Key Takeaways

  • Airbnb lost 80 percent of its business within eight weeks in March 2020, putting 12 years of growth at risk of immediate collapse.
  • Board member and former American Express CEO Ken Chenault warned Chesky that the pandemic's fallout on travel would surpass 9/11 tenfold.
  • Faced with corporate death, Chesky discarded conventional executive detachment and took direct control of operations for the first time in 15 years.
  • When the business stabilized, Chesky rejected employee requests to return to hands-off delegation, keeping direct control over operational details.

Ken Chenault Warned Travel Was Facing Ten Times the Damage of 9/11

In March 2020, twelve years of building evaporated in eight weeks. Airbnb saw 80 percent of its business disappear as borders closed and travelers canceled their reservations. Up until that point, running the company meant delegating authority and managing expansion from high above daily execution.

The pandemic destroyed that comfort. Former American Express CEO Ken Chenault, who served on Airbnb's board of directors, called Chesky with an urgent warning. “Ken calls me and said, 'Remember 9/11? This is going to be 10 times the size of 9/11 for travel as far as impacting what it was,'” (play from 25:17) Chesky recalled. The company had spent over a decade constructing a global platform, only to face immediate collapse. Outside observers openly debated whether the company could survive. “People were asking, 'Is this the end of Airbnb? Is Airbnb going to exist?'” (play from 25:35) Chesky said. “And it was that moment that the board rallied behind me and my co-founders rallied behind me. I think it was the people who believed in me that told me to keep going. It was me feeling like I can't quit.” (play from 25:39)

Operating in the Foxhole Changed Chesky as an Executive

The crisis forced Chesky to rethink what it meant to lead. Standard executive advice tells founders to hire managers, set abstract targets, and let subordinates handle operations without interference. Chesky realized that delegating during a tailspin was a formula for corporate death. If the company died, the responsibility was his alone.

“It was a crucible moment,” (play from 0:00) Chesky explained. “It was the first moment I had to be a good CEO, and it was a life-or-death moment. Because before that, it was a nice-to-have to be CEO: 'Well, we could grow faster, it'd be less chaotic.' But at that moment, either I'm a great CEO and the company survives, or I'm a bad CEO and the company dies. So it became life or death.” (play from 0:00)

Instead of reviewing dashboards, Chesky jumped directly into operational details. He audited expenses, stripped away corporate sprawl, and worked shoulder to shoulder with his team. “Basically, it was like we're all in the foxhole,” (play from 45:37) Chesky said. “So now I'm running the company hands-on for the first time in 15 years, not telling you what to do, but like we're in the foxhole together.” (play from 45:39)

Chesky Refused to Return to Conventional Management

Operating in the weeds worked. Airbnb halted its tailspin, cut its cost base, and stabilized the business. Once the acute danger passed, employees expected a return to hands-off delegation. They wanted leadership to retreat to high-level strategy and leave daily execution alone.

Chesky refused. “We get out of the tailspin,” (play from 45:46) he said. “And then, I think a bunch of employees thought, okay, let's go back to operating the way we were, and I'm like, no way.” (play from 45:47)

Chesky realized that distance between executive leadership and daily operations had created bloat and waste. Conventional corporate advice creates layers of insulation that blind leaders to basic operational flaws until a catastrophe hits. For Chesky, direct involvement was not a temporary emergency measure. It became his permanent operating model.

What to Do With This

Pick the single project in your company that is slipping on its delivery date this week. Cancel the status meeting, sit down directly with the person building it, and review the raw work together line by line.