Remote Year should be a pretty appealing idea to anyone with a serious case of wanderlust: Participants spend a whole year working abroad, moving to a different city and country each month.
But is it just a fun, one-time experiment, or the seed of a big business? The team at Highland Capital Partners is betting on the latter — it just led a $12 million Series A in the company. Other investors in the round include WeWork Labs co-founder Jesse Middleton and Airbnb co-founder/CTO Nate Blecharczyk.
Remote Year founder and CEO Greg Caplan told me that he first had the idea about two years ago, and when he announced it, 25,000 people ended up applying to participate in the first group of 75 — which recently completed its year abroad. Now the company has expanded to include 500 traveling professionals across six programs.
With the new funding, naturally, one of Caplan’s goals is to increase the number significantly, something that will be helped by tapping into two “mega trends.”
“First, productivity has moved to the cloud,” he said. “Great work can be done anywhere. People are more creative and productive when they’re inspired by their surroundings … The second is that we no longer value the things that we own, but the experiences we share with other people.”
To expand the program, Caplan said he will continue to grow Remote Year’s team, which is currently  85 people (As you might expect, that team is all over the world — there’s no central headquarters.) Remote Year will also be building its own physical infrastructure.
“In Croatia, for example, there wasn’t an existing coworking opportunity for us to tap into, so we created an amazing coworking space right on the beach [in Split],” Caplan said.
Remote Year participants make a $5,000 downpayment and also pay $2,000 a month for the first 11 months. That’s meant to cover travel, living accommodations and a workspace with Internet. Caplan said a cohort of 75 people feels like the right size and allows for continuity between the different programs. However, the itinerary can change from program to program — for example, some groups may consist of travelers who need to work US hours, and will therefore avoid traveling to Asia.

“The diversity that’s been most exciting for us is vocational,” he added. “We have people from all different backgrounds — a lot of engineers and designers, but the biggest category is marketing. There are journalists, writers, even a few lawyers. It’s a very, very diverse group of people in terms of where they’re from and in terms of what they do.”
Of course, it’s an intense experience, and not everyone completes the program. From a personal perspective, you can take breaks and rejoin as you please, and as for the remote working, Caplan said, “We don’t believe we can make a bad employee [into] a good remote employee, but we can make a good employee a good remote employee.”
