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Ep: 199: How this digital nomad creates income with remote real estate investing with Matthew Bowles

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In this episode, I speak with Matt Bowles who is the co-founder of  Maverick Investor Group which helps individual real estate investors buy performing rental property in the best U.S. real estate markets, regardless of where they live.  

As a location-independent business owner, Matt runs his company from epic locations around the world and has lived in over 50 different countries since 2013. 

He is a sought after speaker at events and conferences around the world relating to real estate investing, entrepreneurship, long-term world travel, and the digital nomad lifestyle.

Listen on to find out how Matt has been location independent with remote real estate investing. 

Listen Below:


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Hey everyone. Thank you so much for being here. I am really excited to speak with our guest today, Matthew.

Hey Matt, how are you?


Hey, Debbie. I’m great. Good to be here.


Thank you so much. I’m so excited to speak with you because what you are doing is something that I am extremely interested in, but before we get to that, can you tell us about you and why you live an offbeat life?


Yeah, so all of my academic background and all of my professional work experience up until the age of 30 has absolutely nothing to do with what I’m doing today.

So I have a bachelor’s degree in sociology. I have a master’s degree in international peace and conflict resolution, and I worked in the nonprofit advocacy space all the way up until the age of 30. And I was doing really important work. It was really meaningful. It was really affecting positive change in the world, I was very passionate about it but I wasn’t making a lot of money.

And so I started investing on the side in rental properties and learned all about remote real estate investing and all of that. And then I started having my friends come up to me, they say, “How are you doing that real estate investing?” And so I was showing them how to do remote real estate investing and all of this.

And then one day, at the age of 30, totally unexpected, we had a change in management. Everything in the organization shifted around. All of a sudden I walk into work, long story short, I get fired from my job completely unexpectedly at the age of 30. And they said, “You got to hand in your phone and your laptop and all this kind of stuff. And out of the office by five.”

And then there I was – no phone even. I’m driving to the cell phone store to buy a phone so that I can call my mother and tell her I was fired. And on that drive, Debbie, I started doing a lot of thinking, a lot of reflecting. And I said, “You know what? If this happened to me now, this could happen to me at any point. So I am going to make a decision at this moment and I’m not going to apply for another job. I am going to figure out how to create my own business and generate my own income.

And then I started realizing that I had no idea how to do that. So I got the phone. Then I went to the bookstore and then I started reading books on how to start a business. Now, this was back in 2007. And one of the days that I went into the bookstore, there was a brand new book on the shelf called The 4-hour Workweek by Timothy Ferriss.

I picked that book up and I read it the day it came out and I said, “That is what I’m doing.” And so I then realized that I didn’t have all the skills myself to start a business. So I reached out to a couple of business partners that had complementary skill sets. And I said, “One of the things I know how to do is to help people buy rental properties.

I know there’s already a demand for that because my friends are already coming to me, asking me to help them to buy rental properties. And so if we could start a real estate brokerage, we could get paid for helping people buy rental properties without having to charge the clients any money. Because in the United States, the seller pays all of the real estate commissions.

“So I could still help my friends buy real estate, this time gets paid for it, but I don’t have to charge my friends any money at all.” I was like, “That is my business model. I don’t have to sell anything. I just help people for free and I still get paid. That’s amazing.”

So that’s what we did. We founded Maverick Investor Group in 2007. It’s a real estate brokerage and we help people to buy rental properties in the United States, turnkey, they’ve already been renovated. They already have a qualified tenant in place paying rent. They’re already cash flowing and performing on the day that our clients close. They can buy them in the most investor-advantaged US real estate markets, regardless of where they live.

They can live anywhere in the world because they don’t have to be the rehabber or the landlord and they don’t have to live near their properties. But they get all of the benefits of owning the actual deeded real estate. So that was our business model.

And we built that with a location, independent infrastructure so that we, and all of our staff, could live wherever we want. Travel the world as much as we want and our clients obviously could live wherever they want. And we’ve been running that business since 2013 and I have lived in about 65 different countries since then.


Wow. Well, that’s definitely what most of our listeners want to do. How were you able to actually transition this business to become location independent? Because most people will think, “Well, if you’re in real estate, you have to be there. You have to make sure that things are running smoothly.” And you created a business that you don’t need to do that.


