Mathew Owens - The $500 Million Playbook

Mathew Owens is a CPA, real estate investor, and founder of OCG Capital. He shares with us the strategies behind building a real estate empire that spans more than 1,500 units, over 1,000 home flips, and more than $500 million in loans to investors. Matt has also raised over $200 million in private capital, giving him a unique perspective on what separates successful investors from those who struggle to scale. 

We dive into his disciplined approach to investing, including the 200-point due diligence checklist he uses to evaluate opportunities and minimize risk before committing capital. Matt shares lessons learned from decades of experience as both an active operator and passive investor, offering practical insights on finding quality deals, raising private money, building passive income, and creating long-term wealth through real estate. This episode is packed with actionable advice from someone who has successfully navigated nearly every corner of the real estate investing world.

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Transcript

Cold Open On Investor Trust

SPEAKER_00 0:00

I've been doing this for 20 years now, since 2006. And so, you know, having them around this long uh really is huge because they give me tons of referrals all the time and things like that. And I was able to build that through short-term flips and short-term lending where they got their money back right away, right? Where, you know, in a 12-month cycle, if tons of investors are consistently getting their money back and being able to redeploy into new capital or new deals over and over again, the trust gets built when they get their funds back.

Show Mission And Guest Setup

Mike Swenson 0:32

Welcome to the Real Freedom Show where we inspire you to pursue your passion to gain time and financial freedom through opportunities in real estate. I'm your host, Mike Swenson. Let's get some real freedom together. Hello, everybody. Welcome to another episode of Real Freedom Real Estate Leverage Freedom, where we talk about different ways you can build time and financial freedom in real estate. I'm your host, Mike Swenson. If you want to get started on your real estate journey, check out our website, freedom throughrealestate.com. It's where we put all of our content, all of our amazing interviews, really with the goal just to inspire you to take some action, move the ball forward, and do something to get closer to your goals in real estate. We don't want to have a lot of people that just sit and listen to podcasts and not do anything. So take some action. Super excited to talk today with Matthew Owens. So Matthew is a CPA real estate investor. You've done a ton, flipped a thousand homes, lent out on more than $500 million, raised $200 million in capital, own over a thousand units, close to $1,500 units. You have your company OCG Capital, and super excited for you to be able to share your wealth of wisdom with us and your journey that you've been on. So welcome to the show, Matthew. Excited to have you.

SPEAKER_00 1:47

Thanks, man. I really appreciate it. You know, all that stuff I look back at that and I just remember the pain that I had to go through on each one of those different strategies to get through the hump and learn my lessons the hard way, you know, in each one of those. So, you know, while we did a lot, we I have also taken a lot of punches in the face and stood back up. And that that that is what I think makes uh you know someone successful long term is is is the perseverance through trials and tribulations we all go through, especially in real estate and nowadays in real estate where interest rates are you know higher and it makes it more a little bit more difficult to cash flow and needed to buy a little bit better of a discount and things like that in order to make things cash flow well.

CPA Roots And First Flip

Mike Swenson 2:26

Absolutely, and you've you've been in it for a long time. So take take us back kind of at the beginning here. CPA, how did that get started? And then tell us about your journey into real estate.

SPEAKER_00 2:35

Yeah, man, no problem. So I I actually became a CPA because I was going to UC Santa Barbara and uh I actually wanted to be an architect, but didn't have architecture school there. And so my dad was a CPA, and my dad was kind of like my hero. He was a ranger and a sniper in Vietnam and uh and uh black belting up keto and you know that kind of and I could always rely on him to to talk with them and he was talking to me about it, and you know, he's like, Why do you want to become a CPA? I was like, Dad, there's there's girls with squirt gun fights here everywhere in Santa Barbara. I'm not leaving, Dad. You know, and he's like, You're gonna become a CPA because of girls. I'm like, Yep, that's what I'm doing right there at 18 years old, you idiot, right? And uh so I ended up getting my degree in economics with an emphasis in accounting and got a job at a CPA firm, um, uh doing audit and tax and learning the inner workings of internal controls and things like that, which was pretty interesting. But after a while, it just got monotonous. And like a lot of people that have W-2s have got a career they got going, it becomes painful and just like you don't want to do it anymore. And I remember wanting to cry going to work, going, I can't can't do this. I can't do audit and tax like for the I hate the IRS, like you know, so I'm like, I can't talk to these people, right? So uh I ended up uh going to getting some real estate courses, and I think it probably gave me a little bit false sense of security to jump into real estate in 2006 to when I got my first flip under contract, and uh we started flipping houses right away.

