Stop Waiting for Money in Real Estate (Do This Instead)

In this episode of The Wisconsin Investor Podcast, Corey Reyment sits down with South Central Wisconsin investor Tim Dougherty, a full-time real estate entrepreneur who has been in the game since 2008.

From surviving the 2008 crash to completing 50+ deals in the last five years alone, Tim breaks down what it really takes to build a sustainable real estate investing business in Wisconsin.

Tim currently owns 17 rental units and operates Doc The House Buyer, helping distressed homeowners in Rock, Jefferson, and Dane Counties. He shares how he left his W-2 job, raised millions in private money, structured deals creatively, and built long-term wealth through flips, rentals, and wholesales.

In this episode, you’ll learn:

• How to raise private money even if you have zero capital
• Why “the deal attracts the money” is more than just a saying
• The mindset shift that helped Tim leave his W-2 job
• How mentorship accelerated his investing career
• Why networking is the real shortcut in real estate
• How to structure your schedule while building your investing business
• Lessons from investing through multiple market cycles

If you’re investing in Madison, Janesville, Rock County, Dane County, or anywhere in Wisconsin, this episode is packed with practical strategies for scaling your portfolio and building financial freedom through real estate.

Connect with Tim Dougherty:
 📧 yresllc@gmail.com

For off-market investment opportunities across Wisconsin, visit:
 👉 WisconsinDiscountProperties.com

Transcript

Imposter Syndrome And Learning From Any Deal

SPEAKER_01 0:39

What's up, my people? Welcome back to another episode of the Wisconsin Investor. I have yet another amazing Wisconsin investor here with us today. I got Tim Dockerty, which you know it's not Doherty. We solved that prior to this. Uh but Tim, you guys, this guy's a full-time real estate investor and he's been in the game since 2008. So he's been through some things. He's seen some cycles here. We'll get into that a little bit today. But he's down in the South Central Wisconsin area. And in the last five years alone, Tim and his team have completed more than 50 deals across different flips, rentals, wholesales. And today, dude owns 17 rental units, and he's continuing to build the portfolio side of things along with the flipping business and everything else he's doing. So he's also the owner of Doc the House Buyer, which is uh him getting involved with some distressed homeowners down in the Rock, Jefferson, Dane counties. And um, and they're they're meeting directly with these folks and doing deals and solving problems. And what I really respect here about Tim, we had a great conversation at the uh Madison Wisco RIA, him and I talking faith, talking family. Uh, you know, he really operates from a very similar core value standpoint. Uh another thing about Tim left his W-2 over a decade ago to go all in on real estate. So I'm sure we're gonna get into that. Dude's raised millions in private capital, which I know you guys in the audience always love hearing how people are doing that. So I'm gonna I'm gonna be peppering Doc with uh a little bit of those those questions today on private money and uh all those other things. So, Tim, welcome to the show, my friend.

SPEAKER_00 2:11

Well, thank you for having me, dude. I I really appreciate the invite. And uh uh to be honest with you, I was uh a little bit surprised on the invite. I'm like, humble old be like I don't know, like and I genuinely mean that. Like, you know, dude, you got a ton of activity yourself, and uh I'm I feel uh honored to be here. So however I can serve you, yeah, let's do it.

SPEAKER_01 2:31

I love it, man. Well, everybody I ask, honestly, it's really interesting, Tim. The uh what do they call it, imposter syndrome?

unknown 2:38

Sure.

SPEAKER_01 2:38

Anybody I ask to be on the show, typically everybody's like, well, I surely I don't have enough value to provide. And it doesn't matter if it's somebody who's done like a hundred deals or or three deals. I always say I love doing this. I one of the reasons selfishly I love doing the podcast is because I can learn from everybody. Like I don't care if they just got this deal or they did a hundred deals, there's like always some good content in there somewhere that we can glean from it. But it's interesting, everybody has the same response. They're like, I don't know if I would be worthy enough to be on this show. So interesting that you uh you must have there.

SPEAKER_00 3:12

I I seriously like that's that was my thought. And uh honestly, you you're you're 100% right. Like whether you whether you've done one deal or you know hundreds or anything like that, there's always something or some angle that you learned. So every single every single puzzle, I learned something new. So but uh well, thank you for having me. For sure. I appreciate that.

SPEAKER_01 3:31

Yeah, well, take take us back, man. So you got started in 2008. So anybody that's in real estate, at least, you know, maybe now we're getting old, so maybe some young young bucks don't uh don't know too much about 2008. Maybe it's that old again, you know. Like I talked to people about like were you on 9-11? Like, yeah. People people on our team, I'm like, hey, do you guys remember 9-11? They're like, I wasn't born. Like, oh my gosh, that's crazy, right?

SPEAKER_00 3:57

Oh, wait, it's gonna be this similar.

SPEAKER_01 3:59

Yeah, well, that you know, 9-11 was when I walked both ways of school in the snow, you know, two feet all both ways, you know. Uh, but but what was that like, man? So what were you doing that made you say 2008? This is a good time. I'm gonna get into this real estate thing. Take us back to that.

