Airbnb CEO Brian Chesky says ‘founder mode’ cost him almost his entire executive team: ‘They left or they didn’t want to work for me’

Brian Chesky, the CEO of Airbnb, once described his approach to leadership as "founder mode," which led to the departure of nearly his entire executive team. Chesky, who founded Airbnb in 2008, found that stepping into the CEO role was vastly different from being a founder. He had been preparing for the CEO role for 20 years, but found himself struggling with the hands-on management style that came with it.

Chesky believed he was naturally a great founder but a terrible CEO, and his attempts to take a more active role in day-to-day operations led to resistance and turnover among his executives. He began his hands-on approach in 2020, when the COVID-19 pandemic disrupted Airbnb's IPO plans and caused a 72% drop in revenue. Chesky implemented "founder mode" by treating roughly 50 employees as direct reports, making decisions on hires, firings, promotions, and managing them himself.

He listened to experienced executives, even when their advice contradicted his instincts, but often deferred to them, which he later realized was a mistake. Chesky also shied away from difficult conversations about performance and took on the work of struggling employees himself, causing resentment. To improve, he began hiring people who had worked for founders like Steve Jobs and Jeff Bezos, who already understood his approach.

Chesky defended detailed oversight as a way to help employees improve and make decisions faster, but acknowledged that indefinitely staying involved in every detail isn't sustainable. He famously said, "If you want to be autonomous, start your own company."