Give Them the Pickle

August 19, 2025 00:39:47
Give Them the Pickle
Short Term Rental Management
Give Them the Pickle

Aug 19 2025 | 00:39:47

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Show Notes

On this week’s episode of Short Term Rental Management, Luke chats with Jeremy Udovich of Sheboygan Vacation Rentals, who’s building a thriving short-term rental business in Wisconsin while still working full-time in tech. Jeremy shares how he and his sister grew from one property to a co-hosting portfolio of 19 units—without burning out. They discuss automation, working with family, market seasonality, and the importance of hospitality (including the golden rule: “give them the pickle”). Jeremy’s measured, sustainable approach to growth highlights how keeping your day job can actually accelerate real estate success. 

 

How to connect with Jeremy: sheboyganvacationrentals.com

 

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

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For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation PropertiesBuy it on Amazon

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Episode Transcript

[00:00:02] Speaker A: This is Short Term Rental Management, the show that is all about short term rental property management with your host, yours truly, Luke Carl. Short Term Rental Management. Jeremy is here. Jeremy's got some of his own properties, manages properties for other folks and he is in Wisconsin. Jeremy, how you doing buddy? Tell us a little bit about yourself. [00:00:28] Speaker B: I'm good man, thanks for having me. Yeah, so running a lean and mean co hosting and investment firm here that specializes in short term rentals in the Sheboygan Wisconsin market. I've been at this since 2021, late 2021. We own five units of our own and then we manage 12 others for other investors, homeowners in the area, most of whom were kind of doing it themselves for a while and just didn't want to deal with the hassle anymore. [00:01:01] Speaker A: The folks that bought during COVID and then eventually they kind of said, you know what, maybe, maybe I'll get somebody to do this for me. That kind of thing. [00:01:09] Speaker B: It's kind of a lot of work. [00:01:11] Speaker A: Yeah, it is. It can be for sure. So talk to me about the market itself. What does it look like? Is this a vacation town or is it just a regular town? [00:01:19] Speaker B: Yeah, it's, it's sort of a regular town. Maybe emerging as a, a tier three vacation town. They spend a lot money under the visit Sheboygan brand to try to get people here. We're right on Lake Michigan so we have some spectacular beaches. We're actually known as the Malibu of the Midwest. We have a pretty big surfing community here, believe it or not. And largely it happens in the winter when it's like under 30 degrees. [00:01:46] Speaker A: Oh wow. [00:01:47] Speaker B: It's, it's pretty wild. We also have a five diamond golf resort destination here. People literally fly in from around the world to play golf here. And then we also have a international racetrack that brings in about a, sorry, about a million people a year all within this little county. [00:02:07] Speaker A: Fascinating. And why, why, why no long term rental? I mean could you get it into a long term rental and do that as well? [00:02:15] Speaker B: Well, we probably could. This is one of those areas that I think has been very good to long term rental investors over the years because our cost basis is still really quite low. I thought that's where I wanted to get started in rental or in rental real estate until we bought our first short term rental and then it was like, I don't know how interested I am in 3 or 400amonth when we can do 3 or 4000amonth in any way. [00:02:45] Speaker A: Can you get, still get that today though. [00:02:47] Speaker B: That sort of return short term rental? [00:02:51] Speaker A: Yes. [00:02:52] Speaker B: Yeah, 100%. [00:02:53] Speaker A: So if I buy a house in your market, how much is it? [00:02:57] Speaker B: A good one that's a little bit unique, that's not on the lake. Maybe five or four or 500,000, maybe a little bit more. Lake houses, anywhere from million to maybe 2, 2 and a half million that can do 2, 300,000 in rent. [00:03:16] Speaker A: And I'm sorry, the. I missed the gross income on the $500,000 house. [00:03:20] Speaker B: So the ones that are, you know, have maybe some lake access near the traffic drivers, somewhere in the 100 to 150,000 range a year. [00:03:29] Speaker A: Oh, wow. And these are very seasonal, right? Like you're not renting year round. [00:03:32] Speaker B: That's the hard part. Super seasonal. Memorial Day to Labor Day. You got to make, make the hay while the sun is shining. There's not a lot of room for error. [00:03:44] Speaker A: I see. Okay. Why not sell them if you can. If you can sell a house, in other words, do you have your real estate license? [00:03:51] Speaker B: I do not. [00:03:53] Speaker A: This seems like it would make sense because if you have a $500,000 house that I