Real Estate School And Finding A Mentor

Coaching, Belief, And Taking Action

SPEAKER_00 4:13

All right, all right, careful here, because if I if I go back, like I'm gonna have to go back from like the very beginning, which I mean for me, that was Yeah, that's great. Like, dude, that was I've been a serial entrepreneur since I was a kid. I had a uh a can collect business when I was like seven years old, and I, you know, took that money and put it into a lawnmower and then had a lawn business all throughout high school. And uh in high school, basically read Rich Dad Poor Dad, I think was like my sophomore year, which that that kind of dates me as well, too, because most people are like, Oh yeah, I read that old book. I'm like, well, it just came out at that time. So um and and so um I was literally ready to drop out of high school after I read that book. I'm just like, why like I was getting you know pretty decent grades uh trying to set myself up for college and things like that. And I'm like, this is silly. Like I'm starting to build my future so I can just go work for someone else and build their business. I'm like so you know, I wanted to invest in real estate for a really long time. Um I remember before, you know, oh five and uh the boom that we had. And they I'm like, oh man, is this the time to get in? I don't have the capital, I don't have money, and things like that. Um and then um somewhere let's see, like so 2006, I actually um uh went to MATC, Madison Area Tech, and and uh and I don't think it's called Madison anymore, but here in Madison, and they actually had a real estate program. So um you can get your associates. You just get your associates in real estate. So it was pretty cool. Like um they'd have a uh uh you at the end of the program, if you took an exam, you'd have your realtor's license. If you took a different exam, you have your appraiser's license, different exam, you have a uh, you know, your property manager's license. So it had all sorts of like exits uh you know after you finished it. And I purposely went to that and I got I got the degree, but I didn't want any of those licenses. I didn't want to be a licensed realtor and have to maintain um any of the uh you know to the annuals and things like that too. So um what ended up happening was uh um I went I I so for budget constraints, I pushed all my core classes toward like the end of the two year period. Um and I um I'm so thankful I did that because uh Chris H, who we both know, was actually the teacher of uh one of the core classes which was real estate interesting. And so I I look at the um oh what do you call it, the the syllabus of the class, you know, what it's about and things like that. And uh it literally says like, you know, if you ever want to know how to own a duplex or you know, buy a rental property and run the numbers and everything like that, and it's it's just like it literally was like words pulled out of my head. I'm like, this is my class, like this is exactly what I want to do. And so, like you you could ask Chris, I literally followed him to his car in the middle of February, almost every single time that we had a class, and like there was I'd say up to hours where we're sitting out in the parking lot, it's freezing cold. Dude has to go home, and I am like holding him hostage, just asking him all these questions, and I'm like, But he he was always so generous with his time. I mean, like he had me over to his house, and yeah, you know, eventually, you know, we formed a mentor relationship that was, you know, pretty critical to you know me getting started in real estate. And uh um, you know, so 08 is kind of just like that's the first deal that I did. But it literally took me, you know, it was a decade in the making almost, and also uh, you know, years of wanting to do it, getting ready to get started, and not you know, using the I don't have money, I can't get into this type of mentality. And finally, I'd I'd say Chris was uh one of the key uh key breaks to that in that my mentality mindset. And you know, he uh uh uh he helped me, you know, with some of my very first deals. Um so but uh yeah before I start. I mean anything else, yeah. Um anything else you got closer?

SPEAKER_01 8:27

Yeah, Chris. Well, Chris, Chris was on, guys. If you haven't uh if you're not familiar with Chris, he is uh he's an OG in the Wisconsin real estate investing world, and he he was on. I think I had him on maybe five or so episodes ago. So if you guys go back and if you're listening to this on Spotify or if you go to YouTube or wherever you're watching, or you're listening to this, go back down, you'll see the episode with Chris. There's a lot of great nuggets Chris shared in there as well. Uh take me back to though, I think what what's interesting for me is you know, I talked to a lot of people who are interested in getting into real estate, as I'm sure you do as well. And there is kind of like what you mentioned, you had it sounded a little bit of analysis paralysis, maybe, or like there were some, you know, some limited, some limiting beliefs that held you back. If you could go back and rewind the clock and you start this thing over today, you're you're Tim, you decide you're gonna do this real estate investing thing, you read which, dad, poor at. How would things be different? What would you do differently if if you knowing what you know now, 17 years later, uh to either speed that process up, slow it down, what would you do? What would what would be some of the things you would do maybe differently going back?

SPEAKER_00 9:30

We got to understand the parameters of this question. So, okay, so I get to go back in time. I have all my present memory of what happens in between, or just a couple of these things too.

SPEAKER_01 9:40

I mean, I've been called more than you got an NVIDIA stock the minute it hits. Yeah, exactly. No just as an investor, like like maybe you just take you know some of the things if you could go back into your uh situation. You read Rich Dad Port, it's 2026, you won't know much about real estate investing, or then you know you want to do it. And now you're you made the decision. At some point you're gonna do real estate investing. You know, it's not like it took you a little while to get in the game from making that decision. What would you do differently today if this was you starting over today?

