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Ben Thompson on Beating Analysis Paralysis, Small Wins, and Building a Real Estate Portfolio

By September 5, 2025Real Estate Pros Show

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Show Summary

In this conversation, Ben Thompson shares his journey from a military background to becoming a successful real estate investor and project manager. He discusses the importance of work ethic, learning from failures, and the role of education in his career. Ben also talks about establishing his property management company, Sunshine Property International, and how he balances multiple responsibilities while pursuing real estate opportunities.

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    Investor Fuel Show Transcript:

    Benjamin Thompson (00:00)
    Yeah, you know, I, I’m one of those guys, and I’ve been told this by my brothers too,

    that I tend to dive in ⁓ feet first and then figure it out.

    So that’s kind of my personality

    In my opinion, I’ve said this many times, but it’s also, I think just worked out in my favor.

    You know, when I, when I come up to the start line and you can have guys that have had a lot more experience that are a lot more ready. ⁓ but a lot of people, they, they want to take a lot of time and almost overanalyze things and do the research kind of like the analysis paralysis thing. Right. Meanwhile, I’ve already started, I’m already, you know, 15 feet ahead because even though I started and I tripped and fell and then got up and ran again and then, and then tripped and fell probably 10 more times.

    Dylan Silver (00:32)

    Hey folks, welcome back to the show. Today’s guest is a Chicago based real estate investor with a military background from the Marine Corps, went on to earn an MBA, now works in project management while also running SPI, Sunshine Property International, a property management company. Please welcome Ben Thompson. Ben, welcome to the show.

    Benjamin Thompson (02:41)
    Thanks, Dylan. Appreciate it. I’m happy to be here.

    Dylan Silver (02:44)
    It’s great to have you on here. And as I was saying that bio right there, it struck me again how much you’ve been involved in. It sounds like two lifetimes worth of experience right there.

    Benjamin Thompson (02:56)
    ⁓ Yeah, maybe, ⁓ People tell me all the time they they always wonder how I get any rest and I say I just like to attack life and have a good time. So this to me and stay busy is it’s good purpose, you know.

    Dylan Silver (03:13)
    Does it feel like that to you? mean, when you look back, because I’m thinking about it as just meeting you here, but also as someone who’s talked with so many investors, does it feel like you’ve really progressed or does it all feel like, know what, I had a goal at the end of the day and I was thinking about that from the beginning?

    Benjamin Thompson (03:31)
    you know, I think

    like all of us as human sapiens, get it when we grow up, our backgrounds kind of shape who we are a little bit. And I would say, ⁓ my drive really comes, you know, cause if you look at my background coming from small farm, didn’t have a whole lot as far as, ⁓ money monetarily. ⁓ but, but work ethic was very important because we were doing it for survival. Mazel’s hierarchy of needs, right? You survival then all the way up to the top of self actualization.

    For me, think even I never lost that. And so for me, it was always a matter of ⁓ trying to make sure that we maintained that level of safety and security. Because, when you grow up with that, that when it’s when it takes away from that a little bit, ⁓ when you’re younger and you don’t have that, you keep striving to do that. And so one of these ways for me that’s given me comfort is to be able to do that and keep striving for more. So take it for what it is. Right.

    Dylan Silver (04:13)
    Yeah.

    I think there’s a lot of people who, mean, I can say for myself personally in listening to this, but certainly our audience, hearing your stories inspirational, but it’s also a testament to the fact that, you you don’t have to necessarily have every single thing plotted out from the beginning in order to end up at the end destination. Did you know, for instance, when you went into the Marine Corps that you were gonna be a real estate investor?

    Benjamin Thompson (04:52)
    No, I had no idea. had I had an idea that I wanted to be in technology because I’ve always really enjoyed technology.

    When I was in high school, I was in computer class for college computer classes. And so there’s a funny story behind that. I don’t know if we have time for it, but the long and the short of it is the Booster Club purchased some computers. It was in the library. The librarian went on lunch. I snuck into the library and took it apart. She caught me and the principal. ⁓ I thought I was in big time trouble.