Surviving The Crash With Integrity

SPEAKER_00 4:00

And I got an office at the World Trade Center in Long Beach on like the 23rd floor um that was like overlooking all of Long Beach, sold a ton of houses, we're killing it all of a sudden, and thought I was dope and realized nope, you're not dope. Here's the market crash coming to just wipe you out and take away everything. And I ended up taking out 290 grand of my credit cards to you know try to float and pay my investors back and get them paid off because we had to sell a bunch of properties at discounts and things like that, and was able to save my investors' capital, but I ended up taking the hit personally. Um, but that's how they all started reinvesting with me. I just hunkered down, kept pushing forward, and um and and kept moving that that needle and they kept starting reinvesting with me and getting more referrals. I started going to four to five networking events every single week for like two to three years to develop capital relationships and partnerships, chamber of commerce events, real estate events, other monthly events that are piqued my interest, right? And that kind of thing, just to develop these relationships. And um, they all started reinvesting. We started flipping and flipping and flipping to do where we were doing about 10 a month at that time and using all cash. We weren't using bank money at all, which that's what hurt us is we had a strategy where we were buying and renovating and selling with seller financing, and then they would go um they would go refinance right away afterwards and then pay us off. And the appraisals just magically were higher in 2006 and seven, of course. And I thought we were dope from doing that, right? Of course, and realized no, you you don't know what you're doing yet. Here, just take a seat, son, right? And um, and you know, since then we just kept pushing forward and pushing forward and grinding, and you know, we've had multiple people steal from us in the past and multiple trials and tribulations and foreclosures we had to deal with, but we you know we now flipped over a thousand houses and lent out over 500 million and raised over 200 million for multiple deal types, and we invest in all different types of asset strategies.

Diversification For Real Freedom

SPEAKER_00 5:58

I really personally believe, hey, own your own personal portfolio, do your own active business, invest passively also so that you can, you know, maybe invest in large multifamilies or self-storage or other assets that you can participate in without having to be the subject matter and operations expert in. And then on the other side, we also invest in alternatives where I have own gold and silver as an insurance policy. Uh, we invest in litigation or accounts receivable financing, or I also own a cannabis farm in Maine. So there's all different types of strategies to try to uh mitigate the risk of the market. And you know, some of the things I learned after just being in one strategy, thinking I was, you know, really solid and realizing no, you're not. You need a diversified pool of cash flow coming in uh to really solidify that base to give you the not just the financial freedom, but the time freedom and the location freedom to be able to move. Like I just got to go to Vietnam for three weeks with my son this last year, my 10-year-old, and we're gonna be going like pretty much every year, and we travel all the time to different spots and can work from anywhere. So, you know, at the end of the day, it's how do you build this business to build the life you want with that time freedom and not being the sole business owner, which I made the mistake of, and a lot of people do, you know, the same thing uh with uh through their career, right?

Mike Swenson 7:16

So and obviously you didn't get there by yourself, you know, you've got relationships, you know. I'm just thinking you mentioned about your cannabis farm in Maine, right? It's like the exact opposite of California. So you've got to find great people and great relationships. So before we dig into that, let's quick touch on kind of the CPA stuff.

Short Term Rental Tax Levers

Mike Swenson 7:33

So in terms of wearing your CPA hat, investing in real estate, just touch on like some of the benefits for people that maybe they don't think of or they just don't, they might hear it, but they don't realize the power and the impact of those great benefits investing in real estate, whether you've got a W-2 or you know, or not.

