The Maverick Show: Remote Entrepreneurship and World Travel

Hear stories surviving 4 days with no food in Patagonia, landing in a Honduran jail, and driving Bolivia’s “Death Road” _____________________________ Subscribe to The Maverick Show’s Monday Minute Newsletter where I email you 3 short items of value to start each week that you can consume in 60 seconds (all personal recommendations like the latest travel gear I'm using, my favorite destinations, discounts for special events, etc.). Follow The Maverick Show on Instagram ____________________________________ Emmy-winning filmmaker and motorcycle adventurer Alex Chacon traces the roots of his life on the road, beginning with his upbringing on the U.S.–Mexico border in El Paso and the identity questions that shaped his early years. Alex shares how soccer, motorcycles, and a deep sense of not fully belonging pushed him toward long-distance travel at a young age, including a solo cross-country motorcycle journey at just 17. He recounts leaving medical school to ride from Alaska to Argentina with paper maps and no cellphone, and reflects on formative experiences across Latin America—from corruption at border crossings and getting lost in Bolivia’s salt flats, to life-or-death moments in Patagonia and the Darien Gap. Throughout the episode, Alex explores how travel became a vehicle for self-discovery, cultural reconnection, and a deeper understanding of inequality, education, and human resilience. FULL SHOW NOTES WITH DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE. ____________________________________ See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads 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? Please Leave a Rating and Review. It really helps the show and I read each one personally.  You Can Buy Me a Coffee. Espressos help me produce significantly better podcast episodes! :)

Learn about parenting with political awareness & building diaspora connections and political solidarity across borders. _____________________________ Subscribe to The Maverick Show’s Monday Minute Newsletter where I email you 3 short items of value to start each week that you can consume in 60 seconds (all personal recommendations like the latest travel gear I'm using, my favorite destinations, discounts for special events, etc.). Follow The Maverick Show on Instagram ____________________________________ In Part 2 of Matt’s conversation with Courtney Orgias—recorded in Rio, where her family is currently based—they dive deeper into the political, ethical, and emotional dimensions of digital nomad motherhood. Courtney explains how she talks to her young children about power, oppression, genocide, and policing in age-appropriate but honest ways, and why cultivating empathy is central to her parenting philosophy. She reflects on experiencing anti-Blackness around the world, connecting with the African diaspora, and why understanding local struggles is essential for ethical travel. Courtney also shares her evolving sense of identity, how travel has transformed her marriage and personal growth, and the origins of The Village Abroad, her new community-building initiative for digital nomad families that is launching its first retreat in Grenada. They close with reflections on home, belonging, raising kids globally, and the radical possibilities that travel opens for Black families. FULL SHOW NOTES WITH DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE. ____________________________________ See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads 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? Please Leave a Rating and Review. It really helps the show and I read each one personally.  You Can Buy Me a Coffee. Espressos help me produce significantly better podcast episodes! :)

Learn about leaving the U.S. to become a digital nomad family—how to raise kids and build community all over the world. _____________________________ Subscribe to The Maverick Show’s Monday Minute Newsletter where I email you 3 short items of value to start each week that you can consume in 60 seconds (all personal recommendations like the latest travel gear I'm using, my favorite destinations, discounts for special events, etc.). Follow The Maverick Show on Instagram ____________________________________ Courtney Orgias sits down with Matt in Rio, where her and her family are currently based, and they talk about attending the Black Travel Summit and why Courtney feels Rio is a great place for raising her kids.  She then talks about growing up in Duval and Atlanta, studying abroad in Copenhagen, falling in love with her husband Justin, and choosing to leave the U.S. to raise their kids in the digital nomad lifestyle. Courtney explains the concept of worldschooling, how she structures he family’s digital nomad life, and how she builds community around the world for herself and her kids. She shares her experience participating in work-travel programs for families like Boundless Life, reflects on building connections with locals vs. other travelers, and talks about living in Mexico and how she responded to the ongoing transnational gentrification problems there.  Courtney then reflects on how she developed her social and political consciousness growing up that now shapes her ethical travel decisions, and how she is able to course-correct in real time upon learning new information such as the UAE government’s role in supporting the genocide in Sudan. FULL SHOW NOTES WITH DIRECT LIINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE. ____________________________________ See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads 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? Please Leave a Rating and Review. It really helps the show and I read each one personally.  You Can Buy Me a Coffee. Espressos help me produce significantly better podcast episodes! :)