Yeah. The answer to that question is preplanning and then reverse engineering a business model.

So when you go to start a business, most people think, “Okay, I need to have a business plan. And that business plan should be how my business is going to make money. What are my costs? What are my expenses? What’s my revenue? How much profit am I going to make?” And they just limit it to the financial aspect of what the business is going to deliver for them.

What we did is we said, “We also want this business to deliver the ideal dream lifestyle to each of us and to our staff and to our customers for that matter.” So we said, “How would we do that?” And then we reverse-engineered the business model to facilitate our location independence and to facilitate and deliver our lifestyle design, which we viewed from day one as just as important, if not more important, than the financial success of the business.


When we look at your life right now, Matt, we’re thinking to ourselves, “Well, this is amazing. This is perfect.” But how did you even find out that this is really the niche for you? Because like you said, you didn’t start doing this until you were 30. And I think a lot of people assume that if you’re successful, especially in the remote real estate investing business or really any difficult industry out there, you need to have a lot of experience and it doesn’t come overnight.

And obviously, it didn’t happen to you either. You had to do a lot of work. But there’s a lot of fear also that goes into it. How did you figure out that this is what you needed to do? And I’m sure getting pushed out of a job was a huge indicator for that. But why did you realize that this was something that you needed to go into?


Yeah. I think your point about the fear thing is a good one. And I think a lot of people hesitate to jump from their stable job because of fear. And to be honest, you’re right. I got kicked in the pants, right? I mean, I kinda got abruptly thrust into this. But I had built up enough along the way.

I had been studying remote real estate investing. I’ve been investing in real estate myself out of state – rental properties. I had been helping other friends of mine do this. And so that was something that I knew. I understood. It was a product that I knew I could sell. It was a service that I knew was in demand.

I was already doing it and helping people, all I had to do was monetize it. So I think the way that people can think about it is what do you already do? Or what do you love to do? And maybe it’s a hobby or maybe it’s a part of what you’re doing professionally right now. But you could recreate that in an independent way and monetize that as a business.

And that’s really the way I would encourage people to go. That’s really what I did. I said, “Okay, what do I know how to do? What do I know how to sell? What can I do? How can I deliver value? What are people already coming to me for that I’m doing that’s delivering value to them already?” I’m just not getting paid for it, right?

And then that’s how this model came about. And then we said, “Okay, how are we going to build this business and help people to buy rental properties in the best real estate markets around the country, no matter where they live, no matter where we live, and then we had to go and design each piece of that?”

We said, “Okay, this is what we want to do. And now this is how we’re going to design it.” So then what you do is you come up with this business plan, you say, “Okay, well, these are some challenges. These are some obstacles.” You made the point, Debbie, that a real estate brokerage is not a traditionally virtual business model, right?

Most people think a real estate broker is that the person that drives you around to look at houses and sits at open houses and lists properties, or drives homeowners around to see if they like the kitchen to the bathroom and they want to buy the house. That’s a traditional real estate brokerage. And so what we did is we developed and created a non-traditional model for that.

We said, “We want our clients to be able to buy in the best markets regardless of where they live.” A regular real estate broker only has properties in their local market to sell. They can’t sell your property out of your local market because they don’t have access to those.

So we said, “Instead of telling everybody they should buy our product and they should buy our market because it’s all we have to sell, how can we flip that around and put the client first and say, ‘We want to be able to do a consultation with each individual investor-client, find out what their remote real estate investing goals are, find out what their buying criteria are, and then help them identify the best real estate markets for them to buy in, regardless of where they live and remove those geographic restrictions on them so they can buy the best markets’?”

So we said, “How would we do that?” And then we start asking these questions and we started saying, “Well, what are the obstacles to doing that? What are the challenges going to be? How could we overcome those?” And so you just start asking yourself those questions and then brainstorming about it and then coming up with solutions, right? Because entrepreneurship is really just continual, nonstop, problem-Solving


I can attest to that because every day there’s a problem that I have to solve with my business.


Yeah. And as long as you keep solving problems, your entrepreneurial journey will continue. You are only going to fail at business the day that you decide to stop solving problems.


And the thing is it’s exciting because it is, it’s really exciting. I know it seems like we’re masochist in some sense because we like having all of these issues and the problems. But it’s so exciting when you finally figure it out. You have an adrenaline rush.


