How Jacob Capeles Turned a Business Setback Into His Next Real Estate Opportunity

Jacob Capeles (00:00)

When we came back to the States, we had Fort Campbell, and we looked into it really hard. So we actually bought our first house with never seeing the property, just with the real estate agent on a video call showing us a house, and sent my wife back early so she could close for us. But

it was kind of scary, but we knew like, “Hey, this is how you get started.” It starts with that first one, and that’s the hardest one.

Issa Hanna (01:54)

Welcome back to another episode of the Real Estate Pros Podcast. I’m your host, Issa Hanna, and today we have Jacob Capeles with us, ready to share his knowledge and his experience in the real estate world. Jacob, welcome to the show.

Man, thank you for coming on. For my people at home right now, and they’re wondering, “Okay, who is Jacob? What does he do?”, can you kind of give them a rundown of what you’re doing nowadays, and then what’s your day-to-day kind of look like? You wake up, what do you do every day?

Jacob Capeles (02:19)

Yeah, so nowadays, I recently just got my brokerage license—a little hard work and dedication got me there—but my day-to-day is: I’m IT by trade, so I do help desk for companies, it’s my nine-to-five. I have a long-term rental out in Tennessee that I’ve had—I’ve filled for many years now, that’s been very successful.

We recently just closed on a short-term rental in South Haven, Michigan, where we—we’ve been kind of slowly making updates in between bookings, while also trying to scale it to where we don’t have many empty calendar nights. And so it’s been a learning process.

Issa Hanna (02:59)

Love that, man. Yeah, you invest, you learn through the fire. Mistakes will be made, but you’ll learn and you’ll get a lot of knowledge. I love that you went and got your broker’s license. That is literally amazing, because real estate school doesn’t really teach you how to do contracts or really move in the real estate space like that, but one thing it does teach you: guidelines, rules, laws,

so that inside and out. And another thing I want to highlight is a lot of people are getting into that short-term rental space. South Haven, Michigan is beautiful—it’s a great place to get into that short-term rental space. I love that you’re getting into it. You took your nine-to-five and you’re growing your rental portfolio out of a nine-to-five. That’s a dream, that’s what real estate does, man. Eventually, Jacob will have

five, ten rentals and you won’t have to do IT, or he’ll go up—he’ll be able to go open his own business, and wealth builds itself when you own real estate. I wanna rewind just a little bit, right? You have the IT background, you work—I’m sure it’s a comfortable living, the insurance and the guaranteed paycheck and, you know, all that good stuff.

What made the light bulb go off and say, “Hey, I wanna invest into real estate”?

Jacob Capeles (04:06)

So when I was young, my grandpa actually—he had apartment complexes, and I would remember watching him do everything from painting, cleaning them out, fixing sewer issues over the years. And he sold them all, moved to Texas, lived a retired life. And so then when I was in the Army, me and my wife, we had a kid already and we’re like, “Hey, wherever we go next, like, we’re gonna buy a house.” And so

we got Germany and we were like, “Dang, we’re not buying a house.” But

when we came back to the States, we had Fort Campbell, and we—and we looked into it really hard. So we actually bought our first house with never seeing the property, just with the real estate agent on a video call showing us a house, and sent my wife back early so she could close for us. But

it—it was kind of scary, but we knew like, “Hey, this is how you get started.” It starts with that first one, and that’s the hardest one.

Issa Hanna (05:49)

Definitely, man. Taking that first step off that ledge is super scary sometimes. One thing I want to highlight about your service and people who do serve: VA loans. The best loan to have, and you’ve got to be a hero and you’ve got to serve to get that loan. So VA loan, you can get in with zero percent down. Amazing thing they do for our vets—

they don’t do enough, but that’s one thing that they do have right, and it’s a great program. So all you—all you guys in the military right now, and I’m sure, Jacob, you can attest: When you get out, look into buying that first home ASAP with a VA loan. So I—I love that, Jacob. I love that answer. It takes a lot of guts to join the military, so I wanna definitely commend you on that for sure, too. Let’s talk about

a strength you told me that you have, right, which I think a huge asset for any investor to have, and that’s your creative problem solver, right? We talked about it: Our business is full of nightmares, our business is full of variables. Every day something different is going to get thrown at you. So can you kind of shed light a little bit about how you’ve been able to solve some problems that you’ve had in your investing past?

Jacob Capeles (07:00)

Yeah, so recently we were running a full RV rental business. We were renting out a camper van and it had an accident, but the accident was gonna be so much where the vehicle’s value wasn’t there no more. So we went back to the insurance officer to say like, “Hey, can you reappraise that value? Like look into the numbers again,” because this year with that much mileage, we were on our fourth summer,

and essentially they totaled out the vehicle. We got our money—the money as if the vehicle wasn’t damaged back, which was like—the timing of it was perfect. We just kind of closed on the South Haven house, so it was like all our down payment was now refunded back to us essentially, and it felt nice because we were like, “All right, how are we gonna do all our plans?” And it takes money, we need more money, and so

we didn’t want to wait, we wanted to move a little faster, and that kind of helped speed things along. But we took something that was really negative—like, “Hey, one business is now crippling away”—but it’s now we’re reinvesting that energy and focus into this one.

