James Gleeson - How He Built a $60M Real Estate Portfolio in Just 8 Years | Real Estate Educators Podcast with Kevin Amolsch

Description

James Gleeson started investing in real estate at just 21 years old. Eight years later, he's built a portfolio worth approximately $60 million with around 470 rental units, without using syndications.

In this episode of the Real Estate Educators Podcast, Kevin Amolsch talks with James about how he got started using the BRRRR method and hard money, including his first deal: a $25,000 property with a $14,000 renovation that appraised for $65,000 and is worth roughly $180,000 today. James also explains how relationships with property managers, lenders, contractors, and other investors helped him scale.

They also dig into the operational side of owning a large rental portfolio. James explains why he eventually brought property management and construction in-house, the hidden costs he experienced with third-party management, and why investors can't afford to ignore operations while focusing only on finding deals and raising money.

Whether you're trying to buy your first rental or already managing a growing portfolio, this episode offers practical lessons on BRRRR investing, leverage, liquidity, property management, relationships, systems, and knowing when it might be time to stop chasing growth.

00:00 – From college basketball to real estate investing

04:10 – Buying his first property at 21

06:15 – Using the BRRRR method and hard money

08:30 – How relationships helped James get started

14:20 – The hidden costs of property management

17:10 – Bringing property management in-house

22:15 – Paying off debt vs. continuing to leverage

25:00 – Why liquidity matters as much as equity

30:15 – Why net worth can become a vanity metric

32:20 – Building systems instead of chasing more growth

Connect with James Gleeson

Learn more about James's real estate investing education and coaching at MultifamilyMethods.com.

You can also find him on Instagram and TikTok at James Gleeson Real Estate.

Learn more about Pine Financial Group at pinefinancialgroup.com

Hosted on Ausha. See ausha.co/privacy-policy for more information.

