Matt Bowles: My guest today is Mike Wolf. He is a seasoned real estate investor with over 35 years of experience. He and his teams have transacted more than 3,000 real estate deals, and he has appeared on outlets such as NBC, Fox, and the TEDx stage.

Today, he empowers audiences with proven strategies for financial freedom and growth through his trainings, online courses, and group coaching.

Mike now lives mostly off of his passive real estate income and devotes his time to philanthropy, family, and traveling the world, having explored over 90 countries on all seven continents. Mike, welcome to the show.

Mike Wolf: Hey, good to see you. Thanks for having me.

Matt Bowles: Good to see you, buddy. Every time I talk to you, I never know where in the world we might find each other. So, let’s just start off by setting the scene. I am actually recording from Rio de Janeiro in Brazil today. And where are you?

Mike Wolf: I am in Genoa, Italy, which is the home of Pesto, just so you know.

Matt Bowles: Amazing. I have been there, and it is a very beautiful place.

Well, I want to start off a little bit before we even get into this entire digital nomad, traveling-the-world lifestyle that you’re currently leading and living off of your passive real estate income. I want to go all the way back and take us on the journey about how you got there, and maybe just start off a little bit, Mike, with where are you from? Where did you grow up? Tell us what that was like and what ultimately led you to decide to buy your very first rental property.

Mike Wolf: All right. Well, first of all, I haven’t grown up, and I hope I never do. But I was raised in Canada. I did most of the beginning of my real estate career in Canada. And how I got started was a really good mistake.

I remember I was in the middle of Grade 12. I had no idea what I wanted to be, you know, what I wanted to do the following year once I graduated. And my parents, especially my mom, it was always like, “Mike, you got to be a doctor or lawyer.” That’s all I ever heard growing up: doctor, lawyer. And I’m terrified of blood, so doctor was not in the cards ever.

But, you know, I used to watch those, like, Perry Mason, those lawyer shows where they have the big fancy offices. And I’d go, “That looks kind of cool.” So, I decided I would make my mom happy, and I went to university and got my first degree.

By the time I got that first degree, though, I had all these student loans. And I decided, you know what? Before I go back and get that second degree, I want to get these things paid off.

So, I got a job at the phone company. A buddy of mine, his mom was a manager there. And at the time it was government, it was union, paid more than it really should have, to be honest, but I won’t complain.

Anyway, so I took this job. And while I was there, I managed to get my credit score was impeccable. I had a government job, so I had a mortgage broker friend of mine who helped me get my first mortgage. And we had to be creative because I didn’t really have a down payment because, remember, I had all these student loans.

So, we got a little bit creative, all legal, but we managed to get my first property. And this was to live in. That was my principal residence. Shortly after that, my mortgage broker friend called me up and goes, “Mike, if you want, I can get you another mortgage if you want to buy another property.”

At the time, like, I’m a single guy, early 20s, thinking, “Why? Why on earth would I want a second property?” It was a totally foreign concept to me at the time.

And he goes, “Well, you buy the property, you put a tenant in there, they pay your mortgage for you. Whatever over and above that there is, there’s your passive income. And eventually that’s going to be your retirement. You hold on to this thing. Twenty-five years from now, it’s going to be paid off, and that’s your retirement.”

And so, I thought, hey, that makes a lot of sense. So once again, we had to be creative because I still didn’t have a down payment, and we managed to buy that second property. That was my first rental property.

And at the time, I didn’t know anything about real estate. It was never even on my radar. The reason I love to tell people this is I get a lot of people coming to me and saying, “Oh, I can’t get started because I don’t have any money,” or “I don’t have any time,” or “I don’t have any this or that.”

The fact that you’re talking about it, you have an interest in it, puts your light-years ahead of where I was because I didn’t have an interest in it. It wasn’t something that I ever thought I would be or could be. And anyway, the rest is history because here I am, 36 years later. And it wasn’t all easy, by the way. There were definitely some ups and downs, especially at the beginning.

