Chesky Says Three Leadership Mistakes Shaped His Airbnb CEO Approach

November 4, 2026 — Brian Chesky says his transition from Airbnb founder to CEO exposed three weaknesses: relying too heavily on experienced executives, avoiding difficult conversations and failing to reject competing priorities. He discussed those lessons on the How I Built This podcast with host Guy Raz.

Chesky said he often put executives’ experience ahead of his own instincts, even when they disagreed. He later concluded that young companies need capable hires who are only somewhat ahead of the founder, with the CEO staying closely involved. He said leaders from larger companies can struggle to build a startup rather than manage an established business.

He also described being reluctant to hold employees accountable, partly because he wanted them to like him. At times, he said, he took on work himself when colleagues were struggling. Chesky warned that a team can spend years correcting a direction set by an executive who has since left.

His move toward greater involvement at Airbnb began in 2020, when the pandemic disrupted the company’s IPO plans and revenue fell 72%. Chesky said he reduced management layers and brought employees doing the work into discussions with their managers so he could make decisions without multiple rounds of approval.

The approach, later called “founder mode,” came with resistance: Chesky said nearly his entire executive team eventually left or did not want to work for him. He has since hired people familiar with working for founders, and said detailed oversight can establish standards before a leader steps back. He has also acknowledged that staying involved in every detail indefinitely is not sustainable.