Airbnb’s Brian Chesky Says He Was a ‘Terrible CEO’

By Grace Kim

Airbnb counted more than 5.5 million hosts and $12.24 billion in annual revenue in 2025, after Brian Chesky led the company from its 2007 founding through nearly two decades as CEO.

In a recent How I Built This podcast interview, Chesky described his early limitations and said he was “naturally a terrible CEO.”

Why did Chesky call himself a ‘terrible CEO’?

“I think I was pretty much naturally a great founder and I was naturally a terrible CEO,” Chesky said on the podcast. He said founder preparation and CEO work require different skills.

Chesky said founder preparation starts in childhood and can accumulate over decades. At 26, when he started Airbnb, he estimated he had “20 years of experience as a founder, starting as a child designing, disassembling Christmas toys.”

He also said a person could spend their “whole life” building and making things. Founding a company therefore was unlikely to be a first attempt, he said. By the time he created Airbnb, Chesky claimed, he already had decades of experience founding or creating something.

CEO work proved less intuitive. Chesky said the main problem with the role is that it is so counterintuitive. When his intuition conflicted with what employees told him, he usually deferred to their experience. Usually, he said, that was a mistake.

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

His early management style also reflected his discomfort with authority. Chesky admitted he was “cautious” about being a boss and “felt shy” about directing people, especially workers who appeared older and more experienced. “I think I was a little bit of a people pleaser,” he said. “I wanted people to like me.”

Takeaway: Chesky’s years as a builder did not remove his early weaknesses in judgment, authority and direct instruction.

What should a young company do differently?

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

Instead, Chesky said, good CEOs should make new hires strategically. They should steer away from experienced people who do not understand the company and choose workers “a little bit ahead” of the leadership team who are smart and hungry. After hiring them, the CEO should “stay really close to them.”

His model runs counter to the common playbook of bringing in seasoned executives, delegating broad authority and stepping back. It also asks more of founders when they may be least inclined to direct strangers closely.

• Chesky says early-stage companies should hire people “a little bit ahead” of the CEO.
• He says those workers should be smart and hungry.
• He says new hires need close coaching rather than space.
• He says trust and delegation fit more mature companies better.

Takeaway: Chesky’s prescription is hands-on development for a young company, not immediate autonomy.

What makes culture harder than profitability?

Chesky also addressed how a CEO builds a culture in which employees automatically do what is expected when the CEO leaves the room. “That’s the hard stuff,” he said. “That’s really hard. Not becoming profitable, expense management — that stuff is easy.”

That comparison separates financial discipline from behavioral change. Chesky described profitability and expense management as straightforward operating tasks. Culture, by contrast, must hold across employees and situations without direct supervision from the chief executive.

Taken together, Chesky’s account links that challenge to his early weaknesses. A people pleaser may soften instructions; a founder who automatically favors employees’ experience may fail to challenge them; a CEO who stays distant may fail to shape behavior. Chesky describes a leader learning to direct people while keeping his judgment open to challenge.

The company’s scale heightens the contrast. The interview profile describes Airbnb’s expansion from its 2007 founding to more than 5.5 million hosts and $12.24 billion in annual revenue in 2025 under Chesky’s nearly 20-year tenure. Yet his advice focuses on the years when a company still needs its CEO close to the work and to its people.

Takeaway: Culture is the harder assignment in Chesky’s account because it must operate when the leader does not.

For early-stage companies, the practical test from Chesky is straightforward: reject hands-off delegation, hire talent that can move ahead of the current leadership team, and coach those hires closely. Mature operators, he said, can rely more heavily on trust once the company and its leadership are ready for it.