Art by Mike Sullivan

Airbnb CEO Brian Chesky is known for his relentless optimism and outsize goals. The company for years has poured hundreds of millions of dollars into pursuing his vision of designing the “perfect trip” for travelers. Determined to think big, Chesky has explored taking the company in unfamiliar directions, such as launching a flight service and a TV production studio. A longtime admirer of Apple, the CEO repeatedly told employees he wants to turn Airbnb into a multifaceted, $100 billion company that does more good for the world than the average corporation. 

But the coronavirus pandemic has put those grand ambitions on hold and forced the company into survival mode. Chesky, one of the world’s most visible startup founders, now faces an unprecedented test of his leadership. While board members say they are behind the CEO, some investors, employees and former executives question whether Chesky can evolve quickly enough into a leader who can make tough decisions in the face of an all-consuming crisis. They point to his past reluctance to walk away from struggling money-losing initiatives, and an unwillingness to remove ineffective or problematic executives.

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