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Today’s episode features an inspiring conversation with Matt Aitchison
, a true example of resilience and growth in the world of real estate and entrepreneurship. Matt is a real estate investor, entrepreneur, and host of the Millionaire Mindcast podcast. His journey—from flipping his first “cat house” in his early twenties using 100% other people’s money to building a diversified portfolio of shopping centers, hotels, medical offices, and mobile home parks—is a masterclass in persistence, creativity, and lifelong learning.
Matt’s story stands out not only for the impressive deals and assets, but for his dedication to surrounding himself with mentors and peer communities that drive accountability and continuous development. Throughout the episode, you’ll hear about how Matt shifted from hustle-driven house flips to cash-flowing commercial properties, as well as his philosophy of becoming a “whole life millionaire”—achieving true wealth across finances, relationships, health, and impact.
Matt shares actionable insights on how to structure your life and investment strategy for long-term success. He offers valuable lessons learned from both his wins and setbacks and highlights the importance of likability, mindset, and creative approaches in today’s market environment.
In This Episode
- Matt’s entrepreneurial start and breakthrough first deal
- The transition from active income flips to passive commercial real estate investing
- Why mentorship, community, and lifelong learning are critical to wealth building
- Practical strategies for thriving in today’s changing real estate market
I’d rather under-promise and way over-deliver than do the opposite. And unfortunately, that’s the challenge we’re seeing with a lot of people that did the alternative.
Welcome to the Wealth Strategy Secrets of the Ultra Wealthy podcast, where we help entrepreneurs like you exponentially build wealth through passive income to live a life of freedom and prosperity. Are you tired of paying too much in taxes, gambling your future on the stock market, and want to learn about hidden strategies for making your money work for you? And now, your host, Dave Wolcott, serial entrepreneur and author of the bestselling book The Holistic Wealth Strategy.
Welcome back to another episode of Wealth Strategy Secrets of the Ultra Wealthy. Today, we’re diving into the entrepreneurial and real estate journey of someone who embodies persistence, creativity, and the long-term mindset it takes to build lasting wealth. My guest is Matt Aitchison, real estate investor, entrepreneur, and host of the Millionaire Mindcast podcast. From flipping his first cat house deal in his early 20s with 100% of other people’s money, to building a portfolio of shopping centers, hotels, medical offices, and mobile home parks, Matt has mastered the art of scaling from hustle-driven house flips to cash-flowing commercial assets.
What I love about Matt’s story is how much it illustrates the true traits of wealth, resilience, resourcefulness, and surrounding yourself with mentors and communities that push you to grow. In this conversation, we’ll unpack not only his real estate strategy but also his philosophy of becoming a whole life millionaire — building wealth across finances, relationships, health, and impact. If you’ve ever wondered how to shift from active income to true passive wealth, why likability may be the most underrated superpower in business…
And how to structure your life so you can say, “Damn, that was a hell of a ride” at the end. You won’t want to miss this episode. Matt, welcome to the show.
Thanks for having me, Dave.
You bet. Awesome to see you again and really looking forward to today’s discussion. And I definitely know the audience is going to enjoy this. Anytime you can get two like minds together who’ve had similar journeys but different paths, there’s so much to learn. In someone’s journey, where did they make those mistakes that I can look out for? Where did they have those successes? Where can I find leverage points in my own strategy?
I know personally for me, I always find so much learning in those success stories and the case studies from other people. So definitely want to unpack that with you today and really just kind of jump into your real estate adventure, what you’re doing today, and how we can help other people really achieve the same success.
So why don’t we start there, Matt? Let’s just jump into your journey. How did it start for you? How did you get into the whole space and get to where you are today?
Well, entrepreneurship, as you said, is quite the journey, right? And obviously everybody has their own path and many different paths. But you know, I’m a big believer. I’ve never been the smartest, sharpest, fastest, strongest guy. So I always try and pay attention to people and learn from the breadcrumbs they leave behind in their own trails and see how those apply to me. My journey started just like most do, right? You have a dream and a desire to achieve something more than what you think you have at that current moment. And so for me, I was getting out of college, and maybe I’ll back up a little bit. I got my first exposure to entrepreneurship in college. Both my parents were in corporate America, divorced when I was young, and kind of co-parented.
