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.

How to be a good CEO

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.

“For example, people tell you to hire great people and trust them and get out of their way to do their job,” Chesky said. “That is what you do once you are very mature. That is a death sentence to a young company.”

Chesky said that good CEOs actually have to be strategic in making new hires. They have to steer away from hiring experienced people who don’t understand the company. Instead, they have to hire workers a “little bit ahead” of them who are smart and hungry — and then “stay really close to them.”

Chesky also addressed the question of how CEOs can create a culture where employees automatically do what is expected of them, even when the CEO isn’t in the room.

“That’s the hard stuff,” he said. “That’s really hard. Not becoming profitable, expense management — that stuff is easy.”

Being a people pleaser

Chesky admitted that early on, he was “cautious” about being a boss. He “felt shy” about directing people to do something, especially workers who seemed older and more experienced.

“I think I was a little bit of a people pleaser,” he said. “I wanted people to like me.”

The difficult part for Chesky was when his intuition would clash with what his employees were telling him. Usually he deferred to their experience, and usually it was a mistake, he said.

“My intuition is telling me this thing,” Chesky said. “It doesn’t mean you’re wrong, but now let’s talk about it.

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.