    But a principal was pretty smart about it. And he said, look, you have two options. You can go to detention for six months, or you can go to computer college. And I was a ⁓ sophomore at the time. So I was like, I’ll go to computer college. ⁓ So it’s funny. That was the beginning of technology. then it’s funny because how that if you want to roll into that, then basically ⁓ I went to the Marine Corps because my twin brother, I’ve got a twin brother and older brother both.

    Dylan Silver (06:24)
    That was the beginning, right?

    Benjamin Thompson (06:39)
    both Marines and they went in and so I did, I still wanted to do technology, but so when I went in the Marine Corps, I did technology, but while I was doing that, I was part of an engineer support battalion and that battalion did humanitarian missions. We talked a little bit about this because you live in the Dominican Republic and that was one of the stops. And so while doing this, of course, I had to, you go as a group and you help out as a group. Well, I learned to build the buildings from the bottom up.

    because my job was essentially to run all the technology in between the walls, the cabling, Cat 45s, RJ 45s, and these kinds of things. And while doing that, I basically learned a little bit more about construction, more so than I did on the farm. Then when I went to Chicago to do my technology degree, so technology led me into all of this. While I was a resident assistant, I lived in a building that was a complex. And then my first job as a resident assistant in college was property management.

    Dylan Silver (07:26)
    Yeah.

    Benjamin Thompson (07:37)
    So I was, yeah, I was taught and I, and it’s funny cause I remember looking over people’s income at the time. And you know, I’m just in college. So I was maybe making maybe 15,000 a year, maybe 20,000 a year. And I’m seeing all these people, I’m seeing all these people come in that are looking for two, three bedrooms or whatever. And these guys are making 150, $200,000 a year. And that was like a 19 or 2000, 2000, you know, I’m like, how are these people doing this? You know, they’re, I’m, and I’m thinking they’re.

    Dylan Silver (07:38)
    is

    Yeah.

    Benjamin Thompson (08:05)
    I’m thinking they’re not smarter than me, you know, maybe that’s ego. but at the time they were just, were learning these were kind of the kinds of people that that’s where my mind started shifting. Like, well, you have to learn how to make money work for you and not work for money. You know, and so.

    Dylan Silver (08:18)
    Right. I want to ask you about

    going from that space to eventually buying properties and then building a portfolio for yourself. Was this like, hey, I saw this in the Marine Corps. I’m able to understand construction and new builds and really can build things from the ground up. When I have the opportunity to I’m going to dive into real estate. Or was this a progressive thing? You’re in the Chicago area and you’re getting involved in tech.

    and then you’re seeing more and more people who are maybe looking at real estate as an investment strategy. How did it come about for you?

    Benjamin Thompson (08:56)
    So it started because ⁓ a building that was fairly cheap in a downtown historic district in Michigan, where I grew up, my sister wanted to open a hair salon because she was doing nails. And, ⁓ I, and I, she knew that I wanted to get into real estate because I was doing property management at the time. And I thought, at 115,000 for a whole building, this is, this is how naive I was.

    I thought for 115,000 for a whole building, this is going to be awesome. I’m going to make oodles of money, you know, and, the long and the short of it, that was, know, right before the 2008 recession hit. Right. And so I’m working two jobs. I’m working the property management. I bartending on the weekends. I’m in college and, I had to then, so, so I bought the building cause I saved up with just a little bit of money to put the money down.

    Dylan Silver (09:44)
    Yeah.

    Benjamin Thompson (09:44)
    and started the salon and the hair salon, I think with maybe five or $6,000 because it was a mixed use space. And the mixed use space had essentially, this is a little bit complicated, but it essentially had a basement level,

    Dylan Silver (09:52)
    brand.

    Benjamin Thompson (10:33)
    a sub-basement level, because back in the day when they built those in 1947, most of the downtown historic buildings had sub-basements where they had oil, big oil containers where they’d heat the whole building. So I found the sub-basement.

    Dylan Silver (10:44)
    Yeah.

    Benjamin Thompson (10:47)
    while I was gutting it, right? And then, um, and

    stuff that we pulled out of there was atrocious. Um, and it’s crazy, crazy, but like old mobster skeletons, you know, no, I’m just kidding. Yeah. So anyhow, long and short of it, I was able to get the hair salon up and running. then luckily the two apartments that were on the second floor, there was another floor that was empty. The second floor was able to at least maintain the building a little bit. Then

    Dylan Silver (10:59)
    believe you. Yeah, was Chicago. was, it was, yeah, I believe you.