Transcription

Speaker #0
The hard money lender referred me to his contractor. So it was like one relationship kind of led to another. And I just did the Byrd method. So I bought it for $25,000 with his money. I renovated it for $14,000 using his money. So I was all in for $39,000. The deal eight years ago appraised for $65,000. And today it's worth like $180,000. That was more difficult. But I think now that we've sort of stabilized, we have the team and it's all said and done, it is much easier. And it's certainly easier than it was to manage a third party management company. And we're making way more money. But the one quality trait that has really helped me is that despite all of those hiccups, I'm still working at it and I'm not giving up. And it sounds cliche, but it's true.
Speaker #1
We were in negotiations for investing in real estate. They're winning. What's up, everyone?
Speaker #2
Welcome to the Real Estate Educators Podcast, where we provide the education you can build on. I am your host, Kevin Amos. We are back. I'm so excited for another fantastic episode of a very experienced investor with us today, Mr. James Gleason. You've been doing this for a while, man. It's in the business for a while. You've built up a nice portfolio, $60 million. I haven't gotten into where yet, but I know you're calling from St. Louis, Missouri. I know you are an investor and a mentor or a coach. You got a lot going on. Welcome to the show, man.
Speaker #0
Thanks, Kevin. Appreciate you having me.
Speaker #2
Well, let's get into it. So you've been doing this, actually it does right here. You've been doing it eight years. So back before COVID even. So tell us eight years ago, why real estate, man? What got you started going this direction?
Speaker #0
Yeah, it is... Pretty simple story. There's really, I didn't have any family members or anyone that was in real estate, but I grew up playing basketball and I always had dreams of playing professional ball. And when I got to college, I played college basketball, quickly found out that that was not going to happen. Everyone was bigger than me, stronger than me. And so I basically just gave up on the basketball dream. Thank you. So that summer, my sophomore year of college, you know, after I had given up the basketball dream, I just lost purpose. I really didn't know what to do with myself because I went to an engineering school because I just heard that engineering was a good degree. You know, I would make a decent living. I was good at math and science. And so it made sense. But when I did the internships, I didn't really enjoy it. You know, I found myself unfulfilled with the actual work that I was doing. And engineering school is very difficult. You know, I went to Missouri S&T here in Missouri, one of the top engineering schools in the country. It is not easy. I'm not one of these naturally gifted math wizards. You know, I had to work very hard to do well in college. And so my whole life, it had just been basketball and pursuing that dream. And so when I lost that, I needed something else to pursue. I always had a natural just... my inclination interest for real estate. I can't really explain why. I grew up watching The Apprentice with my mom. I'm sure that had something to do with it. But I just always knew that I wanted to do real estate. And so I saw a Grant Cardone ad when I was in college for his millionaire booklet. And I saw that ad and I was just immediately hooked. I was like, this is what I want to do. And so from that point forward, I just... completely obsessed with real estate like I did with basketball, read the books, listened to the podcast, hired a mentor, went out for coffees with as many people as I could. And the rest really became history. I never really looked back at that point. And so when I was 21 years old, January of 2018, I bought my first house. I'm happy to get into the specifics of that if you'd like. And then, you know, after I bought that first house, I used the same lender for the next three or four properties. And, you know, that was eight years ago in 2018. Fast forward today, I own a $60 million portfolio, about 470 rental units. I did all that without syndications. So I'm not someone who just owns, you know, 10% of his portfolio. I own the vast majority of my portfolio. I do have a lot of partnerships. But those are all 50-50 partnerships for the most part. And then I own $1.5 million of real estate free and clear. Happy to get into my philosophy with that. I think there's a lot of just leverage till the day you die. Part of me believes in that, but part of me also believes in ultimately paying off that debt for peace of mind and lifestyle. And then I've became vertically integrated as well. So I have a construction company. I have plenty of nightmare stories with construction that I'm happy to talk about. Same thing with property management. And then I have an education platform where I teach other people how to do what I've done.
Speaker #2
Okay. So you have a lot going on. There's obviously a lot of different directions we could take this, but you said it, man, 21 years old. That's when I bought my first house too. Not a lot of people could say that. How'd you make that happen?
Speaker #0
So really just through education, you know, I used the Burr method to buy my first deal. So I found a hard money lender, the hard money lender. So this was a deal I found through Craigslist. All the real estate books that I was reading talked about Craigslist, Facebook Marketplace, door knocking, yellow letters, all these things. So I would go on Craigslist pretty regularly. And I found my first deal for $25,000. I googled property managers near me. And I found a property manager who was so gracious. It was a husband and wife. They were so gracious with their time. They were happy to walk through that house with me, point out things to look out for. Yeah, it was amazing because as you know, when you're starting out, or at least for me, I didn't know what flipping a breaker meant at the time. I didn't know anything. So walking these houses was pretty...
Speaker #2
What are you talking about?
Speaker #0
I was an engineer because I thought I would make a good living, not because I knew how to engineer. So obviously. noted uh yeah it was pretty bad um thus why i didn't enjoy it because i wasn't good at it um but they were so gracious with their time it really gave me the confidence they referred me to the hard money lender that i used um that hard money lender funded 100 of the deal um he charged me um 15 interest and five points so he was pretty expensive um but he funded the whole deal there was definitely some convincing there He had some hesitations because I was 21 years old and had never done this before and didn't really have savings. So the property manager referred me to the hard money lender. The hard money lender referred me to his contractor. So it was like one relationship kind of led to another. And I just did the Byrd method. So I bought it for $25,000 with his money. I renovated it for $14,000 using his money. So I was all in for $39,000. The deal eight years ago appraised for $65,000. And today it's worth like $180,000. So, you know, obviously I got very lucky buying in 2018 before the COVID era. But I've experienced a lot of appreciation and equity benefits since then. But yeah, just educating myself, getting the right relationships and using the BRRRR method.
Speaker #2
So we talk a lot on this show about the power of relationships and who you surround yourself with and how it could really impact your career. It sounds to me like you had several right out of the gate, very powerful relationships, but that one with the property management sounds pretty important. Tell me more about that. You said how you found it because you just Googled them, but how'd you convince them to come take you under their wing and what kind of impact did that have on where you are today.
Speaker #0
Yeah. And I would say, just to add to that, if I could go back in time, one of the things I would have done differently is I would have spent even more time on building my relationships. I am where I am today because of the people that I know, because of the relationships that I have. And that's all the way from the lenders that I know, the wholesalers that I know, the agents that I know, the brokers, the partnerships. Like everything that I have today is a result of those relationships that I have. Um, so if I could go back in time, I would have doubled the amount of people that I was meeting on a weekly basis. Um, I think it was conviction. I think I knew that this is what I wanted to do. Um, hopefully they could hear that passion through the conversations with me. Um, I I'd love to say that it was all my ability to persuade them, but I think part of it is just, they were nice people. Um, here's a 21 year old. You know, he's talking about buying these houses and, you know, buying without using his own money. And I'm sure they saw some. some of them and me potentially, you know, and they just wanted to help this young guy out. But yeah, I think they were very nice people. I had a lot of conviction. And I think at the end of the day, just like those relationships got me that first deal, in a lot of ways, even today, my relationships are what are still getting me, you know, the deals and the money that I need to continue growing.
Speaker #2
We all have relationships in our career. Anyone who has any... any level of success, success has that type of relationship, right? I mean, somebody helped you along the way. This isn't a do-it-yourself business. So I'm just curious, do you still talk to them to this day?
Speaker #0
