Global Travel Stories & Life Beyond Borders

Funding a Life of Long-Term Travel

Learn how people fund long-term travel and build a life overseas through remote work, entrepreneurship, investing, and travel hacking. These episodes explore financial strategies for sustaining a travel lifestyle while working abroad and generating income from anywhere.

How do people actually fund long-term travel and sustain a life overseas? In these conversations from The Maverick Show, guests share the strategies that allow them to work remotely, build sustainable travel lifestyles, and create financial freedom while working and traveling. You’ll hear from location-independent entrepreneurs, remote workers, investors, financial planners, and travel hackers who have created financial systems that support living abroad and working from anywhere. Topics include how to build a location-independent business, land a remote job, invest in turnkey rental property, create passive income, and use points, miles, and other travel-hacking strategies to get free flights and accommodations. Together, these episodes explore how people design financial freedom to support long-term travel and global living.

363: How to Use Points & Miles to Visit Private Islands, Stay in Overwater Bungalows & Arrive by Seaplane in Bora Bora, the Maldives and the Seychelles with Chew from ChewsToExplore

Learn how to get over-the-top luxury bucket list experiences for free that usually cost thousands of dollars per night. 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…

327: Scaling Unbound Merino to a $40 Million Business While Traveling the World as a Digital Nomad with Dan Demsky

Learn the tactics to start a remote business from scratch and scale it to $40 million/year while traveling the world. In Part 2 of my interview with Dan Demsky, we pull back the curtain and do a deep dive into exactly how he built Unbound Merino from a Kickstarer to an 8-figure global brand. He

311: Financial Planning for Digital Nomads with Michael Kim

Learn how to improve your money mindset, set financial goals & avoid the biggest financial mistake digital nomads make. Michael Kim starts off talking about his family’s immigration story of how his parents got to Canada, his experience growing up in Toronto, and how is interest in travel started to develop. He shares his experience…

287: From Middle School Teacher to 6-Figure Freelancer and Digital Nomad with Mashon Thomas

Learn how to work 20 hours a week as a remote freelancer, take 3 months off a year, and make 100K while traveling the world. Mashon Thomas joins Matt from the Philippines and describes her experience there. She then talks about growing up in Ohio, studying abroad in the Basque Country, traveling around Europe, and…

170: Building a Remote Marketing Agency with Your Spouse, Traveling to 70 Countries Together and Diversifying Your Investments with Santiago Sosa

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…

164: How to Land a Remote Job in 90 Days and Become a Full-Time Digital Nomad with Juliana Rabbi

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…

136: Five Ways to Get Free Accommodations Around the World and Being a Professional Hobo for 12 Years with Nora Dunn

Nora Dunn (a.k.a: The Professional Hobo) takes us on her journey growing up in Canada, becoming an entrepreneur, and then selling her financial planning practice to travel the world full time as a Professional Hobo. She talks about her lifestyle design, travel cadence, destination selection, and adventures over her 12 years of full time world…

113: Making 6-Figures/Year on TikTok, Falling into the Ganges River, and Helping People Become Digital Nomads with Christa Romano

Christa Romano takes us on her journey of becoming a full-time digital nomad and financing her itinerant lifestyle for 7 years as a remote employee, a freelancer and eventually career coach. She takes us on some of her most epic adventures and misadventures around the world—from her euphoric moment of watching hot air balloons rise…

107: Designing Your 9-5 Transition Plan, Recession-Proofing Yourself, and Traveling While Black with Dels Ogun

Dels Ogun talks about growing up between Lagos and London, the Afro-Beats music scene in both places, and her Nigerian identity as an international world traveler. She shares her journey going from a minimum wage worker to becoming an international lawyer, world traveler and, eventually, a location independent entrepreneur. She explains the steps she took…

58: Bootstrapping a $3 Million Business in 12 Months and Empowering Female Entrepreneurs to Hit 7-Figures with Erin Young

Erin Young shares her journey growing up in Australia and founding her first business, Zen Green Matcha. She opens up about the mistakes she made in building that company, including leaving her job too early and needing to go back to work until she landed the distribution contracts that enabled her business to fully sustain…

38: Traveling the World Full Time on Passive Rental Income and Coming Up in the Hip Hop Game with Tiffany Green

Tiffany Green shares her experience coming up in the hip hop radio industry, working at WGCI in Chicago and Hot 97 in New York City. She explains what hip hop means to her and shares behind the scenes experiences of meeting A-list musicians, breaking artists as a music director, and interacting with some of the…

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