Learn about parenting with political awareness & building diaspora connections and political solidarity across borders.

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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,

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Learn about leaving the U.S. to become a digital nomad family—how to raise kids and build community all over the world.

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See my Top 10 Apps For Digital Nomads

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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)

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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.

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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

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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

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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.

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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

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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

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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.

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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

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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)

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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. _____________________________

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See my Top 10 Apps For Digital Nomads

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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,

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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.

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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)

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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.

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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)

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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. _____________________________

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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

____________________________________

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 being a Black Muslim activist in the U.S., meeting Malcolm X’s daughter, moving abroad and living in Cairo.

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Imani Bashir joins Matt in Washington, DC and they reflect on their Keynote panel at Nomadness Fest and their experience meeting Malcolm X’s daughter there.  Imani breaks down the neocolonial dynamics that often pervade the travel industry and travel journalism, and then offers tips on how be a more socially conscious traveler and content creator.  Next, she talks about the history of Islam in Black America, her experience navigating her Black and Muslim identities in the U.S., her experience after 9-11, and how her father raised her in an activist home.  Imani then talks about her commitment to Palestine solidarity work and reflects on the history of Palestine solidarity within Black American and other anti-colonial struggles around the world.  She then takes us on her personal journey attending an HBCU, getting her first passport, the impact of visiting London, and recognizing the beauty of immigrant communities.  Finally, Imani reflects on the history of Black-American expatriation, how the death of Sandra Bland motivated her to move out of the U.S., and her lessons and reflections from living in Cairo, Egypt.  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! :)