Hear how losing everything led to family nomad life, 12 years in Haiti, and a new real estate career starting at age 58. ============================ 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 Bill Manassero tells his incredible life story which begins with him getting elected to public office at age 18, becoming a corporate VP by age 21, then becoming an entrepreneur, gravitating into the tech space, getting hired by one of Meg Whitman’s companies, and then losing it all when the tech bubble burst in the late 90s. Bill had 5 kids at the time and decided to make a major life pivot, become a professional musician, and travel the world long term with his wife and kids. Homeschooling his kids and teaching them life lessons through travel, Bill shares what life was like for his family as itinerant nomads for over 3 years before moving to Haiti where they would be based for the next 12 years. Bill explains how he and his family founded “Child Hope International” which established medical clinics, orphanages, schools and entrepreneurial trainings for the people of Haiti, and ended up getting his family featured on a CNN special with Soledad O’Brien and interviewed by Oprah. He explains how incredibly challenging yet incredibly rewarding life was for his family in Haiti. Bill then talks about how he transitioned back to life in the U.S. and started investing in real estate in 2014 at age 58 and explains how he has acquired 88 units since then. Bill gives his top advice for real estate investors over 50, and shares tips on analyzing and conducting your due diligence on out-of-state rental properties. Bill then explains why he started the “Old Dawg’s REI Network” podcast and shares his biggest takeaways from it. → 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!

Real Estate Investing for Old Dawgs, Nomading with Your Kids, and Being Interviewed by Oprah with Bill Manassero  (Ep 26)

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Hear how losing everything led to family nomad life, 12 years in Haiti, and a new real estate career starting at age 58.  ============================  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  Bill Manassero tells his incredible life story which begins with him getting elected to public office at age 18, becoming a corporate VP by age 21, then becoming an entrepreneur, gravitating into the tech space, getting hired by one of Meg Whitman’s companies, and then losing it all when the tech bubble burst in the late 90s. Bill had 5 kids at the time and decided to make a major life pivot, become a professional musician, and travel the world long term with his wife and kids. Homeschooling his kids and teaching them life lessons through travel, Bill shares what life was like for his family as itinerant nomads for over 3 years before moving to Haiti where they would be based for the next 12 years. Bill explains how he and his family founded “Child Hope International” which established medical clinics, orphanages, schools and entrepreneurial trainings for the people of Haiti, and ended up getting his family featured on a CNN special with Soledad O’Brien and interviewed by Oprah. He explains how incredibly challenging yet incredibly rewarding life was for his family in Haiti. Bill then talks about how he transitioned back to life in the U.S. and started investing in real estate in 2014 at age 58 and explains how he has acquired 88 units since then. Bill gives his top advice for real estate investors over 50, and shares tips on analyzing and conducting your due diligence on out-of-state rental properties. Bill then explains why he started the “Old Dawg’s REI Network” podcast and shares his biggest takeaways from it.  → 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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