I don't. I don't even know that they're still in business anymore. I actually got away from property management completely. I do have a lot of relationships that are eight years old with like vendors that I'm still using, for example. my HVAC people, my electricians, partnerships, lenders. I have some very old relationships that have just continued to be win-win relationships. But no, I ultimately fired property management. Every podcast and book and bigger pockets told me, you should work on the business, not in the business. And so just hire a property manager and focus on finding deals and finding money. And finding deals and finding money is one of your highest ROI dollar per hour activities that you can spend your time on as a real estate investor. But if you ignore the operations, the construction management and the property management, you're not going to be able to grow as quickly and you're potentially going to get yourself into trouble. And that's what happened to me. You know, I thought it was as simple as hire a contractor, give them 50% down and then talk to him in three months. And I found out that that is the farthest thing from reality. And with property management, you know, I didn't have as many like crisis things happen with property managers. But what I did find out is that every single month I was making nothing and they were making a bunch of money. you When I dug into it, I was like, what is going on here? Like everyone says hire a property manager. Am I the only one who's not making cash flow? But when I really started digging into it and thinking about it, they have, you know, obviously their 10% management fee, which you can negotiate down a little bit. But on top of that, they have their leasing fee. On top of that, some have maintenance fees. But then even the fees that they don't charge you, which are the most... ones. Number one, there's a lot of maintenance requests that with my vertically integrated management company today, we turn down maintenance requests. If their battery dies in their smoke detector, we put that back on them. If they need a light bulb replaced, we put that back on them. If it's a single family house and there's been no roaches for six months and then they complain of a roach issue, we put that back on them. I've found that property managers don't do that for the most part. They have their own business to run. It's not that these are unethical people. They just have their own business to run, and they make money off their maintenance requests. Turnover is another big one. As you know, your number one expense as an investor is vacancy. And so every time a tenant would move out, they're managing 500 other units. It's probably not a week until they can get to it, probably not another few days until they send me an overpriced. quote, probably another week or two before they actually finish the work. Then a few days later, they finally list it. It takes them longer to fill it up than it takes my team today. And then when it's finally all said and done, they give you a leasing fee of one month's rent. So every single time I was vacant, I'm losing like three months of rent or more. And you don't see that on the spreadsheet. On your spreadsheet, you just have 10%. But in reality, it's so much more than that. So I never made any money.
Speaker #2
So my wife would kill me for saying this, but I got to say it. So I want to know what your opinion is. I think that managing property is actually fairly easy. And it's the turnover, as you're alluding to, that's the challenge. So what we do in our business on the single family detached stuff, anything that's attached, we have professionally managed. anything detached We just hire a management company to do the leasing, like a leasing agent for us. And then we take all of the other management on ourselves. What are your thoughts about doing some type of a la carte? management.
Speaker #0
I used to do that too. I would say that that's better than having a third party property manager do everything. I would argue the next step to that is just doing everything yourself. Because what I found is that I was spending just as much time telling the property manager what I wanted done as it would just take me to do it myself. Now, you might say, hey, I don't micromanage my property manager. I just let them do what they want. I have found when I do that, I don't make nearly as much money as I should be. And so if I have a vacancy sitting for three months, they were hearing from me like, hey, have you tried doing this? Have you tried doing that? And again, they have their own business to run. So they're not going to change their entire business for one client. Why should they? Even though they had so many units with me, it just didn't make sense. for them from a business perspective. So I would say if your wife and you took that next step and brought everything in house, you'd be amazed how much more money you would make, at least in my experience. I don't disagree that property management is difficult. I would say, especially as you grow the amount of units that you manage, it becomes a lot easier because then you have a team who really does everything for you. We have a. We use Appfolio as a CRM. And then we have a workflow CRM called Monday.com. You might have heard of that. We use Appfolio. Perfect. So every single step of each individual's job is there. We don't have to micromanage it. So in the beginning, like setting up all those systems and like really managing everything, that was more difficult. But I think now that we've sort of stabilized, we have the team and it's all said and done, it is much easier. And it's certainly easier than it was to manage a third-party management company. And we're making way more money.
Speaker #2
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Speaker #0
That makes a lot of sense. I've had a similar epiphany. Obviously, I've only been doing this eight years, I have a lot of time left. But one of the things that's come across my mind recently is my net worth is eight figures. even after you take away all the partnerships. So by anyone's standards, I'm doing well. Catch flow is great. If I lose all of that, that would be devastating. If my net worth increases by 10, 20, 30%, my lifestyle changes nothing. Nothing will change in my life. And so the risk of losing it all is far greater than the benefit of growing.
Speaker #2
And so is that why you like the paid off? Is that what we're getting to here?
Speaker #0
You got it.
Speaker #2
Not it. Okay. Keep going. I didn't mean to interrupt you.
Speaker #0
No, you're good. I was just, so my mindset shifted from, you know, continue to leverage to buy more properties to let's, let's take a step back. 2026, I've slowed down the acquisitions a lot. And I've been, you know, saving up reserves and paying off properties as aggressively as possible. But I totally agree with you to a certain extent, it is not worth it to just stress yourself out and keep growing. It does nothing for you.
Speaker #2
Yeah. I, yeah, we're on the same page for the listener. That's still in the growth phase and not an eight figure net worth. It does slow growth to pay off properties. I don't think anybody would argue with me on that. Now, I'm not saying that's good or bad. It does ease life, right? But if you leverage that and go buy two or three properties, then your returns would go up, right? And you have a great net worth and great cash flow. Well, some people have great net worth and no cash flow. And they have great net worth and no cash, right? So to have leverage on your properties and money in the bank sometimes is safer than paying off the properties. Because I got to tell you, man, there's businesses that are profitable that go out of business. And real estate is one of them. And the reason I say that is... Every month you make a payment on your mortgage and a piece of that goes to principal, right? Well, that's profit, but that's not going in your pocket. So I know I'm going a little bit higher level here, but we need to be careful with how much equity we really have instead of cash in the bank because equity earns 0% return and you cannot buy a beer with it.
Speaker #0
We 100% agree. So if you have $200,000 in the bank and your mortgage is $200,000, it would be a very bad idea. It would be a bad idea to pay off that mortgage, have zero dollars in the bank and a free and clear property, because then any singular thing that goes wrong, you are in trouble. So I would much rather have that liquidity and have a mortgage than to have the free and clear real estate. The next phase for me is building that liquidity. You know, I would like to have a substantial amount of liquidity, even more than, you know, what you would call a rule of thumb. to me, 5% to 10% of your mortgage amount is a good rule of thumb. I want to exceed that because, again, I don't care if I don't buy another unit for the next 10 years. What I do care about is if I get reckless and I start to get into trouble because real estate is a business where a lot of people get into trouble because most real estate is very debt-focused. You have a lot of debt. You could be sensitive to interest rates, depending on the type of debt that you have. You could be sensitive to, you know, rising taxes, rising insurance. Cap rates can continue to increase as interest rates go up. You could get yourself into trouble if you don't have this safety net of liquidity at the end of the day. I think both are important. I think at the same time, you know, if all of your properties are 80 percent leveraged. depending on what market you're in, you could also get into trouble. Oh, that's true.
Speaker #2
I agree with you.
Speaker #0
So I think both liquidity and keeping an eye on your leverage are important.
Speaker #2
Well, you're obviously doing something right, James, because you have this amazing portfolio and you did that without any syndications. Not a lot of people can say that. So give me maybe the top two reasons for your success. What do you attribute where you've been able to come these last eight years? What are the top two that you attribute it to?
Speaker #0
I would say perseverance. So the unwillingness to give up would be number one above anything. I have made a lot of mistakes. I have lost a lot of money. I have been very stressed out in previous years because of just bad financial situations. I think that's another reason why I'm so anti-growth right now is because I've been through the time where I made mistakes. tried to grow too fast and got myself into trouble. And now that I'm out of that, I don't ever want to go back to that. But the one quality trait that has really helped me is that despite all of those hiccups, I'm still working at it and I'm not giving up. And it sounds cliche, but it's true. You know, I've been very, very adamant about just keep going, figuring it out. And, you know, real estate can, there's a lot of... ups and downs for any entrepreneur. You know, there's, there's days where I feel on top of the world and then there's days where everything's going poorly and I'm just not on top of the world at all. Um, so, so I think my, my perseverance has gotten me very far. Um, second quality trade, I would say, uh, collaboration, just my ability to make win-win scenarios with people. Um, I treat every relationship very seriously. So like even something as simple as a real estate agent. Anyone who finds me deals, a wholesaler, if they find me a deal and the numbers work for me. I'm not someone who nickels and dimes them. I want to make sure I'm getting a good deal for myself. So I'm certainly not being reckless. But I think some people might just negotiate because they can. I don't do that. You know, if the numbers work for me, I want to make their life easy because I want them to keep bringing me deals. If it's a partnership, you know, I try not to be too opinionated or hardheaded when it comes to like when we If they want to sell a deal, for example, that's fine. If they want to refinance a deal, that's fine. So I think I approach every relationship that I can in a collaboration. How can this be a win-win? And I treat it as it is, which is the benefit of that relationship long term is a lot more valuable than if I can squeeze somebody out of, you know. $10,000, you know? So I would say those two quality traits.
