The Wisconsin Investor

My Most Expensive Real Estate Mistakes (So You Don’t Repeat Them)

• Corey Reyment

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In this episode, Corey opens up about the deals that didn’t go well — the ones that cost real money, real time, and taught real lessons.

Because the truth is simple: experience comes from getting punched in the face financially… not from the wins.

This week, Corey breaks down several costly mistakes from 2024–2025, including a Jacksonport project that spiraled far beyond the original budget and a series of flips that exposed gaps in process, oversight, due diligence, and team bandwidth.

If you're scaling, flipping, or thinking about jumping into a new asset type, these lessons will save you money, frustration, and months of wasted time.

In this episode, we cover:

  • The Jacksonport deal: why new asset classes require deeper due diligence
  • How skipping well/septic inspections cost $45K–$60K
  • Why “moving fast” without structure is actually chaos
  • How tight numbers push investors into bad decisions
  • The hidden bottlenecks inside growing teams
  • Why contractors must be checked in person — or by someone who can be
  • How to hire, delegate, and avoid burning your people out
  • The real cost of doing too much yourself

These weren’t rookie mistakes — they were scaling mistakes. And if you're growing your Wisconsin real estate business, you’re going to face the same traps. This episode is here to help you avoid them.

If you want 2026 to be your least stressful and most profitable years yet, start with the lessons that cost Corey tens of thousands — so they don’t cost you anything.

Quick reminder — our New Year Giveaway winners will be announced on January 1st, and there’s still time to enter if you haven’t jumped in yet! More details on our pinned post on our Facebook/Instagram.

👉 If this helped you, subscribe on YouTube, drop a review on Apple or Spotify, and share the episode with another WI investor.

Your support helps us grow the community and bring you more real, honest, and actionable content.

Speaker:

