Learn what early setbacks taught him about designing work-travel programs, building community, and leading remote teams. ============================ Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds. ============================ ON THIS EPISODE 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 become 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 with direct links to everything discussed are available here. ============================ FIND YOUR NEXT EPISODE Explore The Maverick Show Starter Packs — some of my favorite conversations curated by theme so you can easily find the episodes that match your interests. ============================ FREE RESOURCES FOR YOU See my Top 10 Travel Apps See my Top 10 Books that Shaped the Way I Travel See my 7 Keys For Building A Remote Business (Even in a space that’s not traditionally virtual) Watch my Video Training on Stylish Minimalist Packing so you can join #TeamCarryOn See the Travel Gear I Use and Recommend See How I Produce The Maverick Show Podcast (The equipment, services & vendors I use) ============================ ENJOYING THE SHOW? Follow The Maverick Show on Instagram and DM Matt to continue the conversation Please leave a rating and review — it really helps the show and I read each one personally Support the show by buying me a coffee — espressos help me produce significantly better podcast episodes!

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

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Learn what early setbacks taught him about designing work-travel programs, building community, and leading remote teams.  ============================  Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.  ============================  ON THIS EPISODE  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 become 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 with direct links to everything discussed are available here.  ============================  FIND YOUR NEXT EPISODE  Explore The Maverick Show Starter Packs — some of my favorite conversations curated by theme so you can easily find the episodes that match your interests.  ============================  FREE RESOURCES FOR YOU  See my Top 10 Travel Apps  See my Top 10 Books that Shaped the Way I Travel  See my 7 Keys For Building A Remote Business (Even in a space that’s not traditionally virtual)  Watch my Video Training on Stylish Minimalist Packing so you can join #TeamCarryOn  See the Travel Gear I Use and Recommend  See How I Produce The Maverick Show Podcast (The equipment, services & vendors I use)  ============================  ENJOYING THE SHOW?  Follow The Maverick Show on Instagram and DM Matt to continue the conversation  Please leave a rating and review — it really helps the show and I read each one personally  Support the show by buying me a coffee — espressos help me produce significantly better podcast episodes!

The Maverick Show is a global travel podcast about what really happens when people cross borders and build lives across cultures. Hosted by full-time world traveler Matt Bowles, each episode features intimate, unfiltered conversations (often over a bottle of wine) exploring the human stories behind global travel and what the journey teaches us about the world and ourselves.  Guests include expats, digital nomads, women and diaspora storytellers, worldschooling families, and human rights advocates, all sharing travel stories that are funny, moving, and deeply human.  In addition to hearing about extraordinary places and the people who live there, you’ll learn what it’s really like to move abroad, build an expat life, or travel long-term, as guests open up about their personal journeys navigating culture, race, power, identity, and belonging in an unequal world. If you’ve ever felt that travel changes you in ways no one talks about, you’re in the right place.  The Maverick Show hit the Top 100 on Apple Podcasts (including #1 in Places & Travel), was ranked in the Top 1% of podcasts globally by Listen Notes, and was named the #1 Digital Nomad Podcast and #1 Remote Work Podcast by Million Podcasts — with hundreds of five-star listener reviews.

The Maverick Show: Global Travel Stories & Life Beyond Borders

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