Speaker #2
You know what I love? I love both of those, James. And I love how quickly you came to them. Like, you really know where you've come from and the success you've had. That's fantastic. Let's talk about like what you're doing now. I'm curious on the coaching, but also you said you're not buying anything right now. So you're just managing your portfolio and doing your coaching thing and hanging tight?
Speaker #0
Yep. So I will take that back slightly. I am buying significantly less. So I'm buying like a duplex here and there. You know, I'm not buying like these big apartment complexes and just I'm not in growth phase anymore. If I find something that's really a no brainer, you know, and it's small, I'll buy it just to keep the guys busy. This year has been 90% focused on just stabilizing and refining the systems in my businesses. My goal up to this point has been net worth. I have found out net worth in a lot of ways is pretty meaningless. It's a vanity metric and it has helped my ego, but it has not helped much more than that. So I would much rather at this point keep the same net worth, not necessarily grow that. But if my active businesses can be spitting out X amount of cash per month, that's going to improve my lifestyle a lot more than buying. more real estate at this point in my career. So I am focusing on the property management company. So switching to Appfolio is something we did this year. Using Monday is something we did this year. Using VAs is something that we started doing this year. Creating all the systems and processes for that management company is something that we started doing this year. So this year, I'm essentially slowing down to speed up. I'm really making sure that the management company is profitable, that it's sort of running itself. Actually, in July, it's mid-August right now, July 1st, we hired our head property manager for that company. So we kind of built all the systems. I found that there was still a little bit of babysitting needed on my end to fill any cracks. And so now the head property manager's job is to 99% take me out of the business. which is very exciting. Same thing with the construction company. We hired a project manager, a construction manager. We have VAs. We're building the systems around that. We're really trying our best to make that company as profitable as possible. And so focusing on the active income businesses is what I'm spending most of my time on and trying to take myself out of those businesses. Not completely, but as much as I can so that one year from now, two years from now, whenever I'm ready to start growing again, I really have a firm foundation to do that.
Speaker #2
I think it's good. Look, we don't know what's coming, right? We have this Iran conflict. We have midterms. There's some concerns, let's say, economically. What I've seen, James, a lot of the more experienced investors, they've shifted their business, similar to what you're telling me, from just a... equity or sponsor position to more of a fee-based business so they can keep generating income regardless of what comes, right? Because look, your $60 million portfolio very well may be worth 50 at the end of the year. We don't know what's going to happen. So I think the way you're structuring it is very smart. Tell me about your coaching program.
Speaker #0
Yeah. So you I teach people how to invest in real estate. We've had dozens, I don't know the exact number, but over 50 students at this point. I have a one-on-one mentorship where I'm coaching people on a weekly basis. They're meeting with me one-on-one. Three years ago when I started that business, I was really excited about that. Great income stream. Also something that I was passionate about, helping people build their real estate portfolio, something that I happen to be very good at. And so my students had tons of success. I'm happy to, you know, people who started with zero units getting to 50 units, 100 units, some quitting their job. I've actually had multiple quit their job. And so that has been amazing. As of last year, I had over 20 one on one students. I was spending like 75 percent of my time just meeting with people, you know. And so I shifted to an online product, a course. And now I have less one-on-one students and I'm trying to focus more so on the online product. And it just gets into all of the weeds of real estate investing. I pride myself in not being the mentor who just says, find the money, find the deal, and then drink Corona on the beach. It's not that easy. No, unfortunately not. So I very much get into the weeds of, you know, this is how you manage a contractor. This is how you manage a property manager. By the way, I recommend that you are your own property manager and your own contractor if you really want to grow this. But, you know, here's I get into the weeds of things very much.
Speaker #1
Cool. Well, I'm going to get your contact information on how we would get a hold of that. But before that. We're at the very end of the show, James, and I want to go through my notes. Every episode, I take notes, what I've learned. That way I could do like a real quick recap for the listener. And then I would love for you to share one thing that I didn't write down that maybe we didn't talk about or we did and I missed, but some piece of advice for the listener. And then obviously your contact information. So we started out going through your story and you got started super young. You were 21 years old. You bought that first house at a pure just like... heart and effort because you didn't have probably great credit, maybe no credit that young. And you said not a lot of cash, but you found the property on Craigslist. You networked with people that got you the money and the property management and the construction. So you used Burr with the hard money lender. You refinanced that and you kept it. You still own it today, it sounds like. You would spend more time on relationships had you gone back eight years to start over again. I thought that was a really powerful lesson there. Finding deals and finding money, that's what most people teach you is important, which it is, but don't neglect or ignore other areas of your business. And we were talking specifically about outsourcing there. You need to manage the manager, which we agree on. Have your systems. As you built your systems, it got easier and easier, and you're continuing to do that today. In fact, you had some big system changes this year alone. Equity is great. Cash is better. The two things that really got you or launched your career was. perseverance and collaboration. And you really just drove it home by just take care of people. How did I do?
Speaker #0
Yeah, great. Cool.
Speaker #1
So what's the final piece of advice for the listener?
Speaker #0
I would say that this would go for someone if you're starting out. This is arguably more important when you're starting out, but even if you're seasoned, real estate is a very enticing business to... be able to get into it without using any of your own money. And that is true. But I would say put a focus on your income would be the other piece of advice that I would give. In my experience, the students that I have who make more money do better in real estate. They can grow more aggressively because if something goes wrong, they have their income to fall back on to sort of make up for those mistakes. They don't have to get perfect creative finance for deals because they are able to put a little bit of money in the deal if they really believe in it and they really like it. And so putting a focus on that income, whatever that means for you, if it means doing a better job at your job or creating a business around real estate like I've tried to do or something else, it really makes a difference in your ability to... Scale not to lose what you've built, which is the most important part to have peace of mind like Money solves a lot of problems in business. And so if you can put a focus on your income, despite what you hear on the podcasts about real estate, I think you will be a lot more successful.
Speaker #1
That's great. Sorry about your career in basketball, James, but man, you really have a great career now.
Speaker #0
Appreciate that.
Speaker #1
All right. How do we get ahold of you?
Speaker #0
Multifamilymethods.com. is if you want to find out about my coaching program. And then Instagram, TikTok is just James Gleason Real Estate.
Speaker #1
All right. And you're obviously busy. You're vertically integrated. You got all kinds of businesses going on. You're coaching maybe more than you want to. It sounds like that takes a lot of time. And you still came out and hung out with me for 45 minutes. So I really, really appreciate your time.
Speaker #0
Yeah, it's been a pleasure. Thank you, Kevin.
Speaker #1
All right. For the listener, you have other podcasts you could be listening to, and you chose the Real Estate Educators Podcast. I am so grateful for you for that. If you got value like I did, I went through my notes, guys. There's a ton of value in this episode. If you got the value, five-star review, share it with a friend, and I hope you make this day a great one. I really hope you enjoyed this episode as much as I did. If you did, please be sure to follow and leave a five-star review. Oh yeah, and tell a friend.
Speaker #0
But the one quality trait. that has really helped me is that despite all of those hiccups, I'm still working at it and I'm not giving up. And that it sounds cliche, but it's true.