Hear award-winning travel creator Nicole Phillip share stories of immersing in Afro-Brazilian history, music and culture. _____________________________ Subscribe to The Maverick Show’s Monday Minute Newsletter where I email you 3 short items of value to start each week that you can consume in 60 seconds (all personal recommendations like the latest travel gear I'm using, my favorite destinations, discounts for special events, etc.). Follow The Maverick Show on Instagram ____________________________________ Nicole Phillip returns to The Maverick Show and records this episode in person with Matt in Rio after spending two weeks together in Brazil.  Nicole is fresh off winning her award for the 2025 Social Media Video of the Year at the Black Travel Film Festival for her video on Reggaeton’s Panamanian roots.  She reflects on the entire Black Travel Summit, the Afrofuture-themed Awards Gala, and why winning this award was such an emotional moment for her.  Nicole also pulls back the curtain and breaks down the biggest leverage points for how she was able to build 350,000 social media followers in just 2 years. She then talks about her trip to Panama where she created the video, as well as her trip to the Dominican Republic, and what some of her biggest lessons were from both places.  Next, Nicole shares her first impressions of Brazil and describes the day she spent touring a favela.  She also talks about spending time in the Madureira neighborhood—the beating heart of Black Carioca culture—both on a daytime tour and partying in the streets at 2am.  Finally, Nicole shares her experience in Sao Paulo visiting a Quilombo and diving into Black history there.  FULL SHOW NOTES INCLUDING DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE.  ____________________________________ See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads 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? Please Leave a Rating and Review. It really helps the show and I read each one personally.  You Can Buy Me a Coffee. Espressos help me produce significantly better podcast episodes! :)

Hear stories and life-lessons from circumnavigating the planet on a bicycle while living on 3 Euros a day for 5 years. _____________________________ Subscribe to The Maverick Show’s Monday Minute Newsletter where I email you 3 short items of value to start each week that you can consume in 60 seconds (all personal recommendations like the latest travel gear I'm using, my favorite destinations, discounts for special events, etc.). Follow The Maverick Show on Instagram ____________________________________ Pablo Mandado talks about his experience growing up in the Aragon region of Spain, how a trip to Greece changed everything and led to a life of long-term travel, and how he quickly transitioned into a spontaneous, hyper-minimalist and hyper-budget travel style.  He reflects on negotiating trust and reciprocity when hitch-hiking and couch surfing.  Pablo then shares an uncomfortable moment while  hitchhiking, as well as a surprising moment of connection, and some incredible stories from his month in Laos.  He then talks about meeting his girlfriend in Latvia and embarking on a 5 year cycling journey to circumnavigate the globe together.  Pablo explains the value of of a loosely planned trip rooted in spontaneous decisions and how he was able to live on just 3 Euros a day for 5 years.  Next, he tells incredible stories of getting caught in a massive snowstorm in Turkey, the heartwarming hospitality he found in Iran, avoiding the secret police in Uzbekistan, and what it was like to cycle across mainland China.  Pablo also talks about his photography journey and how he was able to turn that into a business.  Finally, he reflects on the unique benefits of traveling the world by bicycle, the re-acclimation experience after the trip, how the journey shaped his relationship, and the lasting impact of long-term, hyper-minimalist, spontaneous travel on him as a person.  FULL SHOW NOTES WITH DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE. ____________________________________ See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads 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? Please Leave a Rating and Review. It really helps the show and I read each one personally.  You Can Buy Me a Coffee. Espressos help me produce significantly better podcast episodes! :)

Learn how to get over-the-top luxury bucket list experiences for free that usually cost thousands of dollars per night. _____________________________ Subscribe to The Maverick Show’s Monday Minute Newsletter where I email you 3 short items of value to start each week that you can consume in 60 seconds (all personal recommendations like the latest travel gear I'm using, my favorite destinations, discounts for special events, etc.). Follow The Maverick Show on Instagram ____________________________________ In Part 2 of this interview Darren Chew (“Chew”) breaks down the tactics for using points and miles to fly business class and have the world’s most epic luxury experiences for free. He explains the real value of a free breakfast in the Seychelles, how to plan around blackout dates and peak travel prices, and why flying Alaska Airlines is one of his favorite travel hacks.  Chew then shares his observations about anti-Blackness around the world, reflects on how travel has impacted him as a person and his relationship with his wife, and explains how he balances travel content creation with living in the moment.  He then gives tips for traveling as a couple, traveling with carry on luggage only, and reflects on what travel means to him today.  FULL SHOW NOTES WITH DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE. ____________________________________ See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads 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? Please Leave a Rating and Review. It really helps the show and I read each one personally.  You Can Buy Me a Coffee. Espressos help me produce significantly better podcast episodes! :)

Hear stories from visiting Nubia, the slums of Nairobi, rural villages in Zambia & going volcano-boarding in Nicaragua. _____________________________ Subscribe to The Maverick Show’s Monday Minute Newsletter where I email you 3 short items of value to start each week that you can consume in 60 seconds (all personal recommendations like the latest travel gear I'm using, my favorite destinations, discounts for special events, etc.). Follow The Maverick Show on Instagram ____________________________________ Darren Chew (“Chew”) joins Matt and starts off talking about his Jamaican and Chinese heritage and shares the story of how his parents met in Jamaica and immigrated to New York.  He then talks about his experience growing up in New York with mixed cultural heritage, traveling back to Jamaica to visit family, and the pivotal role of basketball in his life.  Chew explains how he started traveling the world to visit former basketball teammates in Europe and then reflects on his first impression of the continent of Africa.  He tells travel stories from Kenya, Zambia, Senegal, Egypt, Guatemala, Nicaragua, El Salvador, and explains why Rio is his favorite city in the world.  Chew reflects on visiting Nubia, gives a preview of his upcoming talk at Black Travel Summit in Brazil, and ends with a unexpected story of cultural immersion in St. Vincent and the Grenadines.  FULL SHOW NOTES WITH DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE. ____________________________________ See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads 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? Please Leave a Rating and Review. It really helps the show and I read each one personally.  You Can Buy Me a Coffee. Espressos help me produce significantly better podcast episodes! :)