My dad was kind of the bean counter, the safe, not big aspirations and goals, just loved the security, wanted enough to pay for kind of the party of life, but was smart, diligent, good with his money, but nothing explosive. Just your slow and steady, and over time it compounds into something good.
My mom was more of the dreamer, didn’t love corporate America, always wanted something bigger and better for herself. And so she would drag me to real estate investing conferences when I was like 12, 13, 14. I remember seeing my first speakers up on a stage telling me about how to get rich and wealthy in real estate investing. I was like, man, that sounds great. But fast forward, I didn’t do anything with it. I was still in high school, still young. When I got into college, I got my first exposure to entrepreneurship working as a cold caller for a guy who had an insurance book of business in Santa Barbara, where I was going to school at the time. I kind of worked my way up, cold calling for him, then became one of his account managers, then kind of became one of his right-hand guys.
As I was graduating, kind of deciding what I wanted to do with my big expensive piece of paper, he wanted me to take over his book of business but still be working for him. I saw all the fun and freedom that he had as an entrepreneur and said, I don’t know, I think maybe I want to give this a shot myself.
So I moved back to Sacramento, where I’m from, and was interviewing at a bunch of places, but didn’t find anything that really met what I was looking for. And of all places, it’s funny when you look back and see what I call the catalyst moments of life in your journey. Mine was a Craigslist ad: Real estate mentor seeks REAL estate mentee. I quickly learned that meant come and do a lot of work for me for free. And I worked for this guy for a year for free. This was back in 2010, when there were foreclosures everywhere. I said, you know what, I’m going to work for this guy for a year for free. I saw he was making $50,000, $60,000, $70,000 a house flip.
And obviously this was back when you could do that very easily. But I learned the whole process—from acquisitions to project management, to dispositions, to analyzing deals, to structuring deals. And at 21, I had the experience of flipping over 100 houses working with this guy. I said, you know what, I think I can do this myself. So I was going around neighborhoods tacking up bandit signs on telephone poles, and after about a hundred “get your ugly sign out of my neighborhood,” I got that one call that changed my life. It was actually a cat lady house. She had over a hundred stray cats in her home. I made her an offer of $75,000. It still sounds crazy to hear that price tag knowing what prices are today, but $75,000.
I remember she signed the contract. I walked out of that house, got in my car, and mind you, I’m Tiger Woods fist pumping, I’m discount double checking, celebrating. I remember fixing my rear view mirror, and I see myself and go, shit, how am I going to pay for this house? I was still living at home with my dad. I was broke. I had a bunch of credit card debt. I remember an early mentor told me, if you find a great deal, the money will follow. I subscribed to that mindset and was able to get private money first, a private money second. I funded that deal using 100% of other people’s money.
I sold it for $230,000 after rehabbing it about four and a half months later, paid off my private money first and second, and I walked with about $106,000 net. That was my big light bulb moment early in my journey. Real estate was going to be the path for me. Creative finance was going to be the path for me. And this was the journey I was going to be on. Fast forward, over the next five years, I flipped a couple hundred houses. Obviously a lot of failing-forward moments along the way.
As I started generating decent income, I quickly learned I was only as good as my last flip. I had an active income stream, still trading time for money. I had to start thinking about how to unlock more time freedom, more financial freedom, which led me to keeping more of the houses. As I started building my single-family portfolio and managing all the headaches of owning real estate—it’s obviously not passive no matter what anybody tells you unless you’re doing maybe a syndication or a REIT. But for me, I was in the trenches, learning through the school of hard knocks.
I quickly learned that $200 a door per month was going to require a lot of doors for me to get to my financial freedom goal. I’m a big believer in, where do you want to go, when do you want to get there by, and let’s reverse engineer a game plan that allows you to do that.
So for me, I said I wanted to generate $500,000 a year in passive income over the next 10 years. I only wanted to buy one property a year instead of 50. That led me to transition my business and portfolio over to commercial real estate. I created my model: buy one commercial real estate property a year that nets me $50,000. If I do that for the next 10 years, I’ll chip away at that. One property a year was much more manageable. I just needed to understand what types of deals net $50,000 a year, what markets they’re in, and what strategies tie to those asset classes and vehicle types.
