The ‘worst moment’ of Sam Altman’s OpenAI ousting happened just before midnight, Airbnb CEO said

At that point, Chesky said Altman and OpenAI president Greg Brockman said they would go to Microsoft, and it felt like the page had turned. While Chesky said he wanted the two former executives to fight to stay, they were ready to leave if that was best for OpenAI and its employees.

“I thought that was the end of it,” Chesky said. “The miraculous thing was, it turns out Emmett Shear is also a friend of mine and that opened a new line of communication.” While many other things happened, his relationship with Shear, who ran Twitch before stepping down in March 2023 and who did briefly run OpenAI over that long weekend, helped foster dialog, Chesky said.

While the midnight news might have disappointed Altman, Chesky said he was surprised — in a good way — at how he wasn’t acting out of self-preservation throughout the ousting.

“When people are attacked, they typically go to themselves,” Chesky said. “And Sam was focused not on himself, but OpenAI and that made me want to fight for him.”

Chesky was one of the first people Altman contacted when he was fired, and the two have reportedly been friends for a decade. Altman and Shear mentored Chesky at startup Y Combinator. Both Shear and Chesky worked together to bring Altman back as CEO, according to a report from The Wall Street Journal.

Airbnb and OpenAI did not immediately respond to a request for comment.