Accountability And Paying For Guidance

SPEAKER_00 10:17

I mean, man, the I I think I I don't know that there's a whole lot I would do differently based on those parameters. I mean, if I have knowledge about other things, totally different. But I I think the the number one thing that I did that was was right is I found other people who were ahead of me in the game. And if if there was if there's one thing I could like maybe a a better way to say it is like what could I tell myself going back and stuff like that? Um you know, I it I don't know if I'm mixing up your question, but I would say that you can do it. Like that's the number one thing I would tell myself. Like, not only can you do it, you do it and you do it well. Um, and um, you know, just to to have that that confidence and belief in myself. I'd say that that was probably the number one thing stopping was, you know, just believing that I could do it. You know, like you said in the beginning, this call imposter syndrome, you know, that's everybody's got a feeling, everybody's got limiting beliefs and things like that. We're always, you know, competing with our our best version of ourselves. And so um yeah, so basically that would be the the number th one thing I I would change is just instilling some sort of belief that that you can do it. Um and it wasn't.

SPEAKER_01 11:28

It sounds like you got that from a mentor. It sounded like Chris was the guy to instill a lot of that belief, right?

Networking, RIAs, And Community

SPEAKER_00 11:32

Yeah, in fact, I I can tell you exactly the moment where things shifted. It was uh um basically he started a coaching program and I was like the student number two that he picked. Um and uh he's like, dude, I want you to I want you to pay me for coaching. And I'm like, You want me to pay you? And he's he's like, Yeah. I'm just like I've been like hanging around you for like the last four years. I've seen all the flips that you do. Like my mom lent you know private money to her from her IRA, so we're doing all these clever things. I'm like, now I gotta pay you? And and he's just like, yeah. He's just like I'm like, ah man, I'm I'm why why would I do that? And he's just like, well, he's like, Tim, do you believe that you could flip a property? And I'm just like, I I remember where I was on the phone talking to him, like, you know what? If I'm to be honest, I know what I should say, but like you know, I can believe, I could do it, you know, I could do anything I set my mind to. But I'm like, honestly, no. Like, I don't believe I can flip a property. I'm like, if I if I could, I would have done it by now. I've been doing this for you know, following you for how many years and haven't done it. He's like, He's like, Well, let me ask you this. He's like, Do you believe that I can flip a property? I'm like, well, duh, I saw you do ten last year. Of course I believe that. And he's like, that's why you'll pay me. He's because you believe in me, and I'll believe in you. And I don't know what it was when he said that. It just clicked for me that literally anything I do at this point, all I gotta do is follow him, and whether I succeed or fail, it's his fault. Like so, so basically, like literally all I gotta do is everything he tells me to do, and the responsibility just was immediately like off my shoulders. All I gotta do is just do what he told me to do because I know he could do it, and then sure enough, like that was what it was. I mean, I knew what needed to be done. I could have flipped any properties at that point in time. I knew, like most people probably listening, you already have all the information, you've listened to enough podcasts, you've you know looked at enough things, joined enough reasons, all that other stuff. The difference is your belief and the action that follows. So, and that's that's so good. Yeah, so it was that is so good.

Designing A Job To Build A Business

SPEAKER_01 13:44

That's that's gonna be the part that the AI picks out for the viral clips, I think, right there, Tim. That was so good because it's so true, man. Like it is, it is such a mental game, dude. Any business, right? I don't care what business you're gonna get into or start, it's a big mental game, right? Like we were talking before this on our and if you guys want this access, you gotta go to our Patreon account, which we don't have. I'm just kidding. Uh but Tim and I were we had a good discussion before this. Like, I've been in real estate investing now and and employing people for almost a decade, right? And then we've so there's very strict rules about W-2 versus independent contractors. And we got audited by the state last year trying to get money out of us because they're trying to say we didn't all these people should have been W-2, right? And we're like, right, oh, these people, you know. So then you have to go prove yourself, right? But my point to all this is I've been in this a decade. I'm still learning stuff, right? Like, I don't know. I'm just doing the best I can and I'm just trying to operate a business, and then the state comes and tries to mess things up for me, right? And now I'm like, okay, now I know I need a new system for this, I need our team to be doing this, and blah, blah, blah. And I learn this stuff as I go. But if I had to try to sit on the front end of this thing and try to learn everything there is to learn about building a business or doing this business or employing people or whatever the case is, like, none of us would ever get started. So I think what you're saying is like gleaning some confidence from somebody who's already where you want to be or is ahead of you in the game, and just go in with their confidence. So they've already seen a lot of stuff, and they're not gonna see everything, but they've seen a lot of things and they can speed that curve up for you. And you can just basically like suck the confidence from them and wear it every day. That okay, I'm gonna wear their confidence because I don't have my own yet. And I'll just wear their confidence and then we can go do this thing. And then that's that's what it's gonna take, you know. And the part, the other part I think that's interesting psychologically, what Chris is also doing is that you know, I'm sure Chris was successful at this point and probably didn't need whatever$10,000,$15,000,$20,000, you know, you paid him. However, what it did for you probably, Tim, is it made you go take action because now you put your money in and now you had to get at least something back out. Is there some truth to that? Um so say it again, like he he didn't need the the finances and he probably didn't he he it was more for you, because if you if you put money in and you don't have a lot of money, you're gonna work your butt off to get that money back, right?