could gross $100,000 on, I would like to buy one. [00:04:01] Speaker B: I'm afraid a lot of people will definitely. High tide raises all ships. You know, it's definitely getting harder. Right. The market is not as favorable from the interest rate standpoint. But if, if you are willing to do this right. There's still, I mean, all of Wisconsin has really good opportunity. I think up and down the lakeshore for sure. We're about, you know, where we're sitting, we're about two and a half hours from 10 million people. When you factor in the Madison, Milwaukee and Chicago markets. And if you flip to the other side of Lake Michigan, so southwest Michigan, that has been known as a vacation market for or destination for Chicagoland region for a long, long time. For whatever reason, they're just finally starting to realize that this side of the lake is pretty sweet as well. [00:04:52] Speaker A: Cool. Cool, man. So let's see. Are these mostly second homes are people. I mean, I mean the whole neighborhood, like is the whole neighborhood. Second homes are people living there, they're living here. [00:05:05] Speaker B: So there's definitely challenges. Most of the markets near us are still pretty tolerant and favorable to short term rentals. Don't know if it'll last forever. Northern Wisconsin, a lot of the lake communities, those counties have gone to some more stringent regulations. Wisconsin though has a right to rent law in place that doesn't allow municipalities to outright ban short term rentals. They can make it Tougher. So they can say like you may only rent for 180 days in a year. Or they could also layer on top of that the. The minimum night would be a six night rental. [00:05:50] Speaker A: Okay, interesting. And so you bought a few or you bought one and it worked and then grew it from there. You ended up with four of your own, is that correct? [00:05:59] Speaker B: We did. So we bought our first one. It went swimmingly well, like better than I think we could have predicted. And then our neighbo across the street approached us. They were getting ready to put their house on the market, asked if we might want it. These are two houses that are not on. So we acquired it not on Lake Michigan, but have access to the beach just about 500ft away in a, in a sort of a woodsy area outside of the city. Those went really, really well. While we were renovating that second one gentleman, a few families actually bought a home right on Lake Michigan. I met them, they said, hey, you sound like you know what you're doing here. We're going to rent this. Would you be interested in managing for us? So that's how we got our first management dealer or co host deal. Really. And then from there we, we purchased a house near that racetrack that I had mentioned. It's a seven bedroom home, log cabin, Montana style, on five acres, really cool looking. It's done. Awesome. We picked up in the interim. Then we managed a couple of condos right alongside Lake Michigan beach and a park in the city of Sheboygan for a lady. They ended up wanting to sell them shortly after. So we acquired those. I mean those have been a home run for us as well. And then just sort of, you know, growing that diverse locale. Like people around us have just started to ask if we'd be interested in managing their properties. I've spoke at a Wisco RIA real estate investment meeting here about short term rentals. Picked up a couple more co host opportunities there. And now we have the sheboygan vacationrentals.com brand that folks are finding and starting to reach out and saying we'd like to be a part of that. [00:07:43] Speaker A: When you say co host, are you in a state that does not require licenses and permits to be a professional property manager? [00:07:49] Speaker B: Yeah. So you do need to be licensed to be a professional property manager. I think we're very much in that gray area where there's not a lot of law defining specifically what we do. Getting a real estate license is on the docket for this fall and winter. We're going to go that route and hang ourselves with, with a brokerage to begin with. So that there is no question. But yeah, I think right now, you know, we've got a couple of different attorneys look at this and you know, they can't really say one way or another. And yeah, so we're just proceeding forward until we can be straight legal. [00:08:30] Speaker A: In other words, no reason not to do it. Right. I mean it's just a little bit of your time to jump through some hoops. [00:08:35] Speaker B: It's the right thing to do and that way we're, you know, it's becoming a big business and we want to be doing it the right way. [00:08:41] Speaker A: Yeah. And also when you go to pitch yourself to new folks, I think it'd be a little more appealing. You can still use the word co host because it sounds hip and cool. Yeah. And it's a little more like, you know, modern and, and influencer style. Like hip. But, but you can say, hey, you know, we do have our ducks in a row in the back end as well. So we've, we've, we've thought of everything. Or do we