Global Travel Stories
& Life Beyond Borders

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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.

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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…

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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…

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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…

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

Learn how LinkedIn, the hidden job market, and interview preparation can help you land the remote role you really want. Juliana Rabbi takes us on her journey growing up in Brazil, moving to…

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

Learn what travel in Asia & investment mistakes taught him about minimalism, Stoicism, risk, and building real freedom. Santiago Sosa takes us on his journey growing up in Colombia, immigrating to the U.S.,…

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

Learn how house-sitting and other creative strategies can dramatically reduce the cost of a long-term travel lifestyle. Nora Dunn (a.k.a: The Professional Hobo) takes us on her journey growing up in Canada, becoming…

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

Learn the TikTok strategies that turned her social following into six-figure income while funding years of world travel. Christa Romano takes us on her journey of becoming a full-time digital nomad and financing…

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

Learn the mindset shifts, personal branding, and career moves that can turn a 9-to-5 into a life with greater freedom. Dels Ogun talks about growing up between Lagos and London, the Afro-Beats music…

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

Learn the product research, social proof, and marketing strategies behind scaling a fast-growing female fitness brand. Erin Young shares her journey growing up in Australia and founding her first business, Zen Green Matcha….

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

Hear how a decade of patient real estate investing gave her the freedom to leave her career and travel on her own terms. Tiffany Green shares her experience coming up in the hip…

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

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…

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