Airbnb CEO Brian Chesky Opens Up About Loneliness and Success After IPO

Airbnb CEO Brian Chesky’s rollercoaster journey from startup success to IPO disappointment

In December 2020, Airbnb made headlines with its highly anticipated initial public offering (IPO), which saw its valuation skyrocket from $47 billion to $86.5 billion in less than a day. However, for CEO Brian Chesky, this momentous occasion marked one of the saddest periods of his life.

Chesky had long believed that success would be the key to solving all his problems. But as the IPO unfolded, he found himself feeling more isolated than ever, despite the company’s soaring valuation. The once close-knit trio of co-founders, including Joe Gebbia and Nathan Blecharczyk, had drifted apart as the company grew, leaving Chesky with more alone time than he had anticipated.

In a candid revelation, Chesky admitted that he had pinned all his hopes on Airbnb’s success to bring him fulfillment. “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,” he said. However, the reality was far from his expectations.

A Harvard University study spanning decades has shed light on the elusive nature of happiness and success. The research found that financial and career achievements do not necessarily lead to contentment. Instead, the happiest individuals prioritize “social fitness,” or the cultivation of meaningful relationships.

In a bid to address his own feelings of loneliness, Chesky decided to reinvest in his social connections. He opened up his San Francisco home to Airbnb guests, offering them a unique experience that included homemade cookies and tours of Airbnb’s headquarters. This personal initiative eventually led to the launch of Airbnb Rooms, a service that allows hosts to rent out individual bedrooms in their homes.

As Chesky reflected on his journey, he emphasized the importance of not solely chasing external markers of success. “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,” he said.

The story of Brian Chesky serves as a poignant reminder that true fulfillment may not be found in material success alone, but in the quality of our relationships and connections with others.