still have a day job? [00:09:04] Speaker B: I do have a day job. Yes. I'm in the tech industry and this. [00:09:07] Speaker A: Is on the chopping block. Or do we like the day job? [00:09:12] Speaker B: I still like the day job for sure. It pays the bills. We're having a great year. There's no real reason to think about getting rid of it. This has really been a side hustle. Like I said. I have a partner in the deal with my sister. She handles a lot of the day to day running so that I can focus on the day job. You know, we're highly automated. You know, I think when, while this can be a lot of work when you have the right team and the right tools in place and maybe you've done it a little bit. You can you listen to a lot of the short term rental management podcasts. [00:09:49] Speaker A: Oh, thank you. [00:09:50] Speaker B: You learn some tips and tricks to make this pretty, pretty automated. It, it doesn't take a lot of my time during the day. [00:09:58] Speaker A: So for now you like the day job and we think we're going to stick there. [00:10:03] Speaker B: Yeah, for sure. I mean, like I said, it pays really nicely. It allows us, you know, if we want to go and acquire another property, we look a heck of a lot more attractive with, you know, with some W2 good W2 earnings on the books. Not to mention, you know, we have the extra cash. We've been able to take the co host revenue and you know, kind of pivot that into new Acquisitions and keep it in the company. You know, I've got a kind of a ten year plan. I'd like to acquire enough properties on our own where we could retire and you know, from the, the day to day job and potentially even hire management to oversee our portfolio and just live off of the, the proceeds. [00:10:49] Speaker A: So it's almost like we are, we're running on all cylinders at the day job. Things are good there. It's probably a pretty high level, high earner type of a situation and we are side hustling to throw even more fuel on the fire. And the end goal is to live a life that nobody else is living. Possibly a little earlier than, than other folks. [00:11:14] Speaker B: That's, that's the idea. At least give us the option. Maybe we'll keep it all. I, I don't know exactly what it'll be but I like the idea of having options. So really the, the co host business has been designed to accelerate our ability to invest. [00:11:32] Speaker A: Interesting. Okay. Does it get you to real estate professional status or does the day job have more hours than the, the day. [00:11:40] Speaker B: Job has more hours by far than, than the, the real estate business. We've been able to materially participate because we are self managing our own properties. So we have been able to take advantage of a lot of those tax upside. We've done cost segs on just about all of the properties so far and have used bonus depreciation and our, you know, fingers crossed that we'll have 100% bonus depreciation available again this year. We can make another acquisition and erase a bunch of those W2 taxes because it's significant. [00:12:14] Speaker A: Wouldn't that be wonderful? It look, it does. All signs are pointing towards that happening. Don't you think it looks good? [00:12:20] Speaker B: It looks good. I mean it's, it's written in there. I guess they've hit a hurdle here on their first pass at it. Not unexpected I suppose. It doesn't seem like the real estate stuff is on the chopping block. There's some other things there that the Republicans probably want to edit before they let it go through but. Yeah, looks, looks really good. But look if it doesn't, it doesn't matter. Like we're going to proceed anyway, right? [00:12:44] Speaker A: I agree 100% and yeah. And again we don't know when this is going to come out. Hope maybe it's even passed by now, who knows. But. Wonderful, wonderful. Would you say that there's, I mean I find that there's no shortage of people that are looking for somebody else to make money with their property for them. Are you have. You're not having problems acquiring new properties to manage, I would imagine. [00:13:08] Speaker B: We're not. We have not marketed it at all yet. Maybe we will one day. We've been able to grow organically at a good speed that we can handle. I don't want to get out over our skis and, you know, throw out a bunch of ads and. And then all of a sudden, you know, have 10 great houses that want management and we don't want to say no. And then all of a sudden like we're stuck in a position where we're running around with our pants on fire. I hate. [00:13:34] Speaker A: Because that's exactly what would happen. [00:13:35] Speaker B: I hate that feeling. I do everything I can to try to avoid that. [00:13:40] Speaker A: Yeah, yeah. There's no shortage of people that want your services, you know, and whether it's long term or short term. And things have changed obviously in the past 20 years. And I think we are at a pivot point right here in life where, you know, traditionally property management meant you were putting a tenant in there. And I don't think that that's