Long before he cofounded Airbnb\u2014the now-$105 billion short-term rental platform\u2014in 2008, Brian Chesky was practicing being a founder as a kid\u2014designing things, disassembling Christmas toys, and persuading friends to buy what he was selling. By the time he started a company, he figured he\u2019d been preparing for the job his whole life, with 20 years of founder experience under his belt. Stepping into the CEO role, however, was a different matter.<\/p>\n
\u201cI think I was pretty much naturally a great founder, and I was naturally a terrible CEO,\u201d Chesky told Guy Raz on Monday\u2019s episode of How I Built This<\/a>.<\/p>\n As Airbnb grew, Chesky said he followed advice to hire experienced executives, trust their judgment, and give them room to work. But when he rejected that approach and took a more hands-on role, he was met with resistance.<\/p>\n \u201cAlmost the entire exec team left,\u201d Chesky said, adding that the departures happened eventually. \u201cThey left or they didn\u2019t want to work for me.\u201d\u00a0<\/p>\n The longtime CEO wasn\u2019t looking to win over everyone\u2014just 10 people willing to serve on his executive team and see whether working his way produced results.<\/p>\n That approach later became known as \u201cfounder mode.\u201d Y Combinator cofounder Paul Graham popularized the term after hearing Chesky speak at an event for the startup accelerator. In a September 2024 essay<\/a>, Graham challenged the idea that founders must hand off the details as their companies grow, arguing they should stay involved with employees beyond their immediate reports.\u00a0<\/p>\n Chesky began changing how he ran Airbnb in 2020, four years before Graham\u2019s essay, as the COVID-19 pandemic disrupted the company\u2019s IPO plans and sent revenue down 72%<\/a>. He turned to former Apple<\/a> designer Jony Ive, who told him: \u201cYou don\u2019t manage people. You manage people through the work.\u201d He then took a page from Apple cofounder Steve Jobs\u2019 playbook<\/a> and cut layers of management.<\/p>\n For Chesky, that meant bringing the employee doing the work and the managers above them into the same meeting. Everyone could make a recommendation, and he could make the final decision without sending an idea through several rounds of signoffs.<\/p>\n In August 2025<\/a>, Chesky said he treated roughly 50 employees as direct reports, weighing in on decisions to hire, fire, promote, and manage them.<\/p>\n Finding people willing to work his way<\/p>\n Taking a more hands-on role meant breaking some old habits. Chesky said he often listened to executives with far more experience than he had, even when their advice ran counter to his instincts.<\/p>\n \u201cAnd what do I do when my intuition and their experience collide? Usually I deferred, and that was usually a mistake,\u201d he said.<\/p>\n He also shied away from difficult conversations about performance, sometimes taking on struggling employees\u2019 work himself.\u00a0<\/p>\n \u201cI felt cautious about being a boss,\u201d he said. \u201cI think I was a little bit of a people pleaser. I wanted people to like me.\u201d<\/p>\n But that deference came at a cost.\u00a0<\/p>\n \u201cThey\u2019ve gone down a path for two years. Guess<\/a> what happens? They leave. You might spend five or 10 years fixing or correcting that decision that person made,\u201d Chesky said.<\/p>\n As he overhauled how he ran Airbnb, Chesky began hiring people who had worked for founders such as Jobs and Amazon<\/a> founder Jeff Bezos. They already understood his approach and needed less convincing.<\/p>\n