How One Commercial Real Estate Deal Can Change Your Life | Matt Aitchison

Matt Aitchison (00:00)
Yeah, I mean, you know, one of my mantras in life is I’m dumb enough to believe myself every day and I’m smart enough to take action. And there’s something beautiful about having an unwavering belief in yourself and going, “Hey, I may not know it all, but if I surround myself with the right people, if I stay humble enough, if I work my ass off, and I bring value to other people in the process…” That’s a pretty dangerous recipe for stumbling your way into one, opportunity, and two, luck.

Quentin Edmonds (02:04)
Hello, everyone. Welcome to the Real Estate Pros Podcast. I am your host, Q Edmonds, and I am excited to be here today. I am excited about my guests. This gentleman is an investor, operator, been at it for 16 years—commercials, boutique hotels, value-add, triple net. Listen, this gentleman knows what he’s talking about, and I’m so excited that we get a chance to peek through his lens, glean from his experience that way we can just apply his knowledge to what we do. And so I am super excited to introduce you all to Mr. Matt Aitchison. Mr. Matt, how are you doing today, sir?

Matt Aitchison (02:44)
Q, can I call you Q? Is that… I feel I feel I feel like we’re brothers already, you know? I’m doing great, man. I’m doing great. Every day I feel, you know, I feel excited and grateful. There’s there’s always something to be looking forward to, something to be excited about. And, obviously, plenty of challenges to solve in real estate, so I am I’m happy to be here with you guys.

Quentin Edmonds (02:49)
Absolutely. I I love you already starting off with the right mindset. You know, I always say it’s it’s hard to be upset and curious at the same time. So if I can keep my mind in a state of curiosity, then I will calm my nerves down and be like, “Okay, how do we get past this obstacle?” Because if the curious person in me will find a way to get over it, so I love where you’re starting off.

Matt Aitchison (03:30)
No, no doubt. I… Jeff Hoffman, he was the founder of Priceline, sold the company for six billion dollars, and fortunate to, you know, have been mentored by him in in some capacities. And one of the things that he said made him most successful was he was always in a constant state of curiosity. He called it daily info-sponging. You know, sponge, obviously, is always soaking up everything around it, and pretty much all the most successful people I know—and, obviously, successful is relative, right?—they’re always in a state of curiosity. They’re always finding a way to ask great questions. They’re always finding, you know, little things that they think can bring value to themselves, to other people. And when you stay in that state of curiosity, it’s something that, one, sharpens your own sword, but it but it gives you the the ability to go out and bring value to other people. And that’s that’s a great bridge for building relationships, bringing in investor capital. The more interesting you can be, the more knowledgeable you can be, the more you can hold conversation and and elevate other people in the process. So I’ve always found curiosity to be one of the best qualities that, you know, the most successful people I know have.

Quentin Edmonds (04:44)
Well, sir, we—listen, we in an alignment here, so I’m going to continue with that curiosity. And so, Mr. Matt, I’m a little curious of what’s your main focus these days, a little bit kind of how you got, you know, your origin story, kind of how you got to where you are now. And also, man, where are you? Like, where you operating in? And so I’m a little curious. Give us a little bit about that, man.

