- 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 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 the 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.
Coins2Day 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 Obama and Craig 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.
Barack Obama’s wisdom to Chesky was simple: He needed to be more hands-on with his relationships. That means instead of texting or calling a close friend once a year, stay constantly connected with them. Chesky said it’s a lesson he translated into his work as the leader of Airbnb.
“He told me something that I’ll never forget,” Chesky said. “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 is on people.”
Chesky admitted Obama’s advice has made a “really, really big difference” at Airbnb. And while it may sound odd for a former president to effectively give a CEO homework, it’s nothing new for Obama, who spent over a decade in the classroom teaching constitutional law at the University of Chicago before his jump into the political arena.
The ‘life hack’ to find success: Reach out to an old friend
The lessons learned from Chesky and President Obama’s relationship on finding success can be summarized into two simple steps: Seek out mentors and have friends outside of social media.
“For young people, the number one thing they need to learn how to do is how to learn,” Chesky said. “And some of the best ways to learn are from other people, and some of the best ways to learn from people are, again, in the real world.”
Moreover, rekindling old relationships is among what Chesky calls a “simple life hack” to make life happy.
“I think the vast majority of people, if they reach out to someone, someone will want to help them,” he added. “They reach out to an old friend, the old friend will want to reach back out to them, and that is the path for reconnection. It’s a path for relationships, and it’s a path for purpose.”
A version of this story originally published on Coins2Day.com on May 27, 2025.
More on career advice:
- L’Oréal exec cut her teeth at luxury brands Chanel and Kiehl’s. Like Walmart’s CEO, she says the secret to her success was always saying yes
- Once a college dropout, this CEO went back to school at 52—but she still says the Gen Zers who will succeed are those who ‘forge their own path’
- Airbnb CEO Brian Chesky challenges founders with a critical question if they aspire to emulate his success
