Some nights, Brian Chesky wakes up with his heart pounding. It’s a familiar feeling—one that he’s had since the early days of Airbnb, the online lodging company he co-founded nearly 10 years ago. Back then, his fears were not unlike those that plague most entrepreneurs: he worried about running out of money, building a product no one wanted, his company going bust. There is little danger of that now. Airbnb, worth $30 billion, operates in every place in the world except Iran, Syria, Sudan, Crimea, and North Korea. Roughly 100 million people—including Beyoncé, Kendall Jenner, and Gwyneth Paltrow— have used the site. And Chesky, at 35 years old, is a billionaire and one of the most powerful C.E.O.’s in Silicon Valley.
Still, in the quiet dark hours, when there are…