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No one shamed Airbnb's chief for working 18-hour days in COVID

When guests could not stay in strangers' homes, its leader worked marathon days and the company emerged stronger.

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mondaymorning.substack.com · Unapologetic

During COVID, Brian Chesky, Airbnb's chief executive and co-founder, put in 18-hour days while a global lockdown settled over a hospitality business built on guests staying in strangers' homes.

An 18-hour day leaves only a few hours for sleep, meals, and everything else, and a lockdown meant travel was limited and strangers were keeping apart. A company whose product needed movement and closeness, sleeping in someone else's spare room or apartment, was trying to keep going when both were shut down.

No one shamed Chesky for keeping that schedule, and Airbnb came out of the lockdown stronger than it went in. The writer who recounts it, a startup investor writing a personal newsletter, finds that lack of criticism notable. In his view, the greats rarely get shamed for long hours.

In his account, most people leave that type alone apart from saying they can be difficult to work with.

The explanation he offers is one he says he is beginning to hold. He describes such leaders as "unapologetic in their pursuit of their own potential," his phrase for refusing to apologize for chasing what they might be capable of.

He puts the larger point as something you could argue. If someone is working on something big enough, looking after the health of the whole business and what it makes possible for others may matter more than worrying about seeming likable as an individual. By the larger thing, he means the company itself and its effects, and by the smaller thing, he means one person's reputation.

Whether the long hours caused the rebound is not shown. He writes as someone surprised by the outcome, asking who would have thought that kind of business could go through that kind of shutdown. Chesky, in this account, simply kept working.

Questions people ask

Did Airbnb really come out of COVID stronger?

Yes, after a brutal start. Airbnb cut about 25 percent of its staff in May 2020 and raised emergency funding, then demand for long-term stays and homes outside cities rebounded. It went public in December 2020 at a valuation above $100 billion and posted record revenue in the years that followed.

What did Chesky actually do during those long days?

Public accounts say he overhauled the business around its core home-sharing product, paused noncore projects, rewrote policies for cancellations and cleaning, and spoke constantly with hosts, employees, and investors. He has described making rapid, centralized decisions to preserve cash and rebuild trust with hosts.

Why would focusing on the company be called more compassionate?

The argument in the source is that saving the system preserves jobs, listings, and travel options for millions of people. From that view, protecting the business and its impact matters more than protecting one leader's reputation for being easy to work with.