Airbnb CEO Brian Chesky used to think that success would be enough for him to get by in life. However, his thought process made a U-term when his lifetime goal couldn’t really fill the proverbial hole in his life.
Chesky, who co-founded AirBnB and has a net worth of over 9.1 billion dollars, said in Dax Shepard’s “Armchair Expert” podcast that his goal was the IPO of the company. However, after his company’s and personal net worth grew leaps and bounds throughout the 2010s, he didn’t feel successful. He thought the IPO could be what was missing in his life.
His firm bought the IPO in 2020 and the company’s valuation reached from $47 billion to 86.5 billion in a day. However, it didn’t bring him any happiness. He didn’t feel happy, satisfied or even relieved.
The time around the IPO was one of the saddest periods of his life, Brian Chesky told the podcast host.
He used to believe that success would be the answer to all his problems. However, the IPO left him more isolated than ever.
One of the reasons for his lack of happiness was that he was lonely. He had started the company in partnership with his co-founders Joe Gebbia and Nathan Blecharczyk in 2008. They used to spend a lot of time together at work. However, that time together has diminished since the two co-founders are busy with their personal commitments as well. This has resulted in him spending more time alone than desired.
He had thought that working harder to make his company a success would help him plug this hole. However, that didn’t happen.
“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,” he told the host.
To remedy this problem, he listed his own San Francisco home on Airbnb. On some weekends, guests come into his spare room and are treated to home-baked chocolate cookies.
“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,” CNBC quoted him as saying.