SPEAKER_00 15:59

Oh and so psychologically the reason why I kind of chuckled when he said that was because he didn't get$10,000,$15,000. I mean, dude gave me one heck of a deal. Like to this day, I won't let him buy lunch anymore. Okay. On top of that, like, um he's like he would sit there, you know, help me out and you know, teaching me on lunch times and things like that. The guy would buy me lunch. And now like I have a totally different, you know, mindset. Uh now that I've actually had some success in business, things like that. Anytime I'm with anyone, which most of the times if I'm going off to lunch with someone, it's uh hopefully with someone who is my superior, at least in in some regard. Um everybody is, everybody's your superior in some way. But what what I mean is like, you know, they they've got more experience in business, things like that, and more life and things like that. I'm trying to, you know, learn from them. And I'll always, always get them lunch. But dude did this for uh, you know, pennies on the dollar, and he did get paid. Our first deals that we did together, we split 50-50, so absolutely was worth it. Uh you know, as far from a financial perspective. But I think for him, where the big benefit was was one, he had been trying to help me for a long time get off the ground. And then he figured out a way that it it our we were able to align our interests, you know, as opposed to being a charity case and help help someone, he was able to figure out a way to make it profitable for both him and myself. And the moment it became profitable for both him and myself, we both succeeded. When it was a charity case and it was something where he was just trying to help me and get me to come along and stuff like that, there was no accountability between the two of us, no matter how much we wanted it to work. There the accountability wasn't there. Whereas now it's like, okay, I'm paying you. And for me, it was a lot of money what I was paying him, and he knew that. So there was enough accountability for the money. It wasn't free to be by any means, but it it it actually was very fair to me, but um, which was what needed it to be for that accountability piece of it. So um, but yeah, he yeah, he definitely gave me a good deal on it. So that's why I laughed when you said that I'm like, Yeah, yeah, you didn't do it for the money. I know that. So, you know.

Leaving The W‑2 For A Big Flip

SPEAKER_01 18:04

Yeah. And and the reason I bring that one up is well, that was one of the things that got my wife and I into action was we hired a local guy, paid him 10 grand, and then we split like the first three deals with him. And so that 10 grand for me at the time was a lot of cash. Like I didn't have 10 grand just laying around. But what it and the coaching, you know, no disrespect to him, could have been better. Okay, we'll just say there could have been other things that I would have expected for 10 grand, we would have gotten from it. But what it did for me, and I'll forever be grateful, is it got me forced into action because I had to go take action to get that 10 grand back. Otherwise, I was gonna like that. Was so important to me. And I'm like, I'm not gonna let this 10 grand just go away, right? And I think that's the important part. Anytime we get a coach, a personal train, like personal training is another good one, right? You want to get healthy, you go get you go get a health coach, right? We you can go on YouTube and watch videos all day long. And why isn't it work? Because nobody, there's no accountability there. There's nothing, right? You hire somebody, you're like, all right, now I gotta actually do what they tell me to do because I'm paying this person, right? So there's something to that. We've talked about that, guys, on this podcast. If right now, I think we're in like episode 80 something. I don't even know where this one will land, but if you've listened to all of these episodes and you still have not gotten in the game, here's your sign, is my old country friends would say. Here's your sign, right? Go be the coach. Go do this. I think, in fact, I believe Chris is still doing this through Whiskerhea, if I remember correctly. And Tim, you're part of you're opening up a Wisconshe as well, correct?

SPEAKER_00 19:30

Yeah, we actually just had our our our second uh meeting. Um it was uh just a couple of weeks ago down in Rock County, Janesville. So um yeah, we had a really good turnout. I mean, Rock County is definitely awesome county and a lot of hungry people there, which is what we saw. And you know, we had some good attendance two months in a row, and so looking to keep that up. Yeah, uh, awesome.

SPEAKER_01 19:53

So if you guys are down in that neck of the woods, yeah, if you guys are down in the neck of the woods, go check it out. What when do you guys typically meet Tim? When is that Janesville RIA?

SPEAKER_00 20:00

Fourth with the fourth Wednesday of every single month. So if you just take a look at the Wisco RIA website and go down to Janesville, uh it'll tell you the exact location, time, everything. And and that's you know, uh, yeah, that'll have the most updated information regardless of when you're listening to this. So cool.

Private Money Mindset Shifts

SPEAKER_01 20:19

Awesome, dude. And RIA, for those of you guys, if you're not sure what RIA is, Real Estate Investment Association. So that's just an acronym that uh we use in the biz, R-E-I-A. So if you're searching that up, WiscoREIA.com. Yep. And you can check out all the uh the locations and and branches and meeting times and stuff. And we talk about it, I think, literally every episode, Tim. Every episode we talk about networking. As every every guest is like, wow, networking's so important, networking's so important, networking. So if you again, if you've been listening to this for a while, this isn't that to condemn you if you haven't showed up yet, but if you're in Wisconsin and you're near any of the locations, and there's plenty of them out there between us, we also run the REI Success Club in Green Bay. If you can't make it to the Wisco Rias, uh, there's a Wisco Rhea in Green Bay, there's there's locations all over the place. So uh networking is a huge piece. I want to I want to go back real quick, Tim. You know, you you you you mentioned that you left your W-2 after a little while, right? What was the decision? Like what made you decide? What was your W-2? Yeah, and then what made you decide to leave that W 2 and go all in on real estate investing?