Description

00:00 – From college basketball to real estate investing

04:10 – Buying his first property at 21

06:15 – Using the BRRRR method and hard money

08:30 – How relationships helped James get started

14:20 – The hidden costs of property management

17:10 – Bringing property management in-house

22:15 – Paying off debt vs. continuing to leverage

25:00 – Why liquidity matters as much as equity

30:15 – Why net worth can become a vanity metric

32:20 – Building systems instead of chasing more growth

Connect with James Gleeson

Learn more about James's real estate investing education and coaching at MultifamilyMethods.com.

You can also find him on Instagram and TikTok at James Gleeson Real Estate.

Learn more about Pine Financial Group at pinefinancialgroup.com

Hosted on Ausha. See ausha.co/privacy-policy for more information.

Transcription

Speaker #0
The hard money lender referred me to his contractor. So it was like one relationship kind of led to another. And I just did the Byrd method. So I bought it for $25,000 with his money. I renovated it for $14,000 using his money. So I was all in for $39,000. The deal eight years ago appraised for $65,000. And today it's worth like $180,000. That was more difficult. But I think now that we've sort of stabilized, we have the team and it's all said and done, it is much easier. And it's certainly easier than it was to manage a third party management company. And we're making way more money. But the one quality trait that has really helped me is that despite all of those hiccups, I'm still working at it and I'm not giving up. And it sounds cliche, but it's true.
Speaker #1
We were in negotiations for investing in real estate. They're winning. What's up, everyone?
Speaker #2
Welcome to the Real Estate Educators Podcast, where we provide the education you can build on. I am your host, Kevin Amos. We are back. I'm so excited for another fantastic episode of a very experienced investor with us today, Mr. James Gleason. You've been doing this for a while, man. It's in the business for a while. You've built up a nice portfolio, $60 million. I haven't gotten into where yet, but I know you're calling from St. Louis, Missouri. I know you are an investor and a mentor or a coach. You got a lot going on. Welcome to the show, man.
Speaker #0
Thanks, Kevin. Appreciate you having me.
Speaker #2
Well, let's get into it. So you've been doing this, actually it does right here. You've been doing it eight years. So back before COVID even. So tell us eight years ago, why real estate, man? What got you started going this direction?
Speaker #0
Yeah, it is... Pretty simple story. There's really, I didn't have any family members or anyone that was in real estate, but I grew up playing basketball and I always had dreams of playing professional ball. And when I got to college, I played college basketball, quickly found out that that was not going to happen. Everyone was bigger than me, stronger than me. And so I basically just gave up on the basketball dream. Thank you. So that summer, my sophomore year of college, you know, after I had given up the basketball dream, I just lost purpose. I really didn't know what to do with myself because I went to an engineering school because I just heard that engineering was a good degree. You know, I would make a decent living. I was good at math and science. And so it made sense. But when I did the internships, I didn't really enjoy it. You know, I found myself unfulfilled with the actual work that I was doing. And engineering school is very difficult. You know, I went to Missouri S&T here in Missouri, one of the top engineering schools in the country. It is not easy. I'm not one of these naturally gifted math wizards. You know, I had to work very hard to do well in college. And so my whole life, it had just been basketball and pursuing that dream. And so when I lost that, I needed something else to pursue. I always had a natural just... my inclination interest for real estate. I can't really explain why. I grew up watching The Apprentice with my mom. I'm sure that had something to do with it. But I just always knew that I wanted to do real estate. And so I saw a Grant Cardone ad when I was in college for his millionaire booklet. And I saw that ad and I was just immediately hooked. I was like, this is what I want to do. And so from that point forward, I just... completely obsessed with real estate like I did with basketball, read the books, listened to the podcast, hired a mentor, went out for coffees with as many people as I could. And the rest really became history. I never really looked back at that point. And so when I was 21 years old, January of 2018, I bought my first house. I'm happy to get into the specifics of that if you'd like. And then, you know, after I bought that first house, I used the same lender for the next three or four properties. And, you know, that was eight years ago in 2018. Fast forward today, I own a $60 million portfolio, about 470 rental units. I did all that without syndications. So I'm not someone who just owns, you know, 10% of his portfolio. I own the vast majority of my portfolio. I do have a lot of partnerships. But those are all 50-50 partnerships for the most part. And then I own $1.5 million of real estate free and clear. Happy to get into my philosophy with that. I think there's a lot of just leverage till the day you die. Part of me believes in that, but part of me also believes in ultimately paying off that debt for peace of mind and lifestyle. And then I've became vertically integrated as well. So I have a construction company. I have plenty of nightmare stories with construction that I'm happy to talk about. Same thing with property management. And then I have an education platform where I teach other people how to do what I've done.
Speaker #2
Okay. So you have a lot going on. There's obviously a lot of different directions we could take this, but you said it, man, 21 years old. That's when I bought my first house too. Not a lot of people could say that. How'd you make that happen?
Speaker #0
So really just through education, you know, I used the Burr method to buy my first deal. So I found a hard money lender, the hard money lender. So this was a deal I found through Craigslist. All the real estate books that I was reading talked about Craigslist, Facebook Marketplace, door knocking, yellow letters, all these things. So I would go on Craigslist pretty regularly. And I found my first deal for $25,000. I googled property managers near me. And I found a property manager who was so gracious. It was a husband and wife. They were so gracious with their time. They were happy to walk through that house with me, point out things to look out for. Yeah, it was amazing because as you know, when you're starting out, or at least for me, I didn't know what flipping a breaker meant at the time. I didn't know anything. So walking these houses was pretty...
Speaker #2
What are you talking about?
Speaker #0
I was an engineer because I thought I would make a good living, not because I knew how to engineer. So obviously. noted uh yeah it was pretty bad um thus why i didn't enjoy it because i wasn't good at it um but they were so gracious with their time it really gave me the confidence they referred me to the hard money lender that i used um that hard money lender funded 100 of the deal um he charged me um 15 interest and five points so he was pretty expensive um but he funded the whole deal there was definitely some convincing there He had some hesitations because I was 21 years old and had never done this before and didn't really have savings. So the property manager referred me to the hard money lender. The hard money lender referred me to his contractor. So it was like one relationship kind of led to another. And I just did the Byrd method. So I bought it for $25,000 with his money. I renovated it for $14,000 using his money. So I was all in for $39,000. The deal eight years ago appraised for $65,000. And today it's worth like $180,000. So, you know, obviously I got very lucky buying in 2018 before the COVID era. But I've experienced a lot of appreciation and equity benefits since then. But yeah, just educating myself, getting the right relationships and using the BRRRR method.