That led me to buy my first shopping center. It was a 100% creative finance deal as well, because I was still lacking resources. But I was a very resourceful person, which is a great lesson for anyone willing to bet on themselves. I always say, just be dumb enough to believe in you and smart enough to take action on what you think will get you where you want to go.
That led me to my first shopping center, then my first hotel, second, third hotel, buying shopping centers, boutique hotels. Now my portfolio consists of medical office buildings in addition to mobile home parks. Commercial real estate is where I hang my hat today, where I’ve built my wealth, and where I’ve unlocked many of the great things I’m extremely grateful for.
Yeah, really awesome journey. And I want to underscore a couple of those things, like big takeaways for the listeners out there. Number one was, you sought getting a mentor early on. It’s one of the keys. Wherever you are, at whatever stage, you have to always be thinking of being a lifelong learner, right? We can always improve our capabilities, even if we’re at the best. You talked about Tiger Woods. I mean, what do they do? He’s with his swing coach seven days a week, right? Even athletes at the absolute top of their game are working with mentors, coaches, things like that to improve.
So anywhere we can do that through masterminds, mentors, or communities that you can learn from is always essential. And then I thought it was great that you really just took action on that deal, and so many traits really come through as an entrepreneur. You can be in any business; it doesn’t have to be real estate. It could be anything. It’s resilience, it’s persistence — all of these things that you had to get through on your first deal. And then confidence. It’s those four Cs: you make a commitment, you have courage, and then you build a new capability which creates new confidence. Then you just repeat that cycle. But you’ve got to start with that commitment and having the courage to make that commitment 100%.
When you improve other forms of capital-intellectual, emotional, physical, spiritual-financial capital has a way of showing up.
I think a lot of people always feel like they need to know everything before they do anything. I’ve always been, honestly, of the thousand-plus interviews I’ve done with people like you and other successful investors, business owners, entrepreneurs on my pod, one of the things that I find as a common thread amongst most is this immediate default to action. They know there are things they don’t know and therefore have heightened awareness around blind spots and gaps. But they are consistently reiterating ways to optimize, adapt, pivot, and take real-time feedback and data as they’re taking those actions, making small micro tweaks along the way. It’s kind of like that story of the flight path of getting to the moon. They had a goal and a plan of, “Hey, we’re starting here, we’re trying to get there.”
But there were so many different iterations and course adjustments along the way. That came through that feedback loop and hyperactivity around taking the data and making the next best decision with what you have. That’s what I try to do. I know I’m not the smartest, fastest, or strongest. I try to surround myself with the people who are, and I keep my awareness up in the areas that I know are blind spots for me or potential threats or weaknesses. I double down on my zones of genius and in areas that I know I am good at and validated in. Like you said, staying in a constant state of curiosity and learning. I’ve had paid coaches in my life literally since day one of entrepreneurship and business. Those are worthwhile investments from an accountability and growth perspective that obviously give a real ROI on paper from your P&L and balance sheet perspective. But who you continue to grow into and metamorphosize yourself into as a result of that accountability, transparency, and commitment to growth —
To me, that’s been an even higher ROI that doesn’t show up on my P&L and balance sheet: who I’ve become. I’ve always been a big believer that your business and wealth are a reflection of your willingness to work on yourself and keep growing. Your business grows to the extent that you do. That’s something I always try to keep front of mind when I’m consistently setting goals in my own life.
Your business and your wealth are a reflection of your willingness to work on yourself and keep growing.
It’s interesting. You can actually tell what level people are operating at as soon as you start interacting with them — who is being coached regularly and learning and growing. I can always tell within the first couple of minutes how the conversation goes. If someone has a fixed mindset, they’re not willing to learn or are static in some thoughts. It’s so apparent to me. This brings up an interesting point, Matt, and how to bring this full circle for the audience. We talk about real estate being a people business, and we also talk about when you make investments, you’re really investing in the jockey and not the horse. Some of these traits you just nailed are spot on, because the only thing that is certain is uncertainty itself. Who could have foreseen a pandemic? The geopolitics we’re in right now? No one could, no matter how smart you are or what your pedigree is. Nobody can really anticipate some of these things. That’s why the VIX is so high and there’s so much volatility in the market and everywhere else.