Matt Aitchison (05:05)
Yeah, I mean, I I graduated from UC Santa Barbara. I’m a Cali kid born and bred. And I moved back up to Sacramento post-financial crisis, it was 2010. And I really kind of didn’t know what I wanted to do. I knew I wanted to be my own boss, I wanted to have unlimited earning potential, I wanted to be in a space that I could build wealth, bring value to other people, and when I was doing all my research, I just kept coming back to real estate. And of all places, I was scouring Craigslist one day and I saw an ad: “Real estate mentor seeks real estate mentee.” And on the topic of curiosity, I’m like, “Man, I I wanna know, I wanna learn. I wanna see what a great, you know, real estate investor is doing.” And so little did I know, and quickly found out, that that meant, “Come work for me for free and bust your ass for a year.” And so he was scooping up, you know, foreclosures in the droves on the courthouse steps. And I think we flipped over a hundred houses that year. I was doing acquisitions, I was doing, you know, all of the underwriting, I was doing the project management, I was helping with disposition, so I got a firsthand crash course. And I saw he was clipping 50, 60, 70 grand a month on—or per house, not per month, sorry—per house. And, you know, once you get in the process, it’s kind of like sitting down to a chessboard the first time. You’re like, “What the hell? How does this game work? What do the players do? What’s the strategy? How do I win? You know, where are my threats on the board?” But by the 30th time you do it, you’re like, “Okay, I understand the game.” And and that led me to have enough confidence to at 21, I bought my first flip, and I ended up netting a hundred and six thousand dollars on it. I did it a hundred percent seller finance, and that was a big lightbulb moment for me. I was still living at home, I was broke, you know, everybody’s kind of beginning story, right? And I decided that I was gonna be a full-time real estate investor, and so I committed to that journey. That process led me to flipping a couple hundred houses over the next, you know, five-ish years. And as I started going to more business masterminds and learning and growing, I had a mentor say, “You know, that’s great that you’re making good money, that’s vertical income. You’re still trading your your time for that. You need to start holding some of these properties.” And so, like a good student does, you listen to the wise teacher, and I would start flipping two and holding one. And so I started building up my single-family portfolio. And then I quickly saw, one, how much work it was and how much stress it was, but I was moving the needle forward and I was excited about being on that journey. But I knew there were levels to the game, and one of my next mentors said, “Hey, it’s it’s cute that you’re doing all these house flips and managing the single-family portfolio, but you’re only making maybe a hundred, two hundred bucks, you know, a door per month. You should check out commercial real estate. Commercial real estate has a higher ROI on your time, your skills. Same thing, different chessboard.” So I sat down to that chessboard, I bought my first shopping center here in my local market—I’m based out of Sacramento, California—and that was a whole new learning curve. And I started to understand kind of the game of value-add real estate: engineering income, drive the top line, reduce the expenses, you know, increase the net operating income. And, “Wow, I can force value into this property.” So I decided commercial was going to be my space. That led me to my very first boutique hotel in the late 2019 or mid-2019, pre-COVID. And I launched that hotel, the first one, week before COVID dropped nationwide. I thought I was gonna go bankrupt. Little did I know, you know, travel was gonna go insane, and that led me to buying my second, my third hotel up in Lake Tahoe. And I really just became passionate about, you know, hospitality experiences and, you know, value-add real estate in the commercial space. So now my portfolio consists of some medical office, mobile home park, and and shopping centers at the moment. I packaged up my hotels and I sold those off kind of pre-rate hikes. Again, part of real estate is just kind of being lucky. You got to be in the game to get lucky, and oftentimes if you’re in the game, you will find luck if you’re, you know, working your butt off and surrounding yourself with the right people. And so now I’ve got assets in four different states in my portfolio. My core focus is all commercial real estate, and we recently just launched a debt fund that is, you know, focused on the lending component of real estate. So day-to-day is all managing and operating my own commercial real estate portfolio and partnering with, you know, accredited and high-net-worth individuals that want to get exposure to commercial real estate. And now we have the debt arm component that also allows us to drive income and kind of cover both sides of the capital stack.

Quentin Edmonds (11:37)
Yeah. Well, sir, thank you. Thank you for taking me through the journey, showing me what it is that you do, kind of how you got there. And, man, you said two things that got my mind twirling: you talked about chess, which obviously you know there’s strategy involved in chess, right? And I love how you say, you know, you sit down to the board at the first time, you’re like, “What is going on here?” But once you get acclimated, like the strategy starts to get in place, you start to strategically do your moves. But then you also mentioned luck, so there’s a bit of strategy and luck. And so, Matt, I often say destiny has no wasted moments. Destiny has no wasted moments. We’re burnt, we’re learning from the strategic part of it, we’re learning from the luck, we’re learning from the success, we’re learning from the failure. So, Matt, I would love to know throughout your journey, what has the moments revealed to you about yourself? Has it made you more disciplined? Has it made you more strategic? Has it changed your outlook on innovation? What has the moments taught you about you?

