239 - How to Build Your Own Short Term Rental Empire with Taylor Jones

3 Oct 2025 · 53 min · 26 chapters

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In short

How to build and scale short-term rental (Airbnb/VRBO) businesses, emphasizing that STRs are an operations/data-and-art business (not passive real estate), plus market selection, underwriting, and tax strategy (material participation and active depreciation).

Guest

Taylor Jones, founder of strsearch.com. Has overseen 200+ STR investments and $120M+ deployed capital; previously a lifelong sales professional (about 70 sales jobs). During COVID, he and his wife learned STRs by consuming real estate content and became STR hosts.

Key claims

STR success depends on differentiation (amenities/features and location) to avoid price-compression; start with supply-demand imbalances by bedroom count using AirDNA/Rabu; underwriting is “buy price vs revenue spread” and needs enough gross revenue to cover debt/ops (he cites ~15% price-to-rent spread as a rough need in today’s higher-rate environment). STRs can generate “active” tax losses via material participation and cost segregation (depreciation ~25–30% of purchase price).

Notable examples

North Georgia cabin (3-bed) bought with ~10% down; ~$40–42k renovations; launched during early reopening; hit 6 bookings and ~$80k revenue, ~$22–24k free cash flow first year. Second cabin with mountain view: more revenue than a similar “trees” cabin by ~$40–50k annually. He later sold via 1031 into “more ideal products” and discusses Broken Bow, OK: 1–3 beds are 72% of supply, so he targets 4–5+ beds where supply is thinner.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Understanding Short-Term Rentals

0:45 to 2:30

Discussion on why short-term rentals (STRs) are an operations business rather than just real estate.

“And I have the man, the myth, the legend, Taylor Jones, who is the founder of strsearch.com.”

Market Analysis for STRs

2:30 to 4:30

Taylor Jones shares insights on market factors affecting STR profitability, including unique amenities.

“And you don't know what you don't know if you're just kind of really taking this as a passive approach.”

Getting Started with STRs

4:30 to 7:30

Taylor discusses his journey into short-term rentals, including his first property purchase and renovations.

“the host side, which I did back in 2015.”

Scaling the STR Business

7:30 to 11:00

Taylor explains how he scaled his short-term rental business quickly after his initial success.

“If you get 30 days of free promotion and no one's booking your place, that's a signal to the algorithms on Airbnb and Vrbo is like, Hey, this listing sucks.”

Lessons Learned from Early Investments

11:00 to 13:00

Discussion on what went right and wrong with Taylor's first two STR properties.

“So it was on top of the mountain instead of the wooded lot.”

Current STR Market Insights

13:00 to 14:00

Taylor provides an update on the short-term rental market and his strategy moving forward.

“And they're like, hey, I'm in for a hundred grand on the next one.”

Current State of Short-Term Rentals

14:00 to 14:37

Explore the current state and challenges of the short-term rental market.

“I'm breaking even like, how is the short-term rental market looking now?”

Lessons from Early Investments

14:37 to 17:08

Learn key lessons from initial short-term rental investments regarding differentiation and market strategy.

“And what did you learn that you did wrong with those first two properties?”

Mistakes and Market Realities

17:08 to 17:46

Discuss the importance of recognizing market cycles and timing in real estate investments.

“And I think if you treat this professionally, you can get professional results.”

Reinvesting Gains into New Markets

19:48 to 21:06

Understand how to leverage gains from previous investments for better returns in new markets.

“So when you sold it, I'm assuming you took those gains, you 1031'd it into something that you thought would return a much better return?”
Show all 26 chapters

Identifying Market Opportunities

21:06 to 22:46

Learn to identify supply-demand imbalances in various markets for investment success.

“Product styles can be saturated, but technically there is a path to succeed in every market.”

Analyzing Revenue Potential

22:46 to 24:05

Discover how to analyze potential revenue and ensure profitable investments in real estate.

“they're safer air quotes, they're cheaper basis, they're lower costs to build, and they're a lower sale price naturally.”

Evaluating Property and Market Fit

24:05 to 28:00

Delve into the evaluation process for property purchases based on market demand and financial viability.

“How do you, how do you find the market in the first place?”

Estimating Revenue for Short-Term Rentals

28:00 to 29:51

Learn how to estimate revenue and occupancy for short-term rentals.

“So your spreads can be tighter when you have lower operating expenses and they have to be a little larger in places like Florida, Texas, California, high labor, et cetera.”

Balancing Occupancy and Average Daily Rate

29:51 to 31:27

Discover the importance of balancing occupancy rates with pricing strategies.

“or a four bed or whatever that metric is because you won't make enough profit.”

Market Viability and Property Investment

31:27 to 32:25

Understand how to assess market viability for short-term rental investments.

“that you're like, Hey, this was worth it because you have to make the two work together.”

Tax Implications of Short-Term Rentals

32:25 to 33:39

Explore how taxes affect short-term rental income and investments.

“And it's trial and error, trial and error until you find markets that work, markets that have consistent inventory and consistent revenue that you can make profit.”

Understanding Active and Passive Income

33:39 to 36:56

Learn the difference between active and passive income in real estate.

“you know, that's obviously classified that way.”

Maximizing Depreciation Benefits

36:56 to 39:05

Find out how to maximize depreciation benefits from rental properties.

“So when you buy that property for a million dollars, it's made up of two things, the land and the structure that sits on the land.”

Leveraging Cash Flow and Depreciation

39:05 to 41:15

Discover how to leverage cash flow and depreciation for real estate gains.

“Assuming you have the liquid capital, absolutely.”

Long-Term Financial Gains Through Real Estate

41:15 to 42:01

Learn how real estate investments can lead to long-term financial gains.

“depreciation, so you maybe bought a six, six 50 purchase price.”

Understanding Real Estate Cash Flow and Tax Benefits

42:01 to 43:42

Learn how real estate investments can provide tax advantages and cash flow.

“Now, obviously, the goal is to actually make money.”

Short-Term Rental Participation Requirements

43:43 to 45:05

Discover the criteria for classifying a property as a short-term rental.

“I have a house that we moved from that I didn't sell and we're renting it right now.”

Market Trends and Opportunities in Short-Term Rentals

45:06 to 47:22

Explore current trends in the short-term rental market and investment opportunities.

“One couple's getaways or cottages, You know, it is a very unique trend.”

Key Advice for New Short-Term Rental Investors

47:23 to 49:44

Receive essential advice for first-time investors in short-term rentals.

“journey, what's like the one piece of advice you would have known upfront?”

Balancing Tax Optimization with Cash Flow in Investments

49:45 to 51:28

Learn the importance of balancing tax benefits with cash flow in real estate investments.

“raise money, you own these Airbnbs, and then you started SDR search.”
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Transcript

Automatic transcript. May contain errors.

0:00Investing at the polls right now is super hot. I woke up and we had six bookings over seven grand and I was addicted. People look at this as a real estate business and it's not. It's an operations business wrapped around a piece of real estate. We made 80 grand, took home about 22 or 24 grand that first year in free cash flow. Now I'm paying myself instead of paying the U.S. government. I got a 30 % plus return on day one. It became this really good learning experience that really got me started in the real estate game. Why are STRs so sexy when they seem so unsexy from the outside?

