48: Remote Year CEO Greg Caplan on the Future of Work, Nomadic Communities and Building the World's Largest International Work-Travel Program

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.

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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 AND DIRECT LINKS TO EVERYTHING DISCUSSED IS AVAILABLE HERE.

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