No Broke Months For Salespeople - Why Most People Lose Money on Short-Term Rentals: Avery Carl’s Strategy to WIN

Episode Date: February 25, 2025

In this episode of No Broke Months, I sit down with Avery Carl, author of Short-Term Rental, Long-Term Wealth and Smarter Short-Term Rentals, and CEO of The Short Term Shop. Avery shares how she went from making $37,000 a year to building a 250+ door real estate empire in just five years—and she’s here to tell you how you can do it too!We’ll dive into:✅ The best markets for short-term rentals (and which ones to avoid)✅ The biggest mistake investors make when picking a location✅ Why she only buys in vacation-driven markets✅ How to scale your real estate portfolio without quitting your day job✅ A real-life horror story from one of her worst deals—and how to avoid the same fate✅ Why NOT to chase the "next big market" that no one's talking about✅ How to out-host the competition and run short-term rentals like a real business✅ The #1 strategy to protect yourself from short-term rental regulationsIf you’re serious about getting into short-term rentals—or you want to scale your portfolio faster—this is an episode you can’t afford to miss!What you’ll learn on this episodeThe difference between short-term and long-term rental marketsWhy vacation-driven markets with limited hotels are ideal for short-term rentalsThe importance of cash flow vs. appreciation in real estate investingCommon pitfalls to avoid when investing in short-term rentalsHow to scale a short-term rental business efficientlyThe impact of local regulations and why choosing the right market is crucialHow Avery went from one property to a massive real estate portfolioResources mentioned in this episodeThe Short Term Shop – Avery’s real estate agency specializing in short-term rentalsSmarter Short-Term Rentals – Avery’s latest book on running a successful short-term rental businessThe Short Term Show Podcast – Avery’s podcast covering everything short-term rentalsAbout Avery:Avery Carl is the best-selling author of Short Term Rental, Long Term Wealth, host of The Short Term Show podcast, and CEO of The Short Term Shop, a top real estate agency specializing in short-term and vacation rentals. Avery transformed her career from a $37k salary to owning over 250 properties in just five years by focusing on short-term rental investments, which allowed for faster portfolio growth compared to traditional long-term rentals. Her mission is to help investors achieve financial independence through short-term rental investing. Avery is a leading industry expert, frequently speaking at conferences, and her podcast has over 1 million downloads. Her agency ranks among the top real estate teams in the nation, as recognized by RealTrends, NewsWeek, and The New York Times.Connect with Avery:Website: The Short Term ShopLinkedIn: Avery CarlInstagram: @theshorttermshop  To find out more about Dan Rochon and the CPI Community, you can check these links:Website: No Broke MonthsPodcast: No Broke Months for Salespeople PodcastInstagram: @donrochonxFacebook: Dan RochonLinkedIn: Dan Rochon

The biggest mistake that I see people making with short-term rentals is saying, I'm going to go where no short-term rental investor has gone before. I'm going to go where there's no short-term rentals. I'm going to be a first one that nobody's talking about this market. Nobody's talking about this is the market that nobody's talking about. Like if it was good, if the tourism was there, it would have been done already. Welcome to the no broke months for salespeople podcast, the ultimate destination for salespeople, business people, and entrepreneurs. As you immerse yourself in this show,

you'll discover the secrets to unlocking consistent and predictable income. We reveal the new way to persuade human behavior by mastering the art of the teach to sell method. Get ready to transform your approach and achieve unparalleled success. Get ready to transform your approach and achieve unparalleled success. Welcome to the no broke months podcast. Today I am talking to Avery Karl and we are going to share about short term rentals, specifically what types of markets work best for short term rentals and Avery's

a author of Amazon's bestseller, Short-Term Rental Long-Term Wealth, your guide to analyzing, buying, and managing vacation properties. She's the host of the Short-Term Show podcast and the CEO of the short-term shop. She went from a $37,000 salary to a real estate portfolio of over 250 doors in just five years. Today she's gonna tell us a little bit more about that. She's got another book coming up pretty soon as well. So I'd love to hear more about that. Every welcome. How are you?

I'm good. How are you? Good. What were you doing getting paid $37,000? So I was doing what I thought was going to be my dream job working on the business side of the music business in Nashville. And because that sounds so fun, they pay basically nothing because there's always an intern who will do it for free. So, yeah.

