Skip to main content

In an interview with The Globe and Mail, 40-year-old entrepreneur Brian Chesky talks about how Airbnb is changing to capitalize on this trend and satisfy its customers’ wanderlust.Jessica Chou/Handout

Earlier this year, Brian Chesky, co-founder and chief executive officer of Airbnb, embarked on a work-life balance experiment he calls “the year of living anywhere.” His first stop was Atlanta, followed by working visits to cities such as Nashville, Chicago, Vancouver and Ann Arbor, Mich., where he fulfilled a lifelong dream of staying in a Frank Lloyd Wright design, the Palmer House.

Through the summer, Chesky plans to keep up the pace, living and working – for weeks at a time – in Airbnb properties scattered across North America and around the world. His reasons for being a working nomad are twofold. First, he wants to sample first-hand the inventory available on Airbnb’s platform of properties. (It has more than four million hosts in 220 regions and countries).

Second, he is doing it to make a point. “It’s more than two years since the pandemic began, and millions of people are now more flexible about where they live and work,” says Chesky, whose travel accoutrements include his laptop, a carry-on bag and his dog, Sophie Supernova, a golden lab who goes everywhere with him.

“The pandemic untethered many people from the need to be in an office every day, and as a result, they’re spreading out to thousands of towns and cities, staying for weeks, months and even entire seasons at a time. There is a revolution under way in how people, live, work and travel.”

In an interview with The Globe and Mail, the 40-year-old entrepreneur talks about how Airbnb is changing to capitalize on this trend and satisfy its customers’ wanderlust.

Through the summer, Chesky plans to live and work – for weeks at a time – in Airbnb properties scattered across North America and around the world.Jessica Chou/Handout

How has COVID-19 reinvented the game in terms of hybrid work?

The world has completely changed from the world of two years ago, and I don’t think we’re going back to 2019 any more than we’re going back to 1950. Millions of people have office jobs, basically jobs where they can do it from a laptop or a computer, which they can take anywhere because they no longer have to be in an office five days a week. What that means is hundreds of millions of people around the world have more freedom and flexibility.

If they don’t have to be in an office, they can take a long weekend. If they don’t have kids, like me, they can live in an Airbnb for a week or two. If they do have kids, maybe they can go away for the summer. When they travel, they’re staying longer. Half our business by nights is now longer than a week. A fifth of our business by nights are for stays longer than a month. It’s a pretty dramatic shift that we had started to notice before 2020, but the pandemic has accelerated by at least five to 10 years.

You have said the increase in lengths of stays away will have huge implications for the travel sector overall. Please explain.

There has been a blurring of the lines between travel and work, and that has led to a more decentralized way of living. They have more freedom and they have more options. Before the pandemic people tended to go back to the same places. Now they’re not just going to New York, or London or Paris. They’re going everywhere because they can.

For the last 25 years, every travel website has kind of been the same. There is a big search box on the front page where you type in a place you want to go. That’s good if you’re travelling for business. It’s good if you know where you want to go. But nowadays people aren’t sure where they want to go. The changes we made mean when you open Airbnb you are presented with 56 categories that organize homes based on their style, location or proximity to a travel activity, which helps people discover places they wouldn’t have otherwise found.

The changes Airbnb has made are extensive. You now have 56 categories that users can now search by home type (castles, shepherd’s huts), by in-home features (chef’s kitchens, amazing pools), by location (beach, arctic) as well as by activity (surfing or ski-in/ski-out). The other new feature is Split Stays, how exactly does it work?

It speaks to what our customers want when they go away for weeks at a time, because it allows them to book back-to-back stays at multiple homes in and around the same area. If, for instance, you plan to go to Italy for a month this summer, maybe you would like to stay in two homes. With this option, users will typically see about 40 per cent more listings when hunting for longer stays, which is great for our guests and for our hosts.

The other thing is the longer people are away, the more they crave to stay in homes because they feel more a part of the community they are visiting. Hotels are great for one or two nights – and they are ideal for business travellers – but they’re expensive if you are gone for a week. Our whole business model is based on the belief that people love homes, which is why they live in them.

You released new data on Canadian travel trends that found family travel by nights booked for summer stays is the fastest growing segment in the first quarter of 2022, compared with the same period in 2019, while older adults aged 60 to 90 were the fastest growing age group. Why are families and empty nesters heading out in record numbers?

Families are on the move in a way we’ve never seen before for the simple reason that their parents have more flexibility to travel when the kids are out of school because many are no longer tied to their office. As for people my parents’ age? They’re living more nomadic lifestyles for the very same reason. My dad is retired and my mom has a remote work policy so they’re hopping around a lot. They’re doing so because life is short and they want to see more of the world.

I’m travelling around for a year because I can run a company the size of Airbnb from a laptop on someone else’s WiFi. I know not everyone can do what I’m doing. If I had a family I probably wouldn’t take them from city to city. I’m doing it for the reason people travel in the first place – because it’s fun and amazing.

Keep up to date with the weekly Sightseer newsletter. Sign up today.