what it's going to be moving forward. I think that there will be long term managers and short term managers and there are in vacation towns, but those short term managers in the vacation towns for, for the most part are very old school and are not really keeping up with the trends in the softwares. Do you agree? [00:14:15] Speaker B: I definitely agree. I think we see that around here there were quite a few long term managers that were getting into the short term rental business because it was available until short term rental specific managers came in and just had the time to be. And the tools to be more sophisticated and better at it from a revenue management standpoint and marketing standpoint. So we make them look pretty bad, pretty quick. [00:14:40] Speaker A: Yes. Yeah. And I think in general, like, if you're thinking about being a property manager, not you, but the listener, you may consider doing just short term or just long term. But it depends on your market. You know, if you're in the Smokies, long term rental doesn't really exist. You know, I mean a little bit, but not really. And you know, if you're in a vacation town in general, like where I live and in Branson, Missouri, that kind of thing, a property manager is just. That's what they do. Overnight rentals for the most part. And then there are. We are seeing some folks. I've got a buddy in Omaha, actually that's where my home. I'm from originally from a small town in Nebraska. And I got a buddy in Omaha that does both long and short. He seems to be more passionate about the short, but the long is, you know, in other words, I don't know that the town has quite caught on yet, you know. And again, you're talking about a city here where there's a difference between a vacation town and, and what I would call a, you know, a hotel alternative, really, like where you're renting a condo unit or an apartment unit, maybe even arbitrage style and putting it on, quote, unquote, Airbnb. That's a whole different thing than when you're in a town like where I live in Destin, Florida, where literally every house in the whole city, well, south of the highway anyway, is rented on an overnight basis, because that's what happens here is vacations happen here, you know. So I think that slowly, very slowly, the general public is in. The real estate world is starting to realize that. You know, I think there was a period during COVID where people thought that this was some sort of voodoo magic. And really all it is is you're just renting a damn house overnight. It's just a house, you know. So I love the approach you're taking here. And, and to be, I hate to use the word nonchalant here, but you're, you know, you're not, you're not sitting here thinking you created, you know, reinvented the wheel. You just prefer to rent them overnight rather than to put a tenant in there. But again, you know, maybe you could branch out at some point and do long terms, because when you're managing them, you're taking a percentage of the gross. It's much different than owning them and only getting that to, you know, $1 2, 300, which, again, is very boring. I will agree with you there, much as I do love it and I have many of them and I love them. You know, I, I look back at when I was a kid or, you know, when I first started this, I was like, Man, $300 a month. That's a big. That make a difference, you know, that'll make it. I'm happy with that. That's. That's a decent amount of gas money, you know, and then next thing, you know, 15 years goes by and, and you work hard like you're doing, and, and good things happen. But we don't think we're going to consider bringing on any long terms. It seems like there probably would be a big market for that. You can maybe even wipe them out. [00:17:30] Speaker B: Out. [00:17:30] Speaker A: You know, the other managers Yeah, I. [00:17:32] Speaker B: I don't know, maybe. I mean it's definitely something we, we think about. We recognize that diversification is probably not a bad thing. I look at diversification. I've got two options in real estate, right? Well, three, maybe I can go into long term rentals, which maybe multifamily would be a little bit more interesting to me than single family long terms. We could look at other markets, potentially vacation ready rental markets or potentially some commercial real estate. Right now we are loving where we are at and we want to continue to explore that. So I think it's likely that we will look in another market before we go into long term rentals. That said, we're not naive. We recognize that it is possible, despite all the efforts that we take to be really good neighbors and try to encourage other short term renters in our market to be great neighbors that maybe will get regulated out at some point. So we've got to have an exit plan and that will probably look like multifamily. [00:18:44] Speaker A: Do you have issues with the neighbors? You got a story or two you could tell? [00:18:50] Speaker B: Yeah, I do. Not consistent. It kind of ebbs and flows. It's really more around, you know, we