Barack Obama Once Told Airbnb CEO Brian Chesky Not To Lead Like A 'Self-Driving Car:' Here's What Former President Meant

Former President Barack Obama has quietly taken on the role of leadership coach to Airbnb ABNB co-founder Brian Chesky, meeting weekly in what the billionaire calls "night school" and pressing him to steer the home-sharing platform with deliberate purpose rather than on autopilot.

What Happened: In a new podcast appearance, Chesky recounted Obama's warning to shun leaders who act like "self-driving cars" and revealed homework-style assignments that reshaped both his personal life and the direction of Airbnb.

Chesky recently told Michelle Obama's "IMO" podcast that the calls ran a full hour every week, stacked on top of 100-hour workweeks in the run-up to Airbnb's 2020 IPO.

“I basically had my day job during the day, and then I had my night school with the former president,” he said. The former president urged Chesky to think deeply about relationships with colleagues, shareholders and society — and plot an intentional course.

"He told me something that I'll never forget," Chesky revealed. "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.”

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“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," he clarified. Chesky went on to add that Obama's advice made a "really, really big difference" at Airbnb.

Why It Matters: This wasn’t the first instance of Chesky heaping praise on Obama’s advice. In a separate showing on the Rapid Response podcast back in 2024, Chesky revealed how Obama, during a conversation over dinner in 2017, advised him to lock Airbnb's purpose into the company bylaws before going public: "Institutionalize your intentions so you don't compromise your vision." The directive inspired the company's five-stakeholder framework and the creation of a Host Endowment fund.

The mentorship didn't stop at boardroom philosophy. Obama's push to stay "hands-on" with relationships inspired Chesky's $100 million Voyager Scholarship for public-service students and his own habit of phoning friends between busy workweeks, a tactic he says keeps success from becoming isolating.

Even Chesky's now-famous 2008 "Obama O's" cereal stunt that kept Airbnb alive remains a popular anecdote in the startup’s origin story.

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