What if your 9-to-5 job was actually a stepping stone to financial freedom?
That’s how Matt Henick approached his transition from corporate finance to real estate investing.
With a strong strategic approach, Matt grew his business to 60 rental units—all while maintaining a full-time job. In this episode, he shares the key lessons he’s learned along the way, from investing in high-quality renovations up-front to scaling in property management. If you’re looking to break into real estate or expand your portfolio, Matt’s insights are packed with practical strategies you won’t want to miss.
Takeaways• How Matt strategically built his portfolio while maintaining a full-time job.
• Why high-quality renovations help minimize long-term maintenance costs.
• Leveraging strong tenant relations & scale to achieve operational efficiency in property management
• The calculated risks and clear vision Matt used to transition from a career in corporate finance to full-time investor
About Matt Henick
Matt Henick is an experienced real estate investor and entrepreneur based in Dubuque, Iowa. Since 2019, he has built and self-manages a portfolio of 60 small multifamily units. In addition to his personal investments, he co-founded Premier Property Management Group, overseeing properties in Dubuque and Davenport, with a focus on newly developed properties.
Expanding his expertise to larger-scale projects, Matt recently joined JB Capital in Cedar Rapids as Co-General Partner and Chief Financial Officer. The firm is leading the development of 226 build-to-rent townhomes across four projects, with construction on phase one scheduled to begin in early 2025.
Prior to transitioning into real estate full-time, Matt spent six years in Corporate Accounting and Finance, working for two billion-dollar companies. He earned a Bachelor’s degree in Accounting and Finance from Loras College (2019) and became a licensed Iowa Real Estate Salesperson in 2024.
With a strong financial background and a proven track record in property management and investing, Matt is committed to creating value for investors and delivering high-quality housing to the communities he serves.
Contact Info:
Phone: 563-663-5122
Linkedin | https://www.linkedin.com/in/mhenick/
Website: https://premierdbq.com/
[00:00:00] I always say real estate is people business first and numbers second. You can be good at both, you can be good at neither, and you can be successful either way, it just depends on how you want to do it. From cornfields to high rises, office to industrial, houses to hotels, and every other asset class in real estate, we cover the people, the projects, and the profit. Welcome to the Investing in Iowa Show. This show is for go-doers, action takers, and business owners. It's for people like you who are sick of Uncle Sam taking a huge bite of your apple.
[00:00:30] If you're looking to get ahead of what's taking place in Iowa, learn who is doing what and how you can get in on the action, you're in the right place. Hosted by Neil Timmins, an Iowa native who has been involved in over $300 million in real estate right here in Iowa. Recording in studio from West Des Moines, here's your host, Neil Timmins. I've got Matt Henick here on the show. Matt, welcome. Thanks, Neil. Thanks for having me.
[00:00:56] I'm excited you're here. Say for the audience's sake, who are you? Where are you from? What do you do? Yes, my name is Matt Henick. I live in Dubuque, Iowa. I originally from the Chicago suburbs. I'm a real estate investor and property manager. I've been full-time in real estate just about a year now. Before that, I was in corporate finance and accounting and spent the best couple, I guess, eight months of my life being full-time in real estate. From the Chicagoland area, how did you land in Dubuque?
[00:01:18] Yep. So I went to Loras College. That's what brought me there and got my undergrad in finance and accounting. I stayed in Dubuque after for a job at A1 McDonald in their accounting department. And it's been a good, just about 10 years there. Cool. Growing up, you have siblings? I do. I have two older sisters. How far apart are they? Four and eight years older. So my dad would tell you he planned to, he only had to worry about college for one at a time. That sounds like somebody in finance or accounting. But what's he do?
[00:01:45] He was corporate telecom for 25 years and actually owns a campground now in New Jersey. Oh, very. So there was real estate from everyone in the family. Yeah, for sure. Okay. So growing up to baby in the family, how did that influence you going to Loras and or getting into finance and accounting as a choice degree?
[00:02:05] So it's funny. I used to want to be a cop. Like I think most boys wanted to be a cop. And when I went to Loras, it was still criminal justice was one of my options. And then honestly, I kind of figured out you make no money in that field. Then I went finance and accounting just kind of naturally. I'd always been good with numbers. I was never a big reader or anything like that. Numbers always made sense to me. So that's how I ended up in that field. Yeah. What did you think you wanted to do as you graduated college?