don't want you here more than any of our guests doing anything that is out of the ordinary for any homeowner. I think that's what we hear more than anything in and around our markets. So not only in our county, county to the north, counties to the south, up and down the lakeshore. It's not that we're having any of these massive parties that you hear about on, you know, CNN or, or Fox News or something like that. It's, it's definitely more of, you know, these people come and go. I don't know. My neighbors, they play bags, you know, on Wednesday nights until it gets dark. And I'm not used to that, so I prefer they're not here more than anything I say. [00:19:40] Speaker A: It's just, it's a bit of an unknown. I guess they're just not used to it. [00:19:46] Speaker B: It's kind of this NIMBY mentality a lot of people like to call it. Like not in my backyard when I travel with my family and my grandkids. Like I, I, we use vacation rentals, but I just don't want them in my backyard. [00:19:58] Speaker A: I hear you. We have live one on one coaching sessions available with our wonderful top notch coaches at Short Term Shop plus and we would love to help you in your vacation rental journey. The mission remains constant to provide amazing homes so that our guests can Create awesome memories with their families. If you need help to set up your systems and processes, how to communicate with guests, how to improve your systems, how to find and hire housekeepers and all of the above, you are looking for short term shop plus. You can find [email protected] and the best part is the price is right, reasonably priced and if you are a short term shop client, please use the code client at checkout for an even better deal on SDS plus.com what's the relationship, the dynamic, I suppose, with the sister. What does she do in the organization? [00:21:08] Speaker B: Yeah, so she handles all of our procurement, so any reorders? She facilitates with our cleaning team. She manages a lot of the cleaning teams, also our inspector group. So she's responsible for hiring them, scheduling them out, making sure they're covered. She's also kind of more boots on the ground. She's visiting all the properties, making sure we have everything loaded into Breezeway. She communicates then with the cleaning teams and the inspector teams. [00:21:42] Speaker A: Okay. And do you have any issues there with the fact that she's family? Are we butting heads ever? [00:21:49] Speaker B: No, we have not, you know, not knock on all the wood I can find here. It's been really, really great. She's really good at what she does, focuses on that area. She's really trusting on me on the financial, the acquisition, the client side of things. Things have just gone really, really well financially over the last few years. So I would say there's just not a lot of reason to, you know, y. Another nor have we even gotten close. I, I would say so. Think things have been good. It's been a great family dynamic. I think it's been good for her family and it's certainly been great for our family. [00:22:33] Speaker A: Does she have a day job? [00:22:35] Speaker B: She did. She, she has three young girls. So she left that position. Oh, I guess it's probably been just six months now. And she spends all of her working hours now on this business. [00:22:51] Speaker A: Fascinating. Isn't that wonderful for her? [00:22:53] Speaker B: It is. I, I hope. I don't know if she loves it or not. I think her dream would be able to be just spending time with her three kids. But she's realistic also, so she, you know, she knows she has to dedicate some part time hours to this business. [00:23:07] Speaker A: In essence, what you just said was, is she would rather not have a job and I think we would all rather not have a job. [00:23:13] Speaker B: Exactly. [00:23:14] Speaker A: Although sometimes I think to myself, what the hell would I do if I didn't have a job? You know, I mean, Golfer. [00:23:20] Speaker B: But you can only play so much golf. [00:23:22] Speaker A: Yeah, I'm a runner. And you definitely get tired there after an hour or so. But I love the love where you're at thing, man. So I see, you know, I see it all the time. I see almost everybody in this space is not happy where they're at. They want more, more, more, more, more. I hate my job. I hate my job. I want out. I want out. And I'll be honest, you know, I mean, I think you realize this. To get out of your job, you got to have a bunch of money, you know, you have a whole lot of money to invest in cash flow to quit any job, you know, So I love that you're, you know, how do I get that? Where do I get that? You know, like, how do I get to be happy if I'm just a regular guy? You have any advice there? Is it that they hate their day job and they just need to find another day job? Any advice there? [00:24:09] Speaker B: Yeah, I would say that is, I mean, it depends. Right, Depends. It's all relative to the lifestyle that maybe you have or that you expect. I mean, I'm certainly guilty of wanting more. Like I'm not, you