Podcast - David Curry, Lawnmower Turned #1 Real Estate Agent in Wisconsin

Off Market Podcast: David Curry, Lawnmower Turned #1 Real Estate Agent in Wisconsin

In this episode, David shares his fascinating story of how he ventured into real estate at just 18 years old, starting from humble beginnings with his father's part-time real estate business. He recounts the pivotal moments that shaped his career, from struggling to sell his first property to becoming a top agent by 2010. David's unconventional strategies, like focusing on the Lake Geneva market and maintaining a strong sense of local expertise, set him apart in a competitive industry. Whether you're a seasoned realtor or just starting out, David's insights on scaling, specialization, and maintaining work-life balance are sure to inspire and motivate.

Transcript of the Episode

Austin: Welcome back to another episode of the Off Market podcast, this week we have David Curry, the #1 realtor in Wisconsin, and a member of the top half-percent of the top 1% of realtors nationwide. He’s sold over $800M worth of homes since 2010 and closed over $146,000,000 worth of properties in 2023. He’s represented many of Chicago's most iconic businessmen, businesswomen, estates, and universities. And even though he’s accomplished so much, he still thinks of himself as “just a kid from the Bay”. If you are in the market for real estate in Walworth County, David is your guy. David, welcome to the podcast.

David: Thanks for having me!

Austin: So why don't you tell us a little bit about how you got into real estate? I know that there was a story about Herb's gas station. We'd love to hear that and then dive right into it.

David: I have no idea why I thought when I was 17 years old that I should be going to like, you know, Gateway Technical School with a bunch of You know, 50-year-old people to get my license, but I did. And, uh, the reason I did it was my dad was a fifth-grade school teacher, his whole life in Williams Bay. And he sold real estate part-time, right?

Cause you know, it's a new creation. That is the, you know, teachers, you know, don't have summer jobs, right. And in the seventies. In the eighties and probably into the nineties, school teachers sort of had this expectation that, Hey, in the summer I'm gonna work something else. And so my dad in 1977, you know, as a reasonable young man at the time, would've been what, in his early thirties, uh, started selling real estate.

So I grew up in a quasi real estate family. And when I was a senior in high school, you know, schoolwork was not my thing. I really wasn't into studying and I, but I needed something to do. And so my dad being in real estate, I thought, well, you know, that, that would be an easy thing to try to do.

I didn't want to, I didn't want to mow lawns. You know, my whole life, which is what I did all through high school. And so I went to these classes and I started selling real estate. I don't know what I graduated in may and I would, I got my license, I think in early August. So, you know, here I was 18 years old.

My dad has this company, which was a desk in our living room. And, you know, I said, all right, you know, I'm going to go quote unquote sell houses. And I, I, you know, put, put on a shirt with buttons on the front and I went to work and here I am. And I, and I said at the time, I thought, well, I'll do it for a while.

And if it works, you know, whatever. And then 28 years later, I'm talking to you on the zoom. So that's how it all started.

Austin: And what was the specific stint with Herb's gas station? Something about you weren't going to make it because you were too young for the business?

David: Yeah. So in our little town of Williams Bay, which I know you've been to, we had this old gas station in town and it was, it's a shame that they don't exist anymore.

Right. It's, it's in Wisconsin. It's all Kwik trips now. Right. And, but you know, there used to be a little tiny, you know, old gas stations and, you know, the guy that owned it would also repair your car. And in my case, He would fix my lawnmower. And so I knew him from that. He like rebuilt a muffler on my tractor once.

And I, so, you know, and I was always around town. I grew up in, in, in town and there was, I mean, at the time there's probably a thousand people maybe in town. And so I started selling real estate, my office that, that my dad ended up renting part of a building that we could have a little office in. Um, and my dad was still teaching school.

So my dad wasn't like there. I just was there by myself. I was, it was probably within a year of starting and I. I went into Herb's and I was wearing, I was like, you know, not wearing lawn mowing clothes. Right. And I probably went to like the Van Heusen outlet in Kenosha and bought like a shirt. And, uh, and Herb was like, wow, that's, that's neat that you're going to do that.

But he's like, you're not going to sell anything. You know, he's like, you're, you know, you're too young. And, you know, no one's going to like work with you. And I said, well, thanks for telling me that, but we'll just see what happens. And, and, and then, you know, in Herb's defense, he was right.

Cause when I was 18, I don't remember how much real estate I sold, but it wasn't very much, so he had a good point.

Austin: I want you to take me back to that first deal. I believe it was 1996. You sell your first property. Tell me about that first deal, who it was, and how it unfolded.

