The Maverick Show: Remote Entrepreneurship and World Travel

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03: From House Hunters International to Relocating Professional Poker Players: Sustaining a Long-Term Digital Nomad Lifestyle with Kristin Wilson

The Maverick Show: Remote Entrepreneurship and World Travel

10/22/18 • 104 min

Long-term digital nomad Kristin Wilson speaks publicly for the first time about how she completely burned out at age 21 and had a grand-mal seizure just months after winning the U.S. National Collegiate Surfing title, dashing her dreams of professional surfing and forcing a major life pivot.

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She talks about how she reinvented herself and went on to sell tens of millions of dollars of real estate in Central America, and landed an appearance on House Hunters International with a Danish Lord and a Brazilian model. She then tells the story of how she pivoted again when online gaming regulations changed in the U.S. and she saw an opportunity to build a business helping professional online poker players physically relocate outside of the U.S.. She talks about how she founded and expanded that company, attracting the attention of ESPN, Bloomberg and other major media outlets. She opens up about her personal journey living primarily outside her home country of the U.S. since 2003, in over 50 countries, and shares the strategies and tactics she has developed for sustaining an itinerant digital nomad lifestyle over the long-term. She explains how to create community support structures, how to optimize work-life balance amidst the excitement of travel, and how to culturally adapt and form deep connections with each place you live to mitigate loneliness and travel fatigue. She then shares her personal morning routine, productivity hacks, and recommends a very remote travel destination with one of the highest concentrations of plant and animal life in the world, where you can see colorful toucans flying around and very few people. FULL SHOW NOTES AND DIRECT LINKS TO EVERYTHING DISCUSSED IS AVAILABLE HERE.

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01: Building a $2 Million Business at Age 24, Managing a Billion Dollar Hedge Fund Portfolio, and Being Innovative with May Ling Lai

The Maverick Show: Remote Entrepreneurship and World Travel

10/08/18 • 96 min

May Ling Lai tells her story of how she built a $2 million business from scratch in 2 years at age 24, before going on to manage a billion-dollar hedge fund portfolio.

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She talks about strategies for navigating a male-dominated industry as a female entrepreneur, why you should always be open to pivoting, and the rewards of proactive networking. She explains the importance of innovation and discusses how to identify a problem that needs to be solved and then transform that idea into a business-building process. May then talks about scaling, why most small business owners never do it, and how to think about decisions relating to debt and equity for business growth. She then identifies the #1 most important skill for executive leadership. She discusses how to hire the right people, manage them effectively, and explain the “real” responsibility of the CEO. May then explains the importance of company culture, having a purpose-driven business, and building a team that is passionate about your mission. She talks about how to run effective meetings that accommodate different personality types, how to process failure constructively, and how to avoid the biggest mistake entrepreneurs make that exacerbates stress. She also explains how she structures her international lifestyle, books the best flights, and how her childhood trips to China inspired her minimalist packing. She recommends her top 3 travel destinations and offers packing tips for women on how to remain fashionable while traveling the world for extended periods without ever checking luggage. FULL SHOW NOTES AND DIRECT LINKS TO EVERYTHING DISCUSSED IS AVAILABLE HERE.

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See my 7 Keys For Building A Remote Business (Even in a space that’s not traditionally virtual)

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00: Introducing "The Maverick Show: Adventures in Real Estate, Entrepreneurship and World Travel" with Matt Bowles

The Maverick Show: Remote Entrepreneurship and World Travel

10/08/18 • 14 min

Matt Bowles introduces himself and the Maverick Show podcast—the weekly show where he interviews today’s most interesting real estate investors, entrepreneurs, and world travelers.