Matt Aitchison (12:37)
Yeah, I mean, you know, one of my mantras in life is I’m dumb enough to believe myself every day and I’m smart enough to take action. And there’s something beautiful about having an unwavering belief in yourself and going, “Hey, I may not know it all, but if I surround myself with the right people, if I stay humble enough, if I work my ass off, and I bring value to other people in the process…” That’s a pretty dangerous recipe for stumbling your way into, one, opportunity, and two, luck. And so for me, it’s been one of those things where I have always believed that if I’ve got a clear, you know, sight—I call it my North Star of where I’m moving towards—I don’t necessarily always have to have it all figured out, but I know that with those things kind of, you know, in my toolkit, I’m gonna be able to identify where I can, you know, bring my unique value and skills to, and I can cover the gaps with other people who have already, you know, been there, done that, had the success. And there’s, of course, you know, been so many peaks and valleys along this journey. I think in that first year, and really pretty much any time I go and pursue something that’s above and beyond what I’ve ever achieved before, how many times you get stuck in your head and go, “What the hell did I do, man? Like, who am I to think that I’m gonna, you know, be successful in this?” But I’ve always gone back to that mantra of like, “Hey, dude, be dumb enough to, you know, believe in yourself every day, and be, you know, able and capable enough to just show up and know that you’ll figure it out along the way.” And that has led me into some insanely amazing opportunities, amazing relationships, and that’s something that I always try and encourage anybody that’s getting into the game. I mean, the first time I sat down to crypto, you know, and started investing in crypto, I mean, so many people are like, “Dude, that’s insane. What are you doing? Why would you do that? You’re a real estate investor.” And I’m just a curious dude. I like Rubik’s Cubes, I like puzzles, I like trying to solve problems and fit all the pieces together. And I think that’s probably one of the best qualities that I see a lot of successful people have is they know there’s gonna be problems, they know there’s gonna be challenges along the way, and yet they still have this unwavering belief in themselves that they’ll figure it out. And we are way more resourceful than we give ourselves credit. I think a lot of people, you know, bet on their ability to go and do something based on the resources they think they need to have in place. And I’ve always believed that it’s my resourcefulness first, and the resources come second. And that’s always somewhat, you know, been proven to me over time is first mentor told me, “If you find a great deal, you’re gonna know if it’s a great deal or not by how many people want to invest with you or go, ‘Dude, you’re crazy, this is a bad deal,'” right? I mean, those are the types of things that you just have to almost abide by the laws of the universe and put one foot in front of the other. And the universe will either affirm you and give you the tailwinds you need to take those next steps, or it will humble you and give you the lessons that you need to be taught. And so I’ve always kind of looked at those opportunities in life to make sure that I’m just staying aware along the way to go, “Where am I winning? Let’s double down on that. Where am I getting my ass kicked right now? Let’s be smart enough to take a step back and look at what we can do different. What do we need to tweak? What do we need to optimize? Which relationship am I missing that I need to get in this world?” And that’s something that I think has really helped along the way, really in any aspect of life—being a dad, being a husband, being, you know, somebody in business that’s trying to build wealth and real estate. And if you can do those things and keep your awareness level up and keep your humility up, there’s gonna be a lot of great teaching moments along the way that will give you the opportunity to fail forward instead of slip down five or ten, you know, rungs on the ladder.

Quentin Edmonds (17:33)
Man, you said you said so much that I want to heartborn. I’m like, am I brought… like, Q, it’s not about you, condense what you want to say, but I I will say this: this is one of my favorite books I’m finishing up. It’s called Gradually, Then Suddenly. Are you ready?

Matt Aitchison (17:45)
That’s a good one. I’ve read it. It’s a good one. What you got for me? Drop some wisdom though, I know you got something good in that.

Quentin Edmonds (17:49)
So because, you know, in the book he he says it goes from impossible to hard to done. It starts off impossible, then it gets hard, and then you like, “Wow.” You look back and you like, “Hey, we actually did that.” So I love how you said resourcefulness first, then the resource comes. Like, let me apply who I am, my skill, what I have as a big vision. Yes, it’s a big vision, but gradually, then suddenly, I’ll be resourceful, then the resources that come. Man, man, brilliant, man. You said so much good stuff, my brother. Man, I appreciate you, man. Listen, let me ask you this, Matt, because people, you know, let’s let’s give somebody something very simplistic, right? So because people are watching, they wanna know how you got successful, I’m sure, and they like, like, “What is something tangibly I can put in place?” So let me ask you this: what’s one operational thing you’ve put into place, let’s say the last two years, that has really changed the way you do your business?

