Insights from Airbnb CEO Brian Chesky on Leadership and Founding
Brian Chesky has served as the CEO of Airbnb since its founding in 2007. Over nearly two decades, Chesky has overseen Airbnb’s remarkable evolution into a global platform with more than 5.5 million hosts worldwide and projected annual revenues reaching $12.24 billion in 2025. This growth story reflects not only the scale of Airbnb’s success but also the leadership challenges Chesky has confronted along the way.
Despite his long tenure and the company’s achievements, Chesky openly admits that he was “naturally a great founder but a terrible CEO.” This candid reflection came during a recent interview on the How I Built This podcast, where he discussed the distinct skill sets required for founding versus leading a company.
Founder Versus CEO: Different Skillsets
Chesky emphasizes that the role of a CEO is fundamentally counterintuitive compared to that of a founder. While founding a company often draws from a lifetime of creativity and hands-on building, leading a company demands a different approach. He shared that by age 26, when he launched Airbnb, he had accumulated “20 years of experience as a founder,” which began in childhood with activities like designing and disassembling toys. This extensive background provided a strong foundation for creating Airbnb.
However, Chesky points out that the CEO’s responsibilities require stepping beyond the founder’s mindset. “Being a CEO is so counterintuitive,” he said, because it involves managing people and processes in ways that sometimes contradict a founder’s instincts. For example, the common advice to hire great people and then “get out of their way” only works for mature companies. For startups, Chesky warns, this approach can be a “death sentence.”
How to Be an Effective CEO in a Young Company
According to Chesky, successful CEOs in young companies must be strategic about hiring. Rather than recruiting experienced individuals who may not understand the company’s unique culture, CEOs should seek out employees who are “a little bit ahead” of the leaders themselves—those who are smart, hungry, and mission-driven. Importantly, Chesky advocates for staying closely involved with these hires to guide and develop them effectively.
Chesky also highlights the challenge of building a company culture where employees autonomously meet expectations without constant oversight. “That’s the hard stuff,” he said. “Not becoming profitable, expense management — that stuff is easy.” Cultivating trust, accountability, and intrinsic motivation within the team is a nuanced leadership task that takes time and intentional effort.
Challenges of Leadership: Overcoming People-Pleasing Tendencies
Early in his CEO journey, Chesky admits to struggling with being a “people pleaser.” He felt cautious about directing others, especially those older or more experienced, because he wanted to be liked. This hesitation sometimes led him to defer to employees’ opinions even when his intuition suggested otherwise—a decision he later recognized as often mistaken.
His experience underscores a common leadership challenge: balancing openness to input with confidence in one’s own judgment. Chesky advises that while intuition isn’t infallible, it merits discussion and exploration rather than immediate dismissal.
Key Takeaways from Brian Chesky’s Leadership Experience
- Brian Chesky views himself as naturally a great founder but initially a “terrible CEO.”
- The CEO role requires distinct, often counterintuitive skills that differ from those needed to start a company.
- Young companies benefit from hiring smart, hungry workers and maintaining close involvement in their development.
Brian Chesky’s reflections provide valuable lessons for entrepreneurs navigating the transition from founder to CEO. His transparent acknowledgment of leadership struggles and growth reinforces the importance of adaptability, strategic hiring, and cultivating a strong culture to build lasting success.
For more detailed insights, read the full article Here.
