“I think I was pretty much naturally a great founder, and I was naturally a terrible CEO,” Chesky told Guy Raz on Monday’s episode of How I Built This.

As Airbnb grew, Chesky said he followed advice to hire experienced executives, trust their judgment, and give them room to work. But when he rejected that approach and took a more hands-on role, he was met with resistance.

“Almost the entire exec team left,” Chesky said, adding that the departures happened eventually. “They left or they didn’t want to work for me.” 

The longtime CEO wasn’t looking to win over everyone—just 10 people willing to serve on his executive team and see whether working his way produced results.

That approach later became known as “founder mode.” Y Combinator cofounder Paul Graham popularized the term after hearing Chesky speak at an event for the startup accelerator. In a September 2024 essay, Graham challenged the idea that founders must hand off the details as their companies grow, arguing they should stay involved with employees beyond their immediate reports. 

Chesky began changing how he ran Airbnb in 2020, four years before Graham’s essay, as the COVID-19 pandemic disrupted the company’s IPO plans and sent revenue down 72%. He turned to former Apple designer Jony Ive, who told him: “You don’t manage people. You manage people through the work.” He then took a page from Apple cofounder Steve Jobs’ playbook and cut layers of management.

For Chesky, that meant bringing the employee doing the work and the managers above them into the same meeting. Everyone could make a recommendation, and he could make the final decision without sending an idea through several rounds of signoffs.

In August 2025, Chesky said he treated roughly 50 employees as direct reports, weighing in on decisions to hire, fire, promote, and manage them.

Finding people willing to work his way

Taking a more hands-on role meant breaking some old habits. Chesky said he often listened to executives with far more experience than he had, even when their advice ran counter to his instincts.

“And what do I do when my intuition and their experience collide? Usually I deferred, and that was usually a mistake,” he said.

He also shied away from difficult conversations about performance, sometimes taking on struggling employees’ work himself. 

“I felt cautious about being a boss,” he said. “I think I was a little bit of a people pleaser. I wanted people to like me.”

But that deference came at a cost. 

“They’ve gone down a path for two years. Guess what happens? They leave. You might spend five or 10 years fixing or correcting that decision that person made,” Chesky said.

As he overhauled how he ran Airbnb, Chesky began hiring people who had worked for founders such as Jobs and Amazon founder Jeff Bezos. They already understood his approach and needed less convincing.

Chesky has since defended detailed oversight as a way to help employees improve and make decisions faster. But he told Raz staying involved in every detail indefinitely isn’t sustainable. He described reviewing roughly 70 drafts of a single press release to establish the standard he expected. Once employees understood that standard, he could step back.

He put it more bluntly in a 2024 interview with Fortune: “If you want to be autonomous, start your own company.”