What's up, everybody? Corey Reyment here, your host of the Wisconsin Investor Podcast. Guys, I'm really excited to be here with you today. Um, but we're gonna talk about some expensive lessons I just learned, and we're doing it so you guys don't have to. Uh people think, you know, experience it comes from wins. It really doesn't. It comes from getting punched in the face financially. So I paid some tuition recently and a few different investments, and uh today I'm gonna break them down for you guys so you can learn from my pain instead of writing the same checks I did. So, you know, um nobody in real estate shares their losses, or very few people do. You know, everybody posts about the wins, and uh, you know, we're guilty about that on this podcast as well of bringing you know guests on here. And a lot of times, we mean we try to bring up some of the mistakes they've they've learned, but a lot of times we want to talk about the successes. We want to learn from what's working really well for them. But you know, the losses are are where a lot of the growth happens, hopefully, right? The goal is you don't make the same mistakes a few times. And a lot of the mistakes I'm gonna talk about today, they weren't really rookie mistakes. You know, they were mistakes that came from me running too fast, um making some assumptions and having a lack of structure. So if you guys are scaling your business at all, um you're gonna face some of these same traps. And I don't want you to make the same mistakes I did. I want you to win faster than I did. And really, you know, what I'm learning here is when you stop learning, this business starts charging you intuition. So learn from my mistakes and um and don't make the same mistakes that I did. So here's a little first example. I'm gonna just go through a few examples for you guys today on some properties. If you follow me on social media at all, on Facebook in particular, you've seen some property, this property in Jacksonport, Wisconsin, which is up in Door County that uh I've been documenting over the last year and kind of sharing some of the struggles with this one. So, what happened with this property? I had decided uh to sell a few of my properties that I had a good amount of equity in. And I was gonna refinance those properties, or I was gonna sell those properties and then um take that capital and put it into you know bigger deals, or you know, maybe just pull it out and invest it um in a in another property similar purchase price, but a better asset, those types of things, and then refinance that asset, take the cash out tax-free, and go invest that in a fund at 10 or 12% and kind of double dip a little bit. All right. What I should have done is just refinance some of those properties and done the same strategy, uh, but kept the properties that I sold because they were good properties. But anyway, I was in a I was in this spot last year in 2024, uh depending on when we're releasing this when you're listening to this, 2024. And I had sold one of my properties, and I was looking at where I could park this money 1031 style. And an opportunity came up from a seller that I had worked with in the past. She had this property in Jacksonport, and it had a big pole building on it. Um, on the back of the property, it was an acre and a half parcel, pretty close to the beach in Jacksonport. I mean, we're literally like you walk to the beach here, and so I'm thinking like, ooh, Airbnb, that'd be cool. And the house was really run down. I mean, it was it was pretty rough, it was full of stuff. She hadn't lived there in like five or six years, and so you know, we walked in it. We knew, man, there's a lot of work that has to get done here. But it's about 1,500 square feet, had a loft upstairs, and could have probably been saved in rehab, but I mean it was going to need one of everything, siding, gutters. Um, the roof was actually okay. Um, windows, you name it, the floors, it was an old mobile home. And then what they had done is they had taken the built a shell outside of the mobile home and then tore the walls down inside. So foundationally, it was a little like the walls on the outside were starting to slope. So it looked like you know, in the middle of the house, but then on it was that was the high point, and then on the outside of the house it was kind of sinking. So that would all had to been jacked back up and resupported and everything else. Anyway, I saw this vision, I was like, oh yeah, 100 grand, maybe we'll put it in this thing and it'll be great. So contractor goes out there, he comes back after we close on it, and he's doing his bid, and he's like over a hundred grand, and he calls me and he's like, dude, I'm uh I'm at like a hundred and ten, hundred and twenty right now, and I'm not even done. So at this point, he's like, You might be better off just going and like ripping this thing down and putting up like a manufactured house on here and going that route because you can get them for like around that price. I was like, dude, that's a great idea. Then everything's brand new. I don't have to worry about this old house and like trying to you know put put lipstick on a pig kind of thing here. And so I was all excited about it, right? So I'm like, this is great. Well, I just was running 100 miles an hour, so I went, I go meet with the uh I shopped around, found a mobile home design I liked, went to the dealership. It was more expensive right away than what I was originally planning. So I was I was looking at some for around that $110, $120,000 mark. Turned out it was like the one I decided on was like $172,000, I believe. And um, and that was just the house. So I here's what I did. I went into a whole new asset type without doing proper due diligence. I was just again, well, we'll figure it out. Again, I I and I and