The Maverick Show: Global Travel Stories & Life Beyond Borders

Learn how moving abroad became a business and why supporting local staff and social causes matters when tourism grows.

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ON THIS EPISODE

Amanda Gedney begins by explaining her love of hula hooping and fire-spinning, how to do it, how she learned it, and how she manages the fire-spinning performances at the Jai Thep festival in Chiang Mai, Thailand. She then takes us on her journey, starting with growing up in New York, going to college at the Fashion Institute of Technology, studying abroad in Paris, falling in love with travel, and then totally pivoting and moving to Chiang Mai to teach English right out of college. She then explains her entrepreneurial trajectory and her experience building her company, Settle in Abroad, which helps digital nomads and teachers re-locate to Chiang Mai. She explains what is included in her turn-key relocation package, as well as her other shorter-term offerings for tours and experiences in Thailand. She then goes on to talk about “ethical tourism”, how travelers should think about it as they explore the world, and how she ethically vets all of her tours and experiences. Amanda then goes on to talk about building and scaling her business, the biggest challenges, and why she over-pays her staff and supports them in building their own businesses. She also talks about her partnership with One Tree Planted, Warm Heart and explains how and why Settle in Abroad gives back to social causes for every program sold. Amanda then gives her advice to high school and college students who desire remote work options and want to integrate travel experiences into their lives.

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

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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.

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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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Hear how years of nomad life shaped her identity, community, productivity, and approach to building an online business.

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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

Danielle Thompson takes us on her path through entrepreneurship, building multiple different businesses until she finally found her true passion with The Freelance Travel Network—helping nomadic freelancers grow and profit from their online service business while traveling the world. She explains how she grew and scaled that business while traveling the world herself. Danielle also opens up about her personal development journey. She explains the profound impact that Ayahuasca ceremonies and other psychedelic experiences had on her business breakthroughs, personal growth, and development of self-love. She also takes us on her travel journey since 2015 when she became a full-time digital nomad. She shares her biggest takeaways, epiphanies, struggles, identity conflicts and growth moments from long term stays in Costa Rica, Nicaragua, Lisbon, Bali, and Buenos Aires. She discusses her experience participating in the WiFi Tribe work-travel program and the importance of cultivating and sustaining community in the long-term nomadic lifestyle. Danielle then discusses her personal day structure and productivity habits, including how she gamifies her entire life and the app she uses to do it. She reflects on the significance of what travel means to her and shares her #1 travel hack. She also recommends her #1 most influential book, her favorite productivity app, and shares the one person in the world with whom she would most like to have dinner.

→ 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)

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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

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Learn how hiring, systems, communication, and culture keep distributed teams productive across countries and time zones.

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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

Liam Martin tells his story of being ranked one of the top 30 figure-skaters in the world before breaking his knee cap at age 21 and having his dreams dashed. He then pivoted into academia but, after receiving the worst teaching evaluations in the department’s history, he pivoted again, this time into remote entrepreneurship. Liam takes us on his business-building journey, that ultimately culminated in the creation of “Time Doctor”, a productivity software that he scaled into a 7-figure remote-first business which now has over 100 staff in 32 countries. He takes us behind the scenes of his company operations and gives detailed tips on remote hiring, building systems and processes, training and running a remote sales team, project management and communication across time zones, detailed marketing and SEO tactics that are working today. He also shares his approach to executive leadership, remote management and building company culture in remote-first companies. Liam then details his personal productivity and time mastery techniques, as well as the way he manages stress and approaches business problems or setbacks. Liam then talks about co-founding “Running Remote”, the world’s largest conference on building and scaling fully remote teams. He discusses who should attend, what to expect, and where/when the next conference is happening. He then talks about his passion for international travel and explains his travel cadence, how he decides on his remote work locations, what travel really means to him at this point in his life, and shares his favorite travel app and the #1 gadget he never travels without.

→ 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)

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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 bootstrapping, lean systems, and remote operations can help a small team build and scale a resilient company.