When you’re placing capital for a long period of time, what you need to think about is investing in that team and those people. When they have traits like persistence, resilience, necessity — Brendan Bouchard’s top performance traits — that is what will help you get through the difficult times. Having that degree of resilience is key in this day and age.
100%. When you think about investing in people, people are what I call some of my greatest moats around areas I need to protect. Whether that is my wife as a moat — I chose to invest in a woman who creates a moat around a pillar of my life that is critical to what I believe my happiness and success are equal to. If I invested in the wrong relationship, we’ve all seen the downside of what happens to people that end up in divorce or toxic relationships. Many people say the greatest investment they’ve made in life is who they chose to marry and do life with. The same applies to the employees I have in seats on my org chart.
Those people are moats around those departments and their responsibilities in our shared mission. If you’re doing a syndication and investing as an LP into a GP, that team, their skills, track record, reputation, and core values — if you get that right — is a moat around your investment dollars. They’ll act as fiduciaries to make sure they do what they say they’ll do for you, even when times get tough. Nothing is guaranteed, nothing is perfect. But we can all relate to making a poor investment decision in any of those contexts and feeling the pain. There’s a lot of learning that comes from that. And we can all relate to saying, “I’m so glad I decided to invest with Dave,” or “I’m so glad I partnered with Matt on XYZ,” because those individuals with aligned core values are critical to the success and fruition of what you’re doing.
I look at people not only as an investment but as a true hedge to my downside in many areas of life, even when I’m not operating at my best. I couldn’t agree more with you on that statement.
Yeah, that’s an interesting perspective — to look at people building moats around people in your life. So it really opens up a bigger question we can go down. This avenue is really, first of all, what is your definition of wealth, Matt, and how are you organizing your life to achieve the wealth you want to achieve right now for your vision?
Yeah, I mean, I’ve interviewed so many people around this. The whole reason I started my podcast 12 years ago was so I could interview people that had amassed, quote-unquote, wealth and success and really unpack what it meant to them, how they approached it, how they got it, how they protected it, and how they grew it. I’ve heard and seen so many different definitions of wealth. I’ll back up to one of the first high net worth mastermind groups I ever paid to be a part of. I walked into a room of 20 millionaires, multimillionaires, decamillionaires, and a couple centimillionaires. And I saw two different people. I saw one person — everybody was financially abundant and an absolute killer in the room — but they were bankrupt in their health, they were bankrupt in the relationships with their spouses, they were bankrupt in the relationships with their kids.
They were bankrupt in their spirituality, they were bankrupt in their ability to want to give back and be philanthropic. And then there were other millionaires who were financially crushing it in their business, but they were equally as intentional, if not more intentional, in their marriages, with their health, with their kids, with their charity work. For me, one resonated more than the other, which was what I call the whole life millionaire — the individual that is financially savvy and skilled but equally disciplined and intentional in the other categories of life. For me, I believe wealth goes far beyond what dollars can buy. Wealth goes far beyond how many commas and zeros you have in your bank account or how many assets you have on your balance sheet. Jeff Hoffman was an early mentor of mine. He was the founder of Priceline and sold it for a multibillion-dollar exit.
One of the first times I heard him speak, he said, “Of all the successes I’ve had in my life, when people ask me what my definition of success is, it has nothing to do with money. It has to do with me getting to my deathbed and watching a metaphorical video of my life replay in front of me and me not saying, ‘Man, I accumulated so much money. Man, I had so many awards. Man, I had so many articles written about me.’ It has to do with being able to say one statement — and this is my definition of wealth — if you can get to your deathbed and say, ‘Damn, that was a hell of a ride,’ and you enjoyed every aspect of it: the good, the bad, everything in between. That’s how you know you left everything out on the floor of life. And that’s what I want to be able to say.” So, of course, does money make the world go around and fund a lot of those experiences and amplify that statement at the end of the day? Absolutely. That’s why I’m money motivated and driven in a lot of ways, because I know I can do good impact with my money.