Speaker #2
So we talk a lot on this show about the power of relationships and who you surround yourself with and how it could really impact your career. It sounds to me like you had several right out of the gate, very powerful relationships, but that one with the property management sounds pretty important. Tell me more about that. You said how you found it because you just Googled them, but how'd you convince them to come take you under their wing and what kind of impact did that have on where you are today.
Speaker #0
Yeah. And I would say, just to add to that, if I could go back in time, one of the things I would have done differently is I would have spent even more time on building my relationships. I am where I am today because of the people that I know, because of the relationships that I have. And that's all the way from the lenders that I know, the wholesalers that I know, the agents that I know, the brokers, the partnerships. Like everything that I have today is a result of those relationships that I have. Um, so if I could go back in time, I would have doubled the amount of people that I was meeting on a weekly basis. Um, I think it was conviction. I think I knew that this is what I wanted to do. Um, hopefully they could hear that passion through the conversations with me. Um, I I'd love to say that it was all my ability to persuade them, but I think part of it is just, they were nice people. Um, here's a 21 year old. You know, he's talking about buying these houses and, you know, buying without using his own money. And I'm sure they saw some. some of them and me potentially, you know, and they just wanted to help this young guy out. But yeah, I think they were very nice people. I had a lot of conviction. And I think at the end of the day, just like those relationships got me that first deal, in a lot of ways, even today, my relationships are what are still getting me, you know, the deals and the money that I need to continue growing.
Speaker #2
We all have relationships in our career. Anyone who has any... any level of success, success has that type of relationship, right? I mean, somebody helped you along the way. This isn't a do-it-yourself business. So I'm just curious, do you still talk to them to this day?
Speaker #0
I don't. I don't even know that they're still in business anymore. I actually got away from property management completely. I do have a lot of relationships that are eight years old with like vendors that I'm still using, for example. my HVAC people, my electricians, partnerships, lenders. I have some very old relationships that have just continued to be win-win relationships. But no, I ultimately fired property management. Every podcast and book and bigger pockets told me, you should work on the business, not in the business. And so just hire a property manager and focus on finding deals and finding money. And finding deals and finding money is one of your highest ROI dollar per hour activities that you can spend your time on as a real estate investor. But if you ignore the operations, the construction management and the property management, you're not going to be able to grow as quickly and you're potentially going to get yourself into trouble. And that's what happened to me. You know, I thought it was as simple as hire a contractor, give them 50% down and then talk to him in three months. And I found out that that is the farthest thing from reality. And with property management, you know, I didn't have as many like crisis things happen with property managers. But what I did find out is that every single month I was making nothing and they were making a bunch of money. you When I dug into it, I was like, what is going on here? Like everyone says hire a property manager. Am I the only one who's not making cash flow? But when I really started digging into it and thinking about it, they have, you know, obviously their 10% management fee, which you can negotiate down a little bit. But on top of that, they have their leasing fee. On top of that, some have maintenance fees. But then even the fees that they don't charge you, which are the most... ones. Number one, there's a lot of maintenance requests that with my vertically integrated management company today, we turn down maintenance requests. If their battery dies in their smoke detector, we put that back on them. If they need a light bulb replaced, we put that back on them. If it's a single family house and there's been no roaches for six months and then they complain of a roach issue, we put that back on them. I've found that property managers don't do that for the most part. They have their own business to run. It's not that these are unethical people. They just have their own business to run, and they make money off their maintenance requests. Turnover is another big one. As you know, your number one expense as an investor is vacancy. And so every time a tenant would move out, they're managing 500 other units. It's probably not a week until they can get to it, probably not another few days until they send me an overpriced. quote, probably another week or two before they actually finish the work. Then a few days later, they finally list it. It takes them longer to fill it up than it takes my team today. And then when it's finally all said and done, they give you a leasing fee of one month's rent. So every single time I was vacant, I'm losing like three months of rent or more. And you don't see that on the spreadsheet. On your spreadsheet, you just have 10%. But in reality, it's so much more than that. So I never made any money.
Speaker #2
So my wife would kill me for saying this, but I got to say it. So I want to know what your opinion is. I think that managing property is actually fairly easy. And it's the turnover, as you're alluding to, that's the challenge. So what we do in our business on the single family detached stuff, anything that's attached, we have professionally managed. anything detached We just hire a management company to do the leasing, like a leasing agent for us. And then we take all of the other management on ourselves. What are your thoughts about doing some type of a la carte? management.
Speaker #0
I used to do that too. I would say that that's better than having a third party property manager do everything. I would argue the next step to that is just doing everything yourself. Because what I found is that I was spending just as much time telling the property manager what I wanted done as it would just take me to do it myself. Now, you might say, hey, I don't micromanage my property manager. I just let them do what they want. I have found when I do that, I don't make nearly as much money as I should be. And so if I have a vacancy sitting for three months, they were hearing from me like, hey, have you tried doing this? Have you tried doing that? And again, they have their own business to run. So they're not going to change their entire business for one client. Why should they? Even though they had so many units with me, it just didn't make sense. for them from a business perspective. So I would say if your wife and you took that next step and brought everything in house, you'd be amazed how much more money you would make, at least in my experience. I don't disagree that property management is difficult. I would say, especially as you grow the amount of units that you manage, it becomes a lot easier because then you have a team who really does everything for you. We have a. We use Appfolio as a CRM. And then we have a workflow CRM called Monday.com. You might have heard of that. We use Appfolio. Perfect. So every single step of each individual's job is there. We don't have to micromanage it. So in the beginning, like setting up all those systems and like really managing everything, that was more difficult. But I think now that we've sort of stabilized, we have the team and it's all said and done, it is much easier. And it's certainly easier than it was to manage a third-party management company. And we're making way more money.