0:37Taylor Jones, personally, I'm really excited for this because I want to learn about this topic, which is short-term rentals, Airbnb, vacation rentals, VRBO, whatever you want to call it. And I have the man, the myth, the legend, Taylor Jones, who is the founder of strsearch.com. He's also raised a couple of funds. Taylor has overseen over 200 STR investments, over$120 million of deployed capital. so the dude knows what he's talking about. I want to ask you this first question. Why are STRs so sexy when they seem so unsexy from the outside? Yeah, it's kind of interesting. People look at this as a real estate business and it's not.

1:12It's an operations business wrapped around a piece of real estate. So what you're getting into is where art and data come together. If this was just purely a data investment, you're really looking at long-term rentals, multifamily, all the other boring stuff that's very straightforward. where you can kind of get those outsized returns and that little extra that attracts people to this asset class is the art form. Understanding how much extra revenue does a swimming pool add in this market versus not having one. What about a pickleball court? What about a lazy river? What about the size of your deck on the back when you go outside the patio?

1:47These are the little nuances that really coincide with how much you could charge on a nightly rate, how much excess revenue you can achieve amongst your competition and ultimately how much more money you can make than a standard investment. And that part is really interesting because I think a lot of people look at it as a passive income stream. Just hearing what you just said, it's like, if you get into a thing game as a passive income stream and you're competing against guys like Taylor Jones, you're going to get your lunch eaten. Like you're looking at, hold on, how many square feet of pool do I need to add in order to raise rent by 32 %?

2:19Oh, okay. Like you said, it's an operations business rock in real estate. It's not a real estate passive income. And maybe that's just my own observation, but would you say that's a fair observation of people who get into the space? It's very fair. And you don't know what you don't know if you're just kind of really taking this as a passive approach. So for example, if I'm going to go into the Phoenix Scottsdale market, I will not buy a piece of real estate that doesn't have room to install a pickleball court if there's one already there. So your next question is, well, how big of a yard do you and I tell you, well, the playing dimensions are 22 by 44, plus you need a minimum three feet of excess.

2:53So I'm going to go use Google satellite and measure. Can I get a 28 by 48 minimum? Obviously you can make the serving lanes bigger and add more concrete if you have the space, but these are the kinds of things I'm going to instantly look for. So I'm not even going to look at the inside. The very first thing that I'm going to potentially buy in the Phoenix Scottsdale market, for example, I'm going to go straight to the backyard, go straight to Google satellite and measure. Can I get 28 by 48 in the backyard? If the answer is no, I don't care if the inside of the house is Carrera freaking marble.

3:20I'm not buying it. It's not worth it because the ROI on a pickleball court versus not in that market is over$40 ,000 in revenue difference. So it just doesn't make sense to run an Airbnb without one when you get such an insane premium to have one in that market. How did you start out in this? So I've had businesses and I've just always loved the idea of having real estate and having rental properties because I guess that's just what you do to build long-term wealth. How did you get into it? What was your first property? Yeah. Yeah. So lifelong sales guy, I was always chasing commission, 70 different sales jobs over about a decade.

3:51COVID hit at a client facing sales job and I wasn't fired, but I wasn't allowed to go sign new contracts. And so you're kind of in that tough spot. And the one blessing I had in March and April was I had all the time in the world. Naturally, like a lot of people had a niche for real estate and I was like, cool, I'm going to go consume a bunch of YouTube videos, podcasts, bigger pockets. I'm going to read everything I can. And so I spent all my waking moments instead Instead of working, you know, diving in, learning real estate. And I looked at everything. Should I go into wholesaling, broker, flipping, section eight, long term rentals?

4:19I looked at everything and then naturally came across short term rentals. And, you know, me and my wife, we've stayed in 27 different Airbnbs since 2015. So like I've been a consumer of the product, but I never looked at the unit economics from the host side, which I did back in 2015. That'd be a different discussion. But I started looking at it. I was like, oh my gosh, there's a lot of opportunity here. and started diving in, really niched out on that topic, spent about two, three months. And I'm kind of one of the guys that I don't want to get analysis paralysis. Too many people get that in both in business investing and real estate.

4:52You can study, but I always say at some point you got to jump in the pool. You don't have to be Michael Phelps on the first day. You just got to know enough not to drown. And so after about three months and writing five different offers, me and the wife, we got our first cabin in the North Georgia mountains under contract. Flew up to Atlanta, went up there for the inspection. The inspector was like, hey man, a couple of small things. It's real estate. There's always small issues in the inspection, but he's like, overall, man, it's a pretty solid cabin. I was like, sweet. Flew home back here to Florida, back up there for the closing.

5:22And then we did a bunch of sweat equity, new game room, install a fire pit, air hockey table, painted new furniture, and then turn around and listed it on Airbnb. And eventually the job came back. So Florida was one of the earlier states to open up. So I'm starting back work. Hold on before you move on from that. Had you bought real estate before? No. First piece of real estate. And you go up there and the inspector's like, there's little minor things, but you should be good to go. So you buy it. You do a bunch of, I guess, renovations. How much money did you put into it? About 40 grand into it.

5:53Yeah. About 40, 42 grand into it. How much did you put down to buy it? So we did a 10 % down vacation home loan. So the property was 460 grand. So, you know, know, about 46 grand plus closing costs. It was a little over a hundred G's, you know, with furniture, the sweat equity would help. Obviously if I had to outsource that, that tab would run up a little bit more, but the sweat equity helps for sure. Okay. All right. So you put in a hundred grand. What was the monthly nut on that? Like what were you paying in mortgage? It was probably around 16, 1800 interest rates were lower. So that's five years ago.

6:23So that was, that was always very net beneficial and the appreciation run up hadn't happened to COVID yet. So yeah, That was about$1 ,600,$1 ,800 a month there on that one. You've got this little cabin, North Georgia, put$100 ,000 into it,$1 ,600 a month of a mortgage on top of it. Things are starting to open back up. All right. I cut you off. Keep going. So I remember we get this thing launched. It was a Tuesday night. And I was like, okay, here it is. You got your listing. And we've booked Airbnbs. And I was like, okay, I think I know what it looks like. There's obviously not as much resources as there is today.

6:53I remember I woke up and we had six bookings for over seven grand. And I was addicted. it. I was like, Oh my God, this is great. So, so that was, yeah, yeah, yeah. So you, so you launched it, you know, again, and you just kind of sit and you know, the good thing about Airbnb is they do want to help new posts. And so for your first 30 days, you get kind of a lot of free promotion. They shove you up on the first page and it's in their best interest because if you don't succeed, you're going to quit the platform and now they have an inventory problem. So naturally they're going to give you artificial boost in the first 30 days.

7:25And they're going to see like, Hey, do people find your listing attractive? Because if they do, then they know, Hey, we need to keep this near the top. If you get 30 days of free promotion and no one's booking your place, that's a signal to the algorithms on Airbnb and Vrbo is like, Hey, this listing sucks. No one wants it. And so it's going to move it down to page five, six, seven, eight, et cetera. And you'll get buried. So if you come out of the gate with good photos, you know, good, good amenities, good design, and your place looks good and you get bookings, that's telling the algorithm, Hey, you know, this is good because let's not be naive.