Matt Aitchison (18:49)
Yeah, I mean, I I think AI obviously has been the hot topic that is very applicable to process-oriented businesses. And real estate is a very process-oriented business from an operational side, right? Deal finding, raising money—that’s all very relationship-driven. Yeah. But when you really strip a lot of it down, there’s a lot of process behind that: you know, how you go out and find tenants, how you underwrite deals, how you, you know, run and manage the back office of, you know, your assets. There’s a lot of process behind that. So one of the things that we have heavily focused on in my business over the last few years is building out AI agents. So we’ve got an investor relations AI agent, we’ve got an underwriting agent, we have a deal outreach and, you know, kind of relationship-building agent. And these are all things that really, I believe, are transforming the way we look at and do business. It’s really allowed us to… once you create that infrastructure, right, it’s all about just getting data and inputs into the system and tweaking and optimizing it based on the outputs and the outcomes that you desire. So we’ve heavily focused on underwriting models, how we can take an operating memorandum and an offering memorandum and putting that through our AI agent, and, you know, deals and things that took me sometimes days to fully underwrite are now getting done in minutes, right? And being able to go out and, you know, utilize some of the technology that is out there now, it’s really giving… it’s leveling the playing field for a lot of people that are using it the right way. So if you’re not looking at all of the processes in your business that are bogging you down, that you hate doing, that are, you know, really cumbersome, if you really take some of the time to document those things and look at some of the tools and resources in AI that are now available to you, it can drastically enhance your business and really free up a lot of time for you to go and focus on the things that, one, you’re passionate about. I mean, if you can play in your strength zone and play in your passion zone, it makes business so much more fun. It makes getting up every day and going and climbing whatever mountain it is that you’re doing with enthusiasm and energy so much more efficient and effective. So that’s something that we’ve really focused on a lot. And I think just in terms of if you’re a business owner and you’re an investor, you know, I used to tell myself, “I’m I’m the relationship guy, right? Like, I’m I’m somebody that’s high energy.” If you can’t tell, I’m an extrovert. I like to talk to people, I like to learn, I like to ask questions. You get me in the process stuff, and while I can do it, it’s painful for me. And so I used to tell myself all the time, like, “I’m not a numbers guy, I’ll let somebody else figure that out.” But what I can say is if you are somebody that’s either starting to learn how to invest or you’re somebody that’s already investing, I think one of the most important skills that will really elevate, one, the people that you attract into your world and, two, your likelihood of having great success going forward is really committing to the core set of financial skills that are necessary to be extremely dangerous in your vertical of business. And so for me, when I got into commercial real estate and I was… it’s a very numbers-driven, data-driven industry, right? Single-family real estate, a lot more emotion there, different types of clients that are playing in that space. In commercial real estate, it’s about math, it’s about numbers, it’s about spreadsheets, and that was a thing that I knew I was really gonna have to challenge myself. Again, another chessboard to sit down to. Now I can work my way around a spreadsheet in my sleep, but that was something that took a lot of time. But like anything, right, repetition is the mother of all success. If you get in there and you continue to get the reps in the areas that you know are vital to your business, and are oftentimes the areas in business that a lot of people shy away from, like me saying, “I’m a relationship guy,” those are the areas that if you put those tools on your toolbelt, you’re gonna be a really successful real estate investor and you’re gonna start to see things and connect dots that other people don’t. And in real estate, right, all it takes is one deal to completely transform your life, to change your balance sheet, your income. And I believe that if you can truly learn how to engineer a deal, whether it’s a single-family house, whether it’s an Airbnb, whether it’s a, you know, triple-net strip center, whatever asset class it is that you’re focused on, mastering the core functional skills and the the numbers behind it is going to make you extremely successful. And that’s a skill that you can apply in your personal life, that you can bring value to other people along the way. And it’s something that so many people are never taught, right? And so many people choose not to teach themselves it, and that’s—those are the areas that I look at and go, “That’s the alpha that if I can capture that, makes me a little bit more dangerous and gives me an edge and makes me an outlier in my space.” And an early mentor always told me, “If you can be a little bit better than mediocre, you’re going be really successful.” And those are the types of edges that I look for in any aspect of business or life that goes, “Where is everybody else just being mediocre and taking the default route?” I wanna look at how, if I want to live an extraordinary life, I got to do some of these extraordinary things. And understanding finance and financial engineering in in real estate at least is is one of the best skills that you can learn.