Yeah. And then that remains exciting until whatever that solution was no longer works. And then like the floor falls out from underneath you. And then you have to figure out a new solution to the new problem. And then you just kind of keep going. But that really is it, right?

I mean, the core crux of businesses is, first of all, finding a problem that other people are having and how your product or service can be a solution to other people’s problems. That’s the first part of any business. Delivering something of value.

So for us, it was like, “Okay, the problem people are having is they think that they can only buy real estate in their local market. And if they live in an expensive market, like you do, Debbie, in New York City, that’s not going to be a very high return, high cashflow investment for them. So that’s a problem.

Number two, people don’t like trying to rehab and renovate properties because that’s annoying, very difficult, very costly, and very high risk. And number three, people don’t like being landlords for properties because that’s really challenging: getting calls from the tenants in the middle of the night when the toilet doesn’t work or this kind of stuff.

And so these are all the things that people find challenging about real estate. How can we remove all of that for people? How can we let people buy in the best markets regardless of where they live? Make sure that they don’t have to be the rehabbers or make sure that they don’t have to be the landlords.

So if we remove all of those problems that people are having and we let them buy a performing, cash-flowing property that’s already renovated, already cash flowing, and already tenanted and already being managed professionally by somebody else. Well, now we have a value proposition, right?

So the first part of the business is solving your customer’s problem. And then the ongoing number of business problems that will continue to be following you. And as long as you continue to solve them, you will continue to stay in business and continue to thrive.


Yeah. And I find it really exciting too that the more problems and issues we solve, the more money you make. Because you can monetize all of those things as you have, Matt. You’ve solved this issue, you made it easier for people, and now you’re able to have a thriving business from it which is incredible.


Yeah. 100%.


So how did you figure out the right systems when you first started your business? Because this isn’t where you started. Did you have a mentor or did you learn as you go?


So I largely learned by myself before I started the business. So I had been investing in rental properties, as I mentioned in different markets. I’ve been reading everything I could read about it, learning about it through doing, and then I partnered with other people that had different experiences than mine, right?

So one of my business partners was on the real estate sales side. He was a real estate agent and a very successful real estate agent who had been selling investment properties. So he was actually on the sales side and actually had that experience and was able to be our corporate broker so that we could actually have a brokerage.

So I recruited business partners that had experiences that I did not have. And then I knew pretty clearly what my experiences were and what my skill sets were that I could bring to the table. And then I recruited two business partners that had complementary skillsets for all the stuff that I either didn’t know or wasn’t good at.


How do you choose the right people to partner with even though you know that they have the skill sets that you want? Especially if you don’t know them yet, how do you know that they’re the right people for you to go into this business?

And because it may be just me, the New Yorker and jaded be like, “Matt, how do you do this and make sure that it’s a win-win for everyone?


Debbie, that’s a super good question. And I’ll be honest with you, I watch other business partnerships fail all the time because people pick the wrong business partners. I mean, that is a really, really important choice, or a lot of people would just go into business by themselves and don’t have a partner for that reason, I suppose.

But for me, I knew both of my business partners very well. So my business partner, Valerie, was my best friend since graduate school. And we had done all kinds of stuff together. We had done political activism together. We’d done international travel together. We had done all sorts of things. I knew her extremely well. We had worked on all sorts of team projects together.

I knew exactly what her skillset was. She knew what mine was. We knew how we worked together, what our synergies were. We had been basically stress-tested in high-intensity environments and stuff like that. So I knew exactly what she would be able to bring to the table.

And then my other business partner, Mark, actually sold me a number of my rental properties. So I actually saw from the customer side what the experience was like working with him as a real estate salesperson and all of the experience that he brought from that end of it.

I knew these people, I had extended experience with these people and I was able to really carefully select them based upon my personal relationships as well as the skillset assessment of them.


I think that’s a really great idea to do, like you said, stress testing someone especially before you get into a bigger partnership because it can really affect a friendship. I think a lot of people are misled by, “Okay, we’re friends, we get along”, but it’s totally different when it’s a business relationship and it gets really complicated.

And I think your idea of trying out the relationship into a business relationship in smaller doses first and see how that goes before you actually get into a long-term partnership where there are more money and legal stuff happening. Because it can be a headache. I’ve seen it often.