But here I am, 36 years later, still doing it, still loving it. I don’t do it the same way I used to. I now have other people that on my teams, finding deals, etc. And I’m not really on the front lines anymore. But I still love what I do. And I am very glad I did not become a lawyer. That’s all I got to say.

Matt Bowles: Well, let’s talk about how that first rental property ownership experience went when you were brand new to this. And then how did you eventually decide to buy your second rental property and your third and scale your portfolio?

Mike Wolf: Yeah, great question. So that first property, I got really lucky. I find it always, when you start something, you get beginner’s luck.

And this way, it went really smooth. The tenant was good. I didn’t know anything about due diligence back then, so I just thought, well, if I’m going to buy a rental property, I want to buy something close to where I live so it didn’t take me long to go pick up the rent check because, back in those days, we didn’t have all these newfangled ways to pay rent. And I wanted a house that was pretty. And, by the way, those are not the criteria that you should use when you’re picking a rental property. But it actually, surprisingly, went relatively smooth.

And then, a couple years after I bought that property, the market just took off in Calgary, where I’m from. Calgary is kind of the equivalent of Houston. What Houston is to the States, Calgary is to Canada as an oil city. And when oil was booming, so would real estate prices boom. Anyway, a couple of years after I bought the properties, still working at the phone company, by the way, my properties went up in price extremely quickly. And that’s when I got hooked. Even while I was holding, I never thought, “Oh, I’ve got a rental property. I’m going to be a real estate investor the rest of my life.” It was still, “Hey, I’m going to go pay off my student loans, go to law school.”

And once that happened, once these properties took off in price, I was hooked. Anyway, that’s basically how I got into it and how I got to scale. Although I sold that rental property, I took that money, and all of a sudden, I had some money to play with. I remember I quit my job not long after, which—don’t do that either because it made it very difficult to get financing after that.

I also told my mom. My mom was going, “When are you going to go back to law school?” And I told her at that point, “You know what? I’ve decided that’s not my dream. That’s your dream for me. That’s not really my dream. I’m going to be a real estate investor.” And my mom is still pissed at me to this day, by the way.

The next thing I did was I decided, “Hey, well, I quit my job, so I’ve got to make paychecks more frequently. I can’t wait two and a half years till my next paycheck. I’ve got to have some cash flow.” So, I decided I was going to become a flipper. And that went extremely poorly at first because I didn’t know what I was doing at that point. Being in my mid-20s by this point, I remember just thinking I knew everything there was to know about real estate investing because I had that first lucky success. My ego got the best of me, and I just thought, “Hey, I’ll figure it out as I go.”

Don’t do that. Because on my next deal, I lost almost all of what I made on the previous deal and realized that there are a lot of things you have to do if you want to be a flipper that are not the same as just buying and holding an already fixed-up property.

So basically, the only reason I’m really still in this game is because I told my mom not to worry, I’m going to make this work. And I didn’t have the heart to tell her she was right because you can’t tell your parents they’re right, ever. So, I thought, “I’m going to figure this out.”

Shortly after that, I actually found somebody who was flipping properties in Calgary and had them take me under their wing. I invested my remaining money in one of their projects. I said, “I’m only putting money up. I don’t even want part of the profit. I want my money back, but not part of the profit. What I want is for you to show me, step by step by step, what you’re doing.”

So anyway, for many years, I was doing flips. Then I got back into rentals after I realized, “Hey, you know, these homes that I’m flipping and making $20,000 or $30,000 on…” Back then, I thought I had learned how to win the jackpot. I thought I could duplicate it over and over and over again.

But I realized, over time, that when you watch those homes later down the road, they’re worth $100,000, $200,000, or $500,000 more than what you sold them for. Then it’s like, “Okay, well, I’ve got to start holding and buying some more of these rental properties.” So, I took a little bit of a hiatus, but then I got back into it, and I’m so glad I did.

Matt Bowles: And now after doing this for decades and working in all the different aspects of the real estate investing space, can you talk about how you got into to real estate, education, coaching and teaching others how to build their wealth and their passive income through real estate?