How To Present Deals To Lenders

SPEAKER_00 21:22

All right. You want me to go down that road? All right, all right, here we go. Yeah, let's go, baby. Let's go. So basically, I uh I work for Quick Trip. Um and uh Oh, I love me some Quick Trip. Yeah, oh no, that by all means. Nothing but positive things to say about Quick Trip. I've always said that uh I don't want to work for a company like Quick Trip. I want to build a company like Quick Trip. I mean, they got vertical integration, all that other stuff down. I mean, like that was actually really cool working for them and like studying them. And I was just it was actually really cool. I was a low man on the totem pole, so there's no responsibility on my shoulders. And so I'd show up to work and they'd be like, oh, like you're awesome. Like you just take initiative and do things and you know, not toot my own horn or anything, but it was just it's easy to do. Like, I I'll get bored. Like, I don't want to sit around, I want to like go be productive. And so, but just to not have any responsibility was actually really cool for a while. And and being a business owner before that, uh, and then coming into Quick Trip um and kind of you know licking my wounds and stuff like that, uh, that's that's where I was at. So um it it was kind of release. But now um, you know, kind of fast forward uh about like six months into working for Quick Trip, I'm just like I can't do this. Like I can't do this. And I and I know it was something It was a God moment. And it's like I I was thinking to myself, you know, like man, I'm just like, am I a failure? Like, why can't I make it in business? And, you know, what is uh like what what do I gotta do different here? Like what maybe I maybe I'm destined to work for a place like this. And all of a sudden it hit me. I'm just like, you know what? I'm just thinking back, because when you're sitting at the cashiers, like sometimes it gets real boring and you get time to think, but you can't leave it at the cashiers. Um and so I was thinking about it, I'm like, you know what? It's right around six months. Every time I start a job, it's right around six months. I want to get the heck out of there. Like I can't take it. Like I want to just tell everybody what to do, and I want to like, you know, I I wanna I wanna take control, like I can't do this. And then it dawned on me, I'm like, wait a minute, that's what God did designed me to do. Like, so if God designed me to do this, like he built me this way that that I'm built to be an entrepreneur. I've been an entrepreneur since I was seven years old or even earlier. And I'm like, so it's not a matter of if I'm gonna succeed. It's just a matter of when.

SPEAKER_02 23:43

Because he's not gonna change.

If The Deal Is Right, Money Follows

SPEAKER_00 23:45

Like I I can start any job I want, I can go and be tempted by you know a cool corporate ladder, fancy position, and this feeling in six months is gonna come right back. Which means I either figure this out or I keep on trying. Either way, I'm not I'm not failing. And I'm and I've gotta do it. So um, yeah, that was a big, you know, God moment to realize, like, all right, I'm I'm gonna be an entrepreneur, whatever time it takes, I'm just gonna do it. So I set up my job in such a way, and this is you know something that you're getting started, and you have the ability to do this, which a lot of people think they don't, but they they do. Um, so I set up my my work schedule with Quick Trip. Like, I am gonna be your number one reliable guy. And it's only gonna be on this day, so you can't schedule me for Sunday, Monday, and eventually Tuesday came into play. So I worked four days a week, 10 hour days, and I put it all um, I s my shift started from noon until 10 p.m. And the way that I looked at that was noon to ten p.m. is my least valuable amount of time to myself. You know, it it's where I'm the most spent and things like that. So of course, if I'm doing a job, you know, I'm renting out my time. I want to rent out the least valuable time that I have uh and use the most valuable time for myself. And so what I would do from six in the morning till noon is you know work out, take care of health, and then run a business and do little day-to-day things. And then on Monday, you know, Sunday, Monday, Tuesday, what I would do, you know, Sunday took care of personal stuff, and then Monday, Tuesday I built my business. And so I was very, very conscious about it. And, you know, they would try and get me to work on Sundays, and I had a boss that like was like, Oh, you're really good, you can go somewhere with this, but you just gotta work Sundays. I'm like, no deal. I I will work whatever time you want me to work, you know, as long as it's within these hours, and I will be your your major hitter. Like, you know, they always need someone on shift that was really good at the job. And so I I gave them that. I gave them as my best possible hours or my best possible effort while they were renting my time. But it was outside of my time. That's my time. That's for my business to build it. So what what ended up happening was um this is after the coaching program by you know, a couple, I mean, I it was during and after the coaching program. So I I hired a coach, um, Chris, and I followed his his you know, tutelage and mentorship and uh uh started marketing and things like that, and you know, got you know my first uh several deals underneath my belt. And by like deal number five, um I took on a big project that uh was gonna be like uh over a hundred thousand dollars in rehab. So it was just the biggest deal that I yeah that I ever took on. And I had you know one wholesale deal underneath my belt uh where it you know I it netted me a good chunk of change. I think I got like 14 grand off of it, and that was a ton of money. I mean, for me. That was almost like like half my annual salary. So I'm like I went part-time. And it it got to the point where I was um you know, working on my education, you know, working on thoughts in between my ears, and um, you know, where my time was becoming so valuable that when I was at work, I'm like at my job, I'm like, this is a waste of my time. This is a waste of my time. Yeah, I'm gonna do it. It's like costing you money to go to work. Yes. It's literally costing you money to be there. Exactly. And I was telling my boss at that time, I'm like, dude, like, do you know what you're he was starting a new store and uh um I was like, you know what you're doing like right now and how crazy it is for you? That's what I'm doing outside of this. So imagine having a part-time job on top of what you're doing right now. And he's like, Oh, that's yeah. Because he was trying to keep me and he was trying to get me to stay on board. He was an awesome, awesome guy. Um and uh I'm just like, I'm sorry, dude. It's it's I I've got to be three. I gotta go out there eventually. Yeah. I did. I went I went full-time, I gave my notice, and I I focused on that project.

