Airbnb CEO shares the No. 1 thing people get wrong about success: I thought ‘everything in my life would be fixed’

Most people imagine reaching their career goals will result in lifelong happiness. The opposite was true for Airbnb CEO Brian Chesky.

For Chesky, the goal was an IPO, he recently told Dax Shepard’s “Armchair Expert” podcast. Even as Airbnb’s popularity and private valuation soared throughout the 2010s, Chesky didn’t feel successful, he said — and he thought taking the company public would help.

But when the IPO occurred in December 2020 — with its opening valuation of $47 billion rising to $86.5 billion in less than a day — Chesky didn’t feel happy, satisfied or even relieved. Instead, it marked “one of the saddest periods” of his life, he said.

Chesky had believed success would cure all his problems, he said. But the IPO left him feeling more isolated than ever — and not just because he watched his company go public over Zoom.

The Airbnb CEO originally moved to Silicon Valley and started his company in 2008 with co-founders Joe Gebbia and Nathan Blecharczyk. Back then, the trio was constantly together. As the company grew, so did his co-founders’ families, and Chesky gradually found himself with more alone time, he said.

In response, Chesky dedicated all his energy to making Airbnb more successful, hoping it’d fulfill him, he said.

“I had this image that if I got successful, I’d have all these people around me, have all these friends … everything in my life would be fixed,” said Chesky. “I do think people should achieve their dreams, [but] don’t go into it [thinking] that just success is going to fill some hole in you.”

A decades-long Harvard University study may offer an explanation. The ongoing research, which started in 1938, has found that career and financial success don’t make participants feel more content. Instead, the happiest people prioritize “social fitness,” or regularly make time for relationships.

“Money can’t buy us happiness, but it’s a tool that can give us security and safety and a sense of control over lives,” Marc Schulz, one of the project’s researchers, told Reuters in February. “At the end of the day, life is really about our connections with others. It’s our relationships that keep us happy.”

Optimal relationships can put us at ease, make us feel safer and offer opportunities for learning and growth, the study has found. People with positive connections are also more likely to live longer, the researchers have noted.

Chesky, in identifying his loneliness, decided to reinvest in his own social fitness, he said on the podcast. Part of his solution: Last year, he listed his own San Francisco home on Airbnb. On select weekends, guests crash in his spare room. Their stays include home-baked chocolate chip cookies and Chesky-led tours of Airbnb’s headquarters.

Six months later, the company launched its Airbnb Rooms service, which allows hosts to rent out individual bedrooms in their homes. Since that announcement in early May, Airbnb’s stock price has risen to $144.14 per share, up from $118.86.

“I feel like a lot of us try to climb a mountain because we feel like when we get to the top of that mountain, something will be filled inside of us,” Chesky said. “Some of the … most difficult periods in people’s lives [aren’t] when they fail, but when they get to the top of that mountain and realize they don’t feel any differently.”

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