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Airbnb CEO Brian Chesky says he writes just one email a week, if that—because it ‘feels like work’ and is ‘inferior’ to just texting his staff

Orianna Rosa Royle
By
Orianna Rosa Royle
Orianna Rosa Royle
Associate Editor, Success
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Orianna Rosa Royle
By
Orianna Rosa Royle
Orianna Rosa Royle
Associate Editor, Success
Down Arrow Button Icon
October 15, 2026, 4:03 AM ET
Most bosses drown in their inbox. Airbnb's CEO Brian Chesky can barely remember the last email he wrote. “I don’t know if I write an email a week.”
Most bosses drown in their inbox. Airbnb's CEO Brian Chesky can barely remember the last email he wrote. “I don’t know if I write an email a week.”Getty Images
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Most bosses drown in their inbox—waking up at 5 a.m. to get a head start on the never-ending stream of messages. But Airbnb CEO Brian Chesky can barely remember the last email he wrote. And he thinks everyone in the working world should use their inboxes a little less. Or as he put it, “not very often.”

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“I don’t know if I write an email a week,” Chesky told Time. “I respond to emails every day because people email me. But I’m trying to think of the last time I, like, drafted an email.”

His problem with emails? “I just find it inferior to almost every other form of communication,” he said. “Email is subject-based. Text message is person-based. Text messages are much faster. It’s contextual. You feel a deeper connection. The person doesn’t have a subject line. When you get a text message, it doesn’t feel like work to respond. ”

Instead, he says that emails feel like work. That’s why he ranks email as the worst form of communication—and would much rather text his 8,200 staffers because he’s more likely to reach them that way.

“I do think that text is a lot more responsive than mail. Like the notifications pop up right on your phone. If I have a problem, my general philosophy is to try to call someone, text them, meet them in person,” the billionaire boss added. 

“I think the best forms of communication are in person, number one; Zoom, number two; text, number three; probably email, number four.”

After-hours work: encouraged by some CEOs, despised by Gen Z and millennials

Even if, for Chesky, sending out a text feels more human. For workers, it doesn’t matter where the communication is coming from; any message from a boss still feels like work. 

But he doesn’t see it as a problem. 

“Everyone has a right to run their company how they want,” Chesky slammed.

While he tries “not to text people when I think they’re with their family unless there’s a crisis,” he also admitted that his own work-life balance is probably more “blended than the average person.” 

And Chesky isn’t the only CEO who doesn’t mind mixing work into his downtime.

The founder and CEO of Farmer J, a popular healthy fast-food chain in London, told Fortune that he’s never turned on his out-of-office auto-reply—even during his honeymoon. 

Anna Lundstrom, CEO of Nespresso’s U.K. and Ireland business, echoed to Fortune that her workforce can reach her on various platforms at any time, from Teams and email to WhatsApp and LinkedIn.

“I think I’d always rather know something than not,” she explained, adding that her phone is constantly within reach from the moment she wakes up. 

Uber’s CEO Dara Khosrowshahi has even insisted that sending out emails on the weekend are simply “part of working hard”—and that he expects staff to respond swiftly in their time off. “If I don’t get a response on Saturday, sending them an email on Sunday with a question mark: What’s going on?” he said on the Diary of a CEO podcast. 

Ultimately, Chesky and other CEOs may swear by text for a quick reply. But do it too many times outside work hours, and you’re likely to get a resignation notice. 

Research from recruitment platform Reed found that a quarter of millennial workers would quit if their boss ever contacted them outside work hours, and 59% of 18-to-34-year-olds say they’d be willing to move on to new pastures to protect their work-life balance.

Fortune Daily breaks the traditional barrier between audience and newsroom. The show transforms Fortune’s trusted reporting into actionable, conversational, and entertaining insights for an emerging class of business leaders. Watch here.
About the Author
Orianna Rosa Royle
By Orianna Rosa RoyleAssociate Editor, Success
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Orianna Rosa Royle is the Success associate editor at Fortune, overseeing careers, leadership, and company culture coverage. She was previously the senior reporter at Management Today, Britain's longest-running publication for CEOs. 

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