For Brian Chesky, leadership did not arrive with a title. It arrived during a crisis that nearly broke Airbnb in its early years.
In a recent interview on CNBC’s Leaders Playbook, Chesky looked back at a defining moment from 2011. At the time, Airbnb was still young. Trust was fragile. Then a host reported that guests had ransacked her apartment.
The story spread fast. Social media turned hostile. The hashtag #RIPAirbnb began trending. For many observers, it looked like the end.
Chesky remembers it clearly.
“That was our moment of truth,” he said. “People thought this was the demise of the company.”
Pressure to stay silent
Back then, Chesky was a first-time CEO. Advisors urged caution. Some told him to avoid public statements. Others warned against admitting fault.
However, silence only deepened the backlash.
As criticism grew, Chesky realised that waiting carried more risk than acting.
So instead of retreating, he chose to respond directly.
A public apology and a hard decision
Chesky wrote a blog post apologising to the host. More importantly, he announced the Airbnb Guarantee, pledging up to $50,000 to cover property damage.
The move unsettled parts of the company. Internally, teams worried about fraud, abuse, and financial exposure. Some feared the policy could bankrupt Airbnb if claims piled up.
Still, Chesky pushed forward.
“At moments like that, leadership means stepping up,” he said. “You have to make a decision that defines who you are.”
Values over spreadsheets
Chesky did not base the decision on forecasts or risk models. Instead, he asked a simpler question.
“If this goes wrong,” he said, “how do I want to be remembered?”
That framing guided the choice. He believed most people were good. He also believed trust mattered more than short-term protection.
As a result, Airbnb rebuilt credibility instead of losing it.
Long-term impact
Over time, the Airbnb Guarantee expanded into a broader host protection programme, now covering up to $3 million in damages.
The company also grew far beyond its early uncertainty. Today, Airbnb holds a market value above $79 billion, serving millions of hosts and travellers worldwide.
Yet Chesky still points back to 2011 as the turning point.
The moment leadership began
Looking back, Chesky does not describe that crisis as a failure. He describes it as a formation.
“That was the moment I really became a CEO,” he said.
Not because he avoided risk.
But because he accepted responsibility when it mattered most.
The crisis forced clarity.
And clarity shaped the leader Airbnb needed to survive.
Airbnb co-founder and CEO Brian Chesky speaks about Airbnb Experiences and the launch of Airbnb Services during the Airbnb Summer Release keynote in Los Angeles, California, on May 13, 2025.
Patrick T. Fallon | AFP | Getty Images
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