7:52Airbnb makes money when you make money on every book. It doesn't cost anything to list on the platform. So if you don't get bookings, they don't make money. So they want to incentivize, well, which properties are getting a lot of bookings? Let's push those near the top because we make money too. Yeah, man, six new bookings came in. Obviously they were spread out for some allotment into the future, but seeing that money there, that seven grand, I was addicted. Obviously it's probably different today than it was back then, but I'm curious from your perspective, what did you do right with that first flip?

8:22not first flood, but first property. And what did you do wrong? Okay. So what I did right was buying a high demand market. So North Georgia, you're an hour and a half from Atlanta. I didn't have the data again. I got lucky, but I didn't get lucky. I picked somewhere that I like to go. So as a Floridian, if we want to escape the heat and we get in our car and drive North, the first mountain range you hit is the North Georgia mountains. So I knew, Hey, a lot of Floridians go here and Atlanta is an hour and a half away. It was anecdotal market research, but it wasn't data-driven market research. Exactly.

8:53Obviously where things are today versus five years ago, completely different animal, but it was kind of that directional. So kind of what I got right was it was at a high demand market, it's desirable and nailed that part. What I got wrong was I ultimately didn't buy the right product to succeed long-term. I bought a three bed that stared at the trees and that ended up being the most common supply in that market. And so when you have a ton of excess three beds that stare at the trees, it becomes a race to the bottom on price for what you could charge. In that first year, how much revenue did you generate from that one property?

9:28We made 80 grand. And after mortgages, expenses, utilities, cleaning, hot tub supplies, all that good stuff, we took home about 22 or 24 grand that first year in free cashflow. So it was like, great. Wow. Got your feet wet. And this was - Was that better? A really good - Better than you expected? Worse than you expected? I don't know that I really had a ton of expectations of what it is. I think it was so cool back then. And it was like this newer thing. There wasn't these huge million follower influencers that promote the space. It wasn't really there. And so I didn't really quite know what to expect.

10:02And so to me, I think just making money was the objective. And then someone tells you about tax benefits and other things you can unlock from real estate besides cashflow. And it became this really good learning experience that, that really got me started in the real estate game. When did you realize like, oh, this could be something I could go all in on. This isn't just like a cool side hustle. Well, four months later, I bought another cabin in North Georgia. So as soon as I got addicted, I said, okay, let's go, let's go stack and get more. How were you buying those? Cause you said your sales job is like, you weren't allowed to sign new clients.

10:35Like how did you have the cash to go buy another cabin? Had a little bit stacked on the second one. It ended up going 50-50 with another one of the sales guys. So it was like, hey, dude. And he'd had a piece of real estate. And we were like, okay, cool. Let's go in together. So yeah, I didn't have enough cash to do that one myself. But ultimately said, hey, let's go 50-50. So we split, put up half the money and rolled into that second one. Again, you took your wins and your compounds and you just rolled them into that second one. We bought a better product. This one had a mountain view. So it was on top of the mountain instead of the wooded lot.

11:07It was still also only a three bed, which is kind of the most common supply in a lot of markets just because it's the easiest thing to build. Most builders aren't going to go build small couples getaway ones and twos that are 600 square feet. And most builders aren't going to build five, six, seven, you know, mansions. So you get a ton of those two, three, four bed, you know, it's just the most common product. And what you've seen over the last five years is that middle of the market has really been frothy because there's just so much supply of it. And so really investing at the polls has where your opportunity has come.

11:39So what's interesting is, let's say for these two properties, you're what, in$120 ,000, $150 ,000? Yeah. So second one was slightly bigger. So my half on that second one was another about 80 grand. So we bought a slightly bigger place, slightly bigger amenities. So that one would have been about 160, some more sweat equity. We both went up there with both of our spouses. So four people doing hands-on labor to cut costs. But yeah, it was just continuing to compound. And then that one, how much free cash flow did that one generate? That one spent out 48 grand, of which my half was about two Gs a month on that one as well.

12:16Okay. So for the first year, what I'm trying to get at is like$180 ,000 in and in free cash flows, like cash to you, let's call it$45 ,000. That's a pretty good cash on cash return. return but you get kind of capped really quickly right like you were tapped out at that point you were done like you didn't have any more cash to redeploy were you thinking cool this will be long term i'll build some more equity and then i'll cash out refi and then we could buy another property or were you just so hooked that you thought but when can i get my next hit i need my fix like when i get my next property it's kind of crazy you start talking about it and other people kind of lead you into like i didn't even know you could raise money and then i had uncles who worked for Oracle and other jobs.

12:58And they're like, hey man, I want in on the next one because they hear about how great it is. And they're like, hey, I'm in for a hundred grand on the next one. Hey, I'll give you 75 grand. And so like, realize like I'm personally tapped out at this point. I got to recycle cash. I got to work more, save for my W-2, my sales job, you know, kind of stock cash on commissions, stock the cashflow. But that's going to take, you know, another year, two years to kind of restock the farm to be able to go buy a third. But like, hey, these people are offering me 75, 100, 120 grand. And they're like, they want in on the next one.

13:27And then you just go down this rabbit hole of like, oh my gosh, like you can raise money. That just kind of opens and unlocks an entirely different skew. And it's really fascinating how quickly one becomes two and two becomes five in this, you know, very quick. Especially, yeah, especially once you go and raise money. So I'm going to put the raising money to the side for a second. I'm most interested in kind of how as an entrepreneur, you could actually go and get into this space. 2020 was an incredible time it was a beautiful time lots of money rates were low property values hadn't gone nuts so when you buy those those first few short-term rentals that you have probably get in a good basis because the rates are low your your mortgage payment is low and there wasn't as much competition your rates that you could charge other people was good let's fast forward like two or three years where are they now like are they still great or is it still would you say it's like, uh, it's okay.

14:21I'm breaking even like, how is the short-term rental market looking now? Yeah. So personally with those two, I've sold those in 1031 into more ideal products because after you sit there, you realize, Hey, this isn't an ideal product to own good news, how to equity. So cash that out. Okay. Okay. Okay. Then forget my question. I want to, I want to drill in on that. What did you learn that you did right? And what did you learn that you did wrong with those first two properties? Being able to have some sort of a moat. So that second one had the bound view. It was on top and it was, okay, it's so much easier and I'm able to command such a premium.

14:56They were both three bedroom cabins in the same exact market, but one of them was making significantly more. We're talking to the tune of about 40, 50 grand more in top line revenue on an annual basis than the other. And so when you have something that is hard to differentiate, again, a three, two that stares at the trees in the woods, that's the entire mountains and how are you going to differentiate it? It becomes a race to the bottom. So what I learned from that is if you're going to go into this, what is a differentiator for that market? And that can mean a lot of different things. It could be close to the beach.