100%. That is entirely true. And the other thing you should realize is that if you ever go into business with another human being, you are putting your entire friendship on the line because 99.9% chance if that business does not work out, the friendship is gone.


I’ve seen it often. Yes.


That’s a hundred percent correct. So you are very clear about the risk that you’re taking with that friendship. And you should absolutely make sure that you have assessed the business skills and you’ve assessed a whole bunch of things about those people. And making sure that it is an actual synergistic relationship for what you’re going to go into.


I’ve also seen work ethics that were completely different and the working styles that don’t work together. So yeah, you don’t think about that until you actually need to get work done. And you just don’t sink in that.


I mean, this is why that experience right upfront, like being able to observe that and people being able to do joint projects with people of some kind, even if it was different from your business.

My business partners that I have done things together, we’ve done joint together in other spaces where I’ve seen how they perform under deadlines, timelines, high-stress environments, and all this kind of stuff. And how we work together and how that teamwork happens.

Because, absolutely, you are right, everything is different under stress. Everything’s different when money’s involved, everything’s different when you’re going through the entrepreneurial roller coaster and you have those stressful downswings and everything else. So 100% agree with that.


And I tell all of my listeners especially when they see a lot of articles or images from digital nomads and location independent entrepreneurs, that it just seems like it’s really great. And they don’t realize how hard everyone works to get this type of lifestyle if anything more, right?

Because we also have a lifestyle that we’re trying to do and we do it in different places and there’s so much more to balance to it. So it’s not just happy and amazing all the time. There’s a lot of things that go along with it.

So I always want to tell the truth and have reality put in there. Obviously, we all love what we do and we love our lifestyle but there are things that you have to look out for if you want to get into this niche or lifestyle.


Yeah. A hundred percent. I mean, there’s a lot of very short-lived digital nomad experiments, shall we say, and people go out and they do this thing for like a year and then they crash and they burned because they didn’t put in enough work.

They burned out on bingeing on too much social stuff. It’s like anything else, you have to have the right balance in your life. And when you add in the itinerant world travel, you’re adding in another piece that you have to balance.

But it’s like anything else in your life, right? Like even if you’re just sitting at home in your apartment, wherever, you could do no work and you could just binge on Netflix for like eight hours a day.


Which I do sometimes.


Like, you could do those things there. And it’s just like when you’re traveling and you’re in some super epic place and there’s like amazing, exciting things to do at all times. You also just like, with not binging on Netflix too much, you have to structure your time, make sure that you’re giving work the priority that you have to give work.

And then you have to make sure that you’re sleeping enough, exercising enough, eating healthy, and doing all of the regular things that you have to do to live a healthy life. And then you factor in the super amazing, exciting, and absolutely epic things that there are to do in those places, which is one of the reasons that I like to slow down because when I travel, I try to stay in places for a good one to two months.

And that, number one, helps me to feel like a resident of that place. I’m not just rushing through and staying at a hostel or a hotel. I’m actually getting an apartment or whatever in a residential area and I am a resident of that city for one to two months.

I’m shopping at the grocery store and I’m doing all of the regular normal life things. And I can really start to feel like a resident of that city. And also if I’m there for a couple of months, I don’t feel rushed. Like, I have to race out and do this thing because I have a couple of months to do all that stuff. So you can live a regularly paced life. You’re just doing really, really epic stuff when you’re going out to do stuff.


I think also when you first start traveling, you feel like you have to go everywhere and do everything and you are. It’s like a race, right? You’re checking off all of these countries. And now I’m in my thirties and honestly, I’m like you, Matt, I just want to travel slowly. I want to enjoy things.

And it’s really not about taking off countries for me anymore. It’s finding a place that I feel at home every time. And also the people ’cause for me, now more than ever, it’s really about the connection you’re getting. Because as a digital nomad, as a remote worker, you can be anywhere and choosing the right place that feels really good.

It feels like, I don’t know, there’s a lot, I think, of us, that feels like we belong in a lot of different places. So you can feel at home in so many different places but I think, at least for me, that’s what’s more important.


Yeah. And if you have a longer-term horizon, you don’t have to race around and try to pack things in. There’s sort of this model in Europe where they have the gap year, right? Where like after high school or whatever, you travel around and you backpack for a year.

