
Show Summary
In this episode of the Real Estate Pros Podcast, host Quentin Edmonds sits down with real estate investor James Gleeson to discuss his journey from aspiring basketball player to building a $60 million real estate portfolio. Based in St. Louis, James shares how discovering real estate through Grant Cardone sparked his passion for investing. Over the past eight years, he has grown his portfolio to 450 residential units without syndications while maintaining majority ownership. James discusses the importance of perseverance, building strong relationships, staying focused in one investment niche, and creating systems that support long-term growth. He also explains how shifting from aggressive acquisition to strengthening operations and systems can help sustain success in real estate.
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Investor Fuel Show Transcript:
James Gleeson (00:00)
one of the most important things that you can learn to really compound your success is focus.
Quentin (00:08)
Mm.
James Gleeson (00:08)
I am where I am today because I am not doing Airbnbs or mobile home parks or commercial space or development and trust me those things look very attractive to me. ⁓ I’ve certainly considered doing those things ⁓ but I have stuck with a very boring business and I say boring because I’ve been doing the exact same thing for eight years but that’s when I knew that I was on to something is when it became boring and I was making money.
Quentin (00:32)
Yeah.
Hello everyone. Welcome to the Real Estate Pros podcast. I am your host Q Edmonds and I am excited to be here. I have another, I have a guest. I was gonna say another fantastic guest. He is another fantastic guest, but this gentleman is something about him like we syncing up very well. Listen, y’all may not understand this. I’ve got some teasing a little bit, but we even had to speak sign language to each other. And guess what? We was communicating. We were speaking sign language maybe like 30 seconds in.
And I’m meeting each other and we were synced up. I say that to say that this is going to be a great podcast. This gentleman is a wealth of knowledge. trust me, I wrote down stuff. We talked. I know his resume. I know what he do. But I kind of want you to hear it from him. And so I’m excited. I’m excited for you all to get to know Mr. James Gleeson. Mr. James, how you doing today,
James Gleeson (03:03)
Hugh, I’m doing good. Thank you so much for having me. It’s a pleasure.
Quentin (03:07)
Absolutely, man. And I’m the type James, I’m going to dive in brother. I’m going to make full use of our time. So let’s do this. I want you to tell the people what your main focus is these days. I would also love if you can give us a little bit of an origin story, man, like kind of how you got into real estate, how this all came about and tell us where you are geographically. People love to know where you are in the world. And so, man, what you’re doing, the origin story and where you are. My friend, you have the floor, sir.
James Gleeson (03:34)
Yeah, so I’m here in St. Louis, Missouri. I started in real estate investing roughly eight years ago. I grew up playing basketball and I had dreams of making it to the NBA ⁓ since I was a little kid. And I gave my absolute all into basketball. I mean, every waking moment I practiced basketball.
And I kind of gave up on my dream when I got into college and I saw all these big basketball players that were point guards and just better than me and I just didn’t stand a chance. And so I gave up on that dream and really lost purpose ⁓ when I was, you know.
I don’t know, 18 years old or so, because I had been pursuing basketball my whole life. And now I was in engineering school and I really didn’t enjoy what I was doing as an engineer. And so I always knew that I wanted to get into real estate since I was a little kid. I just didn’t know what that meant.
⁓ I just had a fascination for it naturally. And so ⁓ one day when I was in college, I saw a Grant Cardone ad on Instagram telling me to read his book. ⁓ It was called the Millionaire Playbook or something like that. ⁓ So grabbed a copy, read it, and immediately I was hooked.
So that was eight years ago, did all the things, listened to the podcast, read the books, hired the mentor, know, did everything that I possibly could to get into this business.
And so I bought my first single family house in 2018. And now you fast forward eight years later, I own 450 units. I’ve done all of that with no syndications. It’s roughly $60 million worth of real estate. ⁓ And I own over 50%.
of my portfolio. So I’ve done it all while owning a majority interest in my portfolio. I’ve become completely financially free. My wife and I now depend on the income from my real estate. ⁓ We’ve become completely vertically integrated. So we’ve started a in-house construction company. We’ve started an in-house property management company. And I also have an education company where I’m teaching others how to create financial freedom through real estate. ⁓
So
that’s been the story. mean, it’s been a wild ride. It’s been a lot of bumps in the road. It has not been easy.
⁓ And my focus today is residential real estate value add. So I don’t do anything in the commercial space. I don’t do any Airbnbs, any mobile home parks, nothing like that. Everything that I do is residential from single family to small multifamily to large apartment complexes. So that’s my story.
Quentin (07:24)
Man, thank you for walking us through the journey. I don’t know if you could tell, I just writing things down as you talked because so many things, man, just rung a bell as you talked. So I played basketball in high school. now listen, now, I went to a Christian school. know, it wasn’t nothing fancy, but you’ll understand this. I played power forward slash center at five, nine, about 240 pence.