[00:02:32] Well, I wanted to be a CFO. That was like the end goal. I think most people you either... If you're in accounting. Yep. It's the pinnacle. That's it. And I remember my first time on an internship, CFO at my job literally asked me what I wanted to be. And I told him I want to be a CFO one day. So still time for that, but definitely went the route of self-employment and I basically do everything now. Okay. So you get a job in the accounting world, right? In the accounting and finance department. How did you get turned on to real estate at some point?
[00:03:02] Yeah. So actually it goes back to my grandpa. So he's the reason I'm in real estate. He was a broker in New York City for almost his whole career and then became an investor, owned some self-storage out there and other items in the East Coast. So I'd always seen it. My dad was corporate America. My grandpa was a self-employed for basically since he got out of Korea. And I would go visit him over the summer. And I kind of liked the lifestyle of being your own boss and doing whatever you wanted.
[00:03:26] So for me, getting a real estate was kind of a natural progression. I think I grew my portfolio to 60 units while I still had a full-time job. How many? Give me that in your account. 60. 60. Yep. Okay. Thank you. I grew that while I had my full-time jobs and I worked at two, well, three companies during my corporate career. Yeah. One through acquisition and really just real estate for me was I wanted to be financially free. It really wasn't about the dollar value. It was about the ability to do what I want every day. And that's what I do.
[00:03:53] So I'm curious, did your grandfather working for himself, being self-employed, I'm curious about the influence that had on your father who chose to go the corporate route. And then I'm curious about your father's choice of corporate route and the influence that had on you to do the opposite. Yeah, that's a good question. And my dad would be fine with me sharing the story. So he worked for WorldCom. WorldCom went under in 2006, I guess. Right. And that was, you know, he was a senior director of the Midwest region at the time. And I was young enough that I didn't really know what was going on.
[00:04:23] But I decided that I wanted my paycheck to be dictated by me. That was it. That was the genesis. Absolutely. Yeah. And I learned that sometime during college that that was like the thing to do. I had professors that obviously had corporate careers before they went into it. I did not want to go the CPA route, even though I had the required education to go CPA. I wanted to go industry. I did that. I loved it.
[00:04:44] But it was just, again, I was relying on someone else to pay me. I started buying these duplexes and I was making, you know, a thousand bucks a month, 400 bucks a month, whatever it was. And then eventually it was making more than my paycheck. I kind of sat down one day and I said, well, man, I can quit. And I did. So it was a good day. And I don't regret it one bit. Tell me about the very first investment. It was a disaster. Yeah. I still own it. I've never sold anything. Actually, I'm selling something next week. So I have my first sale ever.
[00:05:14] One. But the first one was a duplex 22nd and Jackson in Dubuque. A lot of people didn't like the area. I grew up in the Chicago suburbs. You know, I've seen Chicago. I've seen the good and the bad. And I'm like, there's no bad part of Dubuque. And I still all die on that hill because it's true. It was a simple up down duplex been converted. God knows how many years ago. Literally the day I closed, both tenants moved out. It was a disaster.
[00:05:37] The carpets were disgusting. I didn't know anything about the business. I mean, I knew nothing when I bought this thing. The funny thing is like two days later, a fourplex went for sale and I offered 30 grand under asking thinking, oh, there's no way they'll take it. And they accepted my offer. So now only do I have two vacant units.
[00:05:52] I have no track record. I'm begging the bank for a second loan literally two weeks later. And I need to come up with 50 grand to close out on this fourplex. So it's like that one was also pretty bad because I had a drug dealer, a hoarder, an empty unit, and just a kind of a creep on the fourth unit. So it was like those first six units literally almost killed me in the business. But me and a friend actually emptied the duplex. That was the last time I ever did any physical labor on my business. I decided I didn't like doing it. I didn't know what I was doing. So then I've hired all that out since.
[00:06:21] But that first duplex, though, was a disaster at the beginning. I've now refinanced three times. I bought it for $89,000. It just appraised for $155,000. And I use that basically as my relationship builder with a new bank. So it's like I know I have two stable tenants there. I've rehabbed the whole thing. It'll appreciate a little bit each time I go to do something. So that loan has been at three banks and I have no reason to leave the third one. You're using that ultimate Tapsome equity to open up a relationship. Yeah, I'd like to call that a paper tiger.
