Airbnb CEO Brian Chesky says these 3 mistakes made him a terrible CEO
Brian Chesky runs Airbnb, the home rental website.
The short version
- He admitted he was a terrible chief executive.
- He ignored his own gut and trusted older bosses.
- He hated hard talks and avoided firing failing workers.
- He said founders must stay close to smart new hires.
As Airbnb grew from a startup into a global travel company, chief executive Brian Chesky learned that building it and running it were two very different jobs. Speaking on the "How I Built This" podcast according to Business Insider, 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 chief executive required a completely different set of skills.
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 run a massive company, he found the role counterintuitive.
Chesky said he often ignored his own instincts in favor of listening to older executives with far more experience. "What do I do when my intuition and their experience collide? Usually I deferred, and that was usually a mistake," Chesky said.
He learned that executives from much larger companies often struggled because they only knew how to manage established systems, not build new ones. Chesky also admitted he was conflict-averse and struggled to hold colleagues accountable when their work fell short. He said he sometimes took on employees' work himself instead of having hard conversations about performance.
Another big mistake was not saying no enough, which left the company without a clear focus. "The right way is one way. And one way has to be your way," Chesky said.
Photo: TechCrunch, CC BY 2.0, via Wikimedia Commons, AI-edited