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Each Monday a new episode will be released where you’ll meet an inspiring guest and hear personal stories about their worst failures, biggest breakthroughs, amazing travel adventures, and most valuable lessons learned on their journey to financial success, location independence, and lifestyle freedom. As the host, Matt will pull out actionable tips and advice as well as their personal recommendations for the most influential books, resources, tools, hacks, and practices that can help you take your real estate investing, entrepreneurship, and lifestyle design to the next level. Matt tells his personal story of how he got started investing in real estate back in 2004, and opens up about how getting unexpectedly fired from his job inspired him to become an entrepreneur. Matt tells the story of how he co-founded Maverick Investor Group in 2007 to help individual real estate investors buy rental properties in the best U.S. real estate markets regardless of where they live. He explains how he and his business partners built Maverick as a location-independent business in a space that is not traditionally virtual, and why they give back 10% of their net profits to charities that affect positive change in the world. He also talks about his personal lifestyle design, how he has lived in over 50 countries since 2013, and how his conversations with incredible business owners, real estate investors and long-term digital nomads he met along the way helped inspire the creation of this podcast. FULL SHOW NOTES AND DIRECT LINKS TO EVERYTHING DISCUSSED IS AVAILABLE HERE.

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See my 7 Keys For Building A Remote Business (Even in a space that’s not traditionally virtual)

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313: Finding Love and Partnership in the Digital Nomad Lifestyle and Choosing the Right Travel Medical Insurance with Ebonie Finley

The Maverick Show: Remote Entrepreneurship and World Travel

12/02/24 • 55 min

Learn how to find a romantic life-partner in the digital nomad life & why all travel medical insurance is not the same.

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In Part 2 of this episode, Ebonie Finley talks about her experience reconnecting with the Bahamas as an adult, and shares tips for visiting the Bahamas and Costa Rica. She then talks about navigating anti-Blackness in the digital nomad life, and why she feels Medellin, Colombia is one of the best destinations for Black women. Ebonie then talks about finding love, romance, and long-term partnership in the digital nomad lifestyle, and gives tips on maintaining a long-term nomadic relationship. She then talks about her experience working for SafetyWing after being a long-time customer of their travel medical insurance. Ebonie talks about why SafetyWing’s Nomad Insurance is so unique in the market, and who it is specifically suited for. She then shares tips for making friends around the world as a solo traveler, offers advice for aspiring nomads, and gives tips for sustaining a long-term life of world travel. FULL SHOW NOTES WITH DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE.

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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

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315: Tequila Trains, Volcano Pizza, Rainbow Mountains, and Kenyan Safaris with Sojourner White

The Maverick Show: Remote Entrepreneurship and World Travel

12/16/24 • 59 min

Learn how to take some of the most epic train rides in the world, and hear highlights from spending time in Africa.

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In Part 2 of this interview with Sojourner White, Matt and Sojourner discuss the best long distance train rides in the U.S.. Sojourner then describes her experience taking the Jose Cuervo Express Tequila Train in Mexico. She also reflects on how special and unique it was to take the train through Peru, and then shares her experience hiking the Rainbow Mountain. Sojourner also talks about visiting Panama, and shares a unique experience hiking a volcano in Guatemala for pizza. She then talks about her experiences visiting Kenya, going on Safari, and spending time in Cape Town and Johannesburg, South Africa. Sojourner shares reflections about connecting with the African Continent as a Black American, and the importance of paying attention to social, economic and political dynamics as we travel. Finally, she reflects on how all this travel has impacted her and what travel means to her today. FULL SHOW NOTES WITH DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE.

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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 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! :)

157: Pro-Democracy Protests in Thailand, Rising Fascism in the U.S., and the Anti-Austerity Uprising in Greece with Joshua Stephens

The Maverick Show: Remote Entrepreneurship and World Travel

11/03/21 • 79 min

Joshua Stephens shares his experience in the “Occupy Wall Street” movement in New York City, and explains how he then transitioned into the nomad lifestyle which he has maintained for nearly a decade.

