Running a Remote Real Estate Business with Matt Bowles, Maverick Investor Group

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Matt Bowles has been a full-time digital nomad with no permanent base since 2013 and has run his real estate company, Maverick Investor Group, from 65+ different countries. You wouldn’t think a real estate business could be operated remotely, but Matt demonstrates it’s possible to do all kinds of unconventional things as a digital nomad. In this interview, we talk about the various iterations of his lifestyle, career, relationships, and much more. 

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How do you run a real estate company 100% remotely? Matt Bowles of Maverick Investor Group shows it's possible! #realestate #remotecompany #remotework #locationindependent #digitalnomad #TheProfessionalHobo #interview

Introducing Matt Bowles, Maverick Investor Group and The Maverick Show

Matt co-founded Maverick Investor Group in 2007 as a fully-remote company to help people buy cash-flowing rental properties in the best U.S. real estate markets, regardless of where they live. He has been featured in major national media and was named one of the “Top 50 Real Estate Opinion Makers and Market Leaders”.

Matt is also the host of The Maverick Show podcast where he interviews today’s most interesting location-independent entrepreneurs and world travelers. Matt is a proponent of “stylish minimalism” and travels the world through multiple climates with carry-on luggage only. He is a sought-after speaker and has addressed conferences around the world ranging from the Nomad Summit to South-by-Southwest on topics relating to real estate investing, location-independent entrepreneurship, and long-term world travel. Matt was also featured in the film Roamers (2021), the first ever studio-backed documentary about the digital nomad lifestyle (about which I’m ridiculously jealous). 

We dig into all this and so much more in our interview! 

Matt Bowles recording his podcast The Maverick Show 

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Check out our meandering chat here! Click here to watch it on YouTube, and please give it a thumb’s up; the earlier you do this in the video, the more it helps me with YouTube’s algorithm. 

How Matt Became an Entrepreneur 

Being fired out of the blue was a turning point for Matt, who decided he would never work for anybody else again. But a bunch of stuff happened prior to this defining moment. We talk about: 

  • How Matt fell into studying Sociology
  • Studying abroad in Ireland at an instrumental time in Irish history
  • Doing a Masters Degree in International Peace and Conflict Resolution
  • How a Peace & Conflict study abroad semester focusing on the Israeli / Palestinian conflict led to in-depth comparative studies 
  • Matt’s experience doing peace and advocacy work in conflict regions
  • How Matt worked in the non-profit space for 10 years, doing human rights civil liberty advocacy
  • At 30 he was let go from his job, which informed his decision to never work for anybody else again, which began his entrepreneurial journey
Matthew Bowles contemplating a remote real estate business

Getting into Real Estate 

Being unemployed gave Matt lots of time to figure out what was next. Here’s what happened: 

  • Matt made his first real estate purchase: a four bedroom house, and he rented out three bedrooms to friends
  • In the first year, that house appreciated in value more than his annual salary 
  • He saw an opportunity to invest in various rental markets
  • Friends took notice, and he started helping them buy rental properties of their own
  • Eventually he got a brokerage license so he could turn it into a business

Starting and Running a Remote Real Estate Company

It’s one thing to start a real estate company; it’s another thing entirely to make it remote! Here’s why – and how – Matt achieved this: 

  • Reading The 4-Hour Workweek changed his life and introduced him to the concept of location independence 
  • “Location independence is a currency that facilitates lifestyle design” – and what that means
  • Knowing he wanted a location independent lifestyle, Matt reverse engineered his entire business plan 
  • Not knowing much about business, Matt self-studied business techniques by reading books
  • The brilliance of finding business partners with complementary skills
  • How Matt and his business partners each make different lifestyle design choices with their location independent careers
  • How Matt manages a traditionally location dependent business remotely, and doesn’t have to keep specific hours (which can be tricky with time zone differences)
  • The beauty of making your work tasks asynchronous so you can work as and when you wish
  • Instead of doing business meetings and company retreats in an office, why not on the Glacier Express in Switzerland? Or in a Costa Rican villa? (By the way, that makes it a tax write-off). 
Matthew Bowles Running Maverick Investor Group from the Glacier Express in Switzerland

Challenges of Running a Remote Business 

Running a remote business with a fully remote team isn’t all roses and buttercups. Here are some of the challenges Matt cites: 

  • Market-related challenges (eg: real estate market fluctuations, COVID-19)
  • Human resources challenges (employee direction, management, motivation)
  • Increased chances of losing company cohesion if you’re not very intentional 
  • The upside is that this forces you to become more precise and organized in designing processes 

Matt’s Digital Nomad Lifestyle

Being a digital nomad for more than eight years, Matt has covered a ton of territory, including staying in some unlikely places for digital nomads (like spending three months in West Africa). His travel style has also taken many different forms. We discuss: 

  • The difference between being location independent versus a digital nomad (I said it on his podcast, then he said it on mine) 
  • How the digital nomad lifestyle isn’t the end goal in and of itself, rather it’s a vehicle to have more freedom in life 
  • How he has stayed in locations anywhere from four days to nine months
  • How location independence affords so many options, and how it’s important to consciously choose what’s exciting and interesting to you 
  • The beauty of being able to make choices about where to be and when based on priorities, relationships, and life circumstances 
  • The different ways he has chosen his destinations over the years
  • His experience with Remote Year
  • How his social circle of travelers and nomads allows him to have adventures around the world with different people in different ways
  • The benefits of location independence being not only the choice of place, but also the choice of who you want to spend time with
  • How Matt’s destinations extend far beyond the standard pitstops for digital nomads (like Chiang Mai, Bali, Medellin, etc) 
  • How he selects his travel partners carefully depending on the destination and experience (eg: the people he would explore West Africa street parties with may be different from the people he’d tour the south of France with)
Matt Bowles and his digital nomad friends exploring the salt flats in Bolivia

Being back in the U.S. for 18 months during the pandemic has been a bit of a reset, and Matt has found a few silver linings therein. Let’s see where his life and travels take him next! Check out his most excellent podcast The Maverick Show (he has some incredible guests, and I’m not just saying that because I’m one of them!), and if you’re interested in getting some turnkey investment real estate, put Maverick Investor Group on your radar. You can also reach out to him on Instagram

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