James Gleeson - Financially Free At 28
What if you could build a $60M real estate portfolio without syndications, big money, or insider connections? James Gleeson shares how he went from buying his first rental at 21 to owning 400+ units—using simple, repeatable strategies like BRRRR and value-add investing in his own backyard of St. Louis.
He breaks down the real lessons, mistakes, and mindset shifts that helped him scale. Now mentoring dozens of investors who’ve collectively closed $50M+ in deals, James proves that building real wealth through real estate is simpler—and more attainable—than most people think.
In this episode, you will be able to:
- Understand why real estate growth is compounding and how scaling becomes easier over time
- Learn how James Gleeson built a $60M portfolio and 400+ units starting from scratch
- Discover how to get started in real estate with limited resources by leveraging relationships and persistence
- Identify the importance of building strong relationships to unlock deals, funding, and opportunities
- Learn why focusing on operations, property management, and construction is key to long-term success
- Avoid costly mistakes by understanding the value of starting small before scaling into larger deals
- Explore the differences between single-family and multifamily investing and when to use each strategy
- Gain insight into how to transition from a full-time job to financial freedom through cash flow
The key moments in this episode are:
1:59 - Basketball Drive Becomes Investing Drive
6:25 - The First Deal And Hard Money
11:16 - Relationships That Create Momentum
14:48 - Operations And Vertical Integration
21:13 - Quitting The Job With Cash Flow
24:22 - Slowing Down To Stabilize Systems
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Full Transcipt Here:
James Gleeson
First of all, 60 million absolutely sounds unachievable. Um, I was at 30 million less than two years ago. So it's really a compounding success. It's not linear. And so getting from your first zero to a hundred units, I would say was harder than getting from 100 to 450. Um, so anyone out there listening, it really does get easier as you build your skill sets and you start building your team and you really start to figure it out. Welcome to the Real Freedom Show.
Mike Swenson
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 that people are building time and financial freedom through opportunities in real estate. I'm your host, Mike Swinson. If you want to get started on your real estate investing journey, check out our website freedom throughrealestate.com. It's where we put all of our content, all of our information, blogs, the intent to be able to inspire you to take action in real estate and start your own journey. And so super excited to share today. I love the idea. And I'm obviously I'm not going to diminish our guest today, James Gleason, and what he's doing, but to your own point, a regular guy didn't have anything handed to him and built something pretty cool. So James Gleason, seasoned real estate investor, began his journey at 21 years old with the purchase of his first rental property and in the next seven years built a portfolio valued at over 60 million, over 400 rental units inside of St. Louis, single family, multifamily apartments, and also love your strategy too as your journey is involved. So, James, I'm super excited to have you on the show. Welcome. Thanks for having me, Mike. It's a pleasure. I like to ask people why, you know, why real estate and how did you get started?
James Gleeson
My journey in real estate really started from my journey in basketball. So since I was a young kid, I had aspirations of making it to the NBA one day, playing pro. Um, and I gave it my absolute like every waking moment before school, after school, before bed, uh playing 2K, you know, if I was playing video games to still play basketball. Um and I ended up doing really well in high school. Um, and naturally I wasn't a good basketball player. Um, but through a lot of just hard work and hours, I became really good. Um, and that really set the groundwork for, you know, a lot of what I'm doing in real estate today. You know, I'm not naturally the smartest guy or a rich uncle, rich family member, or anything like that. Um, I've just put a lot of work into my craft. Um, and so fast forward, I ended up playing uh college basketball for uh University of Missouri Science and Technology, and I ended up going to engineering school. And when I played my freshman year of basketball, I quickly found out that I wasn't gonna make it pro. Everyone around me was six foot six, point guards, way bigger, stronger, you know, faster. Um, and so I gave up on my dream sophomore year of college. And I had been pursuing basketball for so long at that point that I felt pretty empty. I mean, that was my entire life's mission, and now I was just doing engineering and I didn't even really enjoy engineering, I was just doing it because I thought it'd be a good career path for me. Um, but I always had a natural fascination for real estate. Um I I grew up watching The Apprentice with my mom. I was always fascinated by the idea of owning property. And so um, when I was in college, I saw a uh Grant Cardone ad on my Instagram for uh uh his millionaire booklet, and I ordered it and I read it, and the rest was best for it. I was up. Um and so real estate in a lot of ways became my new my new sport, you know, it became just what I'm pursuing in life from that point forward. Um, and I I've treated it like a sport ever since. Um, so I bought my first house when I was 21 years old, January of 2018. Um, used a hard money lender for that purchase, purchased another single family after that, then a duplex. And then fast forward eight years later, um I have 60 million dollars in real estate. I've done that with no syndications, so I'm not someone who owns, you know, five or 10% of my portfolio. Um, I own the vast majority of my portfolio. Um it's roughly about 450 units. Um, and real estate's created complete financial freedom for me and it's completely changed my life. Um, so I don't have to work, my wife doesn't have to work. Um, I choose to work every day because frankly, I'd probably be pretty bored if I didn't. Um, and it it's like a sport to me today. So that's my journey.