I still agree, like I've learned so many lessons from going through this project that will hopefully save me maybe from doing something like this again in the future. Or if I do something like this again in the future, I now know a much I know much, I know the numbers much better of how to run the numbers. And so what ended up happening is I I got this thing, and over the last year, um, on a previous episode, I talked about the opportunity cost missed out from doing everything. Well, I'm the one doing everything, I'm the bottleneck on this example, and it's costing me opportunity costs for other deals and or growing my team or whatever else I could be doing, spending time with my family. I I spent so much time trying to figure out this process this year and so much frustration that if I could go back and redo it all over again, not buying that deal would have been the best deal I did in 2024, in all reality. So we're still not fully up and operational on this thing. It's been over a year now. Um, so ordered the house, thought I could reuse the foundation that I had underneath the existing mobile home because I was like, well, if I could just get another one, there was already the steel beams underneath and everything else. I can just plop a new one right on here. And if I got to add a little bit to the concrete, probably no big deal. Again, didn't do any due diligence on that before I signed for the new house. Turns out you can't do that. You got to put a whole new foundation in if it's not the right thickness or the beam where the beams are gonna go is not exactly lined up. You have to have a different type of foundation in there. So I had to put a whole new slab in. All right. Then we found out that the well was a non-conforming well. So I had to redo the whole well. So that was another $18,000 to $20,000 by the time I was done with all the tests I had to do, all this other sort of stuff. So it was a very expensive lesson. Um, a couple other things. You've gotta have skirting on these things. So you either gotta throw up some cheap stuff, which still is not cheap, or you've got to get like uh the there's like these, I don't know what you call them, like decorative stone rock thingies, blocks, whatever that you can go around. Either way, I I didn't understand. I was looking at about $10,000 to $12,000 to get on some kind of skirting on there of anything that looked decent. You know, it's gonna be an Airbnb. That's gotta look pretty good, right? That was that. Then you've got concrete, you know, for sidewalks, patios, all this other stuff. Um I'm not even done with landscaping yet. Like we're just kind of letting it sit. Oh, driveway, you know, $11,000 to get a driveway put in, plus some grating and other other um dirt work that we had to have done. Again, we're still not done with it. So that's just the bill I have now. Um, the electrical on this thing. I didn't I thought, you know, mobile home manufacture house, be normal electrical. Well, turns out it's like a 220 amp service. So I had to upgrade our entire electrical service going into the property. So that was great. So that I mean, overall, this thing is just way, way, way over budget. You know, here's here's the good news. If I hold this thing for the next 30 years, I'll make some money on it. I'm kidding. But not really. Uh it'll it'll be a while before I can make some money on it and actually, you know, have some equity in this thing. Um, but hopefully it'll still we'll be able to rent it and it'll cash flow some money every month um and help us pay our debt down on it. But uh but yeah, so lesson learned. If you guys are out there and you're looking at getting into a new asset class or something else, do your homework first before you're running a hundred miles an hour. All right. Uh another lesson here, this is really I I let I let tight numbers turn into some bad decisions. And again, without processes in place and people in place, this could happen to you guys as well. So a few recent deals in in um 2025 we had, you know, the numbers were pretty tight, but my team was pretty confident, you know, my acquisitions guys, hey man, I think this is an easy one. You know, do this, this, and this, and it's and it's done, and whatever. And I said, all right, cool. And I'm just kind of I'm just moving fast. We're doing a bunch of deals. It was a busy time of year, and I didn't really have like a whole process in there or anything else. I was just like kind of running and wanted to get to a yes or no quick. And so I ran some numbers myself, and then I said, Yeah, okay, it makes sense to me if we stick around this, and you know, budget-wise. Well, a couple of these properties had wells and septics, kind of going back to the same thing. I didn't get them tested before we close. Um, I don't know why. Now looking back, I'm like, I have no clue why we wouldn't have got those tested, but we didn't. And we ended up closing on them and without getting that. And uh I can tell you two properties in particular, that one of them needs a new septic, and the other one needs a well antiseptic. And that mistake alone from those two deals is probably gonna cost me 45,000 to 60,000 just in hard costs. That's just for the the wells and the septics. That's not counting, like again, going back to the time that our team is having to spend on these deals now, the lost rent that we're gonna have until some of those things can be done. Um, you know, one of them we had we were flipping and we had a buyer lined up and they went and got a well and septic inspection done, and they came back and then they failed. And so that um, and then we had to start this whole process of what are we gonna do now, right? And we talk about like this just the capital tied up in these properties now. That's you know, again, opportunity cost, the