David: I'm trying so hard, Austin, to think of what it was. I can't think of what it would have been, but there was a very general theme in my deals for the first three or four years. And, and it was either, it was either somebody from my parent's church that was, you know, buying a, you know, a $60,000 cottage at the time, or, you know, somebody that.

You know, I remember when I was actually early on a couple of my friend's parents were buying little rental houses here and there and I would like to try to help, you know, I didn't, you know, I had no real idea what I was doing. And in ‘96, you know, the internet was sort of a new thing that no one really knew what it was.

You know, I certainly didn't and so it was a very slow start to my real estate career but looking back it should have been expected right? It was 18 years old, you know, and my dad had this company but I've looked back, you know, because when you're a kid, you know, your dad sells real estate you think he's like selling some houses and it turns out my dad really didn't sell very many houses And uh, I think it was in the six years before I started I think my dad sold four houses.

Uh, or for properties in general, I think the total transaction volume was something like 400 and some thousand dollars. So, like, we didn't have a book of business. There was no, like, oh, join this team and go to an open house and you'll sell houses. It was more like. Well, my dad's teaching school down the road.

I'm in this office. I have no idea what to do. I would sit there and simultaneously hope the phone rang and hope it didn't ring. Cause I, I didn't really want to talk to people, which I still don't. And, you know, so it was a slow, it was a slow start, but it should have been expected.

Austin: Right. Yeah. And, uh, and then you start to scale. I would see you get some more deals under your belt and it sounds like you get your stride almost 15 years later in 2010. Now I’d like to double down on what I know and what I love to talk to us about your strategy for scaling. Some people like to go with the old riches in the niches. They'll go after divorces or probates or they'll specialize in certain things.

You actually took a very unique approach and I would love to hear about how you started to specialize.

David: it's funny to hear you ask that. Cause I don't get, you know, I don't talk about it that much. I don't get really asked that. And so it's, it's interesting to kind of reflect on that.

You know, I would say that I have plenty of opinions about the business of real estate and about how realtors function and what they do wrong, I have very few opinions about what they do right. Which makes me kind of an antagonist in our, in our business. But I'll tell you what happened, Austin, you know, I, I struggled when I started in ‘96.

I didn't sell very much real estate from like 1996 till 2010. It, what people see me now, or they saw me then, you know, even in 12. And I thought, well, geez, you're just a young kid. You know, you're, you had this, your dad had this business, which, you know, I'm insulted by, you know, to be honest, because it's like, my dad had a business in the sense that like, If your dad drove fast on the way home from work, he was a race car driver, right?

It's like it wasn't the same thing as people think. But, you know, I struggled for that first, I'd say 14 years. And I like to say in 2008, I had, you know, wife and kids and all this sort of responsibility at age 30. And I, you know, I sold 22,000 bucks, grossed 22,000 that year. And it was a humbling experience on top of a career that had already been humbling.

I, I kind of looked at the market then I looked at my life. I looked at my business and I thought, you know, I'm this far into this and this thing is, Not working. I see the realtors that are doing the business. I wish I did. And I don't even know, I don't know how to do it, but you know, it's different today, even right.

2024 this Instagram world, the coaches the television realtors that have ruined a lot of things for all of us, you know, all of that showbiz wasn't there right. In 2008. And so it wasn't like, Oh, you just. Do a stupid tick tock and you'll be viral and someone will call you, right? There was, there was no means to do that.

So what I did at the time is I started writing a blog and you know, I, I, I didn't know what I wanted to write about, but I knew that the markets were changing. You know, they were changing relatively quickly. And, and this is kind of, it was the pivot in my career because, you know, the world, most people knew things were changing, but something that's very steady in the business of real estate is realtors are very good at.

Telling you it's not changing as long as that viewpoint benefits them. And so I had nothing to lose, right? I just made 22,000 bucks. I was like broke, you know, my, my, there was, there was nothing else to do. So I started writing this blog and in 2008, I think I started it maybe in oh six, I write like one stupid thing, like every six months and it was, It's just meaningless.

And then 08 came, I started trying to be a little bit more consistent with it, and 09 came. Our markets here, um, in 09 started getting a little bit weird, but the Lake Geneva market didn't actually find some meaningful price decline until 2010. And by 2010, I was sort of moving with what I wanted to say relatively consistently.

And, you know, I had approached to it that said, listen, this is actually bad, right? Like, like your house isn't worth as much as it was in 2008, and that's not going to change next month. And for buyers, I took an approach, which I was starting to gain a little bit of visibility that I had never previously had because of this.

I would aggressively tell buyers like, yeah, let's lowball this house. Right? Oh, they're asking eight hundred thousand. I think we should bid, you know, 575,000 and tell them it's best and final. And I started just being a little bit more aggressive and in hindsight, it was now I can see it clearly.

