- Billionaire Airbnb CEO Brian Chesky went back to school prior to the company going public—but it wasn’t to obtain a degree, it was to seek the guidance of a former president. Chesky reveals that during weekly chats with Barack Obama, he would receive “assignments” that revolutionized his leadership.
To build Airbnb into a billion-dollar business, Brian Chesky sometimes worked gruesome 100-hour weeks. However, on top of that, he would regularly carve out time to pick the brains of one of the most important people in the world: former President Barack Obama.
“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,” Chesky has just revealed.
Speaking on the latest episode of Michelle Obama’s podcast IMO, he added: “I just was really shameless about reaching out to him, asking for advice, asking for mentorship, and he would meet with me, and he’d give me advice.”
He recalled that 44th president of the United States advised him to avoid becoming like other leaders who are effectively “self-driving cars” without intention. Instead, he should always be thinking long and hard about relationships—with his friends, his success, and his company—and be more active with the impact he wants to make.
Fortune reached out to Chesky and former President Obama for comment.
Finding a mentor in a president
After building Airbnb into a household name, Chesky faced a problem: he still wasn’t satisfied—nor necessarily happy.
“The thing about being very successful in tech and making a lot of money and all this is no one ever told me how lonely it would become,” Chesky said to Michelle and Robinson. “And I started realizing, well, it’s weird, I had old friends that were middle class, and I’ll be honest, a lot of them seemed happier than me at that point in my life.”
And he credits former President Obama with helping him realize that how he was feeling was completely normal. That “the more success you get, the more isolated you get.”
“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,” Chesky said.
Obama’s…
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