Airbnb CEO said super IPO was a sad period of his life

The rental platform’s shares soared on its debut, rising 113% from its initial public offering price of $68, and the company’s valuation jumped to about $103 billion, up from its $18 billion valuation after its last private placement round last April. USD.

With that in mind, Airbnb’s debut market cap was higher than the nation’s. Three major hotel chains merge: Marriott International, Hilton Worldwide and Hyatt Hotels have market capitalizations of US$43 billion, US$39 billion and US$8 billion respectively.

Its CEO, Brian Chesky, should be ecstatic. Instead, he described the moment of triumph as “one of the saddest periods” of his life.

Chesky admits that growing up, he was “desperate to succeed” because he thought it would bring him adoration. In addition, his parents are social workers and their living conditions are not wealthy. He also believes that a lot of money can “solve all problems.”

“I had this idea that if I was successful, I would have all these people around me, all these friends, I would have all this love, all of this, and my life would be fixed,” he said on his show as told to Dax Shepard. armchair specialist podcast.

But in reality, when Airbnb is valued at $100 billion and “everyone in high school” knows what he’s done, he’s lonelier than ever—and it’s all of his own making.

“I’ve done that, I’ve completely isolated myself from work,” Chesky added.

There is more “hope” at the foot of the mountain

When Chesky moved to Silicon Valley in 2008 to start the company with co-founders Joe Gebbia and Nathan Blecharczyk, he said the three were like family. But as CEO, Chesky said he felt guilty spending time with them instead of growing the business.

“Whenever I took time out to be with friends and family, I felt guilty because I wasn’t working for the company,” he said, while adding that he was plagued by a nagging feeling of “not being enough.”

As a result, he devoted all his energy to working up to 18 hours a day, hoping to develop Airbnb into the rental giant it is today.

“But as we suddenly became more successful, the people who worked for me had families themselves,” Chesky said, while adding that when the boss and his co-founder became employees, there was also a relationship between himself and A clear “power imbalance”.

Then the pandemic hit. While the coronavirus has curbed travel in nearly every country and caused Airbnb sales to plummet 80% in eight weeks, the platform has made a remarkable comeback thanks to the success of its IPO.

By then, Chesky had reached the peak of his loneliness: “I was alone 24/7,” he said. “There were no bells ringing, the entire IPO was held on Zoom.”

“At the bottom of the mountain, you have hope,” he said, summing up his journey from scrappy startup founder to billionaire. “But the problem is, when you get to the top of the mountain, you’re often alone at the top, cut off from the rest of the world.”

Advice from Barack Obama

Chesky met with Barack Obama at a global entrepreneur summit near the end of the U.S. president’s second term. They became “very close,” and Chesky said their relationship grew until they had weekly stand-up conversations.

“He became a mentor to me,” Chesky said, while adding that at the time he couldn’t help but wonder: “Why did he spend so much time with me? — I still don’t understand.”

Months after the IPO, Chesky was feeling “really isolated,” revealing that he wrote Obama a letter asking how he could stay grounded at the peak of his career.

“He said: You are connected to your roots, and your roots are your past relationships,” Chesky said. “He described the idea that you should have 15 friends and you should be very close to them.”

It made the Airbnb leader think about his friendships and whether it would feel “casual” if he suddenly picked up the phone and called one of his friends for a chat.

“I realized that was going to be the case,” he reflects. “I couldn’t just call one group of people because I was so isolated.”

“When I started this journey, no one told me how lonely it would be,” he added. “No one should feel bad and I do think people should achieve their dreams (but) don’t get caught up in (thinking) success is going to fill some holes in you because it’s a long lesson learned.”

Now, he finds satisfaction in taking Obama’s advice and reconnecting with friends from college and high school. While it’s unclear whether he became close to the Airbnb co-founder again, he said that contact with his childhood friend “completely changed everything about his life.”

“The irony is, these are all friends I had before I started Airbnb.”