know, some profit or something like that. Of course I want more. [00:24:24] Speaker A: Right. [00:24:24] Speaker B: I already said, like I want to acquire more properties. I want to have enough where I could choose to leave my day job or not manage my own properties if I wanted to and still upkeep a lifestyle. If I'm comfortable with an $80,000 a year income, you know, I probably don't need a whole lot of really high performing properties. But if I'm used to making a few hundred thousand dollars a year and I want that to last until I'm 90, you know. Yeah, I agree with you. You probably need to have a job and you probably need to take that side hustle and not take a vacation with revenue, but pour it into more and more cash flow positive opportunities. In our case, it just happens to be short term rentals. I think we're, we're good at it. We're in a great market for it. I love hospitality. I was a Golf Pro for 10 years out of college. I grew up working in the golf industry for really like 20 years. Before that. Hospitality is just kind of ingrained in me, treating people well, paying attention to the details, you know, give them the pickle. It was a video I watched in hospitality a long time ago. Don't worry about even though the pickle may cost you 50 cents, if somebody's a little irritated Just give it to them. It's not. It's not worth it. Yeah, I don't know. My sister was in the golf business for a little bit too, in that hospitality side, not in the playing side. So I think maybe she just has a little bit of that attitude as well. And it's. It's served us really good. Like we're kind of a real estate company that. Well, I. Sorry. We're kind of a hospitality company that owns some real estate and has a desire to own more real estate. Not unlike maybe McDonald's is in the burger business. Even though they're kind of a real estate company. We want to flip that script, but it's going to take some time and we're gonna have to pour all of our money into it to get there. [00:26:18] Speaker A: Love that. Avery's dad was a professional golfer. I don't know if you knew that. [00:26:22] Speaker B: I did not know that. [00:26:23] Speaker A: Yes. She actually grew up on tour in a. In an rv. Well, I think for just like her first two or three years. And then he ended up going back to school. But anyway, yeah, he was a pro golfer for 12 years or something. But anyway, out of college, you know. But anyway, let's talk about your stack, your tech. You know, what are we using here on a day to day basis to run the company? [00:26:51] Speaker B: We use. We use a lot. We use Hospitable. It was our first pms. Still have it. Even though we've transitioned most of our operations to owner res, we still use Hospitable for our lock management and our messaging and a lot of our team management. We also use Breezeway. We have Price Labs. We've hired a revenue management firm that really now handles most of the Price Labs work on our behalf. We have a marketing firm called Build Up Bookings that does really all of our digital management. So, I mean, I guess I make this sound like it's just my sister and I, but some of the big parts that are, you know, they take a lot of time. We've outsourced that so that we don't have to do that. We use Relay bank. We are on three of the OTAs. So Google vacation rentals, Airbnb, Vrbo. We use Nest. We use Ring. Depending on the property, trying to think what. We have QuickBooks Online. I mean, our expense burden on the software side is significant. [00:28:07] Speaker A: Yeah. It seems like you're interested in this kind of stuff, though. You said you're a tech guy. [00:28:10] Speaker B: I love it. [00:28:11] Speaker A: Yeah. Well, this is why short term appeals to you as opposed to long term, which Is boring as all hell. [00:28:16] Speaker B: Yeah, probably. [00:28:17] Speaker A: Yeah. I got you. What's the name of the revenue management company we use? [00:28:22] Speaker B: Free Wild. So their RPM product. So it's Jasper Rivers and Eric Mueller. They're out of Idlewild, California and they've got their own podcast that I was listening to as well. And yeah, they started spinning out this revenue management business. I took a look at it. They like to work with companies that do a million dollars in bookings or more. We were just starting to fit into that. And I love it. We meet once every two weeks. We've been with them, I think since last fall. And I'll just say that our while I think we did a really good job of revenue management on our own. Every single property exceeded year over year numbers in our off season, which was like magical to our company. [00:29:08] Speaker A: You're a numbers junkie. [00:29:09] Speaker B: I like diving into the numbers. I mean it's like in sales, right? Like I like the wins and showing the property did better year over year. And in the crummy part of the season, like that's a win. I like seeing that and I like grinding towards that. [00:29:24] Speaker A: And this is why you think you gravitated towards owner as? Maybe. [00:29:28] Speaker B: Yeah, maybe. I