And then you’re going to like go to college, get a job, go into the corporate world and like get married, have kids and whatever else life has prescribed for you. But you get this one year and you could just go have epic bonkers adventures for like this entire year.

You just try to pack everything into that and by the end of that year, you’re probably so burned out. You’re like, “Okay, fine. Now I want to go back.” And I feel like some people with the nomadic stuff sort of subscribing to that type of framework.

They’re just viewing it as maybe like a short term gap year type situation where they’ll go out and do all this stuff for a year. They don’t do very much work, they run out of money and then they basically have to come back. And it was just kind of an adventure that they can talk about for a while now.

Whereas people that want to actually do this long-term and they actually want to maintain an itinerant lifestyle where they’re able to move around and live in different places in the world at their own speed, at their own pace and really design their own lifestyle long-term, that requires more discipline and more structure to be able to do that long-term. To make sure that you have all the sustainability pillars that you need to do that long-term.

I totally agree with you and I don’t try to just chalk up countries either. I mean, I will oftentimes go back to the same country again and again. And oftentimes to see different cities.

I went back to Japan three times over the last two years because I spent a month in Tokyo and I didn’t leave Tokyo then I went and I spent a month in Kyoto. Then I went and spent a month in Osaka. And because I just want to go and see the different parts of these amazing countries which are so different.

So it’s not like, “Oh, I just want to like count my countries and this. I want to go have really amazing experiences.” But my horizon is very long term. I want to spend a minimum of a month in all of these places.


And I think that’s really what the beauty of this lifestyle is. You are not being rushed. It’s not like you only have two weeks of vacation that year, you have to pack everything in, you’re exhausted and then you can’t wait until the next year.

This is a lifestyle. You can make the sustainable but you also have to be very careful because, like you said, Americans, especially, we’re not used to this. We’re not used to long-term travel. We’re used to very quick, very fast. And then you go home and you go back into your reality.

Fortunately, we are able to have the opportunity to work remotely. And now this could be an ongoing thing. I think that’s one of the most beautiful things about being in this type of lifestyle.


Yeah. And the other thing that I would mention is that you are in control of how you structure your lifestyle if you are location independent. So I encourage every single human being to strive to achieve as much location independence as possible because all that means is that you have the choice, right?

So if you want to live in New York City and just like never leave New York City and that’s your choice, great. Like, you can do that if that’s what you prefer. But if you want to become an itinerary, nomad and travel around the world and live in a different place every month, you could also do that. Or if you want to go to one country and stay for a year and then go to another country and then go to another country.

Like, however, you want to structure your life. The fact is that you’re in control and you have options when you’re location independent and it’s you that’s making those choices for yourself. And those choices can change over time as your life changes, your preferences change, you have kids, or whatever. Like, you can always change that. But location independence gives you the control to make the choices for yourself.


It’s really about the freedom. That’s why most of us are doing this.

So let’s go back to when you first started, Matt, how did you land your first client?


So, well, I told you that my one business partner was already in real estate sales, right? So he already had clients that he had sold investment properties to and he had marketing channels through which he was selling them and all of that. So I had friends that were interested in buying rental properties, as I mentioned. Were sort of buying them through, I was helping them to buy rental properties and all of that.

But my business partner, Mark, really had the greater sort of sales landscape on how he was finding clients. Now he was selling them. He was closing them. And that was one of the pieces of value that he brought to the table. So he had already a network of clients that knew him and trusted him because he had sold the real estate before.

And then he had other sorts of marketing channels for how to find those real estate investor clients. And so we just were able to bring that in. And then from there just kind of grow and build.


That’s incredible. And that’s why having the right partnership can work in your favor.




But it has to be the right one.

So Matt, let’s fast forward to 50 years from now and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for?


Oh, that’s a great question. First of all, I mean, I should also tell you that one of the other pillars of our business is that, and I mentioned to you that I have a nonprofit advocacy background and my business partner, Valerie, does as well and we are very passionate about social justice and human rights advocacy and things of that nature, and so one of the things that we did with our company is we built in a part of our business infrastructure is that we would give back 10% of all of our net revenue before we take any money out of the company for ourselves.

Like, for our managerial compensation or anything else, we’re going to donate 10% of our net revenue. So as the company does better so too then do the causes that we care about that receive money from our business. And so those causes, we donate to various different things and we changed them up, but we have that mechanism.

