CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!

In this episode of 'The Diary Of A CEO with Steven Bartlett', Airbnb co-founder Brian Chesky shares his journey of entrepreneurship, the importance of culture, and the unique role of founders in a company's success. Chesky begins by recounting the early days of Airbnb, highlighting the rejection they faced when seeking funding. He shares an email from 2008 where an investor turned them down, citing a lack of market opportunity. Chesky contrasts this with Airbnb's current scale, emphasizing the importance of vision and perseverance in entrepreneurship. He discusses the challenges founders face, including scaling their leadership skills and succession planning, noting that founders bring passion, permission, and deep knowledge to their companies that professional managers may lack.

Chesky then delves into the topic of culture, arguing that it is the most crucial aspect a leader can design. He shares a recent email sent to Airbnb employees, explaining that culture is the foundation for innovation and that without intentional design, an undesirable culture may emerge. He stresses that culture is more than just values printed on walls; it is the behaviors of leaders and the decisions made in hiring and promoting. Chesky concludes by asserting that culture is a company's ultimate intellectual property, as it defines how people and resources are directed towards achieving the company's goals.