capital that I potentially couldn't use for other deals for that. So, you know, if your numbers are really tight, do your homework, um, slow down a little bit. So if you're out there and you're brand new and you're just running up 100 miles an hour, you know, slow down a little bit, get around some other investors, is what I would encourage you to do. And, you know, find out some of these mistakes. What are some of the mistakes you guys have made in real estate? Um, we run the REI success meeting, and that meets typically the fourth Tuesday of every month at the Woods Golf Course on the east side of Green Bay. So that's a great networking opportunity. We typically get 40 plus people out there at these events, and um, it's a great time to come and learn and grow. And, you know, again, just get in that room and ask people, hey, what's what are some of the biggest mistakes you've made in your investing journey? And you'll learn a lot, right? And and you won't need to make those same mistakes if you listen and pay attention and and put that somewhere for your future deals. So those were a couple big things. So now you'll see with Wisconsin discount properties going forward, any property that has a questionable age of a well and septic, you will see a inspection done on those. All right. Sometimes we still won't get them if we have documentation that the well and septic are newer. You know, it'd be kind of unnecessary at that point for the most part to get that done. Um, but we still might. Maybe we'll even just get a water test or something done on the well to make sure that that water quality is still still decent. But um anyway, so that was a big one. Well and septic inspections, but really it came down to just running too fast and not really having a process in place to do this. So now in our process, there are different stops in the process to make sure that before we close on a deal, we've got um a well-inseptic inspection done on it. If there is a well and septic on the property, so that is kind of the same thing. Like we okay, we learned $60,000 lesson, not gonna do that again. Let's make sure we put a process in place for that. All right. Um, another one, again, on the on a previous episode, I talked about you're probably the bottleneck in your business. And in our business, we have people on our team that also can be bottlenecks to our growth. And um, by me not recognizing just the impact that some of these projects and initiatives that we did in 2025 would have, I created a bottleneck in our business. But it was, it was really, I was putting a big load on people on our team. So, Reese, who a lot of you guys know from our team, fantastic uh go-getter, young guy, full of energy, full of piss and vinegar, as people say, right? Wants to wants to take on a lot of things, which I love. I appreciate that. Um, but this year we started doing more of our own flips on the deals that you guys didn't want to do. Or if it was what we would consider an easier one, and again, this is where I got in trouble with a few of those. We're like, oh, those will be pretty easy. He can run them. Well, again, he's running a hundred miles an hour, right? So he's doing he was trying to run our flips from Milwaukee, which is where he was living. Um, he's handling our whole dispositions department, our whole, our whole Wisconsin discount properties team, and he's still doing his own deals on his own. So what happened was we're doing these deals, and again, this is not Reese's fault, but it was we put the the flip project management stuff on his plate, and it ended up being a big mistake. So he got really overwhelmed. Um, he did the best he could, but one of the things that I would recommend for you guys, if you're doing flips, you or someone on your team has to go visit that property on a regular basis and keep your contractors on pace and make sure that they're doing the work that would meet your expectations. All right, so we had a property out west of Oshkosh, kind of in the country, on a big parcel of land. We actually still have this one at the time of this recording, and we will still have it by the time this recording drops, because we haven't even listed it yet. And um it should be done hopefully within the next week of this time of recording. But this is a property by the time it actually sells, we will probably have it for a year. All right, which is that um maybe good for capital gains. Maybe I'll get long-term capital gains on it. I don't know if I talk to my accountant on this one. But uh what happened was we had we had he he went out, found a contractor for it to do the work, had him bid it, came back, he came in, recommended from some other people, and uh bid came back reasonable and decent. And um, you know, I don't know that we set really clear, you know, timelines with the with the contractor or what our process was. Again, I was kind of leaving a lot of this up to to him to figure out which is a big big issue there. And um, and he he gave us the whole green light probably a month and a half ago, two months ago, that this thing was done. And our realtor, Monty, my brother, went out there to go get he got he actually went and had listing pictures done. And there was just a bunch of stuff that was just not up to the standard that we would want, and something we don't want to have, right? And um we realized at that time, you know, that was a challenge for Reese trying to manage these projects from afar without having another who to go and run and look at these properties and do these um, you know, inspections, so to speak, for us as as the thing went along. That, you know, this guy was doing the best he could to he was trying to save us money, is what the contractor was doing, which we appreciate, but we weren't clearly able to uh communicate our expectations