Mike Swenson
Awesome. I think for a lot of people, you know, you you hear 450 units and 60 million, and you think like, oh, that's not possible. And I think for a lot of people, like the most important thing, and this is like what we focus on on the podcast, is take the next right step, right? You're not gonna get to 450 units overnight. It does take time. There's a lot of blood, sweat, and tears in the path to get there. However, if you don't take action today and you wait another year or two, right, then you just continue to delay that. And I see a lot of people that want to build a portfolio or want to do more in real estate from an investing standpoint, and then you talk to them 12 months later, it's like, well, I just didn't get around to it. I was really busy, I was doing my other thing, my main thing, whatever. It's like, no, you've got to start to put some foundation down there to be able to build that. And and for you, you were working and building that to the point to where then eventually you could quit and do real estate full time. So it does take time. So for you, then you mentioned kind of the the first deal. Talk about those first couple a little bit, kind of how you were able to get started and get that momentum going.
James Gleeson
First of all, 60 million absolutely sounds unachievable. Um, I was at 30 million less than two years ago. So it's really a compounding success. It's not linear. And so getting from your first zero to a hundred units, I would say was harder than getting from 100 to 450. Um, so anyone out there listening, it really does get easier as you build your skill sets and you start building your team and you really start to figure it out. Um, but for me, my first few deals, um, I ran into I ran into my hard money lender on bigger pockets. Um, I just put a post out there that I was looking for someone to finance my deal. Um, I found my first deal on Craigslist for$25,000. Uh, this was again January of 2018, so prices have changed quite a bit. That property today is worth$160,$180. Um, and so that hard money lender, it was actually very difficult to convince him to give me money because I was a 21-year-old, didn't have credit, didn't have money, didn't have the skill sets. Um, and I remember him telling me he would do the deal, but then a couple weeks before closing, he called me and he said that he had a change of heart. He spoke with his wife and he wasn't gonna be able to do the deal. And I remember literally begging him, like, please give me a shot. I'm I'm gonna give it my all. I'm not gonna let you down. Um, and long story short, he ended up giving me the money for that deal. Um, bought it for 25, put 14 into it, it appraised for something like$70,000 at the time. Again, this is uh eight years ago that this happened. Um and I was hooked at that point. And so I had built a relationship with that hard money lender. He referred me to a third-party property manager who was gracious enough to walk that deal with me, kind of tell me the things to look out for. Um, today I don't use third-party property management. I'm completely vertically integrated. I have my own construction company and my own management company. Um, I've learned that's the only way to do this business. Um, but after I did that first one and I really built that credibility with that hard money lender, he was the same lender for my second deal, which was also single family, and then my third deal, which was a duplex. Um, and then he funded a couple deals after that as well. So um it was really difficult in the beginning to find those relationships and and build my credibility. Um, but it became easier as I started to build a track record. And then fast forward to today, you know, I turn people down because I just don't have the time for it. So it does get easier as you progress and as you start to build that track record. Um, but yeah, I did the first few deals with a hard money lender, and then I just started branching off, building relationships with other private money lenders, hard money lenders, um, got into creative finance a little bit, um, and I was off to the races.
Mike Swenson
So now to clarify, you you don't use that hard money lender anymore?
James Gleeson
I don't.