Speaker #2
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Speaker #0
That makes a lot of sense. I've had a similar epiphany. Obviously, I've only been doing this eight years, I have a lot of time left. But one of the things that's come across my mind recently is my net worth is eight figures. even after you take away all the partnerships. So by anyone's standards, I'm doing well. Catch flow is great. If I lose all of that, that would be devastating. If my net worth increases by 10, 20, 30%, my lifestyle changes nothing. Nothing will change in my life. And so the risk of losing it all is far greater than the benefit of growing.
Speaker #2
And so is that why you like the paid off? Is that what we're getting to here?
Speaker #0
You got it.
Speaker #2
Not it. Okay. Keep going. I didn't mean to interrupt you.
Speaker #0
No, you're good. I was just, so my mindset shifted from, you know, continue to leverage to buy more properties to let's, let's take a step back. 2026, I've slowed down the acquisitions a lot. And I've been, you know, saving up reserves and paying off properties as aggressively as possible. But I totally agree with you to a certain extent, it is not worth it to just stress yourself out and keep growing. It does nothing for you.
Speaker #2
Yeah. I, yeah, we're on the same page for the listener. That's still in the growth phase and not an eight figure net worth. It does slow growth to pay off properties. I don't think anybody would argue with me on that. Now, I'm not saying that's good or bad. It does ease life, right? But if you leverage that and go buy two or three properties, then your returns would go up, right? And you have a great net worth and great cash flow. Well, some people have great net worth and no cash flow. And they have great net worth and no cash, right? So to have leverage on your properties and money in the bank sometimes is safer than paying off the properties. Because I got to tell you, man, there's businesses that are profitable that go out of business. And real estate is one of them. And the reason I say that is... Every month you make a payment on your mortgage and a piece of that goes to principal, right? Well, that's profit, but that's not going in your pocket. So I know I'm going a little bit higher level here, but we need to be careful with how much equity we really have instead of cash in the bank because equity earns 0% return and you cannot buy a beer with it.
Speaker #0
We 100% agree. So if you have $200,000 in the bank and your mortgage is $200,000, it would be a very bad idea. It would be a bad idea to pay off that mortgage, have zero dollars in the bank and a free and clear property, because then any singular thing that goes wrong, you are in trouble. So I would much rather have that liquidity and have a mortgage than to have the free and clear real estate. The next phase for me is building that liquidity. You know, I would like to have a substantial amount of liquidity, even more than, you know, what you would call a rule of thumb. to me, 5% to 10% of your mortgage amount is a good rule of thumb. I want to exceed that because, again, I don't care if I don't buy another unit for the next 10 years. What I do care about is if I get reckless and I start to get into trouble because real estate is a business where a lot of people get into trouble because most real estate is very debt-focused. You have a lot of debt. You could be sensitive to interest rates, depending on the type of debt that you have. You could be sensitive to, you know, rising taxes, rising insurance. Cap rates can continue to increase as interest rates go up. You could get yourself into trouble if you don't have this safety net of liquidity at the end of the day. I think both are important. I think at the same time, you know, if all of your properties are 80 percent leveraged. depending on what market you're in, you could also get into trouble. Oh, that's true.
Speaker #2
I agree with you.
Speaker #0
So I think both liquidity and keeping an eye on your leverage are important.
Speaker #2
Well, you're obviously doing something right, James, because you have this amazing portfolio and you did that without any syndications. Not a lot of people can say that. So give me maybe the top two reasons for your success. What do you attribute where you've been able to come these last eight years? What are the top two that you attribute it to?
Speaker #0
I would say perseverance. So the unwillingness to give up would be number one above anything. I have made a lot of mistakes. I have lost a lot of money. I have been very stressed out in previous years because of just bad financial situations. I think that's another reason why I'm so anti-growth right now is because I've been through the time where I made mistakes. tried to grow too fast and got myself into trouble. And now that I'm out of that, I don't ever want to go back to that. But the one quality trait that has really helped me is that despite all of those hiccups, I'm still working at it and I'm not giving up. And it sounds cliche, but it's true. You know, I've been very, very adamant about just keep going, figuring it out. And, you know, real estate can, there's a lot of... ups and downs for any entrepreneur. You know, there's, there's days where I feel on top of the world and then there's days where everything's going poorly and I'm just not on top of the world at all. Um, so, so I think my, my perseverance has gotten me very far. Um, second quality trade, I would say, uh, collaboration, just my ability to make win-win scenarios with people. Um, I treat every relationship very seriously. So like even something as simple as a real estate agent. Anyone who finds me deals, a wholesaler, if they find me a deal and the numbers work for me. I'm not someone who nickels and dimes them. I want to make sure I'm getting a good deal for myself. So I'm certainly not being reckless. But I think some people might just negotiate because they can. I don't do that. You know, if the numbers work for me, I want to make their life easy because I want them to keep bringing me deals. If it's a partnership, you know, I try not to be too opinionated or hardheaded when it comes to like when we If they want to sell a deal, for example, that's fine. If they want to refinance a deal, that's fine. So I think I approach every relationship that I can in a collaboration. How can this be a win-win? And I treat it as it is, which is the benefit of that relationship long term is a lot more valuable than if I can squeeze somebody out of, you know. $10,000, you know? So I would say those two quality traits.
Speaker #2
You know what I love? I love both of those, James. And I love how quickly you came to them. Like, you really know where you've come from and the success you've had. That's fantastic. Let's talk about like what you're doing now. I'm curious on the coaching, but also you said you're not buying anything right now. So you're just managing your portfolio and doing your coaching thing and hanging tight?
Speaker #0