mean, at the time where I was thinking owner or sorry, hospitable, didn't have everything that I wanted, I was just paying attention to some folks that were just super hype on owner as. So I migrated to owner as. It's not amazing all the time. It takes some learning. There's a learning curve to it for sure. But it is super robust and I think it'll be able to grow with us as we add on more properties and more ideas on how to drive more revenue and. And do more marketing. I think it'll be a really good tool for us. [00:30:07] Speaker A: And right now people are just finding you are is your inbox getting hey, will you manage my property or no? Do you even want more properties? [00:30:17] Speaker B: Well, so that's a good point. So I was meeting with our marketing agency recently and that was part of their, you know, equ like should we start focusing now on acquisition of new properties? And I kind of said no because we're onboarding a couple of more. We'll have 19 here in the next couple of weeks and I think that's like a good number until we have a little bit more process in place. We're looking to hire a couple of part time W2 employees to help us manage some of this once they're up and running. I think that'll give us the capacity to go bigger. But maybe at the same time, it's time to weed out some of the properties that aren't perfect fit and search for properties that are more interesting to us. Okay, well, because it really, like I've got a property that made you 300,000 this year. It doesn't take much more work to manage theirs than somebody that's doing 50,000. [00:31:13] Speaker A: Yeah, yeah, it's really pretty similar. And you do think you're going to branch out maybe someday to multifamily. What about a hotel? [00:31:22] Speaker B: Ooh. So we've got some really good friends that have acquired a couple motels and a really awesome vacation market in Wisconsin. And it's got me like jealous beyond belief. It's very intriguing to me. I don't know if I'm in a place with my current job to take on a whole new learning curve of running a, like a boutique motel as a short term rental, but it's definitely interesting. The commercial side of it is very attractive. [00:31:52] Speaker A: Okay, well, do you have any advice for somebody starting out that maybe wants to quit their job and doesn't want to drive Uber and would rather co host and. Or maybe somebody that wants to be you and be happy where they are in life? [00:32:07] Speaker B: Boy, I, you know, I would say keep your job, keep it so much longer than you think you need to because you just never know. I mean, we're certainly driving enough revenue where I could probably have already replaced my income in this, this tech business, but if just one of our municipalities regulate us out, it would put me in a really crummy position both for our company and then potentially personally. And like, I don't know, this wouldn't be very fun if we were struggling. So people ask us like, wow, you, you know, you've done a lot really, really fast. What is the secret to doing that? And is like our income, our ability to not have to sweat whether we have to like fix a septic system or spend money to have somebody help us do something that we don't really know well to do, like not having to worry about that because we have the income already to support it, like that has been like the secret sauce. Without question. Both of our families have really good incomes. So like if we need to buy a house and put some money into it, if we need to spend more on a reshoot of photography because the first go around at 500 just didn't really do it and just not even like question it. Like that has been able to provide us the opportunity to move fast on a lot of things, not to mention acquisitions. Like, something really great comes up, we can just go get it if we want it. Yeah, I wouldn't do that if I quit my job. [00:33:37] Speaker A: It's refreshing to hear this. There's a period, it seems like yesterday, but it was really about five years ago, where every single person on the planet wanted to quit their job. And I'm like, what are we doing here? Can. Can we. Can we get back to work? Can we. We. That's why the economy's in the situation we're in right now. Everybody decided to stop working. You know, I mean, that's one small part, obviously, of a million moving pieces, but I like it. I. It's referring. [00:33:58] Speaker B: You get a lot of credit, man. And listen. Listening to your podcast and. And hearing you has kept me really, really grounded. I mean, no lie, like, I love. And you said it earlier, just about all we're doing is renting a damn house. Like, stop overthinking it. Like, yes, you can do some really cool, unique things that not every other house on the block has, and you certainly aren't living in that exact environment. So it's fun, but at the end of the day, that's all we're doing. This is not magic. This is not rocket science in any way, shape, or form. I'm not some brilliant being. [00:34:36] Speaker A: Thank you. For multiple reasons for saying that. And