    Benjamin Thompson (11:16)
    we had the recession hit. Well, everybody was like, you know, just get rid of the building. You can’t afford it. And they were right. I couldn’t afford it, but I stuck with it. I was literally just like by the skin of my teeth. And then Michigan released a grant funding program. Thank God, because I went through like six or seven months of grant funding. And at that time, I was also, then I got a job and then it just, hung onto it. And long on the short of it now, you know, this is where I really learned a lot about real estate with time. Cause people think that you get it, if you get into real estate,

    that you’re immediately got to make money. They don’t understand that you have to be a very patient person, especially in the beginning. If you’re going to going to get where you need to go, I call it the inchworm approach, or this is where the rabbit and the hair thing come in. Right. You have to take the, the, the, the tortoise, the tortoise in the hair, guess I should have said. So you have to take the tortoise approach when it comes to real estate. ⁓ it’s like a snowball. So yeah, that’s what got me into it.

    Dylan Silver (11:54)
    Yep.

    Absolutely.

    And so that deal, I wanna back up a bit here. Did you do heavy underwriting on that deal? Did you have mentors who were telling you about how to get into this thing?

    Benjamin Thompson (12:19)
    Now, you know, I think maybe Michigan, kind of like Wisconsin, if you go to Wisconsin, you see a lot of family owned businesses, know, this or employee owned businesses. And so the nice part about Michigan, think, especially at the time, maybe, you know, it’s kind of like Chicago, I got a guy, but in Michigan, yeah, but in Michigan, it’s a little different. It’s more like, you know, you go to church with these people and it’s the pastors.

    Dylan Silver (12:39)
    Yeah, I got a guy.

    Benjamin Thompson (12:47)
    son’s friend, daughter that does loans or financing, these kinds of things, right? So when I say it’s grassroots, it’s really grassroots. So I found out through some people that, you know, there was like farm, farm, there’s a farm credit union. And then the other one, the other one that I came across was Horizon Bank, not a plug, just the truth, you know? And yeah, there were, there were lower, I would say a smaller, smaller bank that just said, well, you know, if you want to purchase this property, we can utilize the two apartments income and

    Dylan Silver (13:01)
    Yeah.

    Yeah, they help you.

    Benjamin Thompson (13:16)
    and you can afford it.

    Dylan Silver (13:18)
    That

    was a big first deal, Ben. I mean, we talk about multi-use, multiple stories. had two, sounds like two units up above. So the first floor, was it one tenant? Was it the shop or was there multiple tenants?

    Benjamin Thompson (13:32)
    Yeah, good question. So the first the first floor really is the main street level. So if you look at the historic downtowns, they have a main, you know, downtown Main Street. That’s where they did all the parades and where everything came through in the 1940s and 50s. Right. And so but that had on top of it, two more levels. And so the two two more levels, the third one used to be the old moose or elks club. I didn’t know that until I started getting into it because there was a moose thing. Anyhow.

    Dylan Silver (13:57)
    Yeah.

    Benjamin Thompson (14:00)
    So the first floor was empty. That’s where I put the nail salon and hair salon. And that actually ended up didn’t necessarily doing well. We got by, we didn’t lose too much money, but ⁓ it was more so the apartments. And that’s when I was like, let’s just stick with apartments because it’s a first year thing. need, know, responsible, good clean housing.

    Dylan Silver (14:20)
    I wanna ask you about going from that deal into the next deals. And then also you mentioned how it was tough, were using the grants that were available to you, and then you talk about the recession at that point in time as well. From there, what was the mentality like? Were you thinking, okay, I’m gonna get more commercial mixed use spaces? you thinking I’m gonna look at single family? Or were you thinking like, hey, I really have to cherry pick the deals that I get into, because that was tough?

    Benjamin Thompson (14:50)
    Yeah, you know, I, I’m one of those guys, and I’ve been told this by my brothers too, that I tend to dive in ⁓ feet first and then figure it out.

    So that’s kind of my personality. ⁓ In my opinion, I’ve said this many times, but it’s also, I think just worked out in my favor.