15:29It could be riverfront. It could be straight location, straight location could be the features. Is it modern? Is it a tree house? Is it a yurt? Is it like, how can you be different than your competition? Because it's going to give you some sort of an advantage that you don't have to worry about, oh my gosh, I can't differentiate my property amongst guests on the platform. Interesting, because otherwise it becomes commoditized and then you're just competing on price. Then it's just a race to the bottom. You have to have something that differentiates enough to get people to pay more for your location.

16:00100%. And I think that applies to all business across the stack. It's not as difficult for putting in systems as it may seem on the outset. I think that's the toughest thing people think is, you know, Hey, and what automations and systems and tech that there was five years ago versus three years ago versus today is, is absolutely wild. I think like any industry it's continued to grow. Obviously all the buzzwords AI getting mixed in here to, to the asset class. Uh, obviously it hasn't been as adaptive as I would say other industries, cause there is some limitations to hospitality, but you're starting to see it become more systematized, more automated on the backend so that you can run these and not have to be local.

16:37You know, again, like I don't than North Georgia. In fact, I live not even in the state of Georgia. So you can put in systems, have local boots on the ground, help a la contractors, a la cleaners who can go in and execute. And you really kind of systematize this as a business. And I think if you treat this as its own little business and not just as this passive endeavor, as we talked about on the onset here, that's where you can get strategic advantages. Because like anything, if you treat this as a dip in the toe with any business you do, any endeavor, you're going to kind of get the results of dipping your toe in.

17:10And I think if you treat this professionally, you can get professional results. So you found cleaners, you found, let's call it handymen, repairmen, plumbers, people pretty easily for that area in North Georgia. Yeah. A lot of Facebook groups, a lot of asking around, and now it's gotten even crazier. There's entire marketplaces of Airbnb cleaners where you can put in any city in the country and you'll get a whole list of them and you can start cold calling. So it's just, that's the evolution of this asset class, which is incredible. Okay, so what did you do wrong? Like looking back, you're like, man, I'm so freaking lucky because I did this and this wrong.

17:44I thought the gravy train would continue to go forever and had a chance to sell for about a hundred grand more than we did. So that second cabin bought it for 640. And in the peak of the market, I mean, we were talking at 0 % interest rates. Everything was super frothy. and I think like a lot of people I got caught up it was like man the gravy train's gonna keep rolling and we had a chance to sell for 1.025 in 22 months of ownership and was like nah let's just keep it going let's keep it going and then reality kicked in and you're like oh yeah this was like la la land we were living in and ultimately still had you know appreciation and we sold it for 920 So don't get me wrong, they still have very good return on the onset.

18:32But when you look back, I think the biggest mistake was I need to take a step back. Like when sometimes when things are almost too good to be true, when business is cooking, the general economy, the market, that there is such a thing as a downturn. I think to me, like I never been through that personally. And so to me, I'm like, oh, great. Like everything goes up and to the right. This is amazing. And it don't work like that. It don't work like that. It doesn't work like that. And to quote the great Kenny Rogers, you got to know when to hold them, know when to fold down. Like it's, it is hard to build that like muscle memory of like, okay, do I double down on this or do I take the win for what it is?

19:09He still came out great, but that's, that's a really, really interesting observation. Hey, I don't know if you remember this, but when we started this podcast, we entered into a social contract. I would spend time, energy, and money producing this podcast, interviewing these individuals and giving you insights into how to build, buy, start, grow your business. and you would like, subscribe, and leave me five-star review. Now, out of that, we both get to talk to really cool people and hear really cool insights. We both get a ton of value, but I just want to help you keep your word. So would you do me a favor?

19:40Will you go leave a five-star review for me on Apple or Spotify? It would really help. And if you want, even share this with a friend. I think the thing that's most interesting to me is that both of these properties did well and you learned some stuff that for whatever reason made you think, I can take the same money, put it into another market with the things that I've learned and get a much better cash on cash return than 22%. What were those things? So when you sold it, I'm assuming you took those gains, you 1031'd it into something that you thought would return a much better return? Yeah. I think a better long-term asset too, maybe short-term cash flow would have been same or slightly different, but long-term protections, let's just say, hey, buying a three bed cabin in a very heavy three bed market where over a third of the supply is three beds.

20:29So if you just go to the Airbnb platform for that market, over 35 % of the supply is a three bed cabin. And you're like, well, crap, this is a good. So I think the first thing I looked at from a differentiation was what are the supply demand imbalances just on bedroom count for this next market. And that's where I started. This would be somebody like me. I want to skip over the learnings that you did for those first two cabins. I want to get to like wherever you rolled this money into. The first thing that you look at in a market is the supply demand imbalance in a market. That's correct. So there's a common term thrown around the S word saturation.

21:00And I say, uh, that's, that's, that's weak. If you think, Oh, this market is saturated. And the reason being is bedroom counts can be saturated. Product styles can be saturated, but technically there is a path to succeed in every market. It might be difficult. Take a Disney Kissimmee there in Orlando, Florida, probably one of the most cutthroat markets and your path to succeed as slim as could be. But the data will tell you if you go 10 plus bedrooms with certain features in certain locations, you have a chance to win. Obviously, that's not a great recipe for success that you're already buying a 5, 6, 7, 8, good freaking luck.

21:38So that's where we're going to start first is what's the current supply in this market versus the demand like total nights booked for those properties. And where do you go and look for that? There's several different data sources. So we have a couple of really big strategic ones, AirDNA and Rabu that we'll pull from really good data providers in this space. And when you can kind of digest those, you're like, oh my gosh, let's take another big red hot market, Broken Bow, Oklahoma. One, two, and three bedroom cabins make up 72 % of the supply in that market. So you're sitting there going, Nick, would you buy a one, two, or three bed in broken Oklahoma no no it's like absolutely not take tell me about that four bed tell me about that five bed though that's exactly where we want to be so to start looking at there's not great opportunities to service the large families multiple families or groups of friends segment of the market and it's underserved with supply and those that have the supply can charge a premium because there ain't a whole lot of competition and most builders naturally don't go build five, six, seven bed spec mansions.

22:43That's not a great, like there's a lot of risk from a builder. If you're speccing that one twos and threes have multiple uses, multiple exits, they're safer air quotes, they're cheaper basis, they're lower costs to build, and they're a lower sale price naturally. So you have more buyers who can buy that. So from a builder, are you going to go build a six bed, 4 ,000 square foot mansion cabin where you put up your own money carrying costs and you pray you could unload it for a million and change, or you're going to go build a three, two, you could probably sell for six, seven, 800 grand. There's a lot of buyers for that product.

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23:15Well, great. Now there's a ton of those in the marketplace. This is probably going to sound stupid, but let me restate what you're saying. I think a lot of people look at it like me, where they're like on Zillow and they're like, oh, I could get this two bedroom and it's 150 grand. And I think I can make that work. I could put some money into it. And they like, just look at the cost side of getting into that real estate. but what you're talking about is the cost is just one equation. You've got to understand what the demand is going to be for that so that you can model what the revenue piece is going to be.