Mike Wolf: Yeah, so once again, that was a mistake.

As I mentioned, I got my start in Canada. I had a friend move from Canada to Las Vegas, and I’d go visit him frequently because I enjoyed it. It’s very close, a two-and-a-half-hour flight from Calgary. So, I’d go there every couple of weekends. But I’m not a gambler. My addiction was I had back then, I had to look at every open house. I could not drive past an open house sign without going in and having a conversation with a realtor. Next thing you know, I’m asking, “Well, why are they selling?” and “What’s the market like?”

Anyway, back then, a lot of Californians were moving to Las Vegas to lower their cost of living. And I’m thinking, “Man, this is so much easier here than it is in Canada.” So, I started investing in the U.S. as a Canadian, back before it became kind of the in thing to do.

And I remember, all of a sudden I get a call out of the blue, This was a few years after, now the market in Vegas instead of people moving from California to lower their cost of living, we were heading into a recession, and prices in Vegas were actually plummeting. I was only buying one or two properties at a time, so I was actually not affected. Matter of fact, I had a lot of cash sitting around, so I started buying properties to hold in Las Vegas instead of flipping them at that point.

I remember there were auctions that took place in Las Vegas in a parking lot. Monday to Friday, there were going to be so many foreclosures that they’d have auctions from 9:00 to 5:00 every weekday. At first, there were only about five of us there, and none of us were American, by the way. I was a Canadian. I remember there was an Israeli, somebody from China or somewhere else in Asia. Anyway, all of us were from somewhere else. No Americans wanted to touch real estate at that time.

Then I got a call out of the blue—I won’t mention their name—but it was from a very prominent, well-known real estate education company. They were having a hard time getting people to show up at their events in the States, so they decided they wanted to go across Canada. They called me and said, “Hey, you know what? We’re looking to do these events across your country. We’ve asked a few people who we should get. We’re looking for a Canadian who’s invested in the U.S., and your name was the only one that came up. Can you come speak for us?”

At that time, I had never spoken on a stage in my life, and I was terrified. If it hadn’t been such a prominent company, if it had just been somebody with a real estate club or something, I would have said no because I was terrified. But I kind of forced myself to do it.

As I did it, I ended up traveling across Canada for them for a while. But as I saw what they were teaching, I thought, “Okay, well, a lot of this…” I remember sitting there thinking, “Okay, well, I think they just taught people how to do mortgage fraud. That’s not good.” They were also teaching people things that had worked 10 years ago. That’s not good either.

So, I eventually called up the head office and said, “Listen, with a clear conscience, I can’t speak on your stages. If you want, I can help you create courses on stuff that’s actually working right now and that’s legal.”

They didn’t care. They were making millions and millions of dollars. They didn’t care what I had to say.

So, I parted ways with them. After I did, I had all these people reaching out to me who had seen me speak on their stage. They were saying, “Mike, your stuff was the only stuff that seemed actionable. Your stuff worked. How do we work with you?”

At the time, I had nothing. I just had a passion for teaching and showing people what I was doing. I didn’t have any courses, I didn’t have any training programs, and I wasn’t looking for other investors for my projects. I was just kind of a lone wolf, so to speak. That’s my last name—Wolf. I was a lone wolf.

But I decided that, you know what, there are all these people paying for education, and they’re not getting a good education. Why don’t I go teach people, like I said, what actually works?

So, I remember taking a group of Canadians down to Las Vegas. I started bringing them to that parking lot, showing them how to find these deals. Then I had teams on the ground to fix them up and manage them. That was kind of the beginning of that side of my career.

So once again, I wasn’t really looking for it. I certainly was not looking to speak on a stage at that point. It all developed from forcing myself way out of my comfort zone. So once again, another good accident.

Matt Bowles: Well, I want to also ask you about your passion for travel. You and I are both digital nomads. We’ve known each other for well over a decade now. You and I see each other and meet up all over the world. And I’m wondering if you can share a little bit about that lifestyle and because you were so passionate about creating that lifestyle, how you’ve now been able to finance and facilitate, facilitate that lifestyle with your passive rental income.

