Airbnb's Chesky Writes One Email a Week — and Calls Email Inferior

By Amara Osei

Airbnb CEO Brian Chesky says he can barely remember the last email he drafted. "I don't know if I write an email a week," Chesky told Time in an interview. "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 verdict on the medium is blunt. "I just find it inferior to almost every other form of communication," he said.

Chesky runs a company with 8,200 employees, and he'd rather text them. His reasoning, as he laid it out to Time:

• "Email is subject-based. Text message is person-based."
• "Text messages are much faster. It's contextual. You feel a deeper connection."
• "When you get a text message, it doesn't feel like work to respond."

What does Chesky's communication hierarchy look like?

The billionaire boss has a clear ranking. "I think the best forms of communication are in person, number one; Zoom, number two; text, number three; probably email, number four," he said.

Texting also wins on responsiveness, he argues. "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," Chesky added.

Do after-hours texts count as work?

Here's the tension. For Chesky, a text feels human. For the employee receiving it, a message from the boss still feels like work — whatever channel it arrives on.

He doesn't see that as his problem. "Everyone has a right to run their company how they want," Chesky said. He tries "not to text people when I think they're with their family unless there's a crisis," but admitted his own work-life balance is more "blended than the average person."

Other CEOs go further. Dara Khosrowshahi of Uber has insisted weekend emails are "part of working hard" and expects fast responses from staff on their days 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.

Anna Lundstrom, CEO of Nespresso's U.K. and Ireland business, told Fortune her team can reach her on Teams, email, WhatsApp and LinkedIn at any time. "I think I'd always rather know something than not," she said. The founder and CEO of London healthy fast-food chain Farmer J told Fortune he has never switched on his out-of-office auto-reply — not even during his honeymoon.

What's the risk for bosses?

The data suggests CEO enthusiasm for constant contact carries a real cost. Research from recruitment platform Reed found that a quarter of millennial workers would quit if their boss contacted them outside work hours. Among 18-to-34-year-olds, 59% say they'd change jobs to protect their work-life balance.

Chesky and his peers may get faster replies by texting. But push that habit past office hours too often, and the response may be a resignation letter rather than a message read receipt.