23:43Otherwise you don't have a return. That's exactly right. This is simplified as two numbers. What do you buy it for and how much can you generate per night? There's a lot of deep analysis that goes into this, but in really everything boils down to what do you buy it for and how much revenue can you generate? And at the end of the day, you need a spread between those two numbers. If there's no spread, there's no cashflow. It's very simple. Okay. So is there a supply demand imbalance? How do you, how do you find the market in the first place? Like you said, Broken Bow, Oklahoma, like are there just markets that are known to be hot markets or would I just kind of look in my own geography?

24:18Where would I start? Without obviously the level of data access that we have. I think where I would start is, you know, look at where do you personally go? Like, I think, you know, unless you're just a complete outlier and you're like, hey, I'm a weirdo vacation guy, which like that could be true. Where do you travel? And you got to assume there's other people that do that, number one. Number two, there's a lot of just general theses. So let's just take things that have very sound investment thesis behind them. Hey, we want to invest near the national parks. Well, that's a pretty good thesis because last I checked, they're not closing Yosemite or the Grand Canyon anytime soon.

24:53Maybe they will, maybe they won't, but that's a pretty good bet I could make. So it's like, cool. Millions of people are visiting these national parks on an annual basis. There's going to be constant demand. So that's an entire investment thesis that happens. And a lot of people will buy around the country near national parks. Take another one is invest within a two hour drive of a major Metro. So think Atlanta, DC, Manhattan, Chicago, Austin, and go, okay, what are vacation towns within a two hour drive of these huge population hubs. Cause nobody's ever going to get tired of being stuck in their 400 square foot shoebox apartment in Manhattan and want to get away for the weekend.

25:29So why is it that the Poconos and the cat skills, which are both, you know, hour and a half, two hours away, why are those popular vacation destinations? Cause you got a trillion people in Manhattan who want to get away for the weekend. That's why. So it's just like, like, you're like, Oh yeah, duh. That makes a lot of sense. So sometimes you don't have to overcomplicate your investment thesis. And so those are like just two examples that people will kind of start with. Now, should you invest within two hours of Manhattan, two hours of Chicago, two hours of Atlanta, two hours from Austin, two hours from San Fran, LA, et cetera?

25:59Well, that depends. How familiar are you with it? Naturally, I'm a Florida boy. I know the Southeast. I travel to the Southeast. I kind of stayed there because it was familiar. If you live in Cali, you're probably like, dude, North Georgia, I couldn't put that on the map if I tried with some of these mountain towns. So I think you go to where your kind of creature comforts and then you ultimately got to start running math. So to your point, like, sure, you can have demand, but if prices are too high, it doesn't matter. There's no profit. So once you kind of narrow down your list of markets, you have to just start running numbers.

26:30What can I buy real estate for? What can I generate in projected revenue? And is there a spread between the two numbers? What are the metrics that you use to evaluate whether or not the spread's good? Yeah. So that's going to be tied to a couple of different factors. A, your debt and B, your operational infrastructure. So when interest rates were lower, you could get away with tighter spreads naturally. When interest rates are higher as they are today, you know, in the sixes and sevens, that spreads there. So we call it the price to rent ratio, which is just simply gross revenue divided by purchase price.

27:02So the spread today with rates in the sixes or sevens, you're going to need at least about a 15 % spread. So an example of that in big round numbers here is on a million dollar purchase price, you need at least 150 grand in revenue to have some spread, to have some cashflow. In gross margin, you mean? Just gross revenue. So 150 grand would be top line. And then after all expenses, you will have enough leftover to generate some cashflow. If you buy a million dollar Airbnb and you're only generating a hundred grand, so a 10 % ratio, a hundred grand divided by a million, I could tell you that if you back out all your expenses, mortgage, utilities, toilet paper, pool cleaning, landscaping, you will have zero dollars left over.

27:43In fact, you will owe money every month with that spread. It's too tight. Now, there's always outliers. That's the envelope math and it's envelope for a reason. So take a place like Texas, super high property taxes. Take a place like Florida, higher insurance. Take a place like North Carolina, cheap taxes, cheap insurance. So your spreads can be tighter when you have lower operating expenses and they have to be a little larger in places like Florida, Texas, California, high labor, et cetera. Just because again, those are fixed expenses that are going to hit you every month. Your tax bill, your insurance bill, the pool cleaning guy, you can't not pay.

28:19How do I, how do I estimate revenue? I just look at what's the average revenue around and then say, okay, 365 days, I'm going to estimate 50 % occupancy. Like what, which numbers do I use to plug in? Does that make sense? Yeah, absolutely. So that's where of those great resources, AirDNA and Rabu are going to come in handy. So what you can do is dive in there on market specific. So say you do want to dial into North Georgia. So you want to dial into, you know, the Catskills in upstate New York. And the way you can start doing is isolating bench room counts. You're like, Hey, you know what? I think I'm going to buy a three that, or I think I'm going to buy a four or Hey, I can only afford to buy a three or four.

28:52So that's the other thing. The data might say, dude, you should buy a five or a six. Well, if you don't have enough cash to buy a five or six, what's your next best alternative. And so once you understand what you can afford and what you're going to hone in on, then you got to look at, okay, well, what are all the other three beds around me generating? What amenities do they all have? What's their design style? What part of town are they located? Are they only on the north side? Are they spread out northeast, southwest and location doesn't really matter? So all of that's just diving into the data once you've kind of narrowed in that.

29:23And so that'll give you kind of that directionally correct data that you're looking for is, okay, all these three beds in this part of town are generating between 70 and 95 grand in revenue. Well, you can't underwrite and say, you know what? I'm going to do 120. I'm the new best guy. It's just unrealistic to assume. So you need to go and say, well, if I'm only generating 70 to 95 grand on this house, will I make money? And if the answer is no, then you probably can't buy a three bed in that market or a four bed or whatever that metric is because you won't make enough profit. So do you just estimate occupancy based like air DNA will give you all that stuff?

29:59Like every day is going to kind of give you an estimate of what the revenue is going to be. Yeah. You're going to see market level occupancies. And what I always say is our occupancy is only half the equation. So it is interesting because occupancy gets measured a lot in long-term rentals, in self storage and in everything else. But here I could get a hundred percent occupancy in my Airbnb. I'll go charge$10 a night. And guess what? I'll be booked every night of the year. Now I won't make money and that's a problem. And then the flip side is I could be very egotistical and say, you know what? I'm never letting anybody rent my place for under 300 a night.

30:32I'll probably only be 40 % occupied, but I've held high on my average daily rate. So average daily rate and occupancy is what makes up revenue. And so what you have to find is what's the best blend of the two of those together. Now, a market like Michigan or Wisconsin, you're not going to roll 70, 80 % occupants, even if you tried, because there's no, it's too seasonal. now in florida oh it makes sense you could run 100 occupancy but you would be leaving money on the table meaning you're filling your calendar for lower nightly rates than you should that sweet spot on like again very envelope math basis it is somewhere between 68 and 78 occupancy so if you can kind of float between that where you don't get too much lower and you don't get too much higher you're achieving maximum revenue so that's what i'm saying like you want to try to aim for the peak there where, you know, again, you're occupied, but you're also charging enough that you're like, Hey, this was worth it because you have to make the two work together.