[00:06:51] Yep, there you go. We've got that equity and can go make some moves on future property. Yep. Well, that's incredible. Real quick. Zero to six. Real quick. Yeah. All right. So speaking of real quick, how long did it take to go from zero to 60? Three and a half years. So I did my last closing was December of 22. So between August the 19th and December of 22, about 60 units. 52 of those are residential. Then the rest are garages and a couple commercial storefronts on the bottom.
[00:07:18] From extra duplexes, houses, apartments, up to a eightplex. So small multifamily basically. But the hard part for me was I had to rehab a lot of stuff. So December of 22, last closing, spent all of 23 and basically half of this year rehabbing 40 of those units.
[00:07:36] So I have very little maintenance now. I have phenomenal tenants, good maintenance contractors that I was just at dinner with them last night and they said, oh, I love working with you and your tenants because you spend the money to rehab these things and you have low maintenance and good tenants. So what ultimately led you down that path? I've known plenty of investors, heavy concentration here in Des Moines, certainly. And everybody's got a different opinion. Some want to do a heavy rehab. They want to, quote unquote, harden that asset to make sure that it becomes tenant proof.
[00:08:04] And I know others who, you know, some might, some might call them a derogatory name relative to a landlord, but they don't want to do anything. They're like, hey, you know, essentially here it is. And maybe they'll rent it under market value, if you will. But it's like, don't call me. So I, it's a good question because I know some of those other people. Sure. And they're great people. It's how they want to run their business that I will never tell someone how to run their own business. I get some of the highest rents in my area. I mean, I have other people say, how do you, how do you get that for that? You know, I said, well, I don't know. I spent.
[00:08:34] 10 grand redoing it. You know, it's all new floors, all new paint. And really those two things go a long way. I've never bought a used appliance. You put a new, new one in tenants like me. I'm available 24 seven, do them, whether that's good or bad for me. I've had the 2 a.m. phone calls. You know, I've had, you know, I've had it all. I chose, I wanted less maintenance. So I don't want to do turnovers. I want to do it right. The first time you might spend 10 grand, 20 grand, depending on what, you know, what kind of rehab it is now.
[00:09:00] But if you spend five grand six times just to put, you know, lipstick on a pig, I don't think it's worth it. I'm curious too. Are you finding that people stay longer? Yes. They get a rehab unit, they stay. See, that's interesting because then the argument of course is fewer turns, less costs associated on those turns. And, you know, on the totality of, you know, the lifespan of one tenant and one unit, what did it really cost in comparison to not rehabbing the unit, having to go in and spend the money on the
[00:09:29] term? So people don't think about that. I think the thing that sets me apart the most from other investors I know is my finance background. So I'm thinking I'll spend the 10 grand now, or I'll spend four grand 10 times over, over the next 10 years. Now I can't tell you my $10,000 rehab is going to last six years. I don't know that yet, but I'm using good quality flooring. I'm getting good quality paint plus because I buy in quantity. I'm getting better prices. So I'm paying almost 50% off what
[00:09:56] other people are paying on paint. And people don't think about that, but yeah, I'll go buy 15, five gallon buckets at a 50% off sale. Are you kidding me? I'll just sit on it. I have heated storage so I can sit on that for almost ever. So those are the things I think of as a finance guy. I always say real estate's people, business first and number second. You can be good at both. You can be good at neither and you can be successful either way. It just depends on how you want to do it. Yeah. No, you're right about that. You've got to understand that people, that management component is a giant part. Hey, Iowa investors. This is Ava Bowkamp,
[00:10:26] chief of staff at Legacy Impact Investors. Have you thought about adding real estate to your portfolio, but don't have the time or desire to play landlord? At Legacy Impact Investors, we do the heavy lifting. Our team finds the deals, manages the properties and handles all the day-to-day operations. Our select group of qualified investors co-invest with us, gaining ownership equity without opening a tenant email or responding to a maintenance call. They just share in the income
[00:10:54] appreciation and tax benefits. These opportunities aren't for everyone. They are for qualified, accredited investors only. If you want to learn more, please visit LegacyImpactInvestors.com to apply. A lot of people will go down this path, buy units, and they don't want to touch management. You're leaning into it pretty hard. Why? So I love talking to people. I meet different kinds of people all the time. The funny thing is I tell people all the time that want to get into the business, go ahead,