because we weren't able there, we weren't there able to see what he was doing necessarily with the quality of the work, right? And aligning our expectations with the quality that we were looking for along with what he was doing. So, you know, a couple things, you know, we were running 130% capacity. We didn't really have clarity on responsibilities or, you know, enough bandwidth really, didn't really have accountability for the contractor, um, didn't really have any systems in place to support it. And sometimes you're not gonna have systems right away. So I'm I'm also a believer in massive imperfect action, right? And those two things, I I go back and forth with those things, right? Um, you gotta sometimes you gotta build the system as you go. And that is that is the reality of it. The problem is we didn't slow down enough as we were trying to build this process to really put some of these things in place to support, you know, where we wanted to take this thing. Um, we were just kind of running and gunning and figure it out as we go, but not really able to build a process in the place. And the and the hard part with flips and build trying to build a process as you go is if you have multiple going on at the same time, you know, these aren't like you're gonna buy it and a week later you're selling it, right? Like sometimes you're not gonna realize some of these mistakes until four or five months later when you're still working on your project. And now if you've got two or three of those going, you just compounded some of your issues. So um the other issue with happening is you know, we were he he will never say this probably, but he was probably getting a little burned out by doing this process. So he's juggling his normal duties and responsibilities of working with a lot of our buyers out there and trying to help coach them up and help uh move them through the process and connect them to people they need connections to and all those kinds of things. Um, plus sell our deals every week and prepare those, you know, the marketing, all those sort of things. And then he was trying to take this stuff on on top of it. And again, like I said, plus managing his own personal life and his own deals. So there was probably a lot uh mistakes there. So these things are way slower than they should have been. You know, we ended up having to go back and do you know a bunch of rework or have our contractors go back and do a bunch of rework on it. Um, I'm getting pulled back into these processes, right, to try to figure things out. So that's again more opportunities that I'm missing out on um in the future. So what we ended up doing to solve this is we hired another person, and we should have hired another person way earlier than what we did. But we hired another person who's managing the processes now, and that's you know her full-time, one of her full-time responsibilities. She does a lot of stuff for us now, too. We found um a lot of other areas to take some things off other people's plates who are getting overloaded as well. But she's able to come in and and um and and do those things. And so one of the things that we're starting to do too is just find out from people where they're at capacity wise on our team. You know, how are you doing with your workload capacity? So that's another thing. If you guys have some people on your team and you're starting to throw things at them, you know, make sure you're having some some check ins every so often with them, find out how they're doing. On the capacity, right? Uh, another thing that we do as well is um I'm really good at throwing things at our team and just saying, hey, so-and-so, I need you to do this, this, or this, or this, right? And what we're doing is we're allowing now them to open up those lines of communication to me and giving permission to say, Hey, where do you want me to put that on my list of priorities? Right. So for Reese example, if we would have had this established, this communication kind of um rule set up, is if I would have said, hey, dude, I want you to do these flips, right? I want you to manage these projects and manage these flips, you could say, Great, Corey, I'm, I would love to take that challenge on. I love learning, I love doing new things. But you currently have me doing, you know, working with buyers, and you could have listed out all the things I have them doing and asked, where do you want me to put that on the priority list? And that would have been a really good way for us to have some honest conversation about like instead of them, you know, and people on your team just trying to appease you as the business owner and do everything that you want them to do, but really start to burn out and maybe not do everything really well. You know, things might start, balls might start getting dropped because they just don't have the capacity to do it. You know, people only have so many hours in a day. Um, and so now what we're doing is we're having these discussions of if we're delegating and people on our team know this too. If somebody else is delegating to you and you have you have some directives of some other priorities, they have to let you know where they want to put that on the priority list. Otherwise, you know, you gotta let them know. You you, as the person being delegated to, have to let the person delegating to you know all the other things you have going on and ask where do they want that put. Right. So that's been a really good thing that we've learned um through that process. So a couple things that all kind of like the some through lines here. Moving too fast, all right. Again, massive imperfect action, yes. Take massive imperfect action, get started, but make sure you're learning those lessons. And I would say before even you you take that first step, if your brand's spanking