Mike Wolf: I always had a passion for travel. And back when I used to be married, I would drive my then-wife crazy because I’d always say, ” Let’s go somewhere.”

I actually convinced her to travel the world back when my daughter was in grade two. We took our daughter out of school in grade two and grade three, homeschooled her, and traveled around the world. My ex-wife got really kind of sick of it. I could have kept going forever. She got sick of it, and she was missing her parents, which is fine. I’m not faulting her for that.

But when we got back home after that, that’s all that was on my mind—that one day, I’m just going to travel full time. I’m going to travel full time when my daughter grows up.

Anyway, not just because of our differences on travel, but eventually I ended up getting divorced. I’m on really good terms with my ex because, when that happened, I knew I wanted to travel. So, it’s like, “You can have everything. I want you to have all the furniture.” So, I got rid of all my stuff.

A lot of people get divorced and get rid of their stuff, but they’re not really happy about it. I was actually happy about it.

Back when I got divorced, my daughter was 13, so I didn’t want to travel full time yet because I wanted to spend time with her. But then, as she grew up and decided she liked other boys more than hanging out with her dad all the time—we’re very close, but apparently boyfriends are more important than Dad—I decided, instead of me always traveling for a week, coming back for a couple months, traveling for a week, why don’t I travel for a couple months and come back for a week?

I remember, at the beginning of that, I would fly my daughter to come see me, but I wouldn’t bring her boyfriend. So, I got some more father-daughter time, which worked out pretty good.

But now I’ve got two grandkids, so when she got pregnant, that changed things. So, I go back to Calgary three or four times a year for a couple of weeks, and sometimes I bring the family to come see me in different places.

But all this is supported by my real estate. So, once again, I was mentioning how I went from flipping to getting back into having rental properties. Every single one of my rental properties is managed by somebody else. I don’t deal with any of that.

So, it gives me not only the financial freedom but also the time freedom. And that’s so important because I know a lot of people that have a lot of money, but they don’t have the time. They can’t go to their kids’ soccer practices, let alone on long vacations around the world.

So, it’s really important that you protect your time. That’s why I think rental properties are so important. But they have to be managed by the right people. You have to have the right team. And if you don’t, you’re not going to get that, even if you have the financial freedom.

If you have a big bank account, that’s great, but you’re not going to have all those other things. You’re not going to have a well-rounded life because you’re going to be busy working, chasing that next paycheck, and putting out fires.

Matt Bowles: Well, Mike, at this point, I want to ask you if you can just reflect back on the last 36 years of your real estate investing journey.

You mentioned that there were ups and downs, mistakes, and bumps along the way. But obviously, now you’ve been able to create your dream lifestyle, finance it with real estate, and you’re training others how to do what you did.

So, I’m wondering if you can think all the way back on that journey and condense down your top three lessons that you learned along the way that you wish you had known on day one, when you were just starting out. What would lesson number one be?

Mike Wolf: Man, I wish I could go way back in time and have a do-over, or even just talk to my younger version of myself.

Number one was I should have gotten a mentor right from the start. As I mentioned, I did my first deal, didn’t really know what I was doing, and got really lucky on it. Then I did that next deal—something I wasn’t at all versed in. Flipping homes was not something I’d ever done. It’s a lot more dangerous than buying a rental property.

Real estate is very forgiving, and if you hang onto a property long enough, you’re going to look like a genius at some point. So anyway, I got the mentor after I messed up. Had I gotten a mentor right from the start, I could have started off on the right foot.

So, I’d say getting a mentor is definitely one of the most important lessons, and definitely something that I would do if I had a do-over.

Matt Bowles: All right, what is lesson number two?

Mike Wolf: Yeah, well, we touched on this one too. Not too long ago, I went back to Calgary to see my family, and I met a buddy of mine who I used to flip homes with back in the ’90s. We went to Starbucks, and he said, “Mike, remember all those homes that we sold? We thought we had hit the jackpot. Man, don’t you wish we still owned all those homes?”

