies, the very best investment opportunities are almost never the ones that look really popular," Altman said during a recent episode of the "Invest Like The Best" podcast.

Altman said following the crowd can help to a point, but it's only when you pick companies that may look unpopular in the moment that you open yourself up to a potentially transformative opportunity.

"You can do okay just following the trend and being a little early, but to do spectacularly well, you kind of almost always have to do things that are not what everybody else is doing," he said. "You cannot be sort of following the new wave."

Recently, the OpenAI CEO has reflected on what he learned during his days leading Y Combinator, the famed startup incubator which Graham cofounded in 2005, and in the Silicon Valley hustle culture.

Altman said that Graham taught him that being a startup investor is "like being a flight instructor." Founders need guidance, but the traditional model of a teacher lecturing isn't what's going to really help.

"The person who sits next to you saying like, 'Do this, don't do this,' that worked, you missed that thing, or, you're making these mistakes, and I'm just going to talk you about this one," Altman said, adding he appreciated "that very hands-on kind of, here's where to direct this sort of like Brownian motion energy."

Altman said memories of his early days in Silicon Valley came back once OpenAI had the realization after GPT-4 that they were on "this exponential of model improvement" they started calling everyone they could to secure the compute they needed.

"We started calling the clouds. We started calling chip fabs. We started calling energy providers and everyone's like, 'You're totally crazy. This is impossible. No industry has ever moved like this. We've been around. There's these booms and busts. It's not going to go up in a straight line. This is reckless,'" Altman recalled.

The experience, Altman said, reminded him of "fundraising for an early-stage startup."

"Most people tell you no, but all you need is one or two yeses," he said. "Most people told us no. And we got one or two yeses and we were able to start building."

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