[00:11:23] buy a duplex. If you hate it, I'll buy it from you. That's my stupid corny line I use. But people look at the numbers. They say, this is going to be a phenomenal investment. Then they have to deal with people, right? At least in my market, there was not a lot of third-party property management options. I loved being a landlord. So I opened a property management company with a partner on the property management side. And that's been great too, because that added 60 units overnight. So literally
[00:11:48] 120 units under management, whether directly owned or third-party managed. And then that just adds more scale, right? So you have 120 units. Now you can get to 200 units or whatever it is to continue growing, whether that's purchasing or managing. Yeah. And some of that adds to the resources that you're now afforded to be able to do that, which in turn helps you manage your own portfolio. There's more than just a single benefit there. Absolutely. Yeah. I know some of the folks are
[00:12:14] going to be curious. How did you ultimately fund 60 units? How did you get the deals acquired? It almost sounds like there's a burn methodology to that. Just walk me through some of that. So probably 60% of the capital that went into purchasing my properties came from refinances, came from taking cash outs while rates were still low and rolling that right into other duplexes. The rest of it was either everything I ever saved or taking out private debt. So I've taken out from
[00:12:43] maybe three or four people, just high interest rate, basically private debt. But for me, there was a time I was like 95% leverage. I can tell you, you don't sleep well at night when you're 95% leverage, especially when half of it's on credit cards. My banker hated that, but I bought in duplexes on credit cards. You get these 21 months and 0% interest. You pay a 3% one-time fee. And I'm like, yeah, sure. Every time I found 20 grand, I bought a duplex. That was just the market I was in.
[00:13:13] I needed 20 grand to close. You negotiate a little bit, you get a credit. So you really only need 10 grand to close. Then I have 10 grand for the rehab. You play those games with the finance. And the bank knows, so it's really not a game. But if there was one 95% leverage, you won't sleep very well at night. I can tell you that, but it got me to where I am and worked out. Yeah. Today, what's your global leverage? I'm at about 65% right now, dramatically. I suspect that's largely due to the appreciation of the marketplace, not that paydown. That's right. Yeah.
[00:13:42] That's where in order to take advantage, in order to reap the rewards, in order to thrive, you got to survive first. But in order to reap the rewards, you got to play the game. Yep. And I suspect that you have seen dramatic rental increases, which is how you're able to get to a spot where you're able to leave the W-2. Yeah. So I would buy, I think my best deal was like a $65,000 duplex. Needed $25,000 worth of work, plus a service line I didn't know about, but that was covered by insurance. Thank gosh.
[00:14:11] I put 20 grand to work into it, rehabbed it. So I'm buying these things. They're renting for 600 bucks. Both those units right now go for 1100 bucks. So I almost doubled the rent with $20,000 worth of work, which was financed by refinances of other properties. So I've put probably $200,000 into my portfolio and I have $3 million worth of real estate. I mean, it's at least a cash value going in. Yeah. So it's been good for me. So, I mean, you largely ran this on the side. Yes.
[00:14:40] They were very poor. I mean, it really was a side hustle until just this year. Yeah. So very poorly ran. When I left my job, I had 16 vacant units. And if you have vacant units, you don't get money. Yeah. Right. And 16 is a big number to have when you have 60 units. I mean, that's a large percentage. So I had to rehab all those this year. I never could have done it if I cut my job. So it was, yeah, I had a nice paycheck. It was, it was a great company. I liked the people I worked with. The funny thing is I rent an office now in the same building, so I still see them all the time.
[00:15:07] But for me, it was, I either hire a property manager for them to deal with it, or I leave corporate America. And it was always my goal to be self-employed. So I just kind of took the risk. I had money saved. I had some, you know, money coming in, but my rent roll had 16 vacant units. So that's all. I have one vacant unit now, I think. And so I'm moving out the end. So two vacant units now, and they're all ready to go. I mean, rehabbed and ready to rent. So I just, I had to leave my job. Yeah. Or hire someone to do it. And I'm cheap and didn't want to pay someone to do it. That's incredible.