So, start creating passive income as early as possible. Start holding onto properties. All those flips we did were great. I’m not saying don’t flip homes. You can make some good money doing it. But definitely, as you flip homes, start to hold on to property. Start creating passive income for yourself.

The passive income is what gives you the freedom. It’s what allows you to have that time back. And once again, I have a friend who’s an extremely successful flipper, but every time I go to visit him, it’s like I say, “Why don’t we go meet for dinner somewhere?” He goes, “Just jump in the car. Just jump in the car with me. It’ll just be an hour, then we’ll go for food.”

We end up driving around all day while he goes from work site to work site to work site, making sure his team is showing up, things are getting done, and allowing him to micromanage everything. And I’m just so glad I don’t do that anymore.

So, create passive income. Get stuff coming in on autopilot for you. Earned income is great, but it’s even better when it comes in passively.

Matt Bowles: Yeah, I think that’s really, really important. My company, Maverick Investor Group, of course, as you know, Mike, helps people buy these performing turnkey rental properties that are already renovated, with tenants in place and property management. A lot of your clients—you’ve been sending your clients to buy their properties through Maverick and everything else—so that they can build those portfolios.

I think that’s a really important distinction as well between active income, which would be flipping rental properties—that’s a form of active income. But also, just going to the office and working at your job is a form of active income.

So, if you need to generate active income, the important part is to take the money you make from your active work and invest it in buying and holding those rental properties long term so that they can generate passive residual income for you, appreciate in value, have your tenants pay down your mortgage, and allow you to take advantage of the tax benefits and all of those things, which continue to compound over time.

So, I think that’s a really good one as well. And then, what would lesson number three be, Mike?

Mike Wolf: Yeah, so lesson number three would be to, I would say, start focusing on building teams early on.

For many years, I was a solopreneur, and I would do everything. The only thing that was lucky for me is that I still, to this day, can’t use a hammer. I’m disappointed that Home Depot sells a hammer and it doesn’t come with an instruction manual on how to use that thing.

So, I was never handy. Otherwise, I probably would have tried to paint homes myself and fix things up.

But I did everything else. I would go try to find the deals, find the tenants, and collect the rent. I had so many things going on. At one point in my career, I was spending 12, 13, 14 hours a day running around trying to get everything done.

I always thought that having a team would be too costly. It’s actually too costly not to have a team. I would build a team way earlier on if I knew then what I know now. Everybody on my team is actually smarter than me, and they don’t need me to micromanage them because they know what they’re doing better than I do.

So, get your A-team, get it as soon as possible, and be creative. Like I remember, like I said, I’ve never been handy ever in my life. So, I was forced to hire contractors, and that’s the best thing that ever happened to me. I used to look at that as a curse and think, “Oh man, if I could just fix this myself, I could save so much money.”

What it allowed me to do, while contractors were fixing up my homes, was go find more deals. And that’s where the money is. The money isn’t sitting there painting your home. That’s a minimum-wage job. Do the stuff that is going to make you the most money. And to do that, you need teams.

Matt Bowles: And a lot of these people on your team are not even going to cost you any money.

For example, you can get a mortgage lender that probably specializes in doing loans on rental properties, and they’re just going to be able to work for you for free and give you good faith estimates and all of this kind of stuff. That’s not something that you pay out of pocket for them to do.

And the same thing with a company like mine, Maverick Investor Group. We’re a real estate brokerage. We don’t charge our clients any money at all to work with us. If and when a deal closes, we get paid, but the money gets paid by the seller, not by the buyer.

So, you can actually build up quite a team of folks that you don’t actually have to pay out of pocket.

Even a property manager—they’re going to take a portion of the rent that comes in, but they’re going to be, of course, leasing and qualifying your tenants, collecting the rent, handling the maintenance, and doing all of that work so that you don’t have to do it. That way, you can recapture your time and do, as you said, Mike, either the more valuable stuff, which is going to make you more money, or travel around the world and enjoy the lifestyle.

