Running a multibillion-dollar company often requires lots of early mornings. For Airbnb CEO Brian Chesky, however, much of his work gets done late at night.
The 43-year-old is leading his company through a major redesign that enables users to book services on Airbnb in addition to stays. Chesky spent his Thanksgiving holiday weekend working on a 10,000-word plan to bring his vision to life and revising it to 1,500 words over the span of a few days, he recently told Wired.
There’s a good chance that the plan came together at least partly in the late hours of the night. The billionaire told The Wall Street Journal that his creativity begins to peak at around 10 p.m. and lasts until bedtime, which is typically 2:30 a.m.
Before that, at 8 p.m., he exercises for about 90 minutes.
While CEOs like Apple’s Tim Cook and Snap’s Evan Spiegel set aside time in the morning to read and answer emails, Chesky said he prefers to use texts and phone calls since 2020.
Some of his nights include time for “personal stuff” like dinner, watching TV, or drawing. When he’s in work mode, however, he’s checking in with employees who are available at night or doing “heads-down work,” Chesky told Fortune in March.
Chesky said he can afford to go all in on work some nights as a single man with his dog at home.
Airbnb declined to immediately comment further on Chesky’s routine.
He’s not the only CEO who has talked about working on his company late into the night. Aaron Levie, cofounder and CEO of the cloud services company Box, told Fast Company in 2013 that he goes to bed around 3 a.m. And in a 2023 podcast episode, Bill Gates said he once believed “sleep is laziness” before realizing the importance of a good night’s sleep as a man over 40.
As the boss at Airbnb, Chesky said he can largely make his own rules, and emailing was the thing he “hated the most” about his job. He’s also decided that he won’t take meetings before 10 a.m. — about an hour and a half after he wakes up at 8:30 a.m., Fortune reported.
“When you’re CEO, you can decide when the first meeting of the day is,” Chesky told the Journal.
While Apple’s Tim Cook and other CEOs often get into the office early, Berkshire Hathaway’s Warren Buffett, who plans to retire at the end of the year, has said he prefers to start his workday later in the morning.
“I will usually sleep eight hours a night,” Buffett said during a 2017 interview with PBS.
“I have no desire to get to work at 4 in the morning,” he added.
Axel Springer, Insider Inc.’s parent company, is an investor in Airbnb.
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