The Diary Of A CEO with Steven Bartlett CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!
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May 28, 2025 
Brian Chesky, Co-founder and CEO of Airbnb, shares insights from his journey in building a global platform for lodging. He candidly discusses how rejection shaped his resilience and the critical role of company culture over profits. Chesky emphasizes the unique challenges entrepreneurs face, highlighting the need for more founders to drive societal change. He also reflects on how culture can foster innovation and growth, inspired by leaders like Steve Jobs, showcasing the importance of values in shaping an organization.
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Early Rejection and Market Doubts
- Brian Chesky shares an early rejection email when Airbnb tried to raise $150,000 at a $1.5M valuation.
- The market was deemed too small then, yet now Airbnb handles money exceeding the GDP of Croatia.
Founders’ Unique Leadership Role
- Founders uniquely combine passion, permission, and knowledge to run and rebuild their companies.
- Professional managers often lack these core founder attributes, making founder-led companies special.
The Challenge of Founder Succession
- Not every founder can scale a giant company or live long enough to see its full legacy.
- Great companies seek longevity beyond founders, highlighting succession planning's importance.