31:31And if I go and do the math and I'm like, Oh, I could generate about$150 ,000 using that back of the envelope. I could also say like, all right, then that means my max property. The price that I could pay is about a million dollars. Like you're, you're kind of like backing into where you think you could invest. I mean, does that make sense? Exactly. And then what you'll draw is you'll draw your little filter there. So again, let's go back to that Catskills upstate New York. And you're like, okay, well, what's for sale for under a million in this region? And it might come back with zero results or it might come back with 500.

32:00You're like, sweet, I have options here. And that's how you start to learn. Is this market investable or not? And again, if you do that same example and you're like, okay, I did the math. I think realistically I can make 150 grand. So I need to buy something at or below a million and zero query results come back on Zillow or Redfin. Not your market. You're like, hey, I need to go to a different market. And so this becomes process of elimination and just ripping, you know, can it work? Yes. No. Cool. Go to the next one. And it's trial and error, trial and error until you find markets that work, markets that have consistent inventory and consistent revenue that you can make profit.

32:34I think one of the interesting things that I've seen is that like these short-term rentals got really big everywhere. It wasn't just coastal cities in California and Florida. Although it was like Michigan, all of a sudden people were buying. They're like, oh, I'm just going to short-term rental this thing out. and to your point it's like those have very different seasonal effects and then and then when more and more people start doing that eat the limited inventory that was there all of a sudden expands and you have a lot less occupancy that builds on top of it so i've seen people kind of get in trouble here locally trying to do the the str model i just think that's a really interesting perspective so how does taxes play into this because we talked about the revenue and the cost and all that other stuff but then like two taxes are amazing i know that that's why i'm interested in it.

33:18How does it work? Yeah. So easiest way I'll describe this. And again, not a CPA, but we'll pretend to be one on TV here for a little bit today is when you have taxes and depreciation, you have active income and you have passive income. And so active income is obvious. That's your, your W2, your 1099, you're working for it. If you passively invest in something, whether that be a business or another piece of real estate, you receive passive income, you know, that's obviously classified that way. So if you're trying to offset that income, you can only offset passive income with passive depreciation and you can only offset active income with what is considered active depreciation so you're like okay cool where do i find this active depreciation you know is it in the room with me right now is he here i did i did this i sold my businesses and i was like oh i'm gonna save on taxes i invested in some opportunity zones and some real estate and then the end of the year comes and they're like okay you owe uh you know whatever,$500 ,000 in taxes.

34:13And I was like, oh, cool. Well, I have$500 ,000 in passive losses. So just deduct it from those passive losses. And they're like, yeah, it doesn't work like that. And I was an idiot. I should have done some more research. So to your point, where are all these active losses happening? Yeah. So in the IRS, you have three really basic buckets. So you have oil and gas, which I am not a Texas or Oklahomian and can't help you there. So find someone who lives locally and could get you there. So there is oil and gas investments, which can give you that. There is equipment. So if you buy equipment, which falls under section 179 of the IRS code, that will also give you active losses.

34:50The fun one is the G wagon. So I'm sure during COVID and on Instagram, people said, oh, you buy a G wagon because the equipment from a vehicle perspective has to weigh over 6 ,000 pounds, a G wagon, a Chevy Tahoe, a cyber truck, a lot of strategic vehicles you saw that got purchased all qualify as that. So weird. Yeah. Really, really interesting. And then the third bucket is short-term rentals. So I know you joked and said, oh, a lot of people say this is a passive investment. Well, the IRS will tell you, no, no, no, this is an active investment. This is an active investment. That's interesting.

35:19And we will give you tax advantages to prove it because we will classify your tax losses as active losses. Is it because you're managing? Is that why it's active? So the key term is because, and again, the only way to unlock these, you can't just buy an Airbnb and you automatically get them. you have to earn them through what is called material participation, which is in short saying, hey, I am materially participating in the business activities of the short-term rental. There's seven different ways to qualify for material participation. So I don't know which one's the best path for you. You should consult your CPA, but it involves how much your output is in the business.

35:56You can't hire a property manager and do nothing and say, oh, I materially participated. That would kind of go against what the basic definition is. So if you achieve some of these achievable benchmarks, again, not super impossible, and you hit material participation, you could take those active losses to offset your active income. Now, let's put some real numbers behind it because that's where it gets fun. Again, I'm going to give you the envelope example here. Typically, your depreciation, now that we have the big, beautiful bill and 100 % bonus depreciation, so you get to unlock all of it in year one, you're getting roughly 25 % to 30 % of the purchase price in depreciation.

36:36So again, big round numbers, you buy a million dollar short-term rental Airbnb, you materially participate. You're going to order what's called a cost segregation study, which is where a fancy engineer is going to come in. They're going to assign values to every structure on the house. You don't have to do anything. And they're going to say, cool, Nick, here's how much depreciation you unlocked on this house. You give that - Because you can't depreciate the land, right? The land is undepreciable. Bingo. So when you buy that property for a million dollars, it's made up of two things, the land and the structure that sits on the land.

37:05So you can't deduct the land value. So if you invest in a high land value market, think South Beach, Miami, or Big Sur, California, those are going to get less depreciation dollar for dollar versus you buy an Airbnb in rural Vermont where the land is worth three nickels, you're going to get a lot of depreciation dollar for dollar. Okay. I mean, so what I tell people is, what are you investing for? If you're investing for long-term appreciation, yeah, Miami Beach is probably better than rural Vermont. It's probably a better bet. If you're maximizing for tax benefit, rural Vermont is way better than Miami because you're going to spend the same dollars to buy the house, down payment, furniture, et cetera.

37:44But how much depreciation? Now, again, you don't get zero. You just get significantly less because you can't take the land and depreciate the land. You can only depreciate the structure. So that's where that envelope math, again, could be a little bit more, could be a little bit less. But if I hang out in that 80-20 portion, 25 % to 30 % of the purchase price is what you're going to unlock. So your million dollar Airbnb gives you$250 ,000 to$300 ,000 of depreciation. Let's say you and your spouse together, you guys both make$400 ,000 of combined household income. All right? You take your$300 ,000 of losses.

38:16You slap that against your$400 ,000. grand, you're assuming no other write-offs that you and your spouse have. Your new taxable income is a hundred K. So you put 400 grand in your pocket. That went into the bank account. You earned that from working doctor, dentist, lawyer, W2 business owner, 1099, whatever you do, but you, your taxable income is now a hundred K in that example. There's a cap on the depreciation amount, right? Isn't it two and a half million dollars? Think with the big, beautiful bill went up to about 1.25. That might be single, not married, But yeah, it's very high north. But there's a cap of how much you can depreciate.

38:52Correct. Is the point. Okay. And it's not like the SBA, if I go get an SBA loan, 5 million is the limit. It doesn't matter how many businesses I buy, it's 5 million. But with this, that's on a per property basis. Like I could buy 10 properties and depreciate all 10 properties in a single year, theoretically. Assuming you have the liquid capital, absolutely. If you can afford to buy it, absolutely. You can order a cost segregation. You can materially participate. And then when you own multiple properties, again, not a CPA, but we'll talk like one on TV. There's a term called a group election where you can put them in a group election.