It was because I didn't feel like I had really anything to lose. Right? I had no business to protect, you know, and I think that's something that. Most realtors fumble because they're so worried about every single thing and everyone likes them. And how do I make sure I don't offend this person or offend this neighborhood or say something bad about, you know, not bad, but say something potentially negative about the value of.

You know, I would just start saying stuff like that. And it started to, you know, sort of take hold. So it resonated. And, and 2010 was really when my business started to find some traction.

Austin: And from 2010 until 2024, you'd sold $800 million in real estate. So something was working.

David: You know, And I think that blog might have been a big part of it.

Austin: So, this might be a heated question, but I would love to hear where you stand. There's this perception that as a new agent, You don't know what you don't know. And so you're very much encouraged to find a coach and pay that coach to help you in your career. What's your stance on real estate coaching?

Did it help? Did you pursue one and what's your general take on that in 2024?

David: So I had this pretty negative part of my existence, which just assumes that I know better than most other people. And so the concept of me paying someone to tell me what to do, like, I, I personally never do it. I've never done it.

I would, you know, I don't, Austin, this'll, this'll come as probably like a real crazy surprise, but like, I don't use any CRM software. I don't have, you know, my computer in the morning doesn't say like, Oh, it's been three weeks since you talked to Jim. Make sure you send him a note. And Oh, by the way, it's time for your monthly recipe postcard that reminds people that you're their, you know, agent and that you're a neighborhood expert.

Like I, I don't, I don't need that, but I do think that if you're a young agent. Number one, you should get out of the business now before you waste too much time. But number two, yeah, I don't see anything wrong with hiring a coach. Uh, you know, I wouldn't personally do it, but I, I understand why certain people do, you know, I, but I guess I, I don't have a strong opinion either way, aside from the fact of saying that I, I personally wouldn't have any interest in it.

And I've never used one.

Austin: Well, you touched on something there, which I think is important, right? People will have these systems and processes in place to help them find out what are the things they want to accomplish. So maybe you can talk to us about how you keep your audience top of mind and how you keep trying to stay top of mind for those individuals.

Obviously, you can trust over time and that's a process that takes a lot of time to do. So what are some of the things you do to try to make that experience as positive as possible for the customer she serves today?

David: You know, I think a lot of it is just, you know, I have a general sort of feeling about real estate, which is about the business of real estate, which says, you know, I think one of the mistakes that agents make is, is trying to be all things to all people.

Right. And, you know, that's always existed, but, uh, but a lot of it's been exacerbated by this. Sort of geographic schizophrenia that all the fancy realtors have on television. Right. It's like, well, I'm a realtor in LA. So it only makes sense that I would be in Scottsdale this weekend, showing my friend a house, and then I will be in Palm Beach next weekend, showing them a house, and then, Oh, by the way, it's ski season.

So you'll find me in an Aspen. It's like that concept is so poisonous. I think to younger agents, you know, I'm the opposite of that.

I am more okay. Identify your market, like, and don't make it a market that you aspire to make it a market that you know, right? So like, You know, if, if I'm, if I'm starting out, why did I say after some, after, after a million years of just selling anything I could find to try to make a paycheck, why did I just start to say, listen, if it's not on the lake, I don't want to do it, right?

If it's not close to the lake, I don't want to do it. I'm just trying to figure out how to serve one market. Well, it was because that was the market I knew. Right. And it didn't mean I knew the people in it didn't mean I knew the buyers of the sellers, but it meant I knew that that area. Right. And I know if, if you want to get in the car with me and go look at some houses.

And I'll tell you an area of the lake that's called Coffin Corner. And you'll say, well, why is it called Coffin Corner? And I'll say, well, you know, it doesn't make sense as to why. Because there was a coffin factory in this town, but it was on the other corner of the side of the lake. But my grandpa would say that it was called Coffin Corner because they would kill the walleyes there.

Right? So the question is like, does either, does any of that matter? No, it doesn't matter. But if you're with a buyer in a car and you tell them that, you think they think you know that market. Yeah, they know you know that market. And so if I'm fancy pants, you know, New York realtor, and I'm going to go to Aspen, what do I know about Aspen?

I know that it snows there in the winter. I know that there's a boot shop where I can buy expensive boots and hats at. I know that the chicken sandwich at the white house tavern is good. And I know that there's expensive real estate. And so here's the bathroom and that's where the kitchen is. Do you want to buy it?