Quentin Edmonds (24:42)
Yeah, love it. Matt, what’s next for you, man? Like, what’s your next real goal, your next real focus? What are you looking to solve or scale next?

Matt Aitchison (24:49)
Yeah, I mean, right now we’re we’re burning a lot of calories on one of my shopping centers. We just started a build-out for TJ Maxx and Harbor Freight, and so I’ve, of course, you know, getting that thing stabilized, and and, you know, continuing to add new assets into the portfolio that allow the team and our platform to to scale. I think what I’m most excited about right now is our our debt fund. So, obviously, I’ve been an operator and an investor for 16 years, and that’ll always be kind of a core bread and butter. I always tell people, we we may not obviously be using, you know, pens and pencils to be signing contracts anymore, so as long as I can click a button on a mouse and and do a do a contract, I’ll be a real estate investor for the rest of my life. But I think what I’m most excited about, and this kind of aligns with what unlocked during my, you know, my my days in in managing and operating, scaling my hotel portfolio, was experiential side of investing. You know, a lot of investment funds, they focus on one thing, and they get you a return, and that model isn’t broken—we’re not trying to fix that. But the debt fund that we’re doing is, obviously, lending out capital on real assets that are collateralized by real assets, and one of the things that we are doing is bringing an experiential component to it. So not only are we paying our investors 10% on their money and they’re getting that monthly mailbox check, we’ve partnered with a high-end concierge and bespoke access company, and essentially we’re getting our investors in our fund who get to deploy their capital now the opportunity to live the return. And I think most people wait until they’re, you know, they build the wealth, and then, “Okay, when I’m 60 or 70, I’m gonna start enjoying it.” Our focus is to help people not only generate the income and build their wealth along the way, but have access to epic experiences that they wouldn’t be able to find anywhere else on the internet unless you’re a part of one of these… usually they charge you a really high membership to even get access to some of their inventory. Investors in our fund are getting complimentary access to think meet-and-greets, restaurants that are sold out for months, you know, concerts, stadium suites, travel, things that we know and we believe lead to an epic life. And so that’s one of the things that we’re really excited about is is focusing on scaling the debt fund, and obviously paying our investors that return, but getting them access to stuff that they wouldn’t be able to find otherwise.

Edmonds (27:14)
Absolutely. I gotta ask you this because you said you’re the relationship guy, so I have to get your perspective on relationships, building healthy relationships within business. What are some of the relationships that have helped you succeed and still continue to help you succeed? Talk to me a little bit about relationships in your world.

