23 Daily — According to entrepreneur.com, Brian Chesky, co-founder and CEO of Airbnb, opened up in a recent "How I Built This" podcast interview about his early shortcomings as a leader, sharing the challenges and mistakes he faced in his CEO role. Since founding Airbnb in 2007, Chesky has stayed in the top position, overseeing the company’s growth to more than 5.5 million hosts and projected
Distinguishing Founder and CEO Roles
Chesky noted that he was naturally a great founder, having about 20 years of experience starting from childhood with activities like designing and disassembling toys, but being a CEO was a completely different and counterintuitive challenge. While founders typically come from a background of creating and building things from an early age, CEOs face the more complex task of managing and leading an organization effectively.
Challenges and Strategies for CEOs
Chesky emphasized that contrary to common advice about simply hiring great people and letting them work independently, good CEOs must be strategic in recruitment. They should hire people who are slightly ahead, smart, and hungry, and then stay close to them. He said that in young companies, relying too much on employees’ experience can lead to mistakes, and CEOs have to balance their intuition with employee input when making decisions.
Growth in Leadership Style and Self-Reflection
Chesky candidly admitted that early on he was shy about being a boss and tended to be a people pleaser, especially with employees older or more experienced than him. This people-oriented approach caused hesitation and sometimes undermined his leadership strength.
Editor's take: The learning curve of effective CEO leadership
Brian Chesky’s reflections highlight that while founder experience is valuable, becoming an effective CEO requires mastering complex leadership and personnel management skills. The CEO role involves continuous learning in strategic hiring, culture development, and decision-making balance. Entrepreneurs looking to validate these insights can try hands-on management roles, evaluate their leadership and decision styles, and seek team feedback to balance care with goal orientation. Building leadership capacity is essential to forming a competitive core team.