Learn how to use points & miles to perform Umrah with a family and travel the world to celebrate Eid in different cities. _____________________________ Subscribe to The Maverick Show’s Monday Minute Newsletter where I email you 3 short items of value to start each week that you can consume in 60 seconds (all personal recommendations like the latest travel gear I'm using, my favorite destinations, discounts for special events, etc.). Follow The Maverick Show on Instagram ____________________________________ Amena tells the story of how she met Matt and bonded around Palestine solidarity at the WITS Travel creator summit in NYC.  She then talks about her parents experience immigrating to the U.S. from India and Pakistan, her experience growing up in Dallas in a Muslim immigrant home, the impact of the post 9-11 environment on her life, and how she developed her politics and worldview. Amena then talks about her first trip back to India as an adult, performing Hajj in Saudi Arabia, seeing the Islamic architecture in southern Spain, celebrating Eid in Istanbul, and visiting Japan and London.  She then talks about performing Umrah as a family, shares strategies to accumulate points and miles to cover international family travel, and talks about her Umrah Guide. Finally, Amena talks about raising socially conscious kids, integrating travel into their lives, and what travel means to her today.  FULL SHOW NOTES INCLUDING DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE. ____________________________________ See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads 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? Please Leave a Rating and Review. It really helps the show and I read each one personally.  You Can Buy Me a Coffee. Espressos help me produce significantly better podcast episodes! :)

Learn how to coordinate your travel plans with friends, exchange recommendations & connect around the world with Pangea. _____________________________ Subscribe to The Maverick Show’s Monday Minute Newsletter where I email you 3 short items of value to start each week that you can consume in 60 seconds (all personal recommendations like the latest travel gear I'm using, my favorite destinations, discounts for special events, etc.). Follow The Maverick Show on Instagram ____________________________________ Matt Gray starts off describing what he loves about Cape Town and tells the story of taking the world’s highest bungee jump off a bridge there. He then reflects on growing up outside NYC, studying abroad in Vienna, and traveling the world for a decade as part of his corporate job.  Matt tells stories from visiting Reunion Island, Madagascar, Lapland, Greenland, Antarctica, Armenia and Uzbekistan.  He then talks about organizing a group safari to Botswana, building community in the digital nomad lifestyle, and his plans for co-hosting Nomad Week 2026 in Cape Town.  Next, Matt talks about founding the Pangea App which enables you to coordinate your travel plans with friends, exchange recommendations & connect around the world.  He opens up about his own transition into full-time entrepreneurship, his journey building and scaling Pangea, his recent acquisition of the Overlap app, and is 5-year vision for Pangea.  Finally, Matt explains how he designs his digital nomad lifestyle, why he wants to travel to every country in the world, and what impact all this travel has had on him as a person.  FULL SHOW NOTES INCLUDING DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE. ____________________________________ See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads 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? Please Leave a Rating and Review. It really helps the show and I read each one personally.  You Can Buy Me a Coffee. Espressos help me produce significantly better podcast episodes! :)

Hear about living in China, Malaysia, Poland and Mexico as a Black Muslim woman & raising her son in multiple countries. _____________________________ Subscribe to The Maverick Show’s Monday Minute Newsletter where I email you 3 short items of value to start each week that you can consume in 60 seconds (all personal recommendations like the latest travel gear I'm using, my favorite destinations, discounts for special events, etc.). Follow The Maverick Show on Instagram ____________________________________ In part 2 of this interview Imani talks about her experience living in China, Poland, Malaysia and Mexico. She tells stories about how many of these places defied stereotypes and how warmly she was received and treated in Poland when she gave birth there.  Imani then reflects on raising her son across multiple countries and how living abroad has impacted him as a person.  She also reflects on the development of her own politics of collective liberation, how she maintains long-term activist stamina, and how we can all rise to meet this historical moment despite feeling overwhelmed.  Imani then talks about her current role as a co-director at “Resist” and the storytelling and communications work she does.  She explains the history of the organization, their present day work in supporting grassroots initiatives, and how you can support their work.  Imani then reflects on how her travel and activism are so integrally intertwined.  She shares tips on raising socially conscious kids, standing in better solidarity with marginalized groups, and offers specific advice to Black and Muslim women travelers.  Finally, Imani reflects on why she continues to travel and what travel means to her today. FULL SHOW NOTES WITH DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE.  ____________________________________ See my Top 10 Apps For Digital Nomads See my Top 10 Books For Digital Nomads 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? Please Leave a Rating and Review. It really helps the show and I read each one personally.  You Can Buy Me a Coffee. Espressos help me produce significantly better podcast episodes! :)