[00:15:38] If you're a house flipper, execute the burst strategy or do double closings and are in need of money. Little Guy Loans is your go-to lender here in the Des Moines area. Time is money. Loan approvals in 24 hours, closings in five days. Little Guy Loans was founded by Neil Timmons, an investor just like you. Since he has been in over 10,000 homes in Des Moines, there's never an
[00:16:02] appraisal. Houses, multifamily and commercial property loans up to 1 million. Check out www.littleguyloans.com. What are you most excited about in 2025? That's a good question. Good segue. I am hoping, so I joined a fund out of Cedar Rapids and he, Jeff and I have actually been on your podcast. So JB Capital are building, the goal is to build 250
[00:16:27] townhome rentals in the Cedar Rapids corridor. So we are, we have the land for 20 of those now, working on the land for some more. And then after the new year, we'll kick off capital raising for that. And in addition, I'm always looking to grow my portfolio and property management company. So just looking at growth, more so on management and fund-based type items versus my own personal portfolio. I'm pretty content there for now. Yeah. So the fund, I don't want Jeff's up to, you know, it's going to take you into that corridor.
[00:16:57] It takes you outside of Dubuque into the corridor. On the property management side and doing some perhaps syndication sites that you would control, are you in Dubuque only? Are you looking outside? Where do you have them? Yeah. So property manager, we're currently in Dubuque and Davenport. So we have 48 units in Dubuque under management, 11 in Davenport, same owner. I've just kind of worked out for that one. And then we've just taken on a couple more smaller units in Dubuque. But we, I like to say Eastern
[00:17:25] Iowa, you know, that's anything right now between Davenport and Dubuque, we're good to take. Depending on what the building is, we'd go a little further. My partner's a commercial broker on that side. So he knows a lot of the people in the business. So Steve Davis, if anyone needs a commercial broker, a great guy, equity real estate group. From a syndicated standpoint, when I look at bigger deals, I want to stay in Iowa and I would love to stay in Dubuque. Sadly, Dubuque does not have the
[00:17:53] large buildings for sale. There's a couple right now. And when they do list, they're super overvalued, where it's going to require a fund to come in to pay all cash. That's really looking for tax benefits and long-term appreciation. That's my opinion, at least. So I look in Iowa, you know, you get to the Des Moines area, there's a lot of bigger things going on down here. But still, you're buying these things at eight, nine caps. We're starting by a duplex at a 15 cap. Now,
[00:18:17] I used to buy the 20 cap. You can't beat a 15 cap. My goal, and I've said this for years, would be to buy a portfolio of 20 duplexes. People think I'm crazy for that because you have 20 roofs, you have 20 hot water heaters and everything. They say, oh, buy a big building. You have one roof. Well, the roof's 60 grand, right? If I need to replace a roof on a duplex, I can do it for five or six grand. So I go back and forth on what I'm looking for on that. But I also have, you know,
[00:18:44] you can raise soft commits, no issues. People know what I'm doing. People tell me, I got 200 grand in the bank. I'd be happy to talk to you about it. And you write that down in a CRM. And when you finally have something, you give them a call back and say, you remember when we talked too much ago and you have 200 grand that you want to invest in something? Here's the deal. Yeah. Yeah. So that's what I'm trying to do in going into the new year. Yeah. Yeah. It's fantastic. For you, why Iowa? I mean, you're from the Chicagoland. You went to school at Loris, right? I mean, you went to school here. You could have gone anywhere. You could have gone back there,
[00:19:12] but you chose to plant roots here and then choose to stay here. Why? Yeah. So I had a job. I decided to stay in Iowa after college solely because I had a job and I liked the area I lived in. I bought a house right before I graduated college. It's my personal residence. I paid like nothing for it. But relative to what it would go for now, I have a 2.9% interest rate. I mean, it was so staying in Iowa was a good choice for me. Why I invest here, the short answer is because I live
[00:19:38] here and it's, you know, I wanted to manage when you, when I look to invest elsewhere, I'd never invested in Illinois. I think for obvious reasons, if you're a real estate investor, you know, but you know, Iowa's a great place to do business. You know, whether it's landlord, tenant law, general business and property values in Dubuque were relatively cheap and rents were high. In fact, I think, and I don't know if the stat's still true, but Dubuque is some of the highest rent in Iowa. I can compare a two bedroom in the 48 unit building. I managed
[00:20:04] downtown Dubuque to something in Des Moines and I'm getting at least 10 cents more square foot on rent. And I don't know why, and I love Dubuque, but I just, I don't know why. I think it's really a supply and demand issue, but that's why. I mean, I lived there. I wanted to invest where I lived and I, you know, I loved being a community business owner. Yeah. Ready for the final three questions? I'm ready. All right. If you had one piece of advice for your 20 year old self, what would it be? I wish I would have invested earlier, but I started when I was 21. So it was a pretty early for me.