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He shares his experience traveling to Egypt during the Arab Spring to interview local activists, and also reflects on his experiences with Israeli “Pinkwashing”. Joshua then talks about his experience on the ground in Athens during the Greek anti-austerity protests and explains many of the more nuanced dynamics that did not get much coverage. He then defines “fascism” and provides context and explanation for its recent rise in the U.S.. Joshua addresses the role of conspiracy theories in the fascist project, and contextualizes the QAnon and anti-vaccine conspiracies. He also discusses the politics of negation, the proliferation of anti-mask and anti-vax sentiment, and its significance in this political climate. Joshua then talks about the pro-democracy uprising in Thailand which he has been documenting while living in Bangkok for most of the last 18 months. He explains wealth inequality in Thailand, as well as the institutional arrangements with the military and the monarchy. Joshua then explains the class dynamics, as well as the role of skateboarding culture in this uprising. He reflects on some of its most unique attributes, and why it is getting so little coverage in the media. FULL SHOW NOTES AND DIRECT LINKS TO EVERYTHING DISCUSSED IS AVAILABLE HERE.

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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 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! :)

144: Matt Bowles on Building Maverick Investor Group as a Fully-Remote Real Estate Brokerage with 4 Pillars of Purpose

The Maverick Show: Remote Entrepreneurship and World Travel

08/03/21 • 47 min

On this episode, the tables are turned and Lydia Lee of “Screw the Cubicle” interviews Matt Bowles.

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Matt talks about how his Irish-American cultural background and his time living in Ireland impacted his politics, identity, and worldview. He then shares the behind-the-scenes story of how he co-founded Maverick Investor Group to help people buy cash-flowing rental properties in the best U.S. real estate markets from anywhere in the world. Matt explains how he and his business partners built the company as a fully-remote real estate brokerage from day 1, and how Maverick’s location-independent infrastructure provides unique benefits to their clients. He then explains how Maverick empowers all their clients to conduct independent due diligence on their rental properties before buying them, without actually having to see the properties in person. Matt then shares how Maverick was intentionally built on “4 Pillars of Purpose” and how that provides multiple layers of motivation for the company to succeed. And, finally, Matt reflects on his 8 years of full-time world travel with no base, and shares his thoughts on some of the key sustainability pillars for a healthy life of long-term world travel. FULL SHOW NOTES AND DIRECT LINKS TO EVERYTHING DISCUSSED IS AVAILABLE HERE.

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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 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! :)

301: Visiting Every Country in Central & South America and How Not to Cross the Venezuelan Border with Ashley Company

The Maverick Show: Remote Entrepreneurship and World Travel

09/09/24 • 48 min

Learn how immersive trips to the Dominican Republic, Kenya and backpacking through South America can be life-changing.

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Ashley Company starts off by talking about her experiences traveling the world for wine, and why the South African wine region is so unique and special. She then talks about her experience growing up in the U.S., traveling to Turkey as a kid, living in South Korea for a year at age 12, and attending an HBUC for college. She then describes how her first solo trip to the Dominican Republic was completely transformative, as was her first trip to Kenya. Ashley then explains what led her to quit her job and backpack through every country in South and Central America. She shares stories about traveling to San Basilio de Palenque in Colombia and accidentally entering Venezuela without going through immigration. Ashley also talks about the power of her first experience attending Carnival in Trinidad and why she has been back 10 times since. And, finally, she reflects on the impact that a full year of backpacking in South America had on her as a person, and how it shaped her life and entrepreneurial trajectory. FULL SHOW NOTES WITH DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE.

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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 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! :)

317: Centering the Voices of Refugees and Founding "Our World Too" with Hira Aftab

The Maverick Show: Remote Entrepreneurship and World Travel

12/30/24 • 45 min

Learn about the importance of prioritizing the voices, stories, and experiences of refugees in the places we travel.

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Hira Aftab talks about growing up in a Pakistani immigrant home between the UK and Saudi Arabia. She reflects on the life changing impact of her first trip to Palestine, and how that inspired her to become a human rights activist. Hira then reflects on doing two Master’s degrees and working in the international humanitarian sector. She talks about her trip to Jordan, the impact of meeting with Palestinian refugees there, and how that inspired her to start “Our World Too” as a platform to center the voices and stories of refugees. She also talks about hosting the “More than a Statistic Podcast” and shares some of her most powerful interviews. Finally, she reflects on the lessons from her international humanitarian work and unpacks some of the neo-colonial dynamics in the space. FULL SHOW NOTES WITH DIRECT LINKS TO EVERYTHING DISCUSSED ARE AVAILABLE HERE.

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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