Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”

This episode is available on Youtube: https://youtu.be/ZYf-DfxJg1c

Brian Chesky was 26 when he and his co-founders launched Airbnb, turning a few air mattresses in a San Francisco apartment into one of the most successful startups of all time.

But as Airbnb grew into a company worth more than $100 billion, Brian struggled to keep up. He hired experienced executives, trusted them to make decisions, and watched the company become increasingly chaotic. Looking back, he says Airbnb succeeded in spite of his leadership, not because of it.

Then COVID hit, and Airbnb lost 80% of its business in a matter of weeks. Facing the possibility of losing everything he'd built, Brian completely reinvented the way he ran the company—and soon after, much of his life outside work, too.

In this episode, Brian explains why some of the most common leadership advice can be disastrous for startups, what he learned from Steve Jobs and Barack Obama, and why the day after Airbnb’s IPO was one of the loneliest of his life. Plus, how Airbnb.org is providing free housing to people in crisis—and why Brian wants to expand that effort to one million nights a year.

What You'll Learn

How an art school graduate with no business experience became the CEO of Airbnb

Why Brian describes himself as “naturally a great founder but naturally a terrible CEO”

How following conventional leadership advice created chaos inside Airbnb

Why Brian believes "hire great people and get out of their way" can be a death sentence for startups

How losing 80% of Airbnb's business during COVID forced Brian to reinvent his leadership style

What studying Steve Jobs taught Brian about getting into the details