Will Smith always said, money just makes you more of who you already are. For me, I want more tools and resources at my fingertips — i.e. money, currency, or whatever it is — that allow us to unlock and amplify the experiences and impact we as individuals want to have for ourselves, our families, and the people we care about, and also to give that vehicle and opportunity to others. That’s my definition of wealth: can I get to the end of my journey and say, “Damn, that was a hell of a ride”? And, of course, along the way, make sure I’m staying aligned with my core values and making an impact on other people that leaves them better than when I first connected with them.
Yeah, love that. Having a great ride but making sure you don’t blow up along the way is key, for sure. That’s such a good perspective. And I think the interesting part is that if you look at behavioral psychology and neuroscience and everything we’re taught, especially at a young age in this culture, we’re grinding and chasing the dollar. We’re chasing it so much because you need it — you’ve got to pay the rent, you’ve got to pay for the car, whatever it is — just grinding. But in actuality, what you talked about is spot on. We like to talk about that in terms of the dimensions of capital — really having six dimensions of capital: spiritual, intellectual, physical, emotional, all of those outside of financial capital.
When you focus on improving those other forms of capital, it’s amazing how financial capital can just show up when you need it and you’re not chasing it. That’s the really cool thing.
Yeah, I believe that if you just focus on one of those pillars, where attention and energy go, results follow. Oftentimes so many people talk about balance and counterbalance, but it’s a myth in a lot of ways. It’s a swinging pendulum that, if you get too far off kilter, you find a way to recalibrate in some ways. I have an all-inclusive mindset. When I go to an all-inclusive resort, I don’t just go there to get some of what they have to offer, I go to get all of it.
That’s the way I look at life as well. I’m not just here to get successful in my financial pillar. I want to be successful in every pillar of my life. That’s the standard I’ve set for myself and what I’ve seen from other highly successful individuals. Because a lot of these extremely wealthy and well-off people I’ve connected with are also very empty, very unhappy. To me, I wouldn’t trade my happiness for any amount of money. Personally, I know a lot of poor people that are happier than most rich people I know.
So I think ultimately, happiness being an inside job, when we find ways as human beings to challenge ourselves, to grow, and to maintain standards and disciplines in our life, when you do that consistently, like you said earlier, you feel good and confident about who you are and what you’re capable of, even when you have little failures and stumbles along the way. When you’re operating below the standards and capabilities of what you know you can do, we all know that too. You feel the guilt and shame, you beat yourself down. To me, I am a framework guy. I try to build metaphorical bumpers to the bowling lane of each one of those pillars, so I’m not bowling gutter balls. At least I know I’m not going to consistently bowl strikes all the time.
But I also know I’m not bowling gutter balls and putting up zeros. If you can have good quality frameworks in certain areas of life — your business, wealth building, relationships, whatever it may be — that’s going to make sure you keep putting up points on the scoreboard and moving the needle forward. That’s all I try and do every day.
Yeah. So you clearly have the mindset piece wired, Matt. In terms of asset classes and real estate, where we are in the cycle, where are you seeing opportunities for the rest of the year and heading into next year?
Yeah, I have been in and out of many different asset classes. I would say the core expertise of myself, my team, my shop is hospitality and shopping centers. I also own medical office buildings and mobile home parks. Where we’re at in this market cycle — just like the economic cycle — real estate goes through a cycle as well, four quadrants. I believe right now we are in somewhat of a… Let me back up real quick.
Each asset class can be at a different place in the cycle based on what market they’re in and what asset type they are. We’ve had some extremely insulated performers over the last few years, with the top two being retail and industrial storage. Mobile home parks, I think, are really starting to get more attention from an institutional level just because of affordability issues. Mobile home parks are often the last layer of affordable housing before somebody goes homeless. There’s always going to be demand for them, and the ability to develop them is often not as supported or incentivized from city and county perspectives these days. Industrial, of course, is going to continue to be very strong for obvious reasons. Data centers right now are really the new kind of “sexy” date on the block with AI, crypto, and the energy needs of that infrastructure being front and center.