Like, I think that's everything that's wrong with the business of real estate. And I think for younger agents that are trying to figure out their angle, or let's say, unsuccessful agents that are trying to figure out their angle, it's What do you know? Right? You know, if you're in some terrible sort of southern town that's sweaty and hot 10 months a year, And, but that's where you're from and that's what, you know, and you know, what the new gas station used to be called, then express your value.

And they're there, right? Don't, don't pretend you can do all the things. So I think that's, that's something that I think is important for agents that are trying to figure out like where they're trying to go or what they're trying to do, like do what you know. And what you know is not luxury real estate.

What you know is a specific corner of this world. That you know better than someone else and that's how you make a career out of it.

Austin: I agree It's knowing the neighborhood like the back of your hand regardless of where they are in the world. So you obviously didn't start out as The number one agent of Wisconsin took you a while to get there. What are some of the things that you did? Obviously, you focused on Lake Geneva, but what are some of the things that you did along the way that you learned worked and didn't work?

And what did that process look like? What are some of the things you had to give up? What are some of the things that you had to deprioritize? What did that process look like? And ultimately, what did you have to give up in order to get there?

David: So, again, I sort of have a contrarian opinion on most of these things, and I'll use an example. I had a client that would call me once in a while. I wouldn't always call him back, right? He'd call me and call me on a Thursday and I don't know, I'd be busy or I'd be at a, maybe I'd be at a, one of my kid's games when he called or something and, And I would be busy and, you know, I could have called him back at five, but I just, you know, I didn't feel like it.

And so there goes that day and the next morning he would call me and maybe I didn't answer. Cause maybe I was busy then. I mean, it was in a meeting and I'm not the guy that if I'm like, if I'm talking to you, I don't say like, Hey, sorry. And then talk to someone else. Right. I just. And I'm talking to you, my phone's gone and I'm talking to you and I'm going to miss a bunch of stuff while that's happening.

But what that customer told me that was really interesting was he said, by, by like the end of the second day, if I didn't call him back, he said he would have two emotions, he said, number one, he'd be very angry with me and he said number two. He was upset that how at how obsessed he was with then talking to me.

So it was like, he's like, who is this guy? I think he is. He doesn't want to talk to me. I want to buy a house from him. Now I'm just going to bug him all the time until he calls me. And so it's super contrarian. Cause you mentioned this earlier, we were talking offline, like. Agents will just go and chase everything, right?

They will just chase everything, you know? And again, a lot of it's the TV realtors that have told everybody to do this. They'll be at dinner, and, you know, they'll be with their friends or their family, and they'll say, Oops, sorry, I gotta take a call. They'll go in the hallway and they'll dance around and high five themselves when they sell something.

And it's like, I've actually built my business doing the opposite. And I think it's a great lesson for people, but it is very hard and it's basically an exaggerated. An example of deferring gratification, which is, you know, what I did in my business was decided after a long period of time, I decided that I knew the business well enough to pretend that I was good at it.

Right. Uh, I, I think it's, it's insulting when there are agents that have been licensed for a few years that try to pretend they're really good at this business. You're, you're not, you're terrible at it. You know, your grandma might have a bunch of friends and they're all dying and you get to list all their houses, but that doesn't mean you're good at the business.

What I did was I decided that I needed to focus on one thing. I needed to do it as well as humanly possible. I needed to value my own time. The last 14 years that I've been, you know, I guess by, by definition, very successful, you know, my, my two kids grew up. Right. And, but my son, I hope when he's older, we'll have great memories of me taking a Wednesday and going fishing with him all day in the driftles, you know, and, you know, taking them sailing in the afternoon because The wind was blowing the right way, and I think, I think that's something that the agents just, just don't, they just don't understand, and, and it's this frantic sort of, I think it can be explained fairly easily that it's, it's this frantic, like, we have to go grab everything because someone else is trying to grab it at the same time.

And as long as you do that, you're going to look like a clown. You're going to look like someone that will list anything, show anything, you know, that's why our broke agent friend writes his little memes about, you know, booking rentals and then, you know, selling a condo for 150 grand and making, you know, 1800 bucks after the split.

Right. It's like. You know, because agents are just programmed to like, go grab everything and hopefully, you can make a living. And along the line, I said, I don't like this business enough to grab everything. So I'm just going to grab the things I like. I am going to work for the people that I want to work for that are in the market that I want to serve.

And if you called me Austin, 'cause you said, geez, I'm super rich now. And I want to go buy a great big house in Madison. I might go up and show you something on Mendota. I might, but probably not because like, it's not my market. I don't know it. So I've become successful by staying in my lane. I don't run around the country trying to sell real estate to people.