Right? And so, right. So I had to learn how to box out. had to use position. I had to work extra hard because I’m down there trying to box out six, eight guys, six, seven guys. And, know, my vertical ain’t, I’m not, you know, dunking out the building or nothing like that. So I really had to use position, but it taught me how to work hard. It gave me identity. People knew me as a rebounder, as a defender. And so once graduating from high school,
My coach was trying to get me to go at least play like, you know, like at a community college or something. And I’m like, I’m not going to play no polo. I know I did, I did okay here. Like, I made one R star game in my whole college career, right? I mean, school career, but I didn’t try to go get my feelings hurt. And so listening to you talk, it was like, you know, you had that pivotal stage when you trying to figure out what you want to do for your life in basketball was all that I knew, but I knew I didn’t have no future in basketball.
And so, man, just listening to you tell your story, how basketball was your thing, ⁓ how you kind of lost purpose. Man, you’ve been thinking about real estate since you were a kid, And I’m saying all these things because I say once every podcast, James, destiny has no wasted moments. Meaning no matter what you go through in life, destiny has a way to build you to the person that you are today.
And if you have enough insight, you’ll realize that the pieces of who you are has been building all along the journey. And that’ll make you kind of look at life differently. It will make you look at perspective differently. And so I would love to know, man, what has this journey, what has destiny, what is these moments taught you about yourself? Has it taught you humility? Has it taught you resiliency? Has it taught you discipline? Like, what has these moments taught you about you?
James Gleeson (09:46)
The number one thing by far is perseverance, resiliency. So I am not the smartest guy in the room. ⁓
Not necessarily a dumb person, but I’m not the smartest guy in the room.
I didn’t have any rich family members, friends. didn’t have a rich uncle. ⁓ I didn’t have even parents who were familiar with real estate that could teach me. So I didn’t have any of those things. ⁓ and actually with basketball, my friends still joke with me to this day in middle school, I was bad. I was not a good basketball player. was naturally not good at basketball.
And then by the time I graduated, you know, I first team all everything player of the year, all these things, averaged 20 points a game, and then went on to play college basketball. ⁓ And all of that was just from.
once a day, twice a day, every single day for my entire life, practicing basketball and never giving up. And then the same thing with real estate. I mean, I have made quite literally every mistake in the book. And I think that’s why I’m such a good mentor right now. And why I have so much success with my students is because I have literally gotten, you know, bad deals. I’ve gotten money stolen from me by contractors. I’ve had projects go sideways. I’ve had property managers do poor jobs with my projects.
and it’s not my intelligence that got me through, it’s not my skill set and real estate necessarily. It has been my inability to give up for eight years. And even to this day, with a $60 million portfolio,
I am dealing with much larger issues today than I did eight years ago. And to this day, I still have that resilience and that perseverance to continue pushing forward. ⁓ Probably…
I tell my students if there’s any piece of advice that you can take from me throughout the entire mentorship, and obviously we get into the weeds on things, but one of the big things is, bite off more than you can chew and figure it out. And that’s exactly what I did. ⁓ I really took a ready, shoot, aim approach. I perhaps didn’t have all the answers, but I never gave up and…
Quentin (12:36)
Mmm!
James Gleeson (12:48)
You know, real estate is a really long-term game. And if you’re not ready to be in it for the next decade or more, it’s probably not the business for you.
Quentin (12:57)
Yeah, yeah. Man, you said so many things that makes my mind think. First, when you was talking about the way you lead your mentors, your mentees, it made me write down the best leaders, coaches, mentors, they lead by what they have experienced. Not a whole bunch of rhetoric, not a whole bunch of like, this is, know, I’m so much better. No, I’m going to show you and tell you exactly what I experienced. And that’s the ups.
the downs and the fact that not only have you had some tribulation or adversities, you overcame those adversities. So it’s like when I leave, when I coach, I’m gonna tell you about the ups and downs. I’m gonna show y’all how I overcame it at the same time. And then man, you talked about, I’ve never heard somebody say bite off more than you can chew and that as a strategy. And that made me think, hopefully it’s not disgusting y’all, but it made me think about how birds feed their young. Like they,
eat something, they have it in their mouth, but they don’t swallow all of it. They have enough that they can nurture and somebody else and give somebody else nutrients. And so when you bite off more than you can chew, not only are you chewing on something for a long time, trying to figure that out, but you still got more left that you’re still trying to figure out. So you’re still trying to chew on that at the same time. And so it’s like, I can give you what I chewed on.
