Brian Chesky Lessons: Great Founder, Struggling CEO at Airbnb

On the day Airbnb went public in December 2020, despite surpassing a valuation of 100 billion US dollars, Brian Chesky recalled that the following morning was one of the most lonely moments of his life. He did not wake up as a brand-new person, felt no significant surge of happiness, and still had to log into regular Zoom meetings just like any other ordinary day.

Chesky shared this story on the How I Built This podcast to reflect on years of accumulated realization: being the creator of a company does not automatically mean you are the right CEO to scale the organization further. His remark about being born to be a founder but turning out to be a terrible CEO challenges the popular startup belief that founders should step away from details and let professional executives handle everything as the company grows.

Stock photo for illustration only, not from the actual event

For Chesky, however, the answer is not that simple. What he calls Founder Mode is not a license for a CEO to interfere and control every single matter at all times, but rather a method where leaders immerse themselves to set standards, transmit core thinking, and gradually step back once the team absorbs those practices into organizational capabilities. Taking the company public amid the COVID-19 pandemic meant their victory lacked ringing bells, family presence, and early teammates celebrating side by side.

Looking back, he noted that part of his ambition stemmed from a need for validation, though praise acts like an addictive substance whose effects fade faster the more you receive it. He and Joe Gebbia spent most of their early days designing, creating, and convincing people of things that did not yet exist. Being a founder is a skill cultivated over time, whereas the CEO role is filled with counter-instinctual demands. For instance, the common advice to hire great people and step aside may work for mature firms, but for early-stage startups, bringing in senior executives lacking deep company context can cause teams to move faster than leadership and structures can manage.

"I was born to be a founder, but I'm a terrible CEO."

Brian Chesky

The pandemic crisis served as a major turning point when Airbnb faced severe uncertainty and strict cost-cutting measures, prompting Chesky to switch into Founder Mode by diving deep into details and working side by side with his team for the first time in 15 years. He drew inspiration from Steve Jobs during Apple's turnaround, highlighting the necessity to ruthlessly cut unnecessary things, make tough decisions, and sharpen team direction.