I find it to be an absolute. Tragedy that that's what this business has turned into. So, you know, if you need me, I'll, my customers know that there's a good chance I'll be in this office in downtown Lake Geneva and. I'll be working probably, and if I'm not, it's probably because I have a good reason. And, you know, I'm going to just serve one client and serve them as well as I can.

Austin: I love that. if you were to go back to yourself, it's 1996, you have five minutes and you can tell yourself whatever you want. What are some of the things that you would tell yourself just starting out fresh, blue-eyed, bushy-tailed, ready to go rule the world?

David: I would tell myself, number one, don't get into the business of real estate. And people hear me say that and they think I'm joking. I'm not. I would, you know, I'll get to the question with a serious answer in a second, the answer you want to hear, but I'll tell you that the reality of the business of real estate is that it is not a business that's meant for as many people as are in the business.

And, you know, I just went and looked, I think our local association has something like 500 members right now. Are there 50 of them that could support a family doing this? I don't know. Maybe there are only 30. I'm not sure. It's not a business for, for, for most people. And I think it's a shame that the business is so saturated, you know, I don't really understand it.

I think it's leads to kind of a lack of general respect for our business because so many people are doing this as a either as get rich get-rich-quick scheme, or they do multiple things:I sell insurance too and i'll detail your car after work if you want I mean, it's just there's too many things that people are doing at the same time.

And so I think when number one I would sort of tell myself if I were talking to my 18-year-old self that did this I would say “don't go this route”, you know, I say that being you know, kind of successful like you know and the reason is every day my most important deal is the one I don't yet have and that might seem fun when you start doing it, you know, like, I mean, 2010, when we go back to that, that year that my, my sort of career changed, I was very fortunate.

I had a very loyal client who had placed some trust in me that he had no business doing, but he let me sell him a house on the lake that at the time was just under 6 million, which, you know, was an absolute outlier for that era. And, you know, without that sale, I would have never been able to sort of build on that right would have never been able to push to where I am now, but, you know, it was 14 years of scrambling.

And, but what's happened since in the 14 years since is you're, it's still scrambled. Right. And it's, I kind of have I'm thinking of talking to my 18-year-old self I'd say. Right. David, first of all, work on your homework, would you? And maybe get an ACT tutor. That would be a good idea. And then, you know, go to college, right?

And try to figure out a path that builds some variety of annuity, right? And that's the thing in the business of real estate. That's the most, I think the most frustrating. And I, I think it should be the barriers of entry, but it doesn't seem to be, which is there's no annuity in this business.

You have repeat clients, right? That's. Agents would say, Dave, you're wrong. The annuity is repeat clients. And I'd love to help them. Like, that's cute. But like, if I was a partner at a law firm and I'd work forever and lost a lot of sleep and, you know, became partner, you know, as long as I keep my hours going, I'm going to stay a partner, right.

And in that, I'm going to have the profit sharing that comes with being a partner, and I'm going to have the, glassy office in the corner of the floor. And, you know, I'm going to be a partner until I don't do well enough to be a partner in my business in this business.

So I'm a top agent in the state of Wisconsin.

What does that mean? It doesn't mean anything. Somebody tomorrow could replace me. We're, we're ultimately all very replaceable. And, you know, I have this supposed stature in the business that Is as fleeting as anything has ever been. And I think that's the problem with the business of real estate, which is why, you know, if you would have gone, I'm talking to my younger self, a different route, and you know, you might find your way to a career that once you reach thresholds of, of sort of significance, you generally don't lose those thresholds unless you screw up as opposed to this business is no, you'll lose the threshold.

If you don't hustle today, and, and maybe my 28-year-old self or my 30-year-old self, or even my 40-year-old self would have thought, that's okay, just keep hustling. You know, I'm 46. It's not that old. It doesn't feel that old, but it, I guess it's old, like compared to you. And, you know, it's, it starts to get a little bit tiring to try to defend your, your territory, you know, day in and day out.

And so, but besides that, aside from telling myself not to sell real estate, I, I would say, hang in there.

You know, I would say to young agents, if you're convinced that this is the business you want to be in. Which I think again is entered into too lightly, as I've mentioned it for a long time now, I think it's, you know, don't, don't start the way I did, which is, you know, at a one-man shop that has no residual business.

If I were a young agent, I would, I would try to join a, uh, I try to join a team where I could have exposure to deals that I personally have no business earning. You know, and I think that's a great fast track for people. So I think most agents should probably start on a team, you know, with that big top producer, with their fancy initials in the corner of the monogrammed, uh, you know, stationary.

And I think that'd be a great way to go, but for me, I didn't do it. It wasn't possible.

Austin: It's an incredible story and, and so many wise words of wisdom. Thank you so much for coming on the podcast, David.

David: It's my pleasure.