Learn what building a global travel company taught him about hiring, remote culture, leadership, stress, and resilience. ============================ 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 Learn what building a global travel company taught him about hiring, remote culture, leadership, stress, and resilience. Sam Pessin talks about his international upbringing in London, Jerusalem and Beijing, and how that impacted his life and his passion for travel. He then talks about his professional career trajectory and ultimately deciding to co-found Remote Year in 2015. Sam takes us through the evolution of Remote Year, refining the customer experience, scaling it to over 100 employees by 2019, and being acquired by Selina in 2020. He then describes the current Remote Year offerings, ranging from one week retreats and one month workations to 4 and 12 month work-travel programs with a community of location independent professionals. Matt shares his experience on the 12-month Remote Year program in 2016 and why it was the best year of his life. Sam then describes the customer experience on Remote Year programs today and discusses safety, inclusion, positive impact, local immersion, and community building. Matt and Sam also discuss the Remote Year alumni “Citizenship” program and why it is one of the most valuable parts of the Remote Year experience. Sam then talks about the company’s Diversity, Equity and Inclusion priorities, and the progress Remote Year has made on its DEI goals over the last two years. He then opens up about the impact that the pandemic had on Remote Year, the acquisition by Selina in 2020, his current role as President, and his vision for the future of Remote Year. Next, Sam talks about Remote Year’s process for hiring amazing people, building company culture in a remote environment, and gives his tips on executive leadership. He then shares his personal productivity habits, how he manages stress, his biggest lessons learned from building Remote Year, and what he would do differently if he had to do it all over again. And finally, Sam shares his #1 Remote Year memory. → 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 President Sam Pessin on Diversity, Equity & Inclusion and Building the World's Largest Work-Travel Program (Ep 154)

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Learn what building a global travel company taught him about hiring, remote culture, leadership, stress, and resilience.  ============================  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  Learn what building a global travel company taught him about hiring, remote culture, leadership, stress, and resilience. Sam Pessin talks about his international upbringing in London, Jerusalem and Beijing, and how that impacted his life and his passion for travel.  He then talks about his professional career trajectory and ultimately deciding to co-found Remote Year in 2015.  Sam takes us through the evolution of Remote Year, refining the customer experience, scaling it to over 100 employees by 2019, and being acquired by Selina in 2020.  He then describes the current Remote Year offerings, ranging from one week retreats and one month workations to 4 and 12 month work-travel programs with a community of location independent professionals.  Matt shares his experience on the 12-month Remote Year program in 2016 and why it was the best year of his life.   Sam then describes the customer experience on Remote Year programs today and discusses safety, inclusion, positive impact, local immersion, and community building.  Matt and Sam also discuss the Remote Year alumni “Citizenship” program and why it is one of the most valuable parts of the Remote Year experience.  Sam then talks about the company’s Diversity, Equity and Inclusion priorities, and the progress Remote Year has made on its DEI goals over the last two years.  He then opens up about the impact that the pandemic had on Remote Year, the acquisition by Selina in 2020, his current role as President, and his vision for the future of Remote Year.  Next, Sam talks about Remote Year’s process for hiring amazing people, building company culture in a remote environment, and gives his tips on executive leadership.  He then shares his personal productivity habits, how he manages stress, his biggest lessons learned from building Remote Year, and what he would do differently if he had to do it all over again.  And finally, Sam shares his #1 Remote Year memory.  → 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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