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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

Eddie Rich takes us on his journey of founding LoDo Massage during the recession with just $30 and scaling it to operate in 45 U.S. states and land clients that include some of the top Fortune 500 companies.  After losing almost everything in the recession of 2008, approaching 50 years old, and unable to find investors for his business idea, he explains how he creatively bootstrapped it and cultivated competitive advantages based on his expertise in SEO marketing and building efficient systems and processes, which allowed him to scale the company to over $4 Million with only 5 corporate staff. Eddie gives tips for SEO marketing and building businesses with minimal startup capital.  He also talks about his leadership style, his productivity habits, and morning routine, and how he runs his company from different time zones and coordinates with his team. He then talks about the advantages of going fully remote, and how he tripled his company revenue once he made all of his staff location independent and started traveling the world. Eddie also shares his experience doing the Remote Year program at age 56, the Nomad Train at age 57, and why he is so passionate about travel and chooses to continue the nomad lifestyle.  He shares his favorite book, productivity app, travel hack, and gear recommendation, as well as his top 3 favorite travel destinations of all time and what is currently at the top of his bucket list.

→ 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 memorable moments from the first 50 episodes and help shape what The Maverick Show becomes in its next chapter.

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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

On the 50th episode of The Maverick Show, I want to thank you so much for listing to the show. Please enjoy this highlight reel from the first fifty episodes! 

→ 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)

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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 trust, authority, and personal branding can help you stand out online and build real confidence from within.

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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

Ashley Hann shares her journey to location-independent entrepreneurship beginning with her experience being hired as the Marketing Director at one of Mark Cuban’s start-up companies and helping to grow it 500% in a year. She explains how she restructured the customer service policy and exponentially increased their sales on Amazon. After that, she explains why she took a job in a large corporate environment and then, after 7 very successful months, quit the day after presenting to the board about a successful marketing campaign. She talks about that transitionary moment and how she went on to build her own business. She shares the top tips for leaving the corporate world with your skills and the mindset required to enter a crowded market and win. She gives tactical tips on personal and company brand building that are working today and how to build trust and authority on social media. She goes deep on Instagram tactics, sharing the latest techniques that are working for both content and hashtags. She then tells the story of how she met Gary Vaynerchuk, how he became a friend and mentor to her and shares the biggest lessons she has learned from him. Ashely then goes on to talk about her top tips for a high-converting website, optimizing your online brand presence, and the SEO tactics that are working today to generate organic traffic. She then goes on to talk about “Magnetic Confidence”, explains what it is, how to develop it, and tells her personal journey overcoming anxiety, depression, fear and limiting beliefs that led her to write her best-selling book on Magnetic Confidence.

→ 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 what early setbacks taught him about designing work-travel programs, building community, and leading remote teams.

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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

Remote Year co-founder and CEO Greg Caplan shares the behind the scenes journey of starting and building the world’s largest international work-travel program. He tells the story of how his unique upbringing in the Chicago suburbs led him to become passionate about international travel and cultural immersion. He then explains how he was driven to start Remote Year based on his own interest in working while traveling with a community of friends and shares his surprise with the amount of initial demand he received for the concept. He then explains how he went about building the infrastructure for the program, what the initial challenges and setbacks were, and the lessons he learned from them. He goes on to explain how the program functions today—how the onboarding, orientation and city previews work, as well as the overall experience that participants can expect on the program. He then details the concept of the “Remote Nation” and how the “Citizenship” program works to connect the Remote Year alumni network across the globe and offer unique experiences to them on an ongoing basis. Greg also explains Remote Year’s mission and values, and talks about the “Positive Impact” initiative as well as the “Diversity, Equity and Inclusion” initiative that Remote Year is prioritizing for both staff and participants. He then shares his vision on the macro trends that are shaping the future of work, both in terms of employee desires to work remotely while traveling the world, and also in terms of companies increasingly offering remote work as a benefit to recruit and retain top talent.