I think we’re very early in that space, honestly, but that’s going to be something most of the institutions are playing and taking up most of the opportunity. For me, I always say right now, with us being in a high interest rate environment, we do have, as of this morning when I checked, about an 87% chance of a cut from the Fed in September. It looks like the market is already baking in another 25 basis point cut in December. We’ve heard whispers of anywhere from three to six cuts next year. I don’t think we’ll get Trump’s 300 basis point cut that he’s calling for, nor should we, but I think it’ll be the beginning of some easing, which will create some opportunity for challenged assets and sponsors to recapitalize their capital stacks. We’re still at this beginning stage of distress flushing through the market, mainly in multifamily.
But it looks like multifamily has started to bottom out a little. In these environments, I always say some of my best deals are creative finance. For example, a mobile home park I just closed on about two weeks ago was a 100% finance deal. I wired about 10k out of pocket to buy the entire park. I would say this is the season of seller finance. With rates where they are, economic modeling is very challenging for sponsors to make deals pencil and go.
Why would an investor put money in a deal at a five or six cap when they can throw it in a CD right now with no risk and no management? Those challenges have created a lot of staleness in the market. That being said, I’m a big believer — and I don’t know what your thought is on this, Dave — but in every bear market or bear cycle, there’s always some bull opportunity somewhere. In hindsight people say, “Man, how did that guy find that deal? How did they get that opportunity done? How did they acquire that at that price?” There’s always a needle in the haystack if you’re looking for it. These are the markets where deals are made, not found. You’ve got to come to the table with a creative lens and identify how do we create a win-win for both of us in this challenging climate. I know where you stand and I know where I stand, and we’re pretty far apart.
So is there any way, through our own creativity, that we can come to the table, put our minds together, and structure something that works in the short term or near long term? That’s where I’ve been able to find a lot of great opportunities. That’s where I’ve seen a lot of people get great deals — creative finance, getting owners and buyers to the table to creatively structure deals and capital stacks. I do think we’re still in this messy middle. A lot of policy is still being absorbed from the new Trump administration and what that’s going to trickle down into the economy and how it’s going to impact us. In times of uncertainty, I believe there’s great opportunity. As investors, volatility is the price we pay for trying to get wealthy and rich. It’s just something you have to get used to, navigate through, and surround yourself with great people like you.
Having these types of conversations and keeping a pulse on what’s going on in your asset class and industry is critical, because there are opportunities out there — they’re just fewer and farther between right now when things aren’t as abundant.
Yeah, that was definitely a solid overview, and I would concur with most of your points. I think the key thing that investors should be keen to really understand is that from a psychological standpoint, literally, it’s like 90% of the time, we get it wrong because humans are emotional and we get our emotions in the way. So this goes to Buffett’s famous saying, right: be greedy when others are fearful. And that’s really about, I think we’re in that time frame for multifamily. But I know a lot of people have some reservations on multifamily because some performers have not panned out the way they have. And we’ve seen some amazing assets execute super well with renovations, occupancy, the business model—they’ve crushed it. But it’s because of this debt piece that has really challenged everyone.
And frankly, that was artificially manufactured by the Fed increasing rates so high. So, that being said, it is really interesting that if you are going to follow theory and understand some of that psychology, there are going to be some amazing opportunities coming out right now. So it just depends on your risk tolerance and where you want to be. But yeah, I think multifamily is pretty much bottoming out, and there are going to be some really good opportunities for those that are willing to get in probably in the next 12 months or so.
That’s why I just think, to your point, right, is obviously there’s a lot of external factors in the world of investing that are somewhat out of our control. And so I just try and focus on the controllables, and I try and hedge against the uncontrollables. And I think what we saw, at least from a lot of people who got and are in trouble right now, and I think this is a good learning lesson for anybody at any point in the future, is learning from other people’s mistakes. I know a lot of people that were relatively good, seasoned, reputable sponsors doing deals, but they got too caught up in the euphoria and the frothiness of the market. And to your point of the zig versus the zag, when candles are extremely green and frothy, you should probably look at selling. And when things are really down and depressed, that’s oftentimes when there’s the opportunities of buying. For me, I’ve always just been a big believer.
