Most CEOs get their insights from boardrooms and consultants. Brian Chesky went to Barack Obama.
The Airbnb CEO revealed in a recent interview that he spent nearly a year attending a private “night school” of sorts with the former U.S. president. The program was unofficial, but Chesky says it ran with the structure and consistency of a real class. One hour a day. Daily sessions. Homework included.
“I would send him things I was working on,” Chesky said. “And he would come back with notes.”
How it started
Chesky first connected with Obama during his presidency, when Airbnb began to reshape global travel. Their conversations deepened post-White House, and in 2022, they kicked off what Chesky now describes as one of the most formative periods of his leadership journey.
Each evening, the pair would dive into topics ranging from policy to human behavior to leadership under pressure.
“Barack gave me a totally different lens,” Chesky explained. “It wasn’t business school. It was more like leadership school.”
What Obama taught Chesky
The sessions focused heavily on navigating complexity—how to make decisions when there’s no obvious right answer, how to build trust at scale, and how to stay grounded when leading a global company.
Obama, known for his deliberative thinking and people-first approach, pushed Chesky to become not just a better CEO, but a better listener.
“He told me, ‘You don’t have to have all the answers. But you do need to ask better questions,’” Chesky said.
Why Chesky is talking about it now
Chesky shared the story as part of a broader reflection on Airbnb’s evolution—from scrappy startup to travel giant. In recent years, Airbnb has faced regulatory challenges, public scrutiny, and the pressures of going public. Chesky credits much of his resilience and strategic clarity to the time he spent learning from Obama.
He also wanted to highlight the value of mentorship—even for leaders at the top.
“Everyone thinks CEOs have it all figured out,” he said. “But the best ones are always learning.”
Not your typical MBA
While many top executives turn to traditional MBAs or executive education programs, Chesky’s approach was unorthodox. But it was deeply personal—and remarkably high-level.
He now encourages other entrepreneurs to seek unlikely mentors and build their own “night schools,” even if it’s just through books, podcasts, or short weekly check-ins with someone wiser.