So I think those are some great lessons.

Mike Wolf: Well, I’ll give you two parts to that. Number one is start by hiring people that can do things that you can’t do. Then, hire people that can do what you do so you don’t have to do it anymore. And that’s where I’m at now. That’s how you get your freedom.

Once again, if you have your A-team, you don’t have to be there to micromanage them, crack the whip, and drive around all day making sure they show up. So, treat them well, they’ll hopefully treat you well, and that’s how you get freedom.

To me, that’s the most important thing.

Matt Bowles: Well, Mike, can you give us a glimpse into your travel lifestyle? You’ve been to 90 countries; you’ve been to all seven continents. What have been some of the highlights, like the bucket list sort of memories that you still have today that you were able to achieve through the real estate passive income ultimately?

Mike Wolf: Yeah. Well, I mean, there’s so many.

And right now, I’m actually having—I just had a villa built in Bali. I’d gone there many times, and because I always like to talk real estate, I’d go meet people who were successfully building villas there. I never thought I would build one myself. Then, all of a sudden, I’m reading that Bali is the most popular, hottest vacation spot on the planet.

So, I thought, “You know what? I should go and build a villa, put it on Airbnb.” And I have, and it’s doing exceptionally well. So, I’ve been able to mix my passions of real estate and travel.

But there are so many places that I love. Costa Rica, here in Italy where I’m at now, the Greek Islands, going to Antarctica—it was an amazing experience. There are so many. I have so many amazing memories of all these places that I’ve been to, and many of them I’ve visited numerous times. I’m just so grateful that I had that really awesome mistake of discovering real estate investing at a pretty early age.

Even though there were, like I said, some definite down times and times when I thought, “What am I doing in this industry?” I’m so glad that I stuck with it. Because if you would have asked me 36 years ago what my dream life was, and I had given you the most ridiculous life I could imagine back then, it wouldn’t be as good as what I’m actually living now, because this wasn’t even on my radar.

And so, I’m just so grateful for real estate. I think the universe decided I wasn’t cut out to be a lawyer, and I’m grateful. No offense to any lawyers watching, but that would not have been a good career path for me. I just can’t imagine, once again, doing anything else besides real estate and travel.

Matt Bowles: Well, I think the last time you and I actually met up in person was in Bansko, Bulgaria, which is this beautiful place in Bulgaria.

And once you start traveling the world and getting into those digital nomad circles, you and I now know people all over the world who are either from those places or who happen to be itinerant travelers. We meet up with them in those places, and it is really quite an amazing network that you start to develop once you incorporate traveling into real estate as well.

Well, Mike, I want you to let folks know, at this point, maybe share a little bit about some of your coaching services and offerings that you have today. If people wanted to connect with you on that level, or if people just want to follow you, find you, connect with you, and keep up with everything you’re up to, how can people come into your world?

Mike Wolf: Yeah, well, you can come check out my website, which is mikewolfmastery.com, and I’m sure you’re probably going to post the link there.

You can also email me at info@mikewolfmastery.com.

I love talking real estate. I love talking travel. I’m in the midst of creating new recorded training on travel hacking, teaching people how to travel for cheaper and how I get first class for less than what a lot of people are paying for economy, as well as how to get status with hotels to enjoy all the perks.

That’s actually become one of my passions because I meet so many people who are paying way too much for travel. So, if you’re a traveler, or somebody who wants to travel, I’m happy to talk about that. Of course, if you want to talk about real estate, I could talk about that all day long. You’re going to have a hard time kicking me off this show.

So, reach out. Don’t be afraid to reach out. These are my passions, and I’m always happy to talk about them.

Matt Bowles: All right, we are going to link all of that up in the show notes. Everything’s going to be in one place if you want to find, follow and connect with Mike.

Mike, thank you so much for coming on the show, man. It’s always great to catch up with you, my friend. This was great.

Mike Wolf: Yeah, thanks for having me, buddy. And one of these daily is we’re going to be in the same place at the same time. Again.

Matt Bowles: We will indeed.