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Airbnb's Brian Chesky reveals what he learned from his mentorship with Barack Obama

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Airbnb's Brian Chesky reveals what he learned from his mentorship with Barack Obama

Chesky carved out time for a weekly phone call with Obama


Maria Loreto
Senior Writer
MAY 28, 2025 5:12 PM EDT

Brian Chesky, the CEO of Airbnb, is opening up about his relationship with President Barack Obama. In a chat with Michelle Obama and her brother Craig Robinson, Chesky revealed that he and Obama had one-hour phone calls every week, where Chesky learned some tools that he would later use in his company. 

Brian Chesky at Airbnb Open LA in 2016© Mike Windle
Brian Chesky pursued Obama's mentorship after he'd left the presidency

Chesky was featured on an episode of Michelle's podcast IMO, revealing that Obama gave him some homework that he implemented in his day-to-day life and work. 

“At one point in 2018, we had a standing one-hour call every week, and I basically had my day job during the day, and then I had my night school with the former president, where I would get these assignments, but it changed my life,” said Chesky.

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Chesky revealed that Obama helped him deal with his success, something that didn't make him happy and instead made him feel isolated. 

“People dream of success, but what they don’t realize is a lot of with success comes disconnection to your past, to yourself, to your friends, and I think a lot of what I’ve tried to do the last handful of years is to reconnect, to not live a life of isolation,” said Chesky. 

Obama's advice helped pave the future of Airbnb

Michelle and Barack Obama at the unveiling of their official portraits in February 2018© Getty Images
Barack Obama played an important mentor role for Chesky

Chesky revealed that Obama advised him to be more present with his relationships, keeping a better grip on them, and preventing them from fading into the background. 

“He told me something that I’ll never forget,” he continued. “He said you should institutionalize your intentions, so that even when you’re a public company, you can make sure not to compromise your vision. And what he meant by that, I think, was that you should be more thoughtful about what you’re making, why you’re making it, and the impact of what you’re making has on people.”

Barack Obama and Michael Strahan on the documentary "Soul of a Nation" © ABC via Getty Images
Obama told Chesky to keep a hold of his relationships, especially as he reached more and more success

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