Airbnb CEO Brian Chesky says he struggled to lead the company after it grew beyond the founder phase, describing himself as “naturally a terrible CEO.” Multiple outlets report that he links the problem to “founder mode,” where building and inventing come more easily than managing and adapting as a company scales.
Across the coverage, Chesky is presented as explaining how leadership shortcomings affected his ability to keep the right executives in place. Fortune reports that he said “founder mode” cost him almost his entire executive team, with people leaving or choosing not to work for him. Entrepreneur and Business Insider also focus on his self-assessment, with Entrepreneur referencing what makes the CEO role difficult and Business Insider highlighting three specific mistakes he says contributed to his poor performance.
The outlets broadly agree on the central message: Chesky frames his early leadership as misaligned with the managerial demands of running a mature company, and he portrays fixing it as requiring changes to who would work with him.
