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Airbnb’s Brian Chesky Says He Was ‘Naturally a Terrible CEO.’ Here’s What Makes the Job So Hard — And What’s a ‘Death Sentence.’

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Airbnb’s Brian Chesky Says He Was ‘Naturally a Terrible CEO.’ Here’s What Makes the Job So Hard — And What’s a ‘Death Sentence.’

The Airbnb chief executive opened up about his shortcomings as a leader.

Brian Chesky has been the CEO of Airbnb since the company’s inception in 2007. For nearly 20 years, he has stuck with the top job and overseen Airbnb’s incredible growth to become a company with over 5.5 million hosts and $12.24 billion in annual revenue in 2025.

However, being a CEO didn’t come naturally. In a recent interview with the How I Built This podcast, Chesky opened up about his shortcomings as a leader when Airbnb first got started.

Chesky drew a distinction between being a great founder and being a great CEO.

“I think I was pretty much naturally a great founder and I was naturally a terrible CEO,” he said on the podcast.

Chesky pointed out that someone could spend their “whole life” being a founder. It starts in childhood, with making and building things — all prep work for being a founder. The moment a person creates a company is probably not the first time they try to make something, Chesky said. He estimated that when he started Airbnb at age 26, he probably had “20 years of experience as a founder, starting as a child designing, disassembling Christmas toys.”

By the time he founded the company, he claimed to have had decades of experience with founding or creating something under his belt.

Then came the tougher challenge: being CEO. Chesky said on the podcast that the main problem with being a CEO is that it is so counterintuitive .


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