Matt Aitchison (27:31)
Yeah, I mean, I think if I look back on deals, investors that have come in, you know, some of my best friends, some of the most amazing experiences that I’ve had in my life, it’s come through core key relationships. So I’ve always been a big believer in being a part of masterminds. I mean, I mentioned to you before we jumped on the show that, you know, I’ve been in masterminds my entire career. I am, you know, a student of life, so I’m always looking for my next teacher. So I’m always… I kind of look at, you know, mentors like a barrel of monkeys. The best mentors that I know that are out there are obviously always trying to… you know, barrel of monkeys kind of have the two arms, right? One’s up and one’s down. And so I’m always looking for the people that got one arm down that are a little bit higher up than me and are looking to pull me up, and at the same time, you know, I’m always looking to reciprocate that same value and pull others up with me as well that may be a little bit behind me. So the best way I’ve been able to find those individuals are the people who value their own education, value network, value experience, and that’s been mastermind. So GoBundance has been a great mastermind—that’s a high-net-worth, kind of investor-based mastermind group that I’ve been a part of for 12 years. Front Row Dads has been another mastermind. I wanted to elevate my game and be in a better dad and a better husband, so I, you know, immersed myself in in that community, which is full of entrepreneurs, business owners, and investors. And, you know, I think one thing that I always tell people, too, I call it the likability formula. It’s something that I know anybody that wants better relationships can be more likable by exemplifying certain traits. And we all know those people that when you’re around them and then they leave, you’re like, “Man, I like that dude. That that that’s a good guy. I wanna be I wanna be friends with him, or I wanna learn with him, or I wanna help him.” And I’ve had so many people unlock experiences and opportunities and capital for me because of really one thing. When I ask them, I’m like, “Why are you doing this for me?” and they’re like, “Because I like you, and I want to help you, or I want to see you win.” And over the years I’ve asked, “Well, but why? Like, why do you like me?” And I’ve boiled it down to a handful of qualities and traits. And these are qualities and traits that anybody can with more intention elevate in their life. So number one is, of course, being humble. Like nobody wants to be around that arrogant person that just doesn’t think they have anything to learn, and they’re the, you know, the hot shit, right? Like, be humble in whatever it is that you do. But at the same time, number two is be confident in who you are, what you bring to the table. Everybody has their own unique values, skills, experiences, and you should be confident in what those things are and what you can bring to other people. The third one is to make sure that you can… have the ability to outwork anybody else. Work ethic and effort are something that costs you nothing except your own physical drive, right? And so that’s something that we can control. And I believe that if you’re humble, if you’re confident, and you consistently look to add value to people over time and you work hard, it’s really hard not to make you more likable. And you’d be amazed at what those types of qualities can unlock and the doors that you can walk through just by having people go, “Man, I just want to help that person.” Yeah.

Quentin Edmonds (30:55)
Matt, sir, you’re the type of guy I can talk to for hours. Like, I can I can just I can pick tock that’s out of my head.

Matt Aitchison (31:02)
Yeah, yeah, I mean, we can pull back the layers to the onion, Q.

Quentin Edmonds (31:07)
Exactly, exactly. But, man, listen, if if someone wanted to reach out to you, connect with you, collaborate with you, learn more about what you’re doing, how can they get in contact with you?

Matt Aitchison (31:17)
Yeah, I mean, I we’re pointing everybody to the fund, so you can either, you know, look at IMAGOS Capital or the easiest way is just text in the word “INCOME” to 844-447-1555. INCOME is, you know, a way to learn more about our investment experiential fund. I’m on social media as well. My my handle is the same across all platforms: officialMattya M A T T Y A. And I love connecting with anybody that is wherever you’re at in your journey, if there’s any value that I can bring you, if there’s anybody that I can connect you with that would help you based on what your goals are, please reach out.

Quentin Edmonds (31:53)
And listen, man, I want to make sure I cover everything, so spell IMAGOS for me for somebody out there.

Matt Aitchison (31:57)
It’s I-M-A-G-O-S, IMAGOS Group.

Quentin Edmonds (32:01)
Awesome, awesome. Listen, sir, let me say three things to you sincerely. One, thank you for your time. I think time is our most precious commodity, so I I I value the fact that you gave us your time, so thank you for your time. Secondly, sir, thank you for your story. Thank you for the gift of your authenticity, and I even say the gift of your vulnerability. I believe your story plants seeds for people, and that seed may grow at any given time, but the seed is there. So thank you for planting some real seeds. And, lastly, sir, thank you for your mindset. Thank you for the way you think and bringing that mindset to this platform. I greatly appreciate you coming on today, sir. Absolutely. So, listen, y’all heard Mr. Matt. His information is in the show notes, so please get in contact with him, but definitely make sure you’re subscribed here.

Matt Aitchison (32:37)
Thanks for having me on, Q.

Quentin Edmonds (32:48)
Because I keep saying it and I keep telling y’all, call me out an ordinary when it don’t happen. We’re going to continue to bring up amazing guests, just like Mr. Matt. So, sir, I say thank you again. And everyone else, have a fantastic day.