Sam Altman really wants to be liked. “That is his superpower,” says Keach Hagey. “He’s very good at doing favors for people—getting people to see his vision. But he’s bad at telling people no.”
That’s what the Wall Street Journal reporter has taken away from years of covering the tech innovator’s career and the rise of ChatGPT. But it’s also the thread that runs through Atlman’s public life more broadly, Hagey tells Vanity Fair editor in chief Radhika Jones, along with executive editor Claire Howorth and Hive editor Michael Calderone, on the latest episode of Inside the Hive. In it, Hagey, who’s coming out with a book on Altman next month, titled The Optimist, goes deep on Altman’s progressive politics, his friendship with Peter Thiel, his feud with Elon Musk, and his dealings with Donald Trump, along with his brief exit from OpenAI—a.k.a. “The Blip”—and vision for this potentially world-altering technology.
The first thing to know about Altman is that he’s not a “nerd’s nerd,” as Calderone notes. “He could talk the talk of a tech nerd. But at the same time, he had this charm and this charisma…he could try to win over a room.” This, in part, is what scored Altman a partnership at the start-up accelerator Y Combinator, where he met Thiel, who inspired him to take bigger swings on hard-tech development. In 2016, however, their friendship was tested when Thiel “became really the only person just about in all of tech to support Donald Trump,” recounts Hagey. Despite being ardently opposed to Trump, Altman “stood up for Peter Thiel as his friend, but also in general as a philosophical point…that we’re not here to shut down people’s support for major party candidates,” she says.
Shortly after Trump’s first election win, Hagey notes, Altman’s radical self-belief led him to consider a formal entrance into politics. “He had conversations with private folks about running for governor of California and also about one day running for president,” Hagey says. “He figured there would be a millennial president, and why shouldn’t it be him? This speaks to his desire to just be in the room. This is what the OpenAI experience ultimately brought him.” (Altman told Hagey in the book he didn’t want to run for president.)
Incidentally, Altman was nearly booted from the room in 2023, when the OpenAI founder was abruptly fired by the company’s board of directors over a lack of confidence in his leadership. Although he was reinstated after internal pushback, Hagey found the episode revealing: “I learned about a bunch of moments where the board felt that Sam had misled them about safety stuff, about the speed of things, and how deep their distrust was of him.”
Of course, being liked is already proving essential to staying afloat amid the second presidency of Trump, who governs by a loyalty-first approach. So far, from the looks of Trump’s $500 billion partnership with OpenAI, Softbank, and Oracle, Altman has managed to get back in the president’s good graces. But given his yearslong feud with Musk, who’s also competing in the AI space, there’s no guarantee that Altman will manage to stay out of the crosshairs. As Jones notes, there may just be a “bigger target on his back.”
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