SPEAKER_00 7:50

So I'll just tell you uh through the first a story of one of my clients, for example. Um, we purchased a large short-term rental and we bought it, we renovated it, we tinted it, and then we've got the long-term financing on it and got it all up and running uh on a short-term rental, super high-end, like shipping container pools, golf simulators in the basements, like the things that pop from a marketing perspective with movie rooms and all that stuff, right? And it sleeps like 15 people. And one of our clients came in uh and he put the down payment down, which was $300,000 on this project. It was a super high-end property in Missouri. Uh, and and then we were able to front load uh tax benefits to where he's getting a $276,000 tax deduction. And then in short-term rentals, there's a loophole where you don't have to be a full-time real estate professional that's working, you know, 70 hours or you know, 750 hours in real estate to get the front-loaded tax deduction for short-term rentals. If you spend a hundred hours over the last year, then you can go through and claim large losses against not just passive income, but ordinary income and W-2 income. So our client was able to wipe out $276,000 worth of his W-2 income via this strategy by tracking and putting in the work to actually for that first hundred hours. Now, after that, we do everything. Year two, it's all taken care of. He doesn't have to do anything anymore. The only reason he was doing the hundred hours is to be able to take the tax deduction against his W-2. If he didn't want to do that, you still get the tax deduction. You just can only take it against rental income and other passive income versus the active income side. You might get maybe up to 25 grand, but sometimes that gets phased out against active income. Uh, so it depends on how much money you make, if that gets phased out or not. Uh, but there's also strategies that we utilize to create more passive income. So we by doing using our diversification strategy. So, for example, I invest in lending companies. And when we're doing lending, we are in the business of lending. Interest income isn't necessarily considered passive income, it's considered portfolio income. So it doesn't count. You can't take the big cost tech segregation study, uh, studies on real estate against interest income. But if you invest in a company that is in the business of lending and you're a passive limited partner on that, you have passive ordinary income, which then that cost can wipe out. So by using investment strategies that can be uh beneficial to each other by investing in some debt uh that is flat monthly payments that are consistent every month versus real estate that you do get cash flow might be a little bit volatile because of repairs or a tenant turnover or something, um, but it can go up over time with inflation. You have it decimates the debt with inflation, all these major positives, then you also get the tax benefits on top of that. Um, you know, yes, the real estate should always work right whether you are considering the tax benefits or not. Like the short-term rental we did was a 12% cap rate. He's making 12% on his on his funds um just for you know putting the down payment on top of the tax benefits. And so you look at some of these benefits and they really add up from a tax perspective. And there's so many strategies out there to mitigate literally your biggest expense, which is taxes.

Mike Swenson 11:17

Absolutely. I remember uh we were just in a in a meeting the other day and had a person talking about you know, your your largest expense in your life is your taxes, right? And so a lot of people might think it's kids or different things like that, and so it's taxes, so it's finding ways to limit your tax burdens.

Choosing A CPA And Planning

Mike Swenson 11:35

And uh there's a there's a lot of value in that for somebody that's maybe looking who to talk to, who who might be a good resource to help with taxes, what what advice do you have for somebody on finding a good real estate related tax person?

SPEAKER_00 11:48

So when you're looking for a tax help, when you're looking for a CPA or a tax attorney to come in and help you with your taxes, it really fully depends on your personal situation. If you have a W-2 uh type you know situation and no other outside investments and things like that, you can easily go to like you know an HR block or something along those lines and pay a cheap price or do the taxes yourself on turbo tax or you know, you may still want to go and get some tax advice and pay for tax planning because it could save you a lot of money and it you could it could give you the trajectory of how to build so you pay less tax on your W-2s uh and on your in your income. But if you're going out and you're trying, if you have a even a business or you have any real estate that you're holding, it's highly, highly important in my eyes to go get that tax advice. Like I don't I don't go and do tax planning for clients, I actually go get tax planning for other CPAs, and I'm a CPA because I focus in real estate and investments a lot more now. But trust me, I know I understand the law a lot more now of being a business owner than even I did doing taxes as a CPA because I don't want to pay the tax. So I find every way possible to not pay taxes, right? So um, so when you're looking for uh a CPA, uh then I highly recommend doing an interview. Go and use Chat GPT or you know, Claude or something, come up with a list of questions that you should be asking your CPA. They should be teaching you all the ways that you could be potentially saving on taxes. And some of those may be too complex for you. Some of those you may want to take a stab at and and put them in place. For example, I have a self-directed 401k that I can contribute uh uh 25% of my salary as a matching contribution from my own S corporation, plus I can contribute my own personal savings to that. And now I can also control it and put that money into deals and real estate and other assets that I can actually uh you know utilize, right? Uh and build my own portfolio for myself that creates a cash flow stream to where I don't have to deplete the principal. It literally is just producing enough cash flow to live off of. That's the idea, or a health savings account that I can do self-direct as well into real estate and other things where you can put like seven, eight thousand dollars a year into a health savings account on a family plan and start building that to where your um all your medical expenses can be paid for, you know, tax deferred that way. And just little chunks like this, let alone there's trust structures, there's life insurance structures. If you don't want to pay taxes anymore, there are ways to never pay taxes again with the right structures. It's insane to say, uh, but there are absolute structures. Now you might pay something minimal or something, but in comparison, like you're getting rid of like 99% of your taxes with different strategies if you take the time to deep dive. And so that's why I pay outside people to do uh tax planning work for me every single quarter, looking at my tax projections. What am I going to make for the next year? What things can I shift into next year or shift into this year from an expense perspective to mitigate my burden? Can I pay my kids for marketing work or other strategies that I want to pay them for to push income there? Right. There's so many things. There's a thing called the Augusta rule where you could rent out your primary residence to your business for 14 days at market rates for a business purpose and document that.