Got it. And how long ago was that? That was almost 10 years ago now. So that was back in 2016, bought my first rental in 2015. Okay. And so then you went from that role to over 250 doors in a very, very short period of time. Before we get into, you know, what types of markets work best for short-term rentals, tell me a little bit more about your journey from your first rental to your 250th door. Yeah. Yeah. Happy to do it. So at that time,

we had just moved from New York City to Nashville. That was in 2013 that we moved to Nashville. And our real estate agent was really trying to get us to was in 2013 that we moved to Nashville and our real estate agent was really trying to get us to buy in this super hip, fast appreciating part of Nashville. And we were like, no thanks. You know, we're moving from Brooklyn to Tennessee. We want to be out in the country. We are tired of neighbors, no more neighbors. And so we bought something out in the country. Didn't think anything else about it. Year or two later, we got married and had a little bit of money saved up. And we're like, what are we going married and had a little bit of money saved up. And we're like, what are we gonna do

with this little bit of money? It was like $10,000. And we wanted to be all, you know, smart. And we just got married and I was trying to be all, all personal finance conscious and reading all the Dave Ramsey books. And I'm like, let's go to a financial planner. So we went to a financial planner.

She was like an Edward Jones office in the same building as my corporate job. And we went and she basically told us we didn't have enough money for her to bother with. And we're like, OK, great. We're losers. So I went to the bar and we were losers. So we went to the bar because we wanted the bar. Yeah, we did quit drinking back in 2019, I believe. So so we went to the bar and we're like, what are we going to do here?

Because we've got to be able to do something with this other than let it sit in the bank. And so we were like, well, what are we gonna do here? Cause we gotta be able to do something with this other than let it sit in the bank. And so we were like, well, remember those houses that Shelby, our agent was telling us about? What if we bought one of those? You have to save up just a little bit more. If we bought one of those, put a renter in it. And if they're really appreciating, you know, the way they have been in 25 years, whenever we have kids

and they grow up and need to go to college, then maybe we'll be able to pay for their college out of that appreciation. We'll have a renter in it so it's not costing us any money all that time and we'll be these great financial geniuses and we won't have to come out of our own pocket. We'll just sell this house." And so we were like, great idea. So we went and did that, bought a house and luckily we got very lucky that that house was a long-term rental. Our mortgage on it was $647 a month, and we were able to rent it for $15.50 a month. So almost $1,000, which is great for a long-term rental.

Paid $122,000 for it. And coincidentally, after all the deductions on my great dream W-2 job, I was making about $1,000 a month. So we thought, wait a minute, this house is making the same amount of money as me when I'm having to work so much harder. We need to figure something out here. And only then did we actually start research and we didn't even know it was called real estate investing. We bought our first one.

Most people do the research first and by later we did it the opposite. And so we said, we want more of these things and we want to build an actual business out of this. So then we started actually reading. And back then, this was again, 2014 probably when we started thinking about buying one and there were no YouTube channels, there were no people posting on Instagram with yellow captions. Like we just had to figure it out. And we knew we had just a little bit of money left for like one single family

down payment. And we said, well, what can we buy that's going to make us the most amount of money, the fastest so we can go buy more. The intention was not to live off of it or to try to get rich the intention was just to buy more and buy more. And so we landed on short-term rentals we knew we didn't want to do it in Nashville back then because Nashville is just very anti short-term rental. But we had just been on vacation to the Smoky Mountains about four hours east of Nashville and we'd stayed in a rental cabin all our friends who came stayed in rental cabins and we thought, well, that's great. Somebody owns these cabins.

That's the normal thing for people to come and stay in a cabin. Let's do that. So long story short, we bought one. It went really well. We scraped like the pennies out of the bottom of my purse to get that property. And that went well scaled to five of those

over the course of about a year and a half. Keep in mind, back then real estate was much cheaper. We were able to pick these things up for 120 to 150,000. And we also, after we got five, said, okay, you know what? We've got some cashflow coming in. We can pick up some long-terms here and there without really feeling that leave the bank account. So we started picking up duplexes in Chattanooga, Tennessee

for like 80,000, grew that to about 40 of those. And during that time, I started my company, The Short Term Shop, which is real estate agency, because there weren't really any agents in the space who could answer our basic questions like, how much did this make? Like, where's the best place to buy to rent stuff? How do you find a cleaner?

