But Chesky, who at times in his career has been “addicted” to work, regrets the impact his climb had on his relationships.

Speaking on the Diary of a CEO podcast, released on Oct. 9, Chesky said that his “addiction” to work was very productive and as a result, was never highlighted as an issue.

Indeed, Chesky revealed that at one point his obsession with work got so bad that he felt guilty “any second [he was] alive but not working.”

“Life is so much more than just climbing a ladder, and getting to the top, and realizing you’re not much higher than you ever were before,” Chesky told host Steven Bartlett. “That you had everything inside of yourself, mostly, to be happy before the journey started, and probably what you needed most is purpose, health, and relationships.”

Chesky’s—and Airbnb’s—journey has been something of a roller coaster. The business was launched in 2007 out of Chesky and cofounder Joe Gebbia’s San Francisco apartment.

The pair hosted three guests, under the banner of Airbed & Breakfast, before officially launching in October a year later during the SXSW film festival.

Since then the company has grown across more than 220 countries and regions with more than 4 million hosts on the platform.

Chesky and his executives began eyeing an IPO before the pandemic hit and slammed shut the doors of host properties, grounding the company’s widespread customer base.

Airbnb’s team took the pandemic as a time to adjust—not only going through a massive restructuring but also laying off 1,900 people.

By December 2020 the company was back on its feet, valued at one point in its IPO at $100 billion.

But growing a company to a 12-figure sum from a flat with two friends was increasingly isolating for Chesky, who said it was an unexpected downside he was never warned about.

“No one told me…how lonely it would be, and it doesn’t have to be,” said Chesky. “When I started Airbnb, I started with my friends, then we hired people, and those people were our employees but also kind of our friends.

“As we got successful then we became more of a corporation, there was a chain of command, there were more boundaries…it becomes more formal. And that’s the moment your employees become your employees and less your friends, and that gets more and more isolating.”

With a growing corporation comes respect and admiration, Chesky continued, but also a distance between friends and peers who thought the founder was too busy for them.

Lonely leaders

On top of the isolation Chesky was struggling with, the tech titan added that reduced human connection is actually bad for business.

“We need to have some healthy relationships to probably make good decisions,” said Chesky, adding: “Lonely leaders are probably not the best leaders.”

He laid out a gamut of reasons for this: less empathy; a heightened sense of vigilance; an inability to clearly see problems; feeling alone when faced with challenges, so being less resilient as a result; and having no sounding board.

Chesky said he actively had to work to build back and maintain relationships with his family and friends.

During the growth stage of Airbnb, Chesky revealed he would go “weeks” without talking to his sister, purely because he felt he didn’t have time.

“I have high school friends I now do an annual trip with,” said Chesky. “Some of them I didn’t talk to for almost 20 years. I graduated, I didn’t keep in touch with them; it’s one of the great regrets that I have.”

The man reportedly worth $10.3 billion, according to the Bloomberg Billionaires Index, said that despite his isolation, the sacrifice has been “mostly worth it.”

“The journey of Airbnb…has been unbelievable. It’s been the great joy of my lifetime,” he added.