→ 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!

Matt Bowles starts off by explaining what “turnkey real estate investing” is, and discusses the benefits of buying and holding residential investment property vs. other asset classes like stocks and mutual funds.

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He goes through the 5 different potential profit centers you have when buying and holding rental properties—market appreciation, cash flow, tax benefits, mortgage principal pay-down by the tenant, and a built-in hedge against inflation. He explains the benefits of not having to be the rehabber or the landlord yourself and how buying a performing rental property (that is already cash-flowing when you close) can substantially mitigate your up-front risk. Matt then explains the benefits of buying and “holding” (instead of flipping) your rental property, and why it’s important to own the deeded real estate as a hard asset as opposed to buying real-estate-backed securities. And, finally, he explains the benefits of building a portfolio of single-family rental properties as opposed to buying an apartment building. He then teaches how to identify the most investor-advantaged real estate markets—assessing demand drivers, and price-to-rent ratios, calculating capitalization rates properly, and buying in the “real estate investor sweet spots”. He also covers the essentials of conducting due diligence on an out-of-state buying opportunity, the importance of verifying everything independently, and how to find and use third-party services. Matt concludes by explaining the business model of Maverick Investor Group, how their niche has been serving individual real estate investors exclusively since 2007, why it doesn’t cost any money to work with Maverick, and how Maverick intentionally created an incentive structure that puts the buyer’s interests first. He then offers two opportunities to connect with Maverick and either learn more or start building your portfolio of cash-flowing rental properties. FULL SHOW NOTES AND DIRECT LINKS TO EVERYTHING DISCUSSED IS AVAILABLE HERE.

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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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Hear how rebuilding from $300 shaped her resilience, entrepreneurship, and perspective on freedom after deportation.

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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

Agnes Nyamwange shares her experience growing up in an Indian-majority neighborhood in her home country of Kenya, going to college in Kampala, Uganda, and then moving to the U.S. where she completed her Master’s Degree and worked in the healthcare industry for a decade. She opens up about how she struggled through 16-hour workdays, racism, being an undocumented immigrant, and ultimately falling into a depression where she couldn’t get out of bed. She explains how her depression, and the subsequent negative effects of anti-anxiety medications, prompted pivotal self-reflection and life changes that led her to start traveling. Agnes then explains the challenges of being a full-time digital nomad on a Kenyan passport, and shares her experience getting detained at the Miami Airport, held for 36 hours in deplorable conditions, and deported to Brazil. From there, with $300 in her bank account, she explains how she moved to Bolivia and starting to rebuild her life-support-training business with a location independent infrastructure so she could run it from anywhere in the world. Matt and Agnes then recount their experience traveling through West Africa together for 3 months through Nigeria, Ghana, Ivory Coast, and Senegal. They reflect on everything from the amazing music and nightlife to the corruption and military shakedowns they encountered to the history of the West African slave trade.

→ 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 automation, delegation, and a remote team can turn a land investing strategy into a business that runs itself.

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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

Mark Podolsky shares his journey leaving the corporate world and starting his own land investing business.  He explains how land investing works and the systems he created to consistently generate 300% returns. He then discusses the way he turned his land investing into a location-independent business by building systems and processes, automating, delegating, and hiring a team to run the different aspects of it.  He talks about his leadership style, his hiring process, and how he manages an internationally distributed team. He then explains how and why he began creating an information product/service business where he mentors and teaches others how to replicate his methods. He also talks about his podcast “The Art of Passive Income”, shares his top tips on podcasting.  He then talks about his book “Dirt Rich” and explains how and why he wrote it. Mark then shares his biggest business mistakes and how he manages stress and handles business setbacks. He discusses his morning routine, meditation practices, and the creative ways he integrates fitness into his life. Mark also explains his lifestyle design choices now that he has automated his business.  He then shares his favorite book, app, travel destination, the advice he would give to his 18-year-old self and the celebrity with whom he would most like to have dinner.

→ 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!