The Maverick Show: Global Travel Stories & Life Beyond Borders

Learn what travel in Asia & investment mistakes taught him about minimalism, Stoicism, risk, and building real freedom.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Santiago Sosa takes us on his journey growing up in Colombia, immigrating to the U.S., getting married, and traveling the world full time with his spouse.  He shares tips on nomading as a married couple with no base, and recounts some of his top travel stories.  Santiago also discusses the impact his Asian travels had on leading him towards the philosophy of Stoicism and becoming a minimalist.  He then shares his entrepreneurial journey, and how he built a location independent marketing agency with his wife as his business partner.  Santiago shares tips on being business partners with your spouse and explains how they run the company together.  He also unveils the most effective marketing tactics that are working for his business clients today.  Santiago then opens up about his personal investing strategies across many asset classes, ranging from real estate to online businesses to crypto currency.  He shares his wins and losses, and emphasizes the importance of diversification.  Santiago takes us on his cryptocurrency investing journey—From learning about it in 2017, to investing in numerous ICOs, to the way he earns yield on his crypto holdings, to the most costly crypto-investing mistake he made, and how to avoid it.  Finally, Santiago reflects on why he continues to travel full time after visiting 70 countries, and what travel means to him today.

→ Full show notes with direct links to everything discussed are available here.

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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)

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ENJOYING THE SHOW?

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Please leave a rating and review — it really helps the show and I read each one personally

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Hear how her Haitian immigrant upbringing and years abroad shaped her views on race, identity, and America from afar.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

In this episode, Martine conducts a whisky tasting for Matt in her apartment in Queens, NY, over a wide ranging discussion about books, art, immigrant identity, world travel, food, whisky, gender, race, and genocide.  Martine takes us on her journey growing up in Queens, NY in a Haitian immigrant family, being exposed to the cultures of the world in her home borough, and then becoming a remote entrepreneur and traveling to over 40 countries.  She shares stories from her travels to Cambodia, Malaysia, Vietnam, Kenya, Ireland, Paris, Italy and more.  Matt and Martine share their experiences in Phnom Penh and reflect on their encounters with the history and lessons of the Cambodian genocide. Martine also conducts a whisky tasting for Matt live on the podcast, and shares specific techniques for “finding your whisky door” even if you think you don’t like whisky.  She talks about her experiences attending “Whisky Live” in Paris and traveling to other top Whisky destinations around the world.  Matt and Martine also share their experiences wine tasting in the Burgundy region of France.  Finally, Matt and Martine discuss James Baldwin and Martine reflects on American racial dynamics from the vantage point of a world traveler when outside the U.S.

→ 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!

Learn why greater global mobility matters and what to consider when choosing a country for a second citizenship.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Becky Gillespie and Matt talk about their previous travels in Argentina, as well as their recent experience together in the Mendoza wine region where the interview takes place. Becky then shares her experiences trekking La Cuidad Perdida in Colombia, Volcano-boarding in Nicaragua, and visiting Omatepe Island. Matt and Becky also share their experiences traveling through India, and Becky tells the story of when she participated in the “Rickshaw Challenge”. Next, she reflects on her trip to the mountain kingdom of Bhutan. Becky then plays the ukulele live on The Maverick Show and sings the song “I Drink Wine” by Adele. She then breaks down the steps to get started with Cryptocurrency, and why she believes it is important for everyone. Becky shares some crypto investment strategies for beginners, explains the basics of buying NFTs, and also explains how to use cryptocurrency to buy tangible items in the real world.  She then moves on to talk about getting a second passport. Becky first discusses the benefits and what motivated her to pursue it, and she then breaks down the process and timeline for getting a second passport from Portugal.

→ 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!

Learn why historical and political context matters for conscious travel and how to leave the places you visit better.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Kaela Atleework takes us on her journey growing up in California, becoming an international model for Chanel, and then leaving it all to pursue the nomad life.  After 10 years of traveling, she shares her critical reflections on “voluntourism”.  Kaela then takes us through some considerations for being more socially conscious travelers, including the importance of learning the historical and political context of the places we travel.  Next she shares a story about the time she hitchhiked across South America alone, and reflects on how becoming a digital nomad helped her create a more socially connected life.  Kaela then dives into her area of expertise on human connection, talks about her concept of “Instantaneous Intimacy”, and shares techniques for making deep friendships quickly.  She then explains the importance of being more than just environmentally conscious travelers, and shares some specific tactics for how we can be “ecologically regenerative” travelers.  Kaela then talks about founding Montaia Basecamp as a model for ecologically regenerative and socially connected co-living and co-working in connection with the land.  She then explains her “migrational” nomad lifestyle and the unique benefits of this particular travel style.  And, finally, Kaela  offers her observations and analysis of the way a segment of the pseudo-spiritual wellness community has coalesced with the far right wing around narratives around COVID disinformation and anti-vaccine conspiracies, and what she feels is a potential path out.

→ 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!

Hear how her family’s experience of war shaped a mission to build dignity, opportunity, and connection across cultures.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Aline Sara takes us on her journey growing up in a Lebanese immigrant family in New York and reflects on how her family’s experience in Beirut during the civil war shaped her passion for international human rights and conflict resolution.  She shares her extensive world travel experiences through Lebanon, Syria and Turkey, as well as Sub-Saharan Africa and South America. Matt and Aline talk about the international solidarity dynamics among oppressed people around the world, in countries ranging from South Africa to Chile to Ireland.  Aline then talks about her experience working as a journalist in the Middle East during the Arab Spring.  She explains how the Syrian refugee crisis was the main inspiration for founding NaTakallam as a language learning social enterprise.  She explains the mission is to empower displaced persons and refugees to work as online language teachers, regardless of their location and status, and to virtually pair them with students who are also interested in hearing their stories.  Aline talks about how she scaled NaTakallam, how she finds and hires the teachers, and shares some examples of their lives prior to being displaced.  She also talks about the customer experience, the expansion of NaTakallam’s service offerings, and explains how it provides an opportunity for refugees and displaced people to tell their stories across the world, and to build bridges across cultures.