    You know, when I, when I come up to the start line and you can have guys that have had a lot more experience that are a lot more ready. ⁓ but a lot of people, they, they want to take a lot of time and almost overanalyze things and do the research kind of like the analysis paralysis thing. Right. Meanwhile, I’ve already started, I’m already, you know, 15 feet ahead because even though I started and I tripped and fell and then got up and ran again and then, and then tripped and fell probably 10 more times.

    Dylan Silver (16:06)
    Rain.

    Benjamin Thompson (16:19)
    I’m still much further ahead because I failed. And what I learned along the way is that those small failures, if you can just keep those failures small, right? But then obviously learn from them, then all of those, that all gains towards experience. And then you’re able to take that and put it towards the bigger things. Cause now I’m a lot more comfortable going into a deal, looking at a deal and going, okay, now I know exactly what I’m looking for because I screwed up on that one or I screwed up on this one, you know?

    Dylan Silver (16:48)
    Right,

    you’ve seen it before so you know how to pivot faster rather than wait for it to sting a little bit. I want to ask you about how common it is that you see for folks that have an MBA to be involved in the real estate space. I don’t know. It seems like it would be a natural connection, but at the same point in time, it seems like you could dive so far down the corporate ladder that you never think about real estate.

    Benjamin Thompson (16:49)
    Well.

    Yeah.

    You know, I have to tell you, the only real reason I got my MBA is because of my professional career, which I currently still have that I’m trying to basically get to a point where I don’t no longer need, because what I’ve realized is that, and, know, there’s probably going to be a lot of people in Wisconsin and Michigan that I start cheering right now, but, know, you don’t need a high priced education. ⁓ because the, because essentially don’t get me wrong.

    I do think that, that an education, ⁓ we’ll, we’ll, we’ll present things to you that changes your mindset about when it comes to tenacity and persistence, right? If you can get through a bachelor’s course, if you can get through an MBA course, that really takes a lot of persistence and it takes a lot of, patience, but long to answer your question long in the short of it. If also, if also I had, I had stuck with just.

    just continuing to dive in and dedicated that to real estate. I might not have needed that job. there’s, don’t question, I don’t regret things, you know, but I’m just saying for those that are out there that think they can make it through real estate, I would agree. You don’t need a high-pressed education.

    Dylan Silver (18:28)
    I will say it’s a pretty impressive ⁓ line on the resume there. So for folks who are looking at investing with you, or if you’re ever looking for capital partners, it’s nice to have that. I want to ask you about SPI, Sunshine Property International, property management company, how that came about. And then also, was the idea, hey, we’re going to create a property management company, or was it because you had a necessity to manage your own portfolio?

    Benjamin Thompson (18:37)
    Yeah.

    Yeah.

    Yeah, that’s exactly right. The reason I said it well, so if you look at taxes, you know, once you start to dive into this, you basically say, how do I keep my money out of the government’s hands? You know? ⁓ Yeah. And how and what I realize, especially, you know, you read the things like Rich Dad, Poor Dad, and then, you know, and and you start watching a lot of the YouTube clips and channels and people that have been, you know, Grant Cardone and a lot of those that have been down this, you know, similar roads.

    Dylan Silver (19:07)
    That’s right.

    Benjamin Thompson (19:22)
    And one of the things that they teach you more than anything, and I truly believe this too, and I think, I think it kind of works out for everybody is that, you know, you want to use other people’s money to make money. Right. And when I, when I’m really, when I really want to mean by that is, ⁓ not other people as in like individuals, more like the corporations and things that, so long on the short of it, if, if, if you’re being lent, if you’re being landed, ⁓ at a six or 7 % and yet you’re going to make 15%, then that’s kind of a no brainer. Right.

    Dylan Silver (19:51)
    No brainer.

    Benjamin Thompson (19:52)
    Yeah. if, uh, and same thing, same thing with rehabbing, you know, I think a lot of people freak out like, oh my gosh, I have to spend 20, 30,000 to rehab this, but you know, Burr method, you know, buy that rehab, rent, refinance, repeat, right? It’s, it’s, it’s tried and true even, even not, yeah, even now. Um, and, companies out there, what they want, they want to see, they want to see, um, a history of that. When I started thinking about.

    Dylan Silver (20:05)
    Yep. Time test.