new, make sure you're talking to some of the other investors in your market or in our area who have been there before you and find out what are the bigger mistakes that they've made. We talked about that earlier, but that's such a key nugget there, guys, to make sure you're doing, to make sure you're not making those same mistakes. Um, if you're gonna get into a new asset class, as we talked about, study that thing, learn it a little bit before you get into it, and do your due diligence before you go diving in. Um you know, take don't take on too much. Try to just focus on one thing for now. And um, you know, speed is great, as we talked about, but but speed without any kind of structure is just it's just chaos. All right. So always do your due diligence, no matter how busy you are. So, like we talked about, well and septic inspections. If it's not, if they don't have any documentation for you on when that thing was put in or that it's up the code or that's been tested recently, make sure you get a well-inseptic inspection. All right. Make sure you're getting in there with your contractors on a regular basis. If you're not local to where this project is going on, find somebody who knows that what they're doing or that you can train up and have them do these walkthroughs for you. Okay, maybe it's your real estate agent who's good at this stuff. Maybe it's as simple as that. Like, hey man, I know you're busy and you want to sell houses and stuff, but I'm gonna be doing a bunch of flips. Would you be would you mind just going and checking on this contractor for me and sending me some pictures every so often? I'm happy to pay you. Okay. Um, get to know your rehab costs. That was another big one for me. Is you know, we're just kind of I'm just going so fast that I'm throwing in some generalities instead of actually breaking down some of these things. Um I would say another lesson learned here is if the numbers don't work, don't do it. Right. I think I I got I got like sold on wanting to appease some people on my team instead of looking at appeasing my uh my discipline and my structure of the numbers. And I always want to, I'm an optimist in in general, so I want to make these things work. Um, but now they're costing us a lot of time and energy and and money. So another thing, ask where you're overloaded, and then what are the things? This is something else I'm doing this year. What are the things that you really love to do? And what are the things that you do not love to do? And keep the things that you love to do and find somebody to take the things that you don't love to do off your plate. All right. I'm challenge you guys for that for this year. And and again, if you're getting overloaded, if you're taking on too much stuff, in the other another episode we talked about you're the bottleneck. Don't be the bottleneck, it's gonna limit your growth, right? And that was an issue we had here is I was I was playing small with hires and I was trying to squeak out as much as I could out of our team, trying to figure out like without having to go through the hiring process and find somebody else to take the stuff on, it was easier and quicker just to put it on somebody else on our team. All right. And so, you know, try to recognize that stuff ahead of time, guys. If it's you that you're throwing stuff on, try to get out in front of that and start hiring before you think you're gonna need it because you will need it. I remember that first hire that we made. I was like, well, we we we actually just hired her on part-time. We're like, oh, I don't even know if we'll have enough for her for part-time. And like within the first two weeks, we're like, hey, how would you feel about coming on full-time? Because we you'll always find more things that it frees you as you bring people on to do other things, and you'll need people eventually to replace those, or you'll need people on your team to replace some of the other things that somebody on your team is doing so that they can focus on what they're really, really good at. All right. Um, I've talked about some other things I wanted to talk to you guys about here. Again, we mentioned the inspections already and that sort of stuff, but you know, I I think overall I I don't want I don't share this stuff because these are fun things to go through, right? I share it because these are mistakes that are going to happen if you're if you're not learning uh from these mistakes. So hopefully I've saved you guys a lot of pain and money and stress and and other things. And hopefully this year will be a great year for you guys. Take that advice, go go talk to other investors out there. Like I said earlier, continue to listen to this podcast because we'll share the successes and you can certainly learn some great lessons from those as well of where to double down. But we'll also share, you know, we'll make an effort to get some mistakes from some of the guests on here as well uh going forward. So hopefully this has been helpful, guys. I always appreciate if you guys are subscribing on YouTube to the show, if you're sharing the show, that really helps us a ton. And um, if you haven't left us a review yet on Apple or Spotify, we really would appreciate that. We're trying to get those numbers up as high as possible. The goal this year is to have over a hundred of those on both channels. So if you guys could go out and help out with that, that would be awesome. And on YouTube, if you guys comment on here, just let me know what you think of the show, guys, of the episode. Let me know if this resonates with you or if you think I'm completely off. Either way, let's start a little discussion. That'd be fun. So appreciate you tuning in. We'll see you guys on the next episode.

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Corey Reyment

Host