I’m the crock pot believer versus the microwave mindset. I’m in this for the long haul. I’ve been doing it for 16 years now. I’m 37. I plan on doing real estate deals until I can no longer hold a pencil or I’m sure at that time DocuSign something, right. I believe that if you want to win long term, then you have to make sure that you don’t do anything catastrophic in the short term. And so for me it’s all about instead of underwriting rents that are going to continue to go up, or underwriting filling vacancies in a much shorter timeline, or getting a construction project done in 12 months when really I should be putting 24, when it’s selling at a 6 cap and I’m putting it at a 4 cap—that’s where people get in trouble. So I always like to generally overestimate where people underestimate, and I like to underestimate where people overestimate.
And if the deal still works and makes sense there, going back to what we talked about of building a moat around your assumptions, your assets, because that’s what most people did. They modeled and made a lot of different pro formas look really sexy on paper. And guess what? Now you got to bring that pro forma to life in real life execution. And if any one of those assumptions are off, it’s going to start trickling in and having a domino effect into other areas of your economic modeling and your deal. And when you’re raising capital of hard-earned dollars from people that are entrusting you to be a fiduciary and steward their money in a way that you’re telling them you can, you better be rock solid. Because all it takes is one deal to completely tarnish your reputation for a long time. And so for me, that’s always something that I always tell anybody that’s trying to raise money or looking at investing money with people: just be very conservative with those things. Because again, I’d rather under-promise and way over-deliver than do the opposite.
And unfortunately that’s the challenge we’re seeing with a lot of people that did the alternative.
Yeah. So what’s your approach on debt these days, Matt? Right, so that was also part of the issue, right, using floating rate debt. And look, the entire industry was—banks were underwriting to this 2001, 2021 to 2023, pretty much. So how are you looking at LTV and the debt structure nowadays, from the learning lessons?
Yeah, I mean, I think obviously it all depends on your capital stack and what makes sense to engineer the returns that you’re looking for and making sure that you’re still doing it conservatively. Obviously we saw a lot of debt product shift over that timeframe where LTVs got a lot lower, interest rates got a lot higher, and a lot more covenants and teeth in those debt agreements really didn’t give you a ton of wiggle room to screw up. And obviously we’re seeing a lot of that play out right now. I’ll give you an example. On two of my hotels, I had much more favorable adjustable rate debt at the time, and I chose to go with an SBA fixed 25-year loan at almost a full point higher. And the reason I did that was I felt like there was some potential uncertainty. And what I also knew was—and this is why I love fixed rate debt—is because if I know that my model is not going to change, and a critical component being debt not going to change, even if it’s a little bit more and my deal still makes sense, I call it the swan effect. I like to sleep well at night.
And so that’s something that I think a lot of people didn’t account for, thinking there’s no way we’re going to go from 3.75 to 7.5. Are you crazy? There’s just no chance. Well, guess what? It happened. In my 4.75 that I was going to get, instead taking a 5.85, a lot of people were like, why are you doing this? There’s way cheaper debt out there. And I said, the deal still works, and I know that this variance is not going to be anything that comes in and impacts my deal because I’ve already got it baked in. It’s not changing.
So just things like that, going, there’s nothing that’s 100% certainty. And so if we can stress test and mitigate as much risk around uncertainty in our deals, that’s the best way to make sure that we are winning, our investors are winning. And even if we make a little bit less, I’m okay with that. Because look at the people who didn’t do that. They’re not only making a little bit less, they’re doing capital calls, they’re handing keys back to the banks, they’re doing total losses.
So those are things that, for me, I just wanted to make sure that I was doing from a fiduciary perspective to make sure that we’re mitigating as much of the downside as possible. And there’s a lot of different ways: you can do rate caps, you can do insurance around rate adjustments. There’s a lot of different things that as commercial real estate investors and developers, we can look at in the marketplace to hedge some of those risks and mitigate some of those risks. But at the end of the day, investing, there’s always risk.