Issa Hanna (08:02)

And that—and that is what real estate is about. Like when something hits the fan, you can’t freak out. And we were talking about that earlier: You’ve got to know how to get through it, you’ve got to know how to pivot. We’re a game of pivots, we’re a game of variables, and you got to roll with those punches. And the—and the ones that last in our business are the ones that are good at doing that. So I see a bright future ahead. But let me talk about your future a little bit, right? Five years down the line, Jacob, I look you up,

where am I gonna see you at? Are you still in IT? Do you got twenty rentals? What are the goals five years from now?

Jacob Capeles (08:35)

We’ve definitely—I’ve definitely scaled up five years from now. Since I’m at three properties, I’d probably predict I’d be at six by then. I’d probably still be working more part-time, just because I enjoy IT and that type of life. But at the same time, like investing in properties is what I breathe, so by then I have hoped to close many deals for people

in their transaction and assist as a broker along that journey.

Issa Hanna (09:03)

Hundred percent, man. That’s what I love. You said, “I—I love doing IT and I’ll still do it part-time,” but real estate can afford you to live that life. It can buy you something that’s priceless—it’s time, right? If you got money turning, you’ve got rentals, you’re sleeping and you’re—you’re turning dollars, you have that time to be like, “What? I can step away for a few hours and take time with the family.” Man,

I don’t doubt five years from now you’re gonna crush your goals. He’s very bright, very, very smart analytical guy, just by talking to you this last 20, 30 minutes here. I wanna kinda get your advice now. I got a lot of people that are just starting off, right? New realtors just got out of school, maybe they’re thinking about it, right? If you can give that new guy, the new investor,

he’s got the money to the side, he’s got a plan in his brain, he’s just a little bit afraid to pull that trigger and jump in, what would you tell them?

Jacob Capeles (09:54)

You’re not jumping in this by yourself, you’re jumping in with success story after success story after success story. So like the formula is already there. You just taking—hopping in the whip, grabbing control of the steering wheel, and you’re following along a good path. And then you have podcasts such as this one, which could help bring new ideas to help guide you down that path.

Issa Hanna (10:18)

One hundred percent, man. And now that you’ve moved into the broker space, you want to help clients, you want people to come in, deal with you. Just talking to you, just you having gone through the purchase process, you having rentals, you understanding that world, you can help people so much. So if you had to give one message to a potential client that was sitting here watching, say, “Why should I choose you, Jacob?”, what would you tell them?

Jacob Capeles (10:42)

Because you’re getting someone who’s an investor-focused mindset and someone who’s experienced lots of problems in the houses over the courses of the past what, decade—countless issues from foundations to electrical, plumbing—and so you’re getting all that experience with me. Plus, I’m just a good time and I always love a laugh.

Issa Hanna (11:05)

I love that, man. Yeah, very personable guy, very good time to sit down and talk with. And then that experience, right? Not all agents are created equal, and not all agents who’ve been licensed for 10 years know the type of stuff. Jacob can walk you through a house, a buyer, an investor, even just a regular home buyer, he’ll walk you through the house and he can probably tell you a lot more than a normal real estate agent can,

just as his past as investors. When you fix things, when you’ve dealt with maintenance issues, you’ve got such a knowledge on the workings of a home that he’s bringing a whole different dynamic. He’s not just opening the door for you and asking you if you want to buy the house. And then a personable guy—he’s been there, he’s done that, he wants the best for you as his client, right? So that’s the guy you want to deal with. Now I’m gonna give you the floor, right?

If people wanted to get ahold of you and deal with you and use the best new realtor services, where could they reach you at?

Jacob Capeles (12:43)

Yeah, I’m licensed in Illinois.

You can reach me on—Jacob Capeles, you can search me up on Google, I’ll pop up. I work with Pearson Realty Group, broker with them, and then as well as give me a text or a call at (224) 355-6641.

Issa Hanna (13:01)

Nice. And man, you’re an Illinois agent, I love that even more. Former Illinois agent here, Chicagoland. I have a lot of connections, Jacob, so I’m definitely gonna put your name out there to my network, man. Super bright guy, super motivated, just by talking to you for a little bit, man. I can—I can tell you’re gonna crush the real estate world. You’re built for this, man.

And I wanna thank you so much for coming on the show, brother.

Jacob Capeles (13:25)

I appreciate you hosting and having this discussion with me.

Issa Hanna (13:29)

Man, it was super, super fun to talk to you. I know you’re gonna crush these goals. You’re built for this world, man. I wanna invite you back on the show in about a year from now, just so we can—I can prove my theory right, and you could tell us about all the awards you’re winning.

Jacob Capeles (13:43)

Let’s make it happen.

Issa Hanna (13:45)

Hundred per—hundred percent. I enjoyed this conversation so much, man. And to the viewers at home, if you enjoyed my conversation with Jacob and want to see more like it, make sure to hit like and subscribe. I talk to people every day that could bring us different knowledge on every facet of the real estate industry. Until next time, the Real Estate Pros are out.