Airbnb's Brian Chesky On Leadership
As Airbnb approaches its 20th anniversary, CEO Brian Chesky shares his thoughts on company leadership, hiring, and remote work, while addressing critics' concerns over rising housing costs

Airbnb's CEO Brian Chesky is set to mark a major milestone next year as the company approaches its 20th anniversary. In a recent interview, Chesky reflected on his own leadership style and the evolution of Airbnb, which he co-founded in 2007 at the age of 25, along with two other people.
Chesky, now 45, has become a prominent voice on company leadership, frequently examining his own character and decision-making processes. He acknowledges that his immaturity in his thirties was a weakness, but believes it was a long-term bet that paid off. As one of the few founders still leading a Fortune 500 company, Chesky's perspective on leadership is unique. He believes that founders tend to be more detail-oriented, decisive, and willing to take bigger risks due to their moral authority.
The company is set to announce new housing initiatives, a move that comes as critics have called out Airbnb for contributing to rising housing costs in cities where it operates. Chesky has also overseen significant changes to the company's offerings, including the introduction of hotel bookings, a move he was initially ideologically against. In fact, Airbnb's first tagline was 'forget hotels', highlighting the company's shift in strategy over the years.
## What changed Chesky's thoughts on hiring have also evolved over time. He believes that CEOs often think about hiring wrong, a realization he came to after being advised by Sam Altman that hiring should be 50% of his job. This shift in perspective has likely influenced Airbnb's approach to talent acquisition and team building.
## Why it matters As Airbnb looks to the future, its leadership and strategic decisions will have significant implications for the company's growth and impact on the housing market. With its 20th anniversary on the horizon, Chesky's reflections on leadership and the company's evolution offer valuable insights into the challenges and opportunities facing Airbnb and the broader tech industry.
The company's ability to adapt and innovate will be crucial in addressing the concerns of critics and regulators, while also meeting the changing needs of its users. As Chesky continues to lead Airbnb, his commitment to introspection and self-improvement will likely play a key role in shaping the company's future direction.