[00:20:34] I probably would have gone a little faster. I would have ignored the six units that were a disaster and just kept buying if I was able to. Two books that changed a lot. So I'm not a big reader, but Rich Dad, Poor Dad. I think anyone in finance, real estate investing, that's phenomenal book for anyone, whether you're investing or not. Order the deal. I just, you know, one of the best negotiators you'll ever talk to, whether you like him or not. It's just great negotiations. If you were cast away on an island for a year, you can only get three pieces of data about your
[00:21:03] business each and every month. What three things must you know to know how your business is running? This is a great question, but I hate this question. Three is a little rough. So I basically run two businesses now, my portfolio and my property company, though a little different, exactly the same. So definitely some financial report, whether that's P&L or just bank balances. Just you want to know rent's coming in, mortgages are being paid. The second one would be some sort of tenant reporting on maintenance requests. Make sure my tenants are taken care of. That's the most important thing
[00:21:32] in this business. And a third is really just make sure bills are being paid when people are happy, which goes back to number two there. But really finance and tenant relation are the things I'd need to know. Man, I asked lots of questions. It's been a fun conversation. What's one question I did not ask that I should have asked? You would have been pretty good. I would say why did I get into property management as a third party? Because a lot of people thought I was crazy. I told them I was doing that. But the way I looked at it, I'm already doing it. So what's the difference if I'm doing it
[00:22:00] for 60 units or 200 units? It really doesn't complicate my life anymore. And I treat both businesses just like they're assets I own myself. So I think that's one thing I would have covered a little more as property management. If anything, is it fair to say that it oftentimes becomes easier in property management to have more, not less? Absolutely. I'm just thinking about that. I tell people all the time, if you're going to get into this business, you have to do it in scale. There's nothing against the people that own one or two duplexes that one day will supplement your
[00:22:29] income. But it's a pain to manage two duplexes and it's no more of a pain to manage 60. At least that's my opinion. Some people call me crazy for that, but I love it. I mean, at some point you're adding leverage to that. You've been leveraging people, leveraging technology, right? You're leveraging other things that are out there that only come by having more. Yep, absolutely. Otherwise, you know, they're just at a small number. You cannot justify the cost associated with some of the tools. Yep. That goal. No, absolutely.
[00:22:59] Running this business. Yep. That's been fantastic. For people who want to find you, they want to follow you, they want to connect with you. Where can they go? What should they do? Yeah. So I'm pretty active on LinkedIn, especially right now. So it's Matt Hennick on LinkedIn, premierdbq.com is the website for my property management company. And then really the best way to get ahold of me is texting me 563-663-5122. All the details and links are below in the show notes for everybody. Matt, I appreciate you being here. I appreciate it. Thanks for having me.
[00:23:26] Thank you. Thanks for listening. If you're enjoying the show, may I ask a favor of you? Naturally, subscribe so you never miss an episode. But would you rate and leave an honest written review on Apple Podcasts? Does a lot for us here at the show. And I appreciate reading your thoughts. Great guests make for a great show. If you know of another island who would be a great guest, or you yourself have interest in being a guest, well, get on our radar. Visit Investing in Iowa
[00:23:54] to fill out an application or recommend a guest. And if you want to connect with me one-on-one, go LegacyImpactInvestors.com. Click on the Invest With Us button in the top right corner. And there, you can pick a time for the two of us to get on the calendar and connect. Until next time, keep investing in Iowa.