Brian Chesky, head of Airbnb, plans to tour the country in the coming months, but that doesn’t mean he’s taking a break from running the short-term rental platform.
The CEO believes that travel between remote workers will be greater than ever as the pandemic pushes employers to offer more flexible working conditions. To prove it’s possible to work just about anywhere, Chesky plans to spend the next few months living and working at Airbnbs in the US, returning to his home in San Francisco between each one to two week trip.
“All you need is a laptop and someone’s internet in their house and you can do your job. You can even run a nearly $100 billion business,” he told USA TODAY.
Soon updates from Airbnb
Chesky’s first stop on his remote work trip was in Atlanta, where he stayed in a home owned by a… host who lives next door with her two young children. San Francisco street posters collected by the host’s father and uncle in the 1970s were propped up behind Brian during a video interview, one of the“personal details” that the CEO drew to the list while browsingabodes.
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“I generally like houses that feel like they’re part of a community,” he said. “Some Airbnbs feel a bit more occupied than others.”
Chesky suggests that remote employees looking to travel through Airbnb should search for listings with good Wi-Fi and look closely at reviews. The longer the better, he said.
“The more passionate someone is about a better review, the longer they’ll leave reviews,” Chesky said. “So when you see a bunch of reviews and they’re like one or two sentences on Airbnb, even if they’re positive, clearly that property didn’t leave the same impression.”
The CEO plans to use his remote time to find ways to improve the platform. Airbnb has been announcing major upgrades in recent months, and Chesky said “some pretty major updates” regarding remote work will go away before the summer travel season kicks in.
‘A revolution in travel’
Before the pandemic, according to Chesky, customers primarily saw Airbnb as a way to find an apartment in a city to stay for a few days. That has changed in the past two years.
About 20% of the nights booked between July and September were 28 days or longer. Half of the nights booked in that same period were at least seven days long – up from 44% in 2019.
“We are on the cusp of a revolution in travel,” Chesky said. “The world is digitizing. The world is getting smaller. It’s getting more global. And I think this has probably been the biggest change in everyday life.”
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While the pandemic won’t last forever, Chesky believes the remote work trend will continue as the “vast majority” of workers don’t return to the office five days a week. He expects this to be especially big for workers without children who are tied to a school system, but added that remote working could open doors for families looking to travel for extended periods during the summer.
The shift is a boon for employees who want to travel more, but Chesky said it also makes sense from a business standpoint: Why would a company limit their labor pool to just people who live near their office?
“I think eventually people will want to compete for the very best talent,” he said.
‘I feel like I can be anywhere’
Chesky’s next stop is still undecided. Cities with friends he’d like to visit are high on the list, but he doesn’t ignore small towns and rural communities as options.
“I’m still kind of figuring out where my next adventure is,” he said. “I think I’ll go to Nashville and then I think I’ll go to LA. I’m not sure where next time is — maybe Miami.”

Chesky is considering posting a social media poll asking for advice on the next step.
“It’s a really fun adventure,” he said. “I’ve always dreamed of being able to live anywhere… (Now,) as long as I’m in a reasonable time zone, I feel like I can be anywhere and be just as effective here as I am at home So my office is everywhere.”
Follow USA TODAY reporter Bailey Schulz on Twitter: @bailey_schulz.