39:26And in essence, instead of having to put individual hours into each of them, you're putting in hours into quote unquote your business. So if you own two, three, five Airbnbs, now your material participation is an, oh, well, you need to hit a certain amount of activity on every individual, but more or less how much activity did you put in the total business? So it allows you to kind of, in essence, put in less hours versus if you had these as all individual entities. I don't know if you knew this. I just talked to Chris Berg, who was on my podcast and he does car washes. Car washes are also an investment that count as active investment.

40:00I didn't realize that. But as he was talking about it, he was like, dude, it's a flywheel. I have this services business that kicks off a bunch of cashflow. And then I just funnel that into the real estate, buy real estate. So I'm building equity in the real estate. And then I use the accelerated depreciation to offset my taxes. And that money that I saved on taxes, I just put back into the business to grow the business that generates more cashflow that I put into real estate. It just keeps kind of spinning like that. Have you found that as well? Yeah. So when you could take some of these awesome opportunities and we'll nerd out even more here, the best case scenario that you want to try to aim for is a one-to-one ratio.

40:38So let's just say I invest 200 grand into a short-term rental down payment, housing costs, furniture, amenities. Okay. If I can get 200 grand of depreciation, that would be, you know, considered a good, good investment. 60 to 70%. So you invest 200 grand, you get a buck 60 in depreciation. That's good. It's not an amazing deal. Anything North of one, you go get 1.25, one and a half or two to one on your money. It's absolutely insane. You need a lot to go for you. Like I said, cheap land value. Maybe there was already furniture in there. So you didn't have to spend that money. So your out of pocket is lower.

41:11These are all things that could be cheat codes. But if you go spend 200 grand to get your short-term rental and you get 200 grand of depreciation, so you maybe bought a six, six 50 purchase price. Let's just say you're in the blended 32 or 37 % bracket, you know, between state and federal, you're, you're talking about saving 70 ,000 plus dollars in real money. So forget your cashflow on the short-term rental. We talked about the cash flow I got on that very first North Georgia cabin. That was cash in, cash out. But we didn't even talk about the tax savings. So right now out of the get-go, I invest 200 grand into a short-term rental and I save 70 grand that I would have given to the US government.

41:49It's not optional, by the way. Last I checked, it is forced. So now I'm paying myself instead of paying the US government. I got a 30 % plus return on day one, even if the Airbnb breaks even. Now, obviously, the goal is to actually make money. go make one, two, three G's and free cashflow. But even if you didn't, I can tell you last I checked paying the U S government taxes, you get a guaranteed 0.0 % return. You will never see that money again. But if you buy an asset, you pay down principle, you hold it, it grows in value. So you can eke out any level of cashflow. You will get a return on that money to some level.

42:26If you buy these assets, right? If you buy real estate and you get these passive or active losses, whatever you want to call it. What if I get, I accumulate$300 ,000 of active losses, but I only make$150 ,000 a year. What happens to the$150 ,000 Delta? Does it go away? No, that's the best part. You can save it for a rainy day. You could roll it into future years. So that is the best part. So, you know, you see why 90 % plus of millionaires on real estate is they're in the depreciation accumulation business. So they have a very nice cash flowing service business, tech, hedge fund, equities that spits off a lot of cash and that creates tax liability.

43:09So how do you offset that? You offset that with buying real estate. It's not necessarily people don't really start buying real estate to get rich. That's not typically the route. You can do it a way quicker, way more efficient in service business, the S &B world, et cetera. But how do you keep more of what you make in those businesses is by buying real estate. And you can accelerate that tax savings by having active income. And that's where buying a short-term rental just becomes super lucrative to people. We're not CPAs, right? We're just playing one on TV. So I'm just going to brainstorm with you here.

43:39So if anybody's listening, that's our disclosure. Like, don't take what we say as financial advice. I have a house that we moved from that I didn't sell and we're renting it right now. And we just started renting it this year and we're managing it. that's going to be an active, I guess, whatever piece of real estate that we're managing. Could I depreciate that? Like, could I, or would I have to go like, does that count or no? So one of the caveats to material participation is you have to prove, you have to prove it is a short-term rental. And the definition according to the government is your average rental stay is seven nights or less.

44:13So if you are actively managing this and someone's in there for a six month or a 12 month term, the average on that will be significantly more than seven. So that would just be regular depreciation, which again, you can accumulate a lot of passive losses and save those for rainy days whenever you get more passive income, but it has to be a short-term rental. And so obviously proving that the proven, the caveat to, Hey, how do I prove this as a short-term rental? Well, was the average length of stay seven nights or less? Doesn't mean every stay just means the average of all stays. So you could have a 90 day stay, a 90 day booking, and they get a bunch of one night, two night, one night, two night, one night, two night, checks in Friday, check on Sunday.

44:49If the average is seven nights or less, it is classified as a short-term rental. Jeez. Okay. What are your favorite markets right now or favorite trends that you're seeing that you're like, Hey, we got maybe a year for somebody to exploit this and take advantage of it. Like I said, investing at the polls right now is super hot. One couple's getaways or cottages, You know, it is a very unique trend. You can provide things that a hotel just can't, whether that's hot tubs, saunas, romantic hammocks, you're by yourself versus, hey, it's 400 square foot and I share a wall with someone else a la hotel.

45:24So that is a strategic investment on one side of the pole. The other is four, five, six bedrooms that accommodate big groups that again, they're not going to go rent seven hotel rooms. And so you kind of get out of that two, three, four zone and you go to the poles. And right now what you're seeing is the outsized returns are living at the polls, the average group size on Airbnb. So the good news about them being a public company is they release their numbers. You start looking at the quarterly report. It's grown now for 10 straight quarters. How many people are in a booking? So they have all this data, obviously firsthand of, Hey, six people checked in here or nine people or 27 people.

46:02Average total number per booking has gone up for 10 straight quarters. So what does that tell you? The puck is growing to more and more people. They're saving money. You can split the costs amongst more heads in a large group travel. And it's cheaper than a hotel. They get that together experience. So the bigger upstream you swim, you're getting paid off for because the puck is going that direction. So what we're heavily doubling down on right now is bigger properties or again, go the complete opposite. Very customized romantic experiences for one bed couples. because again, no builder is building a 600 square foot, you know, little tree house, yurt, you know, cottage thing.

46:42They're not building those. So if you can get your hands on one or build one yourself, you've got a great opportunity to add nice little fire pit, nice little hammock, maybe the outdoor shower, all the little romantic things that you do. People are like, well, what's my alternative? My alternative is to pay$200 to go stay at a hotel with, you know, powder day continental breakfast and a carpet and share a wall, or I could pay a little extra. I could pay 300 a night and we got one acre by ourselves in the woods. It's an easy decision a hundred out of a hundred times. And that's the direction that honestly, like we're doubling down on right now is go super big or go super romantic and super small.