Mike Swenson 16:09

Awesome. And and and thank you so much for sharing some of those best practices and top tips. I know obviously for anybody listening, like what you just rattled off is a lot of stuff and it's deeper stuff, but at least you just you shared kind of the tip of the iceberg of there's so many great opportunities for people, and you've got to take the time. It's worth the time and the hassle, and and for a lot of people, it's not the most exciting stuff. However, once you start to understand some of these things, yeah, there's a a ton of opportunity to save money, bring in more income, keep more income when you use these strategies. So I appreciate you just kind of sharing, sharing some of the top tips there. Yeah, absolutely, man.

Capital Attracts Better Deals

Mike Swenson 16:46

So talking about kind of what you do today, so you've got a lot of capital that you you raise debt funds, what opportunities you search for and how they come together, and then how you can obviously you work with a lot of investors, you're raising a lot of capital. So help them find opportunities that they're excited to put their money into.

SPEAKER_00 17:04

Really, a lot of the the opportunities get sent to me now where I don't have to look for them anymore. We used to do a ton of pay by click marketing, direct mail marketing, and other marketing strategies to find properties every single month to flip. I slowed down a lot on the single family home flipping. Uh, I do still hold and do projects and have renovation projects and I do different tax credit strategies, but I don't really have to market for them because the capital, the the deals come to us now. When you have the capital to deploy, um, then the deals will come to you and you can structure those deals because you have the capital, right? So um, and whether that's on the lending side or the joint venture side or you know, other other means of creating income through some of these things, right? Um, and you know, and we also used to do direct lending and we do a lot less of that now. We still do some, but we buy the debt now instead from lots of brokers that we work with that have good systems because it's a ton of work doing all that talking with tons of borrowers and stuff like that all the time. You know, I have I have 11-year-old and an eight-year-old, and I'm, you know, I don't want to be talking to people all day long on the phone, which you can this usually with a the game plan with for a real estate investor is to be on the phone negotiating, talking to people, handling contractors, dealing with all that, right? Um, and so being able to cut down some of the more active strategies and focus a lot more on larger strategies, like we just finished an accounts receivable fund uh where we uh raised over 38 million for that. Uh, and the way we did that is very unique, and it creates an income strategy for people with large databases, uh, where um we went out and lent money uh at a 30% interest rate to uh to uh against accounts receivable financing at 25% of what that that project was, uh the the actual collateral was worth. Uh, and then we went and gave our investors 20% and then gave our capital partners 25% if they put in over a million dollars or more. So if they raise a million from their database in their own fund structure, so it's all compliant with SEC purposes, then they are then investing those funds, be getting better metrics and by getting a better share class into our fund. And so we're able to do that. We raised a lot of capital from our own database and our own investors that wanted to invest and get an interest-only 20% return, which is insane, you know, uh, type of return, of course. Um, but then our capital partners were able to raise millions of dollars for us also um via that and make a spread on that capital as well, which makes them, you know, a great return on their on their on their time for doing that. And so we teach other people how to raise capital like this because it benefits us as well, and have that strategy out there where we do trainings on how to raise money in our marketing strategies.

Funds And Alternative Investments

SPEAKER_00 19:53

Um, but then we also go out and we do different direct projects where we manage a portfolio of over 800 mobile home parks uh that we're involved with or mobile home park units, sorry, not parks in total, but uh that we are part of. And then we uh also have own a cannabis farm where we are direct operators. I have a CFO and a COO, and they report to me and I manage that that aspect of things and the capital side of things and uh be able to you know help with the whole project. And now we're uh actually doing an expansion where we should end up at about a four and a half million dollar net income on a $10.5 million capital stack with no debt on that type of asset, which is really an interesting structure where investors get all their money back first before there's a split with the GP on that deal. So really cool. And there's all these deals that I'm working on. Investors are projected to make like 19% cash flow and 28% IRR uh on the cannabis deal. On our litigation financing deal, investors can make 20 to 30 percent on their funds. So that I focus on these alternatives that are higher interest, but then I also focus on the real estate stuff and short-term rentals and long-term rentals so that that way we have a good base of cash flow coming in and inflation hedges that I think is super necessary because I think the government's just gonna keep renting money like crazy, you know, forever. And so owning that, decimating the debt that's uh that's fixed rate debt on there, I think is super important while also investing in these other alternatives that can give you a higher rate of return, a really good cash flow, and diversifying into multiple operators, multiple asset classes, and multiple markets is really the key to that like base base foundation there, you know.