    Benjamin Thompson (20:19)
    The future a little bit more for me, like what this could mean down the road. started thinking, okay, I need to structure my business. And then also with that structure, get some experience in history behind the business, because then what you’re, what I’m doing is I’m building a reputation based around that business. That way it provides evidence and proof that I’m reliable as a, as a real estate person. Right. And then entities are a lot more apt to, to do that. The ones that give you seven, eight, 9 % now.

    Dylan Silver (20:40)
    Yeah.

    Benjamin Thompson (20:47)
    where you can make 15, 20%. I’m throwing, just throwing out numbers. mean, obviously ideal LTVs are a little different now, but you get my point.

    Dylan Silver (20:51)
    Sure.

    I want to pivot a little bit here. We are coming up on time, but I do want to ask you about managing ⁓ a ⁓ management company, managing a management company while also having a full time job and then also looking for deals. Right. So I’m doing one of those things, right. I’m looking for deals and I’m blessed to be able to be a cohost of this podcast, but it does feel like a full time job looking for deals.

    Benjamin Thompson (21:01)
    Yeah.

    Yes.

    Dylan Silver (21:22)
    And I do have to be careful because I’m not at a point yet where I can just go and get everything under contract and just have tons of EMD out there. What’s your process like for managing the attention, time, and focus that is all limited for all of us?

    Benjamin Thompson (21:30)
    Sure.

    Yeah, that’s a great question. ⁓ Have a really good partner. I’ve been really blessed ⁓ to have somebody. My wife is an actress, she’s gorgeous and she is just a really genuine person. more than anything, I really appreciate authenticity. And so when it comes to being authentic and us wanting to build something together.

    Dylan Silver (21:44)
    There you go.

    Benjamin Thompson (22:05)
    She has been very ⁓ open minded in saying, okay, you know, you’re, have to work this full time job for now until we get to a point where we can be bigger. So what do you need for me? And part of that was me being able to shift, Hey, between six 30 and three o’clock every day, I’m going to be at my job, you know, knocking this, this w two wage out. ⁓ you know, can you handle the tenants when they call? Can you, well, at first it was, you know, at first it was a bit of this because it’s, ⁓

    Dylan Silver (22:25)
    Yeah.

    Benjamin Thompson (22:34)
    we’re husband wife, right? But ⁓ then once we understood how to start communicating a little bit better with that, and really for me that meant don’t expect the same things you expect out of yourself from her, try to understand that she’s gonna need, that she’s somebody different and try to mentor and teach that a little bit. I had, essentially I taught myself from a sense of self-empowerment, and then I had to really question and go back. And the nice part now is that

    Dylan Silver (22:36)
    Right.

    Yeah.

    Benjamin Thompson (23:02)
    When you do that, you do that right, then she or vice versa, your partner will then start teaching you too. And then you can feed off each other. yeah.

    Dylan Silver (23:10)
    This is

    an incredible story, Ben. Really, truly congrats to you. I know I and our listeners will keep an eye out for SPI. ⁓ Speaking of which, we are coming up on time here, Ben. Where can folks go if they’d maybe like to reach out to you if they’re in your area? Or maybe they have a deal they’d like you to look at or get some feedback on?

    Benjamin Thompson (23:32)
    Yeah, it’s funny because the last year I

    about 83 different deals. Um, and, it’s funny cause I passed on every one of them, except for the most recent that just came up and that kind of tells you how conservative I am. Um, uh, just, uh, B Thompson at SPI, uh, Chicago.com is perfectly fine. I’m a very personal person. I love having this face to face interaction. And so, uh, is it okay to give my number on here? I don’t want to, yeah. Yeah. 312-972-3412.

    Dylan Silver (23:57)
    Yeah, go ahead.

    Benjamin Thompson (24:01)
    Feel free to reach out to me if you’re looking for, ⁓ we didn’t talk about this a lot, but the section, we try to, we’re more apt to section eight and CHA housing for some of the buildings that we do. So that’s more of a niche market for us. So if you’re looking more so to understand CHA and section eight housing, this is something that we’ve been really taking advantage of and getting to know ⁓ more appropriately. yeah.

    Dylan Silver (24:24)
    Ben, thank you so much for

    coming on the show here today.

    Benjamin Thompson (24:28)
    Dylan, it’s been great. Thanks so much. Have a great day.

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