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When shares in Airbnb opened at $144.71 on the Nasdaq Stock Market in December 2020, it marked one of the most successful IPOs in history.

The rental platform’s shares skyrocketed on their first day of trading, rising 113% above the initial public offering price of $68 and the firm’s valuation jumped to around $103 billion, compared to $18 billion after the firm’s last private funding round that April.

To put that in context, Airbnb’s debut market capitalization was higher than those of the nation’s three largest hotel chains combined: Marriott International, Hilton Worldwide and Hyatt Hotels had market caps of $43 billion, $39 billion and $8 billion, respectively.

Its CEO Brian Chesky should have been ecstatic. Instead, he describes the winning moment as “one of the saddest periods” of his life.

Growing up, Chesky admits he “desperately wanted to be successful” because he thought it would bring him adoration. Plus, having social worker parents who were by no standards rich, he also thought a large sum of money could “solve every problem.”

“I had this image that if I got successful I’d have all these people around me, all these friends, I’d have all this love, all this everything, and my life would be fixed,” he told Dax Shepard on his Armchair Expert podcast.

But actually, when Airbnb hit that $100 billion valuation and “everyone in high school” knew what he did, he was lonelier than ever—and it was all his own making.

“I had done that, I had so isolated myself totally focused on working,” Chesky added.

There’s more “hope” at the bottom of the mountain

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

“Whenever I would make time with friends and family, the guilt was I wasn’t working on the company,” he said while adding that he was plagued by a constant niggling feeling of not being “enough”.

So, he poured all his energy into his work for up to 18 hours a day in the hopes of growing Airbnb into the rental giant it is today.

“But as we got more successful suddenly the people working for me had families themselves,” Chesky said, while adding there was also a notable “power imbalance” between himself as the boss and his co-founders turned employees.

Then the pandemic hit. Despite the fact that coronavirus curbed tourism in nearly every country and caused Airbnb’s sales to tumble by 80% in eight weeks, the platform made its highly remarkable comeback with its IPO success.

At the time, Chesky had hit peak lonely: “I’m by myself 24/7,” he said. “There’s no bell ringing, it’s all on Zoom—the entire IPO.”

“At the bottom of the mountain, you have hope,” he concludes of his journey from scrappy start-up founder to billionaire. “But the problem is when you get to the top of the mountain oftentimes you are at the top by yourself, disconnected.”

The advice Barack Obama gave him

Chesky had met Barack Obama towards the end of his second term as U.S. president at a global entrepreneur summit. They became “really close” and Chesky said their relationship gradually evolved until the point where they were having a weekly standing conversation.

“He becomes a bit of a mentor to me,” Chesky said, while adding that at the time he couldn’t help but wonder: “Why is he spending so much time with me?—I still can’t figure that out.”

Months after hitting IPO and feeling “really isolated”, Chesky revealed that he sent a letter to Obama asking him how he stayed grounded at the peak of his career.

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

It made the Airbnb leader consider his own friendships and whether it would feel “random” if he were to suddenly pick up the phone and call one of his friends for a chat.

“I realized it would be,” he reflected. “I couldn’t just call a bunch of people because I had been so isolated.”

“No one told me when I started on this journey how lonely it would be,” he added. “No one should feel bad and 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 because it’s a very long lesson.”

Now, he’s found that fulfillment by taking Obama’s advice and reconnecting with his college and high school friends. Although it’s unclear whether he became close again to his Airbnb co-founders, he says that reaching out to his childhood friends has “totally changed everything” about his life.

“The irony of all of it was these were the friends I had before I started Airbnb.”