→ 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!

Hear how eight years without a base changed what travel means to him and how he balances documenting life with presence.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Sergio Sala shares his journey growing up in Mexico, studying abroad in Italy, backpacking around Europe, and eventually becoming a full-time digital nomad and YouTube video creator. He shares the top digital nomad destinations for living and working in Mexico, including what he loves about Mexico City and how to get to the hidden beach near Sayulita. Matt and Sergio then discuss the close bond between Ireland and Mexico and reflect on their travels in Ireland. Sergio then opens up about his first trip to New York City, and how it changed his perceptions about people in the U.S. He then shares some of his top international travel experiences including attending the World Cup in Russia, studying at a Buddhist temple in China, and spending two weeks in Tibet. Sergio also explains how he selects his travel destinations, structures his day, and sustains the digital nomad lifestyle with no base. He then takes us behind the scenes of his life as a professional YouTuber, shares some tips on how to do it full time, and reflects on how he balances the video documentation of his life with the importance of being present in the moment. Sergio also discusses the importance of minimalism in his life, and shares some tips on how to travel the world with carry-on luggage only while still looking stylish (including his favorite travel clothing brands). And, finally, he reflects on why he continues to travel after 8 years as a full time nomad, and what travel means to him today.

→ 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!

Learn how LinkedIn, the hidden job market, and interview preparation can help you land the remote role you really want.

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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

Juliana Rabbi takes us on her journey growing up in Brazil, moving to Spain as an ex-pat, transitioning to remote work, and then becoming a digital nomad who travels the world full-time with no base.  She reflects on her experiences living in Madrid, Barcelona and Kilkenny, Ireland, as well as the impact of joining theater and improv groups in Spain.  Juliana also shares her experiences backpacking in Thailand and Nepal, life lessons learned, and how that inspired her to become a full-time nomad.  She then shares the details of how she transitioned to become a location-independent entrepreneur.  Next, Juliana talks about the services she offers today and how she helps her clients find their remote dream job in 90 days.  She explains how to use LinkedIn effectively, how to tap into the “hidden job market”, and how to prepare to crush your job interview.  Juliana also explains how her services work and describes her ideal client.  And, finally, she explains how she designs her lifestyle and how she structures her work and travel as a nomad.

→ 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!

Learn how daily routines, productivity, and lifestyle design can help entrepreneurs build more freedom into their lives.

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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

Jimmy Naraine shares his process for setting and achieving high level goals. He then talks about his day structure and productivity optimization techniques while traveling the world full time. Jimmy also reflects on his 8 Years as a digital nomad, his experience during the pandemic lockdown, and what travel means to him. He then talks about his decision to become a full time online course creator, mentor and educator. Jimmy takes us behind the scenes of how he scaled his online course sales to over 265,000 students. He breaks down the key marketing techniques to launch, create momentum, and become a best-selling course creator. Jimmy then offers the Maverick Show listeners a discount code to get one of his courses for free. And, finally, he shares his favorite books, travel destinations, and his top 5 hip-hop MCs of all time.

→ 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!

Learn how shoestring travel, language immersion, and daily structure can make long-term nomad life sustainable and rich.

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Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds.

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ON THIS EPISODE

Jimmy Naraine takes us on his journey growing up in Poland to mixed parents, getting into graffiti and skateboarding as a form of rebellion, and eventually embracing hip-hop and beatboxing.  Jimmy beatboxes live on The Maverick Show and then explains how he still uses it in his personal and professional life today, as well as in his travels both to connect with people across cultures and to diffuse potentially dangerous situations. Jimmy then talks about how his interest in world travel developed, and how he was able to travel on a shoestring budget before he had much money including a 3,000 kilometer trip across Europe on just 200 Euros. He then explains how he learns languages through intensive immersion and by leveraging the 80/20 rule.  Jimmy also reflects on his sustainability pillars for living a healthy, fulfilling, exciting life as a full-time nomad for over 8 years.  He discusses his selection process for his travel destinations, and explains how he structures his lifestyle.  Finally, Jimmy shares his experience hiking the Annapurna Circuit in the Himalayas, and the profound life lessons that came out of 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!

Hear how family expectations and ancestral homelands reshaped her identity and relationship with travel across borders.

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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

Sally Elbassir takes us on her journey being born in Ireland to Egyptian and Sudanese parents, and growing up mostly in Los Angeles.  She shares the experience of her Muslim immigrant family in the aftermath of the 9-11 attacks in the U.S., and reflects on her identity as a “third culture kid”.  Sally shares her experiences going back to her homelands of Egypt and Sudan for the first time as a teenager, and then again as an adult.  She also explains the context of the pro-democracy uprising in Sudan after the coup in October, 2021.  Sally then takes us on her own world travel journey—from a school trip to China, to studying abroad in Ireland, to interning in Indonesia, and eventually leaving her job in 2015 to become a full-time digital nomad and embark on her first solo journey to Spain.  She opens up about navigating her parents’ traditional cultural expectations in order to pursue her dreams of world travel. Sally then talks about founding her blog, “Passports and Plates”, and explains her passion for experiencing the world through food.  She also talks about misconceptions about Islamophobia, unpacks the concept of “travel safety”, and shares her experiences traveling in the Middle East and North Africa.  Sally then reflects on the impact that world travel has had on her, and shares how she now understands the concept of “home”.  Finally, she shares tips and resources for Muslim travelers, as well as advice on how non-Muslims can be better allies.

→ 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!