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Brian Chesky has been the CEO of Airbnb since the company\u2019s inception in 2007<\/a>. For nearly 20 years, he has stuck with the top job and overseen Airbnb\u2019s incredible growth to become a company with over 5.5 million hosts<\/a> and $12.24 billion<\/a> in annual revenue in 2025.<\/p>\n However, being a CEO didn\u2019t come naturally. In a recent interview with the How I Built This<\/em><\/a> <\/em>podcast, Chesky opened up about his shortcomings as a leader when Airbnb first got started.<\/p>\n Chesky drew a distinction between being a great founder and being a great CEO.<\/p>\n \u201cI think I was pretty much naturally a great founder and I was naturally a terrible CEO,\u201d he said on the podcast.<\/p>\n Chesky pointed out that someone could spend their \u201cwhole life\u201d being a founder. It starts in childhood, with making and building things \u2014 all prep work for being a founder. The moment a person creates a company is probably not the first time they try to make something, Chesky said. He estimated that when he started Airbnb at age 26, he probably had \u201c20 years of experience as a founder, starting as a child designing, disassembling Christmas toys.\u201d<\/p>\n By the time he founded the company, he claimed to have had decades of experience with founding or creating something under his belt.<\/p>\n Then came the tougher challenge: being CEO. Chesky said on the podcast that the main problem with being a CEO is that it is so counterintuitive.<\/p>\n \u201cFor example, people tell you to hire great people and trust them and get out of their way to do their job,\u201d Chesky said. \u201cThat is what you do once you are very mature. That is a death sentence to a young company.\u201d<\/p>\n Chesky said that good CEOs actually have to be strategic in making new hires. They have to steer away from hiring experienced people who don\u2019t understand the company. Instead, they have to hire workers a \u201clittle bit ahead\u201d of them who are smart and hungry \u2014 and then \u201cstay really close to them.\u201d<\/p>\n Chesky also addressed the question of how CEOs can create a culture where employees automatically do what is expected of them, even when the CEO isn\u2019t in the room.<\/p>\n \u201cThat\u2019s the hard stuff,\u201d he said. \u201cThat\u2019s really hard. Not becoming profitable, expense management \u2014 that stuff is easy.\u201d<\/p>\n Chesky admitted that early on, he was \u201ccautious\u201d about being a boss. He \u201cfelt shy\u201d about directing people to do something, especially workers who seemed older and more experienced.<\/p>\n \u201cI think I was a little bit of a people pleaser,\u201d he said. \u201cI wanted people to like me.\u201d<\/p>\n The difficult part for Chesky was when his intuition would clash with what his employees were telling him. Usually he deferred to their experience, and usually it was a mistake, he said.<\/p>\n \u201cMy intuition is telling me this thing,\u201d Chesky said. \u201cIt doesn\u2019t mean you\u2019re wrong, but now let\u2019s talk about it.<\/p>\n<\/p><\/div>\n Brian Chesky has been the CEO of Airbnb since the company\u2019s inception in 2007<\/a>. For nearly 20 years, he has stuck with the top job and overseen Airbnb\u2019s incredible growth to become a company with over 5.5 million hosts<\/a> and $12.24 billion<\/a> in annual revenue in 2025.<\/p>\n However, being a CEO didn\u2019t come naturally. In a recent interview with the How I Built This<\/em><\/a> <\/em>podcast, Chesky opened up about his shortcomings as a leader when Airbnb first got started.<\/p>\n Chesky drew a distinction between being a great founder and being a great CEO.<\/p>\n<\/p><\/div>\nHow to be a good CEO<\/h2>\n
Being a people pleaser<\/h2>\n
Key Takeaways<\/h2>\n
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