That’s one of the things that really, really inspires me to do well in the business. And so for me at this point, the lifestyle design, I’m able to travel around the world. I’m able to meet extraordinary human beings, right? In some cases, it’s other travelers. In many cases, it’s local people in the places where I’m going.

I’m able to learn about the culture and, and people and learn languages and all this kind of stuff through immersion which is an incredibly, amazing fulfilling lifestyle. So I’m really just trying to go to epic places, surround myself with amazing people. And then be able to give back to causes that affect positive change in the world through all of the work that we’re doing with the business.

And I’m also trying to support other people along the way that are trying to achieve things for themselves. Whether it’s people that are trying to get into the nomad lifestyle, they’re trying to become location independent, or start their own businesses I do whatever I can to sort of support them and have that ripple effect.


Isn’t that amazing when you can do both? You can create income while you’re also helping other people and changing people’s lives. I mean, I don’t know if it can get any better than that, honestly.


I’ll be honest with you, Debbie, for me, I feel like that’s imperative to have that deeper incentive and that deeper impact. Because if the only thing you’re getting out of your business is just money for you, I’ll be honest with you. Like for me, I think entrepreneurship is just too hard.


Yeah. It is.


It’s just too hard if you don’t have a greater purpose and it’s not doing greater things. So for us, for our business, I talk to entrepreneurs about this a lot and I tell them that we have what I consider to be four pillars of purpose which I think is really important for our business.

One, is that it facilitates our dream lifestyle, right? The owners and partners of the company. Number two, it facilitates and enables the dream lifestyle for all of our staff. Anyone that we hire, they’re all location independent, and they can go lead their dream lifestyle.

Number three, our customers, right? We’re helping them to buy these cash flowing rental properties, build up their passive income, build their wealth and facilitate their dream lifestyle. So we’re making our customers’ lives better with every single property that we sell. And then the fourth one is that we give back to these causes that affect positive change in the world and donate to these charities and all of that.

And so those are the four pillars of purpose and they’re all four really imperative to motivate you to work as hard as you need to work and endure the level of stress that you need to endure as an entrepreneur because otherwise, it’s just too hard.


No, I totally agree. And like we had mentioned before, every day there’s literally a new obstacle that you’re faced. So if it’s just with money, honestly, stay at your nine to five. You can actually get remote jobs now from anywhere because of COVID and everything. So just stay with that.

You don’t need to have a business because it is really fricking hard. Let me tell you, we both can tell you. If it’s just the money, just get a regular job, your boss will pay you. You’re good to go. But if you also want to make an impact and do this for a long time and be a little crazy as well, then yeah, entrepreneurship is the way to go.




So that if our listeners want to know more about you, where can they find you?


Well, I host a podcast called The Maverick Show, right? Interviewed today’s most interesting real estate investors, entrepreneurs, and world travelers. So these are people that are designing really epic lifestyles. They are really doing the damn thing and they are financing it through either their entrepreneurial location independent business or through their rental properties. And they’re having epic travel adventures.

And so I profiled those people on The Maverick Show podcast, where you can find that – anywhere you listen to your podcasts, just the Maverick show with Matt Bowles, or you can go to and all the episodes are there. And you can see the show notes and everything else.

If you are interested in the rental properties and doing a free video consultation with us, getting to know us, getting your questions answered, let us get to know you in terms of your remote real estate investing goals, buying criteria, and seeing if it would be a good fit for us to work together, we would love to chat with you and to help you to buy out of state rental properties that are being professionally managed already.

And if you’d like to learn more about that, you can go to, and there you will be able to get our free report on how to avoid the seven biggest mistakes real estate investors are making in today’s market. And you can also register for a video consult with us to get to know us and chat with us and see if it would be a good fit to work together. And we would love to get to know you and answer your questions.


Perfect. Thank you so much, Matt, for giving us all of these incredible tips and for sharing with us, your journey. We really appreciate it.


Thanks for having me, Debbie.

Listen to Matthew’s extended interview where he shares how to buy rental properties from anywhere.

What you’ll find:

In this episode, Matt will debunk the misconceptions about rental properties. Learn how to acquire rental properties even if you’re thousands of miles away.

Follow Matt:

Show Credits:

Audio Engineer: Ben Smith

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