Mike Swenson
Yeah. No. Well, because one of the things I was gonna mention, just kind of a few concepts here, a few key things to talk about is number one, what I really love is you didn't give up, right? So 21 years old, there's a lot of people that would sit, you know, listening to this and say, 21 years old, don't have the credit, uh, don't have the history or the track record. I'm just gonna have to wait, right? And and I think people that are successful are resourceful and figure out a way to make it work. So I tell a lot of people when they say, hey, I don't have the money, I say, Well, go talk to a couple local banks, find out, like, hey, here's a type of deal that I'm interested in. What do you need to see to be able to make that happen? And I said, that doesn't have to be you bringing the credit, the assets, whatever that might be, but now you have a puzzle to figure out and go find the pieces. And you found the pieces. And then the other thing is that first relationship that was really important doesn't necessarily be the relationship for life. And so, in some ways, as you're scaling up, you're finding the relationships that work well for where you're at at that time. But to your point, those relationships are really huge. You wouldn't have gotten where you are today without them, and where you are today, that relationship, you know, for whatever reason doesn't make sense, or there's other opportunities or better opportunities, or the niches are different, right? For what you're looking for and what they're looking for. So stuff happens. And so it's just that resourcefulness mixed with finding what you need at that time to get to the next step.
James Gleeson
Indeed. Um, I would say building relationships, if there's any one key area that has influenced my success over anything, it's been my ability to create win-win situations with other people. Um, and those relationships are the reason why I'm here. You know, building relationships with lenders got me the money that I needed for the deals. With banks, gave me the long-term money that I needed. Um, partnerships. I'm currently a part of over 20 partnerships, um, which I recommend and don't recommend at the same time, and we can get into that. Um, you know, finding deals, wholesalers, investor-friendly agents, other investors, you know, so every relationship that I've built has contributed to my success one way or another. Um, and it gets a lot easier to build those relationships. You know, as you start to build credibility um and you meet someone who knows someone, you know, you do what you say you're gonna do, you execute on a deal. Um, they might know another hard money lender or private money lender. Um, this lender in particular, he just stopped lending. He got out of the lending business. Um, and then, you know, I found other fantastic relationships. And today I have a hard money lending business of my own. Um, and so yeah, I would say every relationship that I've gotten has been the number one contributor to my success.
Mike Swenson
Are you looking to get started or scale in real estate investing but don't know your next step? Are you overwhelmed thinking about finding deals, analyzing deals, doing due diligence, and managing properties on top of it? Go ahead and push the easy button and invest with us. Real estate investing is what we do full time. We've done dozens of deals with hundreds of doors. We have the knowledge and experience to handpick the best deals that most investors can't find. We've got large off-market deals all the time where you can hopefully find returns and economies of scale that you just can't find on your own. The best thing is it's 100% costs to you for less capital than you can put down and trying to acquire a property on your own. Don't let this year go by or you don't make the leap, add to your portfolio, or you just did an analysis by brought it. To find out more, visit Freedom Through Realestate.com and click on invest. You can book a call and learn more there. So get to scaling your portfolio now with us by your side. That's freedomthroughrealestate.com and click on invest. I tell people you're you're you're building a resume, right? And so the resume that you need, you know, for for entry level or, you know, kind of first level isn't necessarily the the same resume that you need for the future, but you've got to just kind of get that experience and build the resume. And thankfully you're able to find somebody that took a chance on you, right, without the resume. And so, you know, there's a ton of value in being able to convince people to partner with you where maybe you are lacking a little bit. I remember my first deal, they had asked, like, well, what have you done in the past? And I said, because I was an agent before I invested. And I said, Well, I, you know, here's the properties I've helped my investors purchase, right? Because I'm leveraging the experience and the knowledge that I have. Doesn't mean I didn't have that experience, but I was very clear, like, I've helped investors buy these properties. So it shows I know how to see a deal, analyze a deal, work through, and get something closed, even though I didn't have the personal experience myself. So you've got to kind of find a way to, you know, leverage what you do have, what transferable skills, or maybe it is just the sweat equity to get to that next spot and build your resume.