SPEAKER_01 27:34

So Tim is unemployable, quick trip. You can't have him. Unemployable.

SPEAKER_00 27:41

Nothing but good things to say about quick trips.

SPEAKER_01 27:43

Oh, love me. We do road trips and we with our family, we love traveling and stuff like that, and it's so depressing to go to other states and they don't have anything like a quick trip. You know, down south they do have quick trips. They're different, they're actually quick with a queue. Yep. Those are good buckies, obviously. If you've been in the south, you know buckies, right? Those are great. But if you go out west, it's like there's just nothing.

unknown 28:03

Nothing.

Planting Seeds And Making Offers

SPEAKER_00 28:06

I'm like, you guys have a real business model. And it's crazy, you can't buy stock in their company. It's all venture. I know we integrated three generations of family, and it's like, oh my god, do they have systems now? They have systems, and I have tried to buy in. Yes. Don't let me do it. Yeah, yeah, exactly.

SPEAKER_01 28:26

Uh speaking, yeah. Oh, I do I do very religiously. Uh the the thing I want to talk about here, kind of shifting gears a little bit, Tim, is speaking of investing things and money and those kinds of things. So you know, you've raised a lot of private money, it sounds like, right? Yeah. What what what what's been some of the secret sauce in raising private money? I know this is always a hot topic for people. I always learn something from different people strategies, techniques, mindset, whatever you can share about. What's what's worked well for you and what do you see people doing maybe that uh maybe make mistakes when trying to raise private capital?

Wisconsin Favorites And Local Life

SPEAKER_00 29:03

I I think the so the biggest mistake I would say that people have at least mindset around money and and raising money is that you need it before you can go make an offer on a property. I think that's the the number one mistake. So um the the most important thing to understand is that you're especially if you're starting out and you don't have a lot of capital and it's not like you know your dad's got a nice line of credit or something like that. Uh if you aren't making offers, you're not gonna find money. Um it it's just it's just not it not likely to happen. And it makes sense when you think about it because there's no point. You don't have a deal to find. So one thing that Chris drilled in my head was if the deal is right, the money will follow. Just repeat that. Like literally eat that, drink that, live that in your sleep. When you wake up in the morning, it should wake up and go, the deal is right, the money should follow. So, like, there are so many times where I've gotten properties under contract where I'm like, I don't have the money for this deal whatsoever. Uh, my very first deal that I had, um, I had the$500 earnest money. And I remember talking to Chris and um, you know, going like, dude, I just put my last five hundred dollars in my marketing budget in the earnest money for this deal. And it was fifty-three thousand, I want to say, like three-fifty-three five hundred, something like that. And it's like, cool, I put five hundred dollars down in thirty days I gotta come up with fifty-three grand. How do I do that, dude? He's like, don't worry, I got and and so that's that's where also maybe a second thing would be mentorship is also really important too, because their belief will follow. And they have a network and things like that that you might be able to tap into. Um and that's exactly what what happened was it was somebody that uh my first deal was funded by somebody that we both knew mutually. Um and you know, he uh just gave me the confidence to be able to approach that person. Um he showed me, you know, how to put together a lender packet to present the deal, show the comps, show the repairs, show the timeline, show the rate of return, show the lien position, you know, uh what uh LTV they're at, things like that. Um, and then walk the property with a lender. And you know, sure enough, not only did we get the the property, uh the funds for the property, but we got you know thirty-two thousand dollars on top of it to do the repairs. And it's just boom, it was funded in 30 days. And I'm like, what just happened? Like all these years, like literally. Right. I mean, like we're in that was like 2012, and I had been trying to do deals for years, and that was my number one thing that was, you know, stopping me uh in my belief was just like I don't have the money to do it. And it's like from there on out, it's like because it simply put, you know, if I've got, you know, Corey, the winning lottery ticket. Let's just say we both go to Quick Trip. I got the winning lottery ticket, it's worth$10,000, um, you know, hands down, or$100,000. So let's make it$100,000. But for some reason, I gotta get on a plane and I can't cash it in, and I'm not gonna be back for like five years. So everything's legit. You can verify that it's worth$100,000, you can call up the lottery company, and for sure it's legit. I just gotta get going. And I go, hey, if you give me$10,000, I'll give you this$100,000 lottery ticket. And it's totally legit, right? Would you be able to find the$10,000? Oh yeah. Easy. Like in a heartbeat. And not even, you know, even if you didn't have any money, you'd still you'd you'd find a credit card, you'd find a friend, you'd explain the situation, show the documentation. Like, dude, we do this together. Like, if you give me$10,000, you know, to give this guy, I'll give you 50% of the 90,000, you're still ahead 45. You know, so it's like uh and that's what it is with real estate. And you you go get a property on the top and you're just getting something with so much equity in it that it's like it'd be stupid for the lender not to give you the money. And their worst case scenario is that you pay them back. They're best and they get the deal for what you paid for it. Right.