it doesn't mean you're not special. It doesn't mean you're not special. It's not just anybody can do that, what you're doing. But I think that it's that approach that's made you successful. [00:34:50] Speaker B: Yeah, well, kudos to you, my friend. [00:34:53] Speaker A: Well, thank you. [00:34:53] Speaker B: Because if you do listen to some of the other folks too much, you get rah rah through the roof and go do a bunch of things that probably wouldn't have served us well. So it's really important to have somebody on the other side saying, like, dude, just chill. Just relax. Like, you're just a landlord, for the love of God. It's just shorter. Shorter term. And that. Seriously, it served me really, really well. [00:35:18] Speaker A: Well, thank you so much. That's wonderful to hear. I did not expect that. Thank you. I'm gonna have to send you a gift. And what's. Well, what's next? We're gonna maybe take on one or two more. [00:35:33] Speaker B: Yeah, so. So we're gonna onboard a couple more properties. We had our first investor out of California reach out to us. They wanted to come to this area because they wanted to have a second home here. Wanted to rent it. So we're, they just got an accepted offer. It's an awesome five bedroom house near the lake and we're just super excited that we may get to play a role in that. So that'll be a first for us and is just like, like a cool kind of, you know, new hat to put on. So we're looking forward to that. And, and then we're looking at a property in another market that is pretty unique and I think we're, you know, probably going to try to find a way to acquire that. And that'll be our first foray into another market that is a little bit more vacation oriented already. And you know, there's a infinite amount of opportunity in that market too because I, you know, from the looks of it on the outside, nobody's just doing it really, really well from a co host or management standpoint. [00:36:34] Speaker A: All right. Book suggestion and, or you mentioned a couple. Well, you mentioned some sort of podcast type of a thing. If you have something. I, I could use a new podcast to be honest. So if you have any suggestions. [00:36:45] Speaker B: I have, I'm sort of a nerd. When I said we were going to start this like in 2021, I, I probably, I don't know, I probably listen to 500 or a thousand hours of podcasts. So when I listen to you, I gotta be honest. I mean I listen to it on like 1.75 or 22 speed. Just try to get as much knowledge as I can. So I've listened to a lot of them. I do like Bill Faith's podcast. I really like Avery's podcast. Certainly your podcast. Get paid for your pad. That's Jasper Rivers podcast. I got some good information there. Tim Hubbard has a podcast which is like short little tidbits. Probably the first one I fell into that really helped me early was thanks for visiting. There's two, two lovely ladies and I think they're in the Columbus, Ohio market. I've just learned a lot from them. [00:37:40] Speaker A: Any other topics? [00:37:44] Speaker B: So I've got a problem, Luke. You know, when I find something I like, I, I get pretty siloed. I have a hard time getting into, getting into anything else laser focused. So yeah, yeah, that's, that's probably a downfall. If you ask my wife, I get pretty, you know, pretty blinders on books. Unreasonable hospitality is one that I just really love that fits perfectly for who I am and who I've always been in the golf business. Like it doesn't take a whole lot to go the extra mile and, and look different to the people that buy from you, that. That book just resonates big, big time. I'm a huge fan of that. Maybe. Okay, so I listened to the Ramsey podcasts, ironically. So him, his daughter, and some of the other folks that. That he partners with over there. I forget their names off top of my head, but, you know, again, they're. He's really good at keeping you grounded. [00:38:40] Speaker A: Okay, wonderful. All right, well, how do we get in touch with you? [00:38:44] Speaker B: Yeah. So Jeremy at short term. Sorry. [email protected] SheBoygan Vacation Rentals. [00:38:53] Speaker A: Such a fun word. That's a fun word to say. [00:38:55] Speaker B: Oh, yeah, a lot of Indian names. Names up here. Also on LinkedIn. Jeremy Udovich, Sheboygan Vacation Rentals. On Instagram or Facebook as well. [00:39:07] Speaker A: Wonderful. Well, I appreciate your time, brother. Thank you so much. And if there's one thing we learned on today's program here, short term rental management with Luke and my buddy Jeremy here, is that we need to give them a. Give them the pickle. We got to give them the pickle. Right? I love that. [00:39:23] Speaker B: That was some training video I saw back in the day in one of my hospitality gigs. [00:39:28] Speaker A: All right. Give them the pickle it is. And you're right about that. If they need a pickle, give them a damn pickle. I love pickles. All right, buddy. Thank you. Appreciate it. We'll see you next time. [00:39:38] Speaker B: It.

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