47:21Okay. Last thing for somebody who's just starting this journey, what's like the one piece of advice you would have known upfront? And it could be something we've already talked about, but like, what's, what do you think is the most important thing when trying to make money with short-term rentals that you would tell someone just starting out? Invest where it makes the most sense for where you are today, not necessarily for where you're at. If you have a large tax problem today, you're not necessarily trying to chase, oh, can this Airbnb make two, three grand a month? You're like, Hey, how do I not pay 80 ,000 in taxes.

47:54On the flip side, maybe you are miserable at your W-2. Maybe you want to retire your spouse and you're like, hey, sure, I'm going to get depreciation, but maybe I'm not as hyper-efficient, but how do I buy a glorified ATM machine that can spit out two, three, four Gs a month that I can stack one or two of those to retire my spouse or have her cut back? And so whatever your strategy is, you're going to definitely pick a different market based on whatever that thesis is. And I think people get too caught up in, they're like, well, yeah, I like my job. I just pay a lot of taxes. Well, you don't need to go chase the high cashflow, less tax efficient markets.

48:32Or on the flip side, it's the opposite. So to me, I say, solve what's in front of you today. Now, if sure, you don't want to pay taxes today and that's the first short term rental, that doesn't mean the second one's not allowed to be an ATM machine where you chase yield. But I think people get too caught up in, oh, well, if I'm going to buy two, three, four of these, they all have to be cashflow forward. They all have to be tax efficient. And I say, solve the problem that's in front of you today, because you and me and everybody else, we have a finite amount of liquid capital. So again, if I can only buy one for right now, now, if you're fortunate, you can buy two, that's great.

49:05But if you can only buy one, solve the problem that's in front of you today. And then a year or two years, wherever you're onto your next one, maybe you don't have a tax problem because you had another investment that love that or maybe you do want the wife to cut back at work because you're tired of her slaving. Solve that problem then. And you're allowed to buy two different properties in two different markets with two different strategies. That's okay. So it's a mistake I see people make is when they try to overthink this investment. I said, dude, like Nick, solve the problem that's in front of you today.

49:33Do you have a tax problem? Let's solve that efficiently. If you're miserable at work and you want to quit or the spouse or whatever, like let's go try to find an ATM machine that could spit out cash for you. Is that why you started your second business, right? Because you raise money, you own these Airbnbs, and then you started SDR search. Is it because there are people like me who are like excited at the prospect of real estate and short-term rentals, but then get quickly overwhelmed with like, oh my gosh, that's too much data and research that I have to go and do. So just take my money, Taylor, just tell me where to go invest.

50:01Is that like kind of the thesis behind your new business? Yeah, that's really what we started SDR search for was, hey man, we have four full-time data analysts. We've studied 359 markets. We look at 300 Airbnbs, a day, every day, all day, like you don't have to guess where is a good market. You don't have to guess where the most appreciation is. You don't have to guess. We can just present data. And so we'll come in and we'll be the data guys in the background, but you know, ultimately it's your car, you're driving, you know, it's your house, your money, you get all the upside. I'm just going to make sure you don't crash the car or hit the curb by trying to do this yourself.

50:38Because unlike equities, it's not, oh, I bought Apple stock. It went down. I sold it. I lost 50 bucks. Like you buy and sell real estate, you could lose 25, 50, a hundred grand by making a bad decision. That's what we want to avoid with clients is, Hey, why don't we make a high ROI decision? Because this is, this is where the real tax problem gets people in trouble. It's like, ah, cool. I bought an Airbnb and I saved 50 grand in taxes. But if the house loses 25 grand a year in free cashflow, that net savings, you're upside down in three years now. So now your tax benefit's gone because the house itself can't sustain it.

51:14And that's where we say is, hey, yeah, let's get the tax benefit, but let's also make sure there's enough cash flow on the back end that this is a good long-term hold for you and your family. I see a lot of people who are trying to over-optimize tax so hard that they end up screwing themselves on a real business or short-term decision. Optimizing for taxes is important, but that shouldn't be your sole focus. I totally agree with that. Well, cool, man. Where's the best place for people to come find you? is that strsearch.com yeah kind of search calendaries right there grab time happy to talk about your individual situation and you know we'll show you what we could do and if there's help needed great if not man like we're just a bunch of data nerds and we can dump a bunch of short-term rental air baby data on you and we we love this shit because it's all day every day man i love it i love it all right man we'll talk soon all right hopefully you like that episode and if you've made it this far you're either really committed or you're stuck doing yard work and you can't actually skip on your phone.

52:07So while I have you, the show is growing, but I have a favor to ask of you. Will you please help me grow the show? I want to reach more people. There's a couple of things that you can do. Like, and subscribe is the simplest thing. Obviously you want to get notifications for when the next episode is coming out, but if you go the next step, will you leave me a review five-star on Spotify or Apple? What that does is it tells the algorithm that, Oh, Hey, this is a high value podcast because more people are leaving reviews for it and it then pushes it out to more people. So that's why when people are like, will you log and subscribe and put the five-star rating?

52:41It's not just to make themselves feel better. It's actually to get more exposure for the show. So if you do that for me, I would greatly appreciate it. And I'll see you next time.

From the publisher

MY NEWSLETTER - https://nikolas-newsletter-241a64.beehiiv.com/subscribe


Join me, Nik (https://x.com/CoFoundersNik), as I interview Taylor Jones (https://x.com/MrJonesSTRs), the founder of strsearch.com.

Have you ever wondered if short-term rentals (STRs) are as passive as they seem? I used to think so, but Taylor completely changed my perspective. He breaks down how he went from a sales guy to overseeing over $120 million in STR investments by treating it not as a real estate game, but as an operations business.

We dive into his first investment—a cabin in the North Georgia mountains that he bought having never owned real estate before—and how it generated $22,000 in cash flow its first year.

Taylor reveals the critical mistakes he made, the lessons he learned about market supply and demand, and how a single amenity like a pickleball court can add $40,000 to your annual revenue.

We also get into the incredible tax benefits and how STRs can offer active losses to offset your regular income, something I wish I'd known sooner.


Questions This Episode Answers:

• How can a single pickleball court add over $40,000 in annual revenue to an Airbnb?

• Why is a short-term rental business more about operations than real estate?

• How can you use short-term rentals to legally reduce your taxable income?

• What is the biggest mistake new STR investors make when choosing a property?

• Why are large-group rentals and small, romantic getaways the hottest trends right now?

Enjoy the conversation!

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Love it or hate it, I'd love your feedback.

Please fill out this brief survey with your opinion or email me at nik@cofounders.com with your thoughts.

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This week we covered:
00:00 The Allure of Short-Term Rentals

02:55 Understanding the Operations Behind STRs

05:42 The Journey into Real Estate Investment

09:00 Lessons from Early Investments

12:09 Scaling Up: From One to Multiple Properties

14:56 Market Dynamics and Supply-Demand Imbalances

18:11 Navigating the Real Estate Landscape

20:55 Investment Strategies for Success

26:00 Understanding Market Dynamics and Profitability

30:13 Revenue Estimation and Occupancy Rates

33:25 Tax Implications and Depreciation Strategies

40:27 Investment Strategies for Short-Term Rentals

47:31 Advice for New Investors in Short-Term Rentals

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