SPEAKER_01 33:07

You know, they take it over. Yeah, if you've default, they got and then you've probably already done improvements and work to it, so now they got a partially improved property for the price of what you paid to buy it, not improve.

SPEAKER_00 33:19

Yes, exactly. Exactly.

Closing Advice And Calls To Action

SPEAKER_01 33:21

I love it, man. That is such a good analogy, Tim. I think this is so helpful for our audience because you know, that is for newer people in particular, or people even looking to scale. You know, at my uh my my spot, like we still bring private money in from time to time when we have a good, I never want to pass up good deals, right? That's rule number one for me in real estate is like don't pass up a good deal. So have I always talk about like we have a Burr for Beginners course that we that we launch. So if you guys are listening to this, you're not in the Burr for Beginners course, but you want to be. If you don't know what Burr is, Google it after this. We have or we go back plenty of episodes on it. But in that course, I talk about having different buckets of money, right? Like private lenders, HELOCs, commercial lenders, um, credit cards. If you're if you have zero you know, introductory rates, you can use those partially. Like there's a bunch of different ways you can get money, right? But I think it's always this question of is do I need the money first and then go get a deal or get this? And what you just provided was a very clear, I think, direction and example for people. So, those of you guys out listening to this, what Tim's talking about is like go to networking events, meet people, build your network, right? And not even that, you probably just have people in your current network that aren't even associated with real estate that if you brought a good deal and you showed them the numbers, it would be a no-brainer, right? They'd be like, Oh yeah, where do I sign up? How do I get you the money? What do we do? It's almost like so easy if you have a really good deal that it's like stupid easy. But I think it's I think that's just a really good point because people get tripped up in this. Like, when do I start the conversation? And I I actually think not not to say what you're saying is wrong in any capacity, I'm saying it's an and situation. Like have conversations with people about what you're doing and be making a bunch of offers because you plant then you're planting a bunch of seeds with people along the way. Then when you have a great deal, you go to that, those people you've already did. Well, see, look, I told you I was gonna go get a good deal. Here's me showing you a good deal, and now boom, it's already there. But it it doesn't have to be that way. What you're saying is so true. If you have a hundred thousand dollar lottery ticket and you're gonna buy it for ten thousand dollars, you will find somebody to fund that ten thousand dollars and if you're offering a bigger piece of the pie.

unknown 35:25

Yeah.

SPEAKER_01 35:26

So I love that dude. That's so good.

SPEAKER_00 35:28

It's definitely it's definitely a thing.

SPEAKER_01 35:30

So yeah, that's awesome, man. Um as we get close to wrapping here, Tim, we always ask our uh our uh guests one fun question. And the reason we do this is we have a lot of people that listen to this show that are outside of Wisconsin uh that maybe want to put some capital in Wisconsin, but they don't know a lot about us. And so I like to just give people a little insight on Wisconsin. So for you, do you have a favorite uh Wisconsin tradition or place you like to visit?

SPEAKER_00 35:59

Oh, okay. Um, literally your backyard. Um, I absolutely love like the Fish Creek area, Washington Island. I'm not wearing any of my my gear that's got you know Colorado on it, but uh oh my gosh, Washington Island, like you're you're blessed that you're so close to it. Uh again, that that's my wife and I have like gone back and forth, like, oh man, well if we lived there, would we still love it as much? I mean, I think you'd be able to tell me that. But uh um George County is just absolutely gorgeous countryside, and just the the people there are awesome, and it's just very peaceful, laid back, relaxed, beautiful water, like Michigan, just different kinds of it. It's awesome. So that's yeah, yeah.

SPEAKER_01 36:48

It's actually it's actually grown on me a little bit, Tim, since I moved here. Like I never grew up really coming up here. Like we came up my um my great-grandma lived in Sturgeon Bay, so we never got up to like actually Door County. I don't consider Sturgeon Bay really like true Door County, right? You gotta go a little bit, you gotta go north, right? You gotta be uh so we always came up coming up here, but that was about as far as we would get when I was a kid, and then um we always would go up to like Manaqua Eagle River area, which I think is another hidden gem for people who don't know about Wisconsin. It's just the same thing, very peaceful, beautiful, a lot of lakes, that kind of thing. But now living here, I've gotten to like explore Door County a lot more. And I mean, there's so much cool stuff to do if you're an outdoor fan. It's like uh like you can do any hiking, there's inland lakes even. I never even knew that Door County had inland lakes that you can boat on. I was like, what? This is crazy. Because I'm like, it's so cold out in the water out there, I'm too wimpy. I want it warm. Well, you can just go to the inland lake and go boat, you know. So there's like all kinds of cool stuff, and Washington Island is so unique, man. I I still can't believe people live there. It's cool, like it's awesome.

SPEAKER_00 37:50

I I don't know about living there. That that one would be tough. I I would say if I own my own boat for sure, then then it's uh a little bit different. But we my wife and I, we went an October one year and stayed for like uh five days straight, and by the fifth day, we actually took the ferry back to the mainland just to go visit Fish Creek. And we're like, okay, we can't do the same thing over and over again that much. But you know, I'd say about three days on the island. The island's only so big. Yep, yep, but it's only so big.

