Airbnb CEO Brian Chesky Says Mentorship From Barack Obama Before IPO 'Changed My Life' — Former President 'Made Me Really Be Intentional...'

Airbnb Inc. ABNB CEO Brian Chesky revealed that mentorship calls with former President Barack Obama in 2018 fundamentally transformed his leadership approach before the company’s blockbuster public debut.

What Happened: “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 said during a podcast with Michelle Obama.

The weekly one-hour sessions operated like structured coursework, with Obama providing assignments that Chesky would complete and present back. The former president’s core lesson centered on intentional leadership versus reactive management.

“He literally said, like so many leaders are like self-driving cars. They’re not intentional. They’re like a car, but they never put the destination in,” Chesky explained. “He made me really be intentional about what do I want out of my life, out of the company.”

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Why It Matters: This mentorship proved crucial as Airbnb transitioned from a startup to a public company. The platform went public in December 2020, opening at $146 per share and reaching an $86.5 billion market capitalization on debut day—a 112% surge from its $68 IPO price.

Obama’s guidance helped Chesky shift from entrepreneurial impulsiveness to CEO-level strategic thinking. “A CEO is to realize, like, I’m responsible. I’m a steward for a community of hundreds, millions of people, thousands of people’s jobs depend on me,” Chesky noted.

Currently trading at $129.40, Airbnb maintains a $79.87 billion market cap. The company recently beat first quarter of 2025 earnings expectations with 24 cents per share versus 23 cents estimated, while revenue of $2.27 billion slightly exceeded $2.26 billion projections.

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Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.

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