Airbnb has garnered favorable comparisons to eBay’s $212 billion marketplace, and for most startups this would be a compliment. Not for Chesky. “People went to Dell for the computers, but they go to Apple for everything,” Chesky says. “That’s the difference between a transactional company and a transformational one.” There’s a lot riding on that single sheet of paper.
Chesky gnaws his fingernails and drums his legs in meetings. The CEO’s “endless energy” (everyone I spoke with referred to it in some fashion) is endlessly apparent. Since 2010, he has lived in Airbnbs at least part of each year. He sounds like a walking travel guide, rattling off details from his last half-dozen Airbnb excursions in the course of a conversation. He still rents out his couch to guests. “Staying here [with Brian] is like having Zuck personally stalk your ex or asking Larry and Sergey tons of inane questions,” reads one of his 85 glowing reviews.
For a long time, Chesky’s relentlessness meant he was running the company like a rhinoceros: Point him in the right direction and he’d put his head down and hammer out a solution. When a guest ransacked a host’s apartment in 2011, he managed the potentially crippling PR nightmare with such fierce attention that it actually led to features that improved the service’s professionalism and trust, including 24/7 customer service and comprehensive insurance coverage. When a European Airbnb clone launched seemingly overnight with $90 million in funding, Chesky, with the benefit of advice from Facebook COO Sheryl Sandberg and eBay chief John Donahoe, rapidly boosted Airbnb’s international presence, opening a dozen offices overseas and expanding its service into 30 languages with reps in every global time zone.