Yep. So I will take that back slightly. I am buying significantly less. So I'm buying like a duplex here and there. You know, I'm not buying like these big apartment complexes and just I'm not in growth phase anymore. If I find something that's really a no brainer, you know, and it's small, I'll buy it just to keep the guys busy. This year has been 90% focused on just stabilizing and refining the systems in my businesses. My goal up to this point has been net worth. I have found out net worth in a lot of ways is pretty meaningless. It's a vanity metric and it has helped my ego, but it has not helped much more than that. So I would much rather at this point keep the same net worth, not necessarily grow that. But if my active businesses can be spitting out X amount of cash per month, that's going to improve my lifestyle a lot more than buying. more real estate at this point in my career. So I am focusing on the property management company. So switching to Appfolio is something we did this year. Using Monday is something we did this year. Using VAs is something that we started doing this year. Creating all the systems and processes for that management company is something that we started doing this year. So this year, I'm essentially slowing down to speed up. I'm really making sure that the management company is profitable, that it's sort of running itself. Actually, in July, it's mid-August right now, July 1st, we hired our head property manager for that company. So we kind of built all the systems. I found that there was still a little bit of babysitting needed on my end to fill any cracks. And so now the head property manager's job is to 99% take me out of the business. which is very exciting. Same thing with the construction company. We hired a project manager, a construction manager. We have VAs. We're building the systems around that. We're really trying our best to make that company as profitable as possible. And so focusing on the active income businesses is what I'm spending most of my time on and trying to take myself out of those businesses. Not completely, but as much as I can so that one year from now, two years from now, whenever I'm ready to start growing again, I really have a firm foundation to do that.
Speaker #2
I think it's good. Look, we don't know what's coming, right? We have this Iran conflict. We have midterms. There's some concerns, let's say, economically. What I've seen, James, a lot of the more experienced investors, they've shifted their business, similar to what you're telling me, from just a... equity or sponsor position to more of a fee-based business so they can keep generating income regardless of what comes, right? Because look, your $60 million portfolio very well may be worth 50 at the end of the year. We don't know what's going to happen. So I think the way you're structuring it is very smart. Tell me about your coaching program.
Speaker #0
Yeah. So you I teach people how to invest in real estate. We've had dozens, I don't know the exact number, but over 50 students at this point. I have a one-on-one mentorship where I'm coaching people on a weekly basis. They're meeting with me one-on-one. Three years ago when I started that business, I was really excited about that. Great income stream. Also something that I was passionate about, helping people build their real estate portfolio, something that I happen to be very good at. And so my students had tons of success. I'm happy to, you know, people who started with zero units getting to 50 units, 100 units, some quitting their job. I've actually had multiple quit their job. And so that has been amazing. As of last year, I had over 20 one on one students. I was spending like 75 percent of my time just meeting with people, you know. And so I shifted to an online product, a course. And now I have less one-on-one students and I'm trying to focus more so on the online product. And it just gets into all of the weeds of real estate investing. I pride myself in not being the mentor who just says, find the money, find the deal, and then drink Corona on the beach. It's not that easy. No, unfortunately not. So I very much get into the weeds of, you know, this is how you manage a contractor. This is how you manage a property manager. By the way, I recommend that you are your own property manager and your own contractor if you really want to grow this. But, you know, here's I get into the weeds of things very much.
Speaker #1
Cool. Well, I'm going to get your contact information on how we would get a hold of that. But before that. We're at the very end of the show, James, and I want to go through my notes. Every episode, I take notes, what I've learned. That way I could do like a real quick recap for the listener. And then I would love for you to share one thing that I didn't write down that maybe we didn't talk about or we did and I missed, but some piece of advice for the listener. And then obviously your contact information. So we started out going through your story and you got started super young. You were 21 years old. You bought that first house at a pure just like... heart and effort because you didn't have probably great credit, maybe no credit that young. And you said not a lot of cash, but you found the property on Craigslist. You networked with people that got you the money and the property management and the construction. So you used Burr with the hard money lender. You refinanced that and you kept it. You still own it today, it sounds like. You would spend more time on relationships had you gone back eight years to start over again. I thought that was a really powerful lesson there. Finding deals and finding money, that's what most people teach you is important, which it is, but don't neglect or ignore other areas of your business. And we were talking specifically about outsourcing there. You need to manage the manager, which we agree on. Have your systems. As you built your systems, it got easier and easier, and you're continuing to do that today. In fact, you had some big system changes this year alone. Equity is great. Cash is better. The two things that really got you or launched your career was. perseverance and collaboration. And you really just drove it home by just take care of people. How did I do?
Speaker #0
Yeah, great. Cool.
Speaker #1
So what's the final piece of advice for the listener?
Speaker #0
I would say that this would go for someone if you're starting out. This is arguably more important when you're starting out, but even if you're seasoned, real estate is a very enticing business to... be able to get into it without using any of your own money. And that is true. But I would say put a focus on your income would be the other piece of advice that I would give. In my experience, the students that I have who make more money do better in real estate. They can grow more aggressively because if something goes wrong, they have their income to fall back on to sort of make up for those mistakes. They don't have to get perfect creative finance for deals because they are able to put a little bit of money in the deal if they really believe in it and they really like it. And so putting a focus on that income, whatever that means for you, if it means doing a better job at your job or creating a business around real estate like I've tried to do or something else, it really makes a difference in your ability to... Scale not to lose what you've built, which is the most important part to have peace of mind like Money solves a lot of problems in business. And so if you can put a focus on your income, despite what you hear on the podcasts about real estate, I think you will be a lot more successful.
Speaker #1
That's great. Sorry about your career in basketball, James, but man, you really have a great career now.
Speaker #0
Appreciate that.
Speaker #1
All right. How do we get ahold of you?
Speaker #0
Multifamilymethods.com. is if you want to find out about my coaching program. And then Instagram, TikTok is just James Gleason Real Estate.
Speaker #1
All right. And you're obviously busy. You're vertically integrated. You got all kinds of businesses going on. You're coaching maybe more than you want to. It sounds like that takes a lot of time. And you still came out and hung out with me for 45 minutes. So I really, really appreciate your time.
Speaker #0
Yeah, it's been a pleasure. Thank you, Kevin.
Speaker #1
All right. For the listener, you have other podcasts you could be listening to, and you chose the Real Estate Educators Podcast. I am so grateful for you for that. If you got value like I did, I went through my notes, guys. There's a ton of value in this episode. If you got the value, five-star review, share it with a friend, and I hope you make this day a great one. I really hope you enjoyed this episode as much as I did. If you did, please be sure to follow and leave a five-star review. Oh yeah, and tell a friend.
Speaker #0
But the one quality trait. that has really helped me is that despite all of those hiccups, I'm still working at it and I'm not giving up. And that it sounds cliche, but it's true.

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