Remote Year co-founder and CEO Greg Caplan shares the behind the scenes journey of starting and building the world’s largest international work-travel program. He tells the story of how his unique upbringing in the Chicago suburbs led him to became passionate about international travel and cultural immersion. He then explains how he was driven to start Remote Year based on his own interest in working while traveling with a community of friends and shares his surprise with the amount of initial demand he received for the concept. He then explains how he went about building the infrastructure for the program, what the initial challenges and setbacks were, and the lessons he learned from them. He goes on to explain how the program functions today—how the onboarding, orientation and city previews work, as well as the overall experience that participants can expect on the program. He then details the concept of the “Remote Nation” and how the “Citizenship” program works to connect the Remote Year alumni network across the globe and offer unique experiences to them on an ongoing basis. Greg also explains Remote Year’s mission and values, and talks about the “Positive Impact” initiative as well as the “Diversity, Equity and Inclusion” initiative that Remote Year is prioritizing for both staff and participants. He then shares his vision on the macro trends that are shaping the future of work, both in terms of employee desires to work remotely while traveling the world, and also in terms of companies increasingly offering remote work as a benefit to recruit and retain top talent. FULL SHOW NOTES AVAILABLE AT www.TheMaverickShow.com
Episode #48: Remote Year CEO Greg Caplan on the Future of Work, Nomadic Communities and Building the World’s Largest International Work-Travel Program
Episode Summary
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About the Guest
Greg Caplan
Greg Caplan is the co-founder and CEO of Remote Year, the world’s largest international work-travel program. After building his first company and having it acquired by Groupon, Greg then founded Remote Year in 2015, which went on to raise $12 million in their Series A round, and now has over 110 employees around the world, generates. Remote Year enables location-independent professionals to live and work in different cities around the world as part of an immersive cultural and community experience. Participants get to work and live like a local for 4, 6, or 12 months in some of the world’s most vibrant cities with a group of other professionals from different backgrounds and industries. For a monthly fee, Remote Year plans all the logistics including flights, accommodations, workspace access with 24/7 wifi, as well as connecting you with locals and planning activities on the ground in each city. And Remote Year has now over 2,500 participants at the time of this recording.
What You'll Learn
- The macro-trends that are shaping the future of remote work.
- How to leave a positive impact on the communities where you travel.
- How to travel with a community and to be part of a global nomadic social network.
Links From the Episode
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GET YOUR $200 DISCOUNT ON A 4, 6 OR 12-MONTH REMOTE YEAR PROGRAM WITH THIS LINK:
- Remote Year ((Use this link to get a $100 Credit on Remote Year))
#1 BOOK GREG RECOMMENDS
#1 TRAVEL TOOL GREG RECOMMENDS
WHERE THE INTERVIEW TOOK PLACE
TOP #3 MOST FAVORITE TRAVEL DESTINATIONS
TOP #3 TRAVEL BUCKET LIST DESTINATIONS
OTHER PLACES MENTIONED IN THIS EPISODE
- Asia
- Australia
- Chicago
- China
- Colombia
- Europe
- Tbilisi, Georgia
- Jerusalem
- Nairobi, Kenya
- London
- Kuala Lumpur, Malaysia
- New Zealand
- Prague
- Peru
- Ljubljana, Slovenia
- Austin, Texas
CHECK FLIGHTS TO ANY OF THESE DESTINATIONS
CONTACT GREG
Time Stamped Show Notes
[3:44] HOW GREG DEVELOPED HIS PASSION FOR TRAVEL AND CULTURAL IMMERSION
- Growing up in the Chicago Suburbs
- Having internationals from around the world living with his family
- What travel means to Greg
- Greg’s desire to travel the world for an extended period of time with a community
[12:50] HOW REMOTE YEAR WAS FOUNDED
- Creating a simple webpage
- Getting 1,000 opt-ins the first day
- Getting media attention and going viral
- Getting 50,000 opt-ins in the first 3 months
- Recruiting his co-founder and COO
- Refining the high-level program itinerary details
- Interviewing 600 people on the phone to curate the first Remote Year community
- Kicking off the first Remote Year trip in June 2015 in Prague
- Forming the initial Remote Year team of 6 people (all in their early to mid 20s).
- Building relationships with co-working spaces and accommodations
- Welcoming the first remotes off the plane in person
[26:33] THE OGs: LESSONS FROM THE FIRST REMOTE YEAR GROUP EVER
- Quality control challenges with workspaces and accommodation
- Lessons, refinements, and institutionalizing quality control
- Thoughtfully vetting participants to ensure they are the right fit for the community.
- Building an ‘employer solutions’ team to help participants get employer permission to join the program
- Building an ‘onboarding team’ to get participants ready and set them up for success
[36:02] THE VALUE OF “COMMUNITY” AS THE CENTERPIECE OF THE REMOTE YEAR OFFERING
- Matt and Greg’s prioritization of community while traveling
- The unique depth-level of community building on Remote Year
- The doing Remote Year was the best year of Matt’s life
[41:15] REMOTE YEAR’S MISSION AND VALUES
- Greg explains Remote Year’s mission and vision
[47:01] REMOTE YEAR’S POSITIVE IMPACT INITIATIVE
- The ethics of international travel and being a socially responsible traveler
- How Remote Year helps participants be positive members of the communities each month
- Examples of Remote Year’s “Positive Impact” initiatives in different cities
[52:33] THE “REMOTE NATION” AND THE “CITIZENSHIP PROGRAM” FOR ALUMNI
- Greg explains the “Citizenship program” for Alumni of Remote Year
- Launching “Citizen Houses” and rolling out a Citizen Summer Camp
- How the “Remote Nation” is organized on Slack around interest-areas and geography
- “Dinners Around the World” and meeting up monthly around the globe
[59:40] REMOTE YEAR’S “DIVERSITY, EQUITY AND INCLUSION” (DEI) INITIATIVE
- Greg’s reflections on Remote Year being less inclusive and diverse than desired
- Remote Year’s initiative to increase diversity and inclusion
- Learning, listening and understanding
- Bringing in external experts to build inclusivity trainings for the Remote Year Team
- Requiring an inclusivity training for all participants as part of the onboarding process
- Incorporating “DEI” into the Remote Year orientation and the monthly “City Previews”
[1:04:36] THE FUTURE OF REMOTE WORK
- The macro-trend that is shaping the future of work
- The best employees desire the freedom to work when, where and how they want
- Companies are attracting and retaining top talent by offering remote work
- Companies experience partnering with Remote Year as a perk for their peak performers
- Why employee excitement for remote work is leading the trend from the bottom up
[1:13:34] THE LIGHTNING ROUND
- The #1 Book Greg recommends
- The #1 Travel hack Greg uses
- Greg’s #1 stress reduction technique
- Greg’s Top 3 favorite travel destinations
- Greg’s Top 3 bucket list destinations
[1:17:30] CONTACT GREG
- Get a $200 Discount on the Remote Year program
- Email Greg
- Follow Greg on Twitter