SPEAKER_01 38:18

Yeah, exactly. Exactly. So well, Tim, this has been awesome, dude. I I I learned a lot already on this episode. I think our episode I think we gotta have you back on again because we could probably you and I could probably talk for hours about real estate. We only got a part way through some of your experience. So I think next time we'll have you back on again here, maybe in a few episodes, and we'll we'll do Tim part two and uh and have you back on a pick back up where we left off, dude.

SPEAKER_00 38:43

I gotta ask you a couple more questions too and get some more information from you. Yeah, I want to hear your story, dude. That'd be awesome.

SPEAKER_01 38:49

So yeah, so for yeah, for those of you guys that haven't heard this, uh I got started in 2016, same exact way Tim did, red rich dead port ad. And I'm like, okay, we're doing real estate investing. Leading up to that, I was unemployable as well. I'd I'd go somewhere, work like three years in sales, and then I'd be like, all right, kind of conquered this. Like, what's next? And then I'd start causing problems with bosses, and I either get fired or have to quit. Right. And uh and so uh my wife and I, we've always had like I've always had like side businesses like you, Tim, and um we did network marketing for like five years, and we got burned out on that pretty heavy, but we liked like the residual income piece of it. So when we were at Rich Head Point, we're like, whoa, we could do that with real estate. Okay, cool. So we started, you know, got that local coach, same thing you did. We're like, all right, we need somebody to teach us how to do this stuff. Got a local coach, started doing it, kind of did a buffet of real estate, I always say. So we did a bird deal, we did a rent to own on our our primary residence that we were living in, we did a seller finance joint venture deal with some somebody else. Um, we wholesaled a deal, we flipped a deal, we kind of did all of them. And then we're like, gosh, we really got into it for rentals. We really wanted rentals. Um, but I the reason I want like, and I think this is good for anybody listening to this. If you think you want a certain thing, like I thought I wanted rentals, start asking why do I want the rentals, right? And the real reason was because I wanted to leave my job, right? And so when I got my first couple burs, I realized like it's gonna be a long time before I can then build consistent passive income. I always do this with real estate passive income because it's still it's still never really truly passive. Yep. Um, and so we we had wholesale deals, and I was like, you know what? I think I really like the wholesaling thing and flipping thing. Like it's quick money, it'll get me out of my job a lot faster. Let's just like learn this. Actually, my wife was way smarter than me. She's like, we should just focus on one thing. And I was like, No, we can do everything. You know, classic. And she's like, no, let's do one thing. And it is so true. So we we focused on wholesaling. We got a coach specifically for wholesaling, and we did exactly what you do with Chris. We just did exactly what they told us to do. And I think it was the same realization I had, bro. I was like, in my job, and I'm like, it's literally costing me money to work right now. Like I could be out getting more deals that are way more fruitful for me. And so I ended up resigning way earlier than I thought in 2018. And from there, you know, we still added, then we started adding rentals once we had a decent whole wholesale portfolio or wholesale business going in some systems and stuff. But yeah, that's that's it, man. And now we're I think 13 employees in, and we got uh did about 170 wholesale deals last year and looking to hopefully expand on that this year. And we're coming down by you guys in the Madison market this year, so we're excited about that. We got our first couple deals uh hitting the buyers list uh probably when this episode drops, maybe even the week before this thing drops, they'll have gone out. So we're excited about it.

SPEAKER_00 41:51

You got it. You got it, man. Are you on the buyers list, Tim? Uh you know, I don't know, honestly. Uh received a text message or an email.

SPEAKER_01 42:01

You you would you would have to go to our website. And so here's our plug, Wisconsin Discount Properties.com. Go on there, put your information in, and then you'll get added to the buyer's list. And then uh Connor, who I think you met at the Wisco Ria, he will probably be the one to give you a call and uh and you know get you set up, make sure you understand how all our emails work and the deals work and all that kind of stuff, and you'll start getting the weekly emails and text, man.

SPEAKER_00 42:25

Okay, well then I gotta get on that. So I see that didn't know that. There's an opportunity I gotta take advantage of.

SPEAKER_01 42:31

There it is. Deal flow coming right here, live on the podcast. So doing deals. Awesome. Doing deals, man. Well, Tim, it's been great, guys. If uh if you got some value out of this episode, please share the episode. Not only does it help us grow the audience, but it helps you let your network know that you're doing real estate investing. So when you go to raise private capital or you've got a deal that you need a JV partner on, somebody in your network is gonna see that because you posted this episode on your social platform. So get the word out there for yourself and help us grow as well. If you get some value, please go and do some ratings for us. I know people ask about this stuff on every podcast, and it's kind of sickening at this point, but it is really, really helpful for us also to can help us continue to do these shows. We want to keep bringing you guys valuable people like Doc the House Buyer here and other great people who we've had on before. So share this stuff, guys, and uh thanks for tuning in weekly. Tim, any last words for the audience?

SPEAKER_00 43:24

Uh don't be afraid to make an offer. Just go make some offers, buddy. Or whoever's listening.

SPEAKER_01 43:29

I love it. I love it. Well, they're all buddies now. They're beautiful.

SPEAKER_00 43:33

Yeah.

SPEAKER_01 43:34

All right. Thanks so much, Tim, for being on. Thank you guys for listening. We'll see you on the next episode.