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Remote Year

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Company or group
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Other company
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The profile

Remote Year, a Chicago startup that sold year-long work-and-travel programs, lost half its revenue in days when borders closed in March 2020, laid off half its staff and paused its programs. Selina bought its brand that October; Remote Year shut down in December 2024. SBA's PPP loan data list no borrower named Remote Year.

  • Category: travel and hospitality
  • Pandemic layoffs: about 50 roles, 50% of staff (TechCrunch, March 2020)
  • Last updated: 2026-11-01

In the archive

Founders, executives and investors

TechCrunch identified Greg Caplan as Remote Year's founder in March 2020. By October 2020, Sam Pessin was co-founder and CEO. TechCrunch reported that Remote Year had raised $5 million from LightBank less than six months before the layoff, bringing its total funding to $17 million, according to Crunchbase data.

Business before the pandemic

Remote Year's website in September 2014 described a one-year program for 100 people, who would spend two to five weeks in each of 18 places while working remotely; the first group was due to leave on June 1, 2015. In 2020 the program took people to 12 cities in 12 months, at $2,000 to $3,000 a person per month. By October 2020 the company also offered one-, four- and six-month programs.

What the pandemic did to the business

"The borders sort of froze up with the virus and a lot of our folks decided not to travel and go home," Caplan told TechCrunch on March 19, 2020. "Half of our revenue dried off in a couple of days, and there's no end in sight when this situation may change." The company said it still had runway from its last round.

Layoffs.fyi noted in May 2020 that small travel startups such as Lola, Remote Year and WanderJaunt had cut dozens of jobs each before Airbnb and TripAdvisor made any cuts. Remote Year's website told prospective customers that its programs had paused and that it was not accepting new participants.

Pandemic-relief role

SBA's PPP loan data list no borrower named Remote Year.

Layoffs

Caplan told TechCrunch on March 19, 2020 that Remote Year had laid off half its staff, about 50 roles in sales, marketing and product, and that its three-person team that placed people in remote jobs was coaching the laid-off staff. How Remote Year handled layoffs →

After the first shock

On Oct. 5, 2020, the hostel-and-hotel group Selina announced an all-stock acquisition of Remote Year's brand and customer base. Remote Year kept its own name and began using Selina's properties, then spread over 19 countries on three continents. Pessin said the company was "planning for a surge in demand" for its four- and 12-month programs as travel resumed. In 2023, Remote Year members were offered 10% or 20% off Selina accommodation and coworking, depending on their membership.

Where the company is now

Remote Year has shut down. Selina declared insolvency in July 2024 and was delisted from Nasdaq. In late August 2024, Collective Hospitality, a Singapore-based group, bought most of Selina's business assets, including about 100 hotels and Remote Year. Destination Group CEO Gary Murray, whose company owns Collective Hospitality, called Remote Year a "fabulous business" at the time. Four months later, on Dec. 21, 2024, Skift reported that Remote Year was shutting down after nearly a decade. The company's statement cited "circumstances beyond our control" and said its new owner had "blocked our last opportunity to continue."

Sources

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