Yeah, I think you nailed it there with basically taking the things that you can control and really trying to fix those. If you can do that with debt, which is one of the biggest components in a deal, then get that fixed and you don’t have to worry about it. And then not worrying about some of the things you just can’t control that are outside of our control. That’s a pretty key formula in terms of looking at a deal the right way in terms of your due diligence. Matt, if you could give just one piece of advice to the audience about how they could accelerate their wealth trajectory, what would it be?
For me, it might be a different answer than what you’re used to hearing. I call it “be more likable.” What I mean by that is, and I’ll just relate it to my own journey, it has unlocked more doors, more opportunities, and more wealth for me. If you’re an investor raising capital with people, if you’re an investor parking capital with people, if you’re an investor looking for more opportunities—for me, the doors that have opened and the opportunities that resulted came because people told me they liked me.
I think everybody can be more likable; it doesn’t matter who you are. These are controllables, and I’ll share them with you because I call it the Likability Formula. As I started getting more opportunities and getting connected with people who were way higher net worth than me, way more successful than me, and with a much better track record than me, they allowed me in their rooms, their deals, and connected me with their networks. I would ask, “Why are you helping me? Why are you giving me this opportunity?” The overwhelming answer oftentimes was, “I just like you. I want to see you win.”
I was like, okay, that’s amazing. Thank you. I’m humbled by that. But what really makes you like me enough that you’d actually gift me this opportunity? Across many conversations, four variables came up, and I’ll share them with you.
Number one is confidence—not cockiness, but confidence in who you are, how you show up, whether you know something or don’t know something. You’re confident in your ability to solve problems, figure things out, and take action. Like I always say, be dumb enough to believe in yourself and smart enough to take action.
The second component is humility. One of my early mentors told me, “No matter how successful you get, don’t read your own press clippings.” Always show up with humility, no matter what people say about you. Have that insatiable curiosity and humility of being here to learn.
Which ties into number three: bring value to individuals. Wherever you go, bring value to people. That can be kindness, positivity, or a connection. For example, “Hey Dave, I know a relationship that can help you out, let me just make the introduction. No, I don’t need anything in return.”
The last one is hard work. I don’t know anyone with those four qualities where successful people walk away saying, “I hope that person fails.” It’s always the opposite.
When I meet people with those qualities, I think, “I like that person. I want to see them win. I want to help them out.” If you spotlight those qualities with intention, you can be much more likable.
I can’t tell you how many times I’ve been invited onto private planes or into deals and wondered, “How did I get here?” Most of the time it’s because people said, “I just like you, man. I enjoy being around you.” That’s where many deals, investments, and opportunities that have grown my wealth have come from—not just financially, but also in meeting mentors and friends who made me a better husband, a better dad, healthier, or connected me with philanthropy. That, to me, is true wealth.
By being more likable, you’ll have the opportunity to open more of those doors.
Really appreciate you sharing that, Matt. That’s such unique advice. You’re right—no one has pointed that out before. I’d kind of refer to that as your unique ability—likability and what you bring to the world. What’s your superpower? If you can have that likability, you make a difference to others.
That’s also why I like real estate. It’s a people business. At the end of the day, it’s about people. Not only are we seeking financial freedom, but also freedom of relationships—choosing who you want to work with and spend time with. Family, friends, professional—you’re 100% right.
When someone is likable, you want to see them succeed. You want to help them. It’s attraction—you become that attractive character and attract positive people into your world. It really creates positivity. I appreciate you sharing that unique perspective. That’s why I love doing these shows—so listeners can learn from all these lessons.
So, if people want to connect with you or learn more about what you’re up to, what’s the best place?
If they want to know more about me or my investment company, they can text the word “deals” to 844-447-1555. That’s a great way to get into my ecosystem. My Millionaire Mindcast podcast releases three episodes every week around real estate, investing, stocks, and personal finance. Or, I’m on social media—my handle on all platforms is @OfficialMattyA (M-A-T-T-Y-A).
We’ll make sure to link those in the show notes. Matt, thanks again for coming on the show. Really appreciate your time.
It was a pleasure, Dave. Thanks.
Thanks for listening to this episode of Wealth Strategy Secrets. If you’d like a free copy of the book, go to holisticwealthstrategy.com. If you’d like to learn more about upcoming opportunities at Pantheon, visit pantheoninvest.com.