James Gleeson
Yeah, I would say the most important skill sets in real estate is finding deals and finding money. Um, those are the two highest dollar per hour activities. Um, but I think what a lot of investors end up ignoring are the operations, the construction management and the property management. And what I've found is that the better I got at the operations, the construction management and the property management, which you don't really hear much about on the podcast or the books. It's all about find the deal, burr out of it, and you make money, you know, and that's it, then it's over. Um, but I've found that by really lasering in on those operations, it has become much easier to build those relationships and much easier to build that resume. You know, I can go up to just about any private money lender and say, hey, I have my in-house construction uh company and my in-house uh property management company. Um, and here's what we're doing. Here's the reason why I started those companies and why we're better, in my opinion, than 99% of the property management companies out there. Um, additionally, when I'm partnering with someone, I have complete control over the success of that project. You know, I hired, I can't even tell you how many contractors I hired when I got started, where money was stolen from me, or just even ethical contractors, the project got behind schedule or over budget or whatever it is. And some of those projects ended up being a disaster. And then the same thing on the property management side, you know, every month I would look at my statements, I wasn't making any money because they have their leasing fee and they have their 10% management fee, and maintenance is a lot more expensive than it should be, um, and lack of urgency because they're managing 500 other units, and they're not going to change their whole business model for you. And, you know, all these things that I learned. So now when I go up to a partner or an investor and I can say, you know, here's all of the successful projects that I've had as a result of having in-house management and in-house construction. And this all started, you know, for those listening, if you don't have a management company or a construction company, this all started because I really focused on operations. You know, it started with really getting good at managing the manager and getting good at managing construction. And then it sort of pivoted into what it is today. Um, but that focus on operations and not just focusing on the finding deals and the finding money really made everything a lot easier for me.
Mike Swenson
Now you do have a mix of single family, you know, smaller multifamily and apartments. Talk a little bit about that journey of starting and scaling, and then maybe for people, you know, kind of thinking about where to get started on that, um, on that sliding scale, kind of maybe what you would recommend for people.
James Gleeson
Yeah, sure. Um, it started with me with single family, and then you know, got into a duplex and then a quadplex. I always knew in the back of my mind that I wanted to get into apartments. Um, I was a big Grant Pardon fan. I, you know, he always preaches going bigger earlier. Um, and so that's something that was always in my mind, and I'm glad I did it because it really quantum leaked my net worth and my success and my journey to financial freedom. Um, I will say I think it is absolutely a must. It's imperative that you start with a smaller deal, in my opinion. Um, because those larger deals, when you're talking millions of dollars in loans, I mean, it can be really catastrophic if you mess up, um, especially if you're signing personal guarantees and all these things. I mean, it can it can really um slow down your success and make things harder. Um, one of my first apartment complexes was a 17 unit when I was roughly a year and a half, two years into the business. Um, and everything that could have gone wrong with that property went wrong. And it really set me back a couple of years because I had to work, you know, um a couple serving jobs and door dashing just to get a little bit more money to be able to, you know, service that debt and um make up the payments for that 17 unit. So it really slowed me down by perhaps going too fast too quickly. Um, so the advice that I would give is, you know, take those baby steps, you know, maybe small stretches every step along the way. Go for a single family, then a duplex, quadplex, eight unit, 16 unit, you know, maybe something like that would be appropriate. Um, or if you really want to get into those bigger deals uh faster, partner with someone who has that experience. Um, partner with someone who's a seasoned operator. Um you could even invest in a syndication if you really want to, and you know, learn from the the operators or the GPs of that um apartment complex. Um but I certainly don't recommend getting into that apartment too early. However, I will say I am where I am today because of apartment deals. You know, those apartment deals that really, especially the value add apartment deals, um, they've really allowed me to quantum leave, you know, my net worth and you know, uh get to that next step uh much more quickly. Um so start with the single families. I will say from an ROI perspective, single families are my favorite. You know, I have the best tenants in my single families, um, they pay for their own utilities, they cut their own grass, uh vacancy is a lot lower, they fill up a lot more quickly. They're just better tenants um because they treat the house like a home, you know. Um, whereas the apartment deals, the tenants are not as good. There's higher turnover, higher vacancy, and all those things. Um, so there's certainly pros and cons. Um, if you have a set amount of money and you want to invest in one deal, I think the single family is the better deal. But if you're looking to scale and get to financial freedom more quickly, um, I strongly suggest inching into those apartment deals slowly, slowly but surely.
Mike Swenson
Talk about your journey going from you know working your job to then eventually being able to quit your job. Walk us through what that was like and kind of assessing like when can I make that leap? What else do I need to accomplish on the investing side so that you feel comfortable being able to quit?
