Airbnb CEO Brian Chesky has revealed how the day after the company went public at a $100 billion valuation turned out to be the “saddest day” of his life. The remarks from the founder and chief executive of the company come despite the Airbnb IPO marking a major milestone for the company. Speaking on the “Invest Like the Best” podcast hosted by Patrick O’Shaughnessy, Chesky described how the emotional high of Airbnb’s public listing quickly faded.“We go public, we have a hundred billion dollar valuation. It’s one of the best days of my life. The next day, I go on a Zoom meeting, and it was like it never happened. It became like the saddest day of my life. Because I realised, I got all this adulation, and I don’t feel any different,” Chesky said at the podcast.
What are Airbnb CEO Brian Chesky’s thoughts about external validation and recognition
Chesky said the IPO experience led him to reflect on the limits of external validation and recognition. He said, “Adulation is like a cup with a hole at the bottom. You keep filling it in, thinking it’s love, except it just keeps coming out the bottom.” According to him, the moment prompted a shift in how he views his work and motivations as an entrepreneur.“That made me reevaluate what I’m doing this for. I want to do things for pure intrinsic reasons. Do the work like you used to do, like when you were a kid. It was light. Just make stuff. Make it for yourself,” he added.Chesky also spoke about how many founders approach success, suggesting that the focus often shifts too heavily toward status rather than creation.“So many entrepreneurs focus on what they want to be. “I want to be a giant tech founder. I want to run a billion-dollar company.” Instead of focusing on, “What do I want to make.”He said that building something meaningful might give a more consistent sense of purpose. “There’s no way to fail if you’re making what you love,” Chesky noted.Airbnb’s public offering was a big moment for the company, but Chesky’s comments highlight how personal fulfilment may not always coincide with financial milestones or public accolades.
