Running a Fortune 500 in "Founder Mode"

Airbnb's CEO questions the value of autonomy.

“No one’s born a good CEO. It is such a non-intuitive job.”

So says Airbnb CEO/founder Brian Chesky in a new interview with Fortune. Very true.

But the main theme of the interview is that Chesky has learned to disobey leadership orthodoxy around employee autonomy. “If you want to be autonomous, start your own company,” Chesky says.

How did he come to a belief so seemingly out of step with 2024 leadership?

In 2016 Airbnb’s business dropped like a rock, by 80%. It was in this crisis that Chesky abandoned the traditional approach to hiring great people and staying out of their way. Instead, he plunged back into the details and learned what was going on in every corner of the business to help right the ship.

Chesky has now emerged on the other side of a successful rebound (Airbnb hit the Fortune 500 for the first time in 2023 and is currently profitable) with a different perspective. Today, he wants to know what his executives are doing. He wants to ensure they are working on the right things…