Because I know about that, but then I can go learn some more and then I can pass it on to you. I know it may sound a little disgusting, y’all, but y’all get the point I’m trying to make, is that you can pass on to people things that you have chewed on and really had a chance to really kind of ⁓ really like ruminate on, know, and really kind of like figure out. And so I love it, man. I love it. I would love to know what’s the next real goal for you? Like, what are you looking to solve a scale next, man?
James Gleeson (14:45)
So for the past eight years, it has been acquire real estate, build the net worth. You know, when I got started, 50 % of my motivation was because I disliked my career so much. You I really did not like being an engineer
and I loved real estate. So real estate was my way out of the nine to five rat race. And so for the first five and a half years, I worked my freaking tail off, you know.
engineering job, I had two serving jobs on nights and weekends, swinging a hammer at my properties, door dashing, everything. Eating ramen noodles, I slept on a couch for two years with my best friend, ⁓ subleasing our bedrooms as Airbnbs so that we didn’t have to pay rent, all the things to just save every single penny and put all of it into real estate. And so that was it the first five and a half years. And then from the time I became
Quentin (16:02)
Yeah. Woo!
Mm.
James Gleeson (16:24)
financially free and quit the job to the time ⁓ to now, you know.
It has been just full offense mode because all I bought my time back. All of my time is now put into the real estate investing. ⁓ and I don’t have to work 40 to 50 hours at an engineering job. And then, you know, let alone a serving job and all these other things. So now that all of my time has been put into real estate, I’ve been able to start the construction business, the property management business, the education business, and put all of my time into real estate. And so over the past two and a half years, I went.
from 93 units when I was financially free to now 450 units and $60 million worth of real estate. So now, you know, I’m at a point where I’m reasonably happy with where I’m at financially. You know, we have liquidity. We own or I own one and a half million dollars worth of real estate free and clear with no mortgages, including my primary residence. No debt, no credit card debt, no car loans, nothing like that. So we’re at a place financially
we’re not flying private jets or anything like that, but we can basically do whatever we want. ⁓ And so now my goal has shifted in 2026 from acquiring more, which really doesn’t change my lifestyle all that much, except for just the numbers game. And there’s that competitiveness in me where I wanna just achieve, which is great.
But I also don’t want to be reckless because there’s people who are a lot smarter than I am who have lost their shirts in real estate from just trying to grow, grow, grow. So that’s why I shifted last year. I paid off a lot of my real estate and cash. And now this year I am buying very, very slowly. I’m buying maybe a house here, a duplex there. I bought a 10 unit last month, but it was with a partner that I trust. ⁓
one of my students actually that I trust. ⁓ And so much more slower growth. And so this year I’m focusing a lot more on defense. So I’m really building my property management team. I am getting dialed in on my CRMs, monday.com, at Folio. I am creating systems that I don’t have to micromanage. You know, it’s like a McDonald’s system. All the systems are there for them and they have to check off on them. ⁓ And so
And then I’m focusing a lot on my active income businesses. So I’m focusing on my construction business, pivoting from being vertically integrated and doing mostly my own jobs to now doing other people’s jobs to produce income ⁓ and things like that. ⁓
Rather than just continuing to expand, I’m taking a year, maybe even a year and a half to really build my systems, build my team and set an extremely solid foundation. And then next year we’ll see, perhaps I’ll start growing again. But this year I’m very excited to be on defense mode and set that super solid foundation.
Quentin (19:32)
Man, I love it. I love it, James. And I want to say this too. ⁓ If we should lose any internet connection on either part, if you lose it, just come back up. I’ll be here. If I lose it, you come back up. I mean, I’ll come back up and you just stay put. I just want to say that because I don’t know, internet is going a little slow. So just want to put that out there just in case. Amanda, bro, I love it, man. I love what you’re doing. I love how you’re stepping into the education space, how you want to help people.
And so to me, it seems to me that the relationship aspect of business matters to you. And so I would love to talk a little bit about relationships from your point of view. ⁓ Is building good relationships within business? Is that important? And I mean from an educational standpoint or just business partnerships, tell me from your vantage point how important relationship building is within this business space.
James Gleeson (20:25)
There is probably no other singular aspect or contributor to my success than the people that I know. ⁓ The people that I’ve met have turned into business partners. They’ve turned into ⁓ people on my construction team.
Quentin (20:35)
Mmm.
James Gleeson (20:45)
They’ve been hard money lenders, private money lenders, commercial lenders, wholesalers and investor friendly agents to find the deals. I mean, I am where I am today largely because of the people that I know. And I, I.
Quentin (20:59)
Yeah.
