Airbnb – Brian Chesky

Initially a website that connected strangers to sleep on air mattresses on each other’s floors, Airbnb defied the odds as it exploded to become one of the breakout tech unicorns of the early 2010s. However, Brian Chesky remembers worrying, “this is just one accident away from being a dead idea.” That accident finally came in 2011 when a host’s apartment was ransacked. More than a PR crisis, it was an existential reckoning—but it fostered a transformation that led to Airbnb becoming the beloved go-to global travel behemoth it is today. The questions Chesky learned to ask himself would guide him through navigating the company’s next crucible moments, including a pandemic that shut down global travel: “What’s the principle decision?” and “How do we want to be remembered?”