James Gleeson
Yeah. So the goal was always to retire from cash flow. Um, it took me up until 93 units. I was making roughly 13,000 a month in passive income. Um, that's of course on my spreadsheet. I had some good months, I had some bad months, but that was the amount of units that you know, the goal was always 10,000 a month. If I could get to 10,000 a month, I'll put my job in return. Um I took the old school approach, which is I kept my job and I did not. Quit until I had enough units to be able to become financially free and quit the job. Um I highly recommend that approach. I know other people who have dived into entrepreneurship. And when you're negotiating a deal because you have to have that deal to pay your rent or eat food, um, there's a level of desperation and fight or flight that just doesn't allow you to be creative and make good deals work. And so I didn't have that problem because my rent and my food was taken care of with my job. And I was just able to work nights and weekends on the real estate. And I was fortunate enough to have a job where I was in front of my computer all day. And so just during the day, I was able to do real estate most of the time. Um hated my job, did not enjoy engineering at all. So I always knew from the beginning that I wanted to become a real estate investor full time. Um, and so it was just living below my means to the most extreme extent. Um, at 21 years old, me and my best buddy uh slept on our couch in our family room and Airbnb'd our rooms in our apartment. Um, worked multiple jobs, ate very cheap food. You know, I worked at a restaurant, I was able to eat my dinner there for free. So did all the things, you know, all the classic fundamental financial things of living below your means and just making as much money as I could. Um, and it was a very, you know, five and a half years to become financially free is very quick in the scheme of things, you know, rather than going 40 or 45 years like a typical W-2 job. Um, but in the moment it felt very slow. You know, if you're working a job that you don't like every day and um you have this dream of just creating financial freedom through real estate, it it feels like a very slow process. Um, but I can say on the other end of it with 100% certainty that it is so totally worth it. I am so glad that I put that work in, and now I get to wake up and just focus on what I actually enjoy doing.
Mike Swenson
And what is what does today look like for you in terms of you've you know, you've got the the mix of properties, you're there in the St. Louis area, you've got your construction company, you've got your property management company. Kind of what does that day look like? Where are you looking to grow or what are you looking to acquire or kind of firm up in your businesses?
James Gleeson
Yeah, every day's different, um, which I like. Um, I have a mentorship as well where I teach other people how to get into real estate. So I'll have you know a couple sessions of one-on-one mentorships per day. Um, there's always something going on in the construction business. So I might be walking projects, I might have meetings with my partner and our project manager, um, might be going over financials. Um, there's always stuff going on in the property management business. So just operating that business, whatever that means, team meetings, looking at numbers, refining systems. Um and then there's the real estate investing, you know, uh actually buying the deals. Um I doubled in size in 2025, so I had a lot of drastic growth. Um, and I've I've just heard stories of so many people in 2008, for example, that lost their shirts. And I've come too far to potentially lose everything. And um, so so I've decided to really slow down this year. You know, I've still bought a few properties. I bought uh I bought a 10 unit earlier this year. I bought a couple duplexes, a couple single-family homes, but I'm not looking to buy like 200 units or anything crazy like that. I'm just buying a few units to keep my guys busy, make a little bit of money. Um, but I'm really focusing on just stabilizing the portfolio and refining my systems. So really making the construction company be able to operate itself. Um, same with the management company. Um, I'd like to have less involvement in those businesses. And it's not as easy as people think to make that happen. It's not just hire people and it does its thing and it takes a lot of work. Um, so that's my main focus this year. And then hopefully in 2027, I'll be able to start doing my favorite thing again, which is you know, looking for deals and and buying deals. Um, but every day in the life for me is a little bit different.
Mike Swenson
It's it's exciting to hear like points where it's like you push the pedal down, points where you kind of plateau and you kind of firm things up, a little mix of offense, a little mix of defense back and forth. Um, and so kind of going back to the basketball analogy, like, yeah, you it's uh you know, we talk about I coach basketball, it's a game of runs, right? And so you've got a run, and then you you hold and you you play some defense, you you get things firmed up and better, and then you can push again and pull back. And so, yeah, really cool. Just a cool story of how you're able to to build and grow and build something really cool. Like to your point, it takes a lot of other people, but I'm saying, you know, you you're the the lead engine there in terms of pushing forward. But uh yeah, James, congratulations on on everything that you're accomplishing and excited to hear your story. And for people listening, like it's very possible. And so uh just love how you have built what you've built. For people that do want to reach out to you, learn more about what you got going on and in your mentorship and stuff like that. How can they do so?
James Gleeson
Yeah, you can check out my website, multifamily methods.com. Um, everything about the mentorship and the education program is on that website. And then you can also follow me on the social medias, Instagram, TikTok, and that's at James Gleason Real Estate.
Mike Swenson
Awesome. And I should add Gleason with two E's, people that uh that don't see the name on the podcast. So cool. Well, James, thank you so much for coming on, sharing your story, um, and best of luck as you guys uh continue to grow in the future. Thank you, Mike. I appreciate you having me. It's been fun.