James Gleeson (21:01)
I would say even today, the people that I’m meeting are the reason why I’m learning. My mentors teach me how to build all these systems in my monday.com and at folio. It’s all the people that I’m meeting that’s allowing me to either learn from them or collaborate with them or partner with them.
or help them or whatever it is, it’s all because of my relationships. Of course, the skill sets that I’ve learned along the way, reading the books, listening to the podcasts, the experience that I’ve gotten through my mistakes, those have all been a tremendous piece to my success. ⁓ But I would say nothing comes close to my relationships. I would venture to say if I were to start all over again,
I would spend the vast majority of my time meeting other people in the business. So I would go to all the networking groups, the Facebook groups, all the things, because everything that you need in this business is just someone that you meet. Like I said, the deals can come from your relationships. The majority of my deals to this day come from my relationships. ⁓
Quentin (21:52)
Hmm.
James Gleeson (22:10)
Multifamily deals are gonna come primarily from brokers. You got your lenders that you need to meet, your short-term lenders that you need to meet. A lot of my capital has come from my ability to partner with other investors and purchase that real estate. So money, money, deals, lending, the construction, everything you need can come primarily from relationships.
Quentin (22:34)
So well said, So well said. Normally, I can piggyback on that, but that was so eloquently said, man. I’m like, that’s to drop the mic right there. ⁓ Listen, we got about two minutes. And I feel like I could talk to you for hours. But let me open this up. Is there anything, James, that I have not asked, a subject that I have not brought up, that you want to talk about?
Or is there any other words, maybe motivation, education, inspiration that you want to leave to people? Like, I kind of want to open it up for you. Is there anything on your mind or your heart that you feel like people need to know?
James Gleeson (23:11)
Yeah, you I would say if you’re going to get into this business or even if you’re seasoned,
one of the most important things that you can learn to really compound your success is focus.
Quentin (23:25)
Mm.
James Gleeson (23:26)
I am where I am today because I am not doing Airbnbs or mobile home parks or commercial space or development and trust me those things look very attractive to me. ⁓ I’ve certainly considered doing those things ⁓ but I have stuck with a very boring business and I say boring because I’ve been doing the exact same thing for eight years but that’s when I knew that I was on to something is when it became boring and I was making money.
Quentin (23:50)
Yeah.
Mm.
James Gleeson (23:55)
When you’re making money and it’s just this repetitive thing, a lot of people say, okay, well now I’m going to start the e-commerce business or now I’m going to start the coffee shop or now I’m going to pivot into a different real estate sector. And for me, I’ve always just stuck with what I’ve become an expert at and that’s why I’m successful. So if you’re starting out in this business, you don’t have to do residential value at real estate. It’s not really important what you pick, but just that you pick
something and you stick with that one thing for the entire duration of your business because you you’re always going to get distracted you’re never going to really become an expert in your sector if you’re constantly changing what you’re doing. So I would say focus is one of the number one reasons why I’ve been able to scale so quickly in eight years. So if you’re listening to this and you’re just getting started make sure you pick one thing and you focus on it.
Quentin (24:52)
Such good advice. This is of my mentors told me just with life, putting in a system in for my life. It’s like getting used to being bored. I get used to the mundane. I get used to the same thing over and over because you want to be an expert at doing the right thing consistently over and over. so he used to say consistency beats intensity any day. So just be consistent. And so I love it, man. Great, great stuff, James. Listen, if someone wanted to reach out to you.
Connect with you, collaborate with you, learn more about what you’re doing. How can I get in contact with you,
James Gleeson (25:27)
Yeah, thank you. So you all can follow me on Instagram or TikTok, James Gleeson Real Estate. You could also go on multifamilymethods.com if you want to learn about the mentorship program. We’ve helped dozens and dozens of students create financial freedom. We’ve had students get over 10 units in their first year, 20 units in their first year, 50 in their first year, 80 in their first year.
⁓ just depending on the student and the circumstances. But if you want to learn about myself or about how you can get into real estate investing, go on those platforms and someone will reach out to you.
Quentin (26:02)
Love it, James, let me say three things to you, sir. First, let me thank you for your time, because you could have been anywhere in the world, but you was here with us. And I think you know you could put a premium on your time, right? So thank you for your time. Thank you for being here. Secondly, man, thank you for your story. Thank you for the gift of your transparency and vulnerability. I tell people all the time that I put a premium on stories. Stories have a way.
that you planted seed in somebody, you never know when it’s going to grow, but your story has planted the seed that can of course correct everything that they was doing. And so I appreciate your story. Lastly, man, thank you for your perspective. Thank you for your mindset and bringing that mindset to this platform. I greatly appreciate you being here today,
James Gleeson (26:45)
Thank you for having me.
Quentin (26:46)
Absolutely, absolutely. Well, listen, y’all heard James looking to show notes, get in contact with him, reach out to him. Definitely make sure you are subscribed here because I promise you we’re going to continue to bring up amazing people just like Mr. James. So, sir, I say thank you again. And everyone else, listen, y’all have a fantastic day.