Mike Swenson 21:39

And obviously a big part of that is you know building good relationships and trusts with your trust with your people because they want to know that their money's being taken care of. Obviously, some people have different risk tolerances in terms of what they want to do. Just out of curiosity, how many of these folks have been with you for the the longer haul, you know, from the the flipping days or you know, have kind of stuck. With you through it because I know you talked about you know having to take on debt yourself to keep your investors whole. Um, that's everything that I know about capital raising, right? Is to make sure that you're you're you kind of eat last your investors, you're trying to keep those great relationships and to help them. So, you know, curious to hear those the journey of some of these investors that you've had for a while.

Passive Investing With Our Team

Mike Swenson 22:20

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Retaining Investors For 20 Years

SPEAKER_00 23:18

Yeah, for sure. And and a lot of those investors have been with me for years. I mean, I'm talking for I've been doing this for 20 years now, since 2006. And so, you know, having them around this long uh really is huge because they give me tons of referrals all the time and things like that. And I was able to build that through short-term flips and short-term lending where they got their money back right away, right? Where, you know, in a 12-month cycle, if tons of investors are consistently getting their money back and being able to redeploy into new capital or new deals over and over again, the trust gets built when they get their funds back, right? That's and and so I was able to build a big base of people that had built the trust for me early through my flipping and through my lending business and doing that over and over again. We also have have our debt fund that we have in place that you know has been running since 2018, have never missed a uh a single preferred return. So all those investors that are in our debt fund, you know, are consistently there, right? And it takes a long time. And don't get me wrong, I've taken major hits. I've when when the interest rate environment, you know, for you know, uh took took uh everything kind of real estate in a different direction, I'll say. We had multiple foreclosures that we just had to deal with and we paid our investors anyways, and we took the hits and took them over and handled the projects and renovated them and tinted them and refinanced them and did all the work so that our investors didn't miss a B. That's how you retain those long-term relationships. Most of these investors can't handle the ups and downs that we deal with in real estate all the all the time, right? The I swear sometimes before before noon on a Monday, you're like, Did I just deal with 20 problems right now? Like it's insane. You know, you're just like, did this really just, you know, how many problems can I really just have to laugh it off, right? So, um, and or or go medit meditate and breathe, you know, sometimes. But uh, but you know, at the end of the day, keep them consistent and take care of them. If you can take the hit, take the hit for your investors and they will always reinvest with you. I hope an instance comes up where that never has ha happens where I can't take the hit or something like that for my investors. Um, but at the end of the day, uh my investors have never lost money with me on any deal that I've I've worked on uh as far as like that I've taken you know capital on. Uh, I think we we had a few other single family home people that um maybe had a bad tenant here or there or something like that and cost them 20 grand and you know, tenant stuff. But we actually did an audit on all of our rentals, and um, we only 7% had a variance on uh and under underperformance on uh the our projections, our initial financial projections on them uh after like a five-year term, which was pretty cool. And we've sold hundreds and hundreds of you know, over a thousand of these now, which is crazy, you know. So, but yeah, you that that's how you take care of them. And then at the end of the day, you have to constantly build relationships with your investors and add value. We do masterclasses all the time on our different investment strategies. We lead with due diligence, where every single time we have a deal, we put a full giant due diligence package together for them to review in detail. And then we we try to make it easy and continue to develop the relationship with them, even when we don't have a deal as well. So these are the things that are super important, and and capital is a lifeblood to real estate investing. And so if you don't have that a system systemized place for capital raising in your business, you're going to be limited at some point with how much you can actually accomplish.

Resources And Closing Thanks

Mike Swenson 26:50

Well, there's so many good things that we could still touch on, but thank you so much for for sharing what you shared with us. You know, you've just got so many different irons in the fire, you've been doing it a long time and still alive to tell about it. And that doesn't mean it's easy, however, uh, you know, very fulfilling. And so thank you so much, Matthew, for coming on and sharing. For people that want to learn more about what you're doing and and the deals that you have and the opportunities that you have, where can they do that?

SPEAKER_00 27:14

Um, they can go to my website, which is MatthewOwens.com, um, when T and Matthew, because my parents couldn't spell. So that's what I tell them because they I've had to explain that my whole life. Uh, but we also have 200-point due diligence spreadsheets because everything should start with the due diligence side on our site for free. We have masterclasses on different topics on capital raising and things like that, and finding deals and analyzing them. So it's all for free in our site if you guys want to go. But yeah, MatthewOwens.com.

Mike Swenson 27:40

Awesome. Well, thank you so much for coming on and sharing. Excited to see where things continue to go for you in the future. So thank you so much. Thank you.