Airbnb's Brian Chesky on the 3 mistakes that made him a 'terrible CEO'

As Airbnb grew from a startup into a global travel company, CEO Brian Chesky said he learned that building it and running it were two very different jobs. Speaking on Monday's episode of the "How I Built This" podcast, Chesky opened up about the steep learning curve he faced as Airbnb expanded. "I think I was pretty much naturally a great founder, and I was naturally a terrible CEO," Chesky told podcast host Guy Raz.

Chesky said being a founder came more intuitively to him, while becoming a CEO required a very different set of skills. "When you're a child, you're making things, you're building things. You're practicing being a founder, and so the moment you found a company is probably not the first time you try to make something," Chesky said.

He said he had been developing the instincts of a founder since childhood, from designing and taking apart toys to persuading friends to buy what he was selling. But when he suddenly had to become a CEO, he said he found the role "counterintuitive." Here are the three mistakes Chesky said he made: Chesky said that as a CEO, he was often advised to hire highly experienced executives and get out of their way. He said he later came to see how that approach isn't the best for a young company: "You've got to hire people just a little bit ahead of you that are smart, hungry, and you got to stay really close to them." Chesky said he also often ignored his own instincts in favor of listening to executives with far more experience than he did, who were often much older than he was.

"The hard part for me was sometimes my intuition would tell me one thing, and they'd tell me another. And what do I do when my intuition and their experience collide? Usually I deferred, and that was usually a mistake," Chesky said.

He said that those executives who came from much larger companies often struggled to apply what had worked at a larger business to the demands of a smaller startup. "They also come from companies where they didn't build it. They managed it.

And now they have to build it," Chesky said. Chesky said he found it difficult to hold colleagues accountable when their work fell short. He said he struggled with knowing "when to tell people what to do" and had trouble having hard conversations about an employee's performance.

He was "conflict-averse to the point that if somebody wasn't working out, I would not take action," he said. "I felt cautious about being a boss," Chesky said. "I think I was a little bit of a people pleaser.

I wanted people to like me." He said he sometimes took on employees' work himself, without realizing he might either be failing to give them enough room to succeed or be propping them up in an unsustainable way. Another mistake Chesky said he made was not saying "No" enough, which left the company without a clear focus. He compared executives pursuing competing priorities to passengers in a car who all want to go somewhere else.

"The right way is one way. And one way has to be your way," Chesky said. He said that if an executive takes a team in a direction the CEO does not believe in, the company could be left dealing with the consequences long after that person leaves.

"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.