So bridge that gap, got my license, became that agent, started what would eventually become The Short Term Shop as just a single agent in the Smokies. Now we've got like 60 agents across the country, 20 different markets. We went from zero to the top team at EXP, the largest brokerage in the world. We became the top team in the world. Within five years, we've been the top team for three years running. 2021, we sold a billion dollars worth of real estate.

We sold about three billion total since we started in 2019. So helped over 5,000 investors buy and sell short-term rentals, grow my own portfolio throughout that time, got up to 250 doors myself. Still don't live off of my rentals, only buy more rentals with the rental money. And that's about it. Thank you for sharing that with me.

First of all, it's impressive. And it's also a journey that I think a lot of people can, I think the only hesitation somebody would have listening to your story is, okay, well, how do I do this because prices are, you know, in some places 20 to 50% higher today than when you started, maybe even more than that, right? So that could be an objection somebody may have, but outside that, I can't imagine that somebody listened to your story, couldn't imagine, you know, couldn't see themselves doing the same.

Hey, hey, salesperson, are you struggling to close deals or struggling to gain trust? Or you're struggling to create consistent and predictable income? I'm Dan Rochon, and I've seen it all. Salespeople stuck in uncertainty, guessing their way through the business. And that's why I created the Consistent Predictable Income CPI Inner Circle. To give you the tools to master, teach to sell, and finally eliminate the struggle. Learn how to influence, close, and turn doubt into trust on repeat. No more trial and error, just results.

Ready to take control? Visit www.nobrokemonths.com. That's nobrokemonths.com. Click login and get started today. What do you say, you know, so you're all, you're all across the country now in different markets. Is that true? And what vacation hotspots, you know, a lot of people talk about like vacation hotspots. What, you know, touch of like non-touristy markets would you say that short-term rentals are thriving? And why do you think they are thriving? Sure. So, and I will say I have not stopped buying. So, the most recent property I bought was December of last year.

So, still buying short-term rentals. It's a great time to buy because there's not a lot of competition. The real estate market is completely dead. People, I think sometimes don't realize that. Fewer homes were sold in 2024 than the entire last 65 years. So more homes were sold in the 2008 crisis than last year and in 2023.

So not a lot of competition, but deals are definitely harder to find. So markets where short-term rentals work really well. The type of market that I buy short-term rentals and the type of market that I buy long-term rentals are very different. I only buy in very tourism-driven vacation markets. So like the Smoky Mountains in Tennessee,

Destin, Florida, places where there's very little hotel presence and the economy is driven by the tourism that's coming to stay in the vacation rentals that they've been staying in for decades and decades. So like my grandmother, for example, has been coming and renting houses in Destin since the 30s. So all those regulation battles were fought generations ago. Everything's very stable. You're not really having to worry about, oh, they're going to outlaw short term rentals. So I like to buy my short term rentals in those types of markets so you don't have having to worry about, oh, they're going to outlaw short-term rentals. So I like to buy my short-term rentals in those types of

markets. So you don't have to really worry about that. You have a very, very deep proven tourism driver and you're not trying to like fish in a pool of 10,000 when you can fish in a pool of a pond of 10 million. So areas that people may not think about, I think the biggest mistake that I see people making with short-term rentals is saying, I'm gonna go where no short-term rental investor has gone before. I'm gonna go where there's no short-term rentals,

I'm gonna be a first one. Nobody's talking about this market. Nobody's talking about, this is the market that nobody's talking about. Like if it was good, if the tourism was there, it would have been done already. It's kind of my theory on it. I'm not into trailblazing.

At this point in my investing career, at this point in my life, I've got two little kids. I want it to be easy. I'm not trying to trailblaze. I want to do where it's easy to do it. So for me, it's just vacation markets all the way. Are there overlooked markets that you would say have been a surprise for you that maybe, I know you're not trailblazing, right?

But has there been a market where you initially you had to consider it? And then after you're thinking through it, like, oh wait, that does meet all the criteria. That does. It is a vacation destination. And, you know, has there been a market like that? Yeah. So Scottsdale, for example, or like the Sarasota, Florida area. Initially, when we started looking at potentially opening up offices in these

markets, I was like, no vacation markets only. These are metro markets. I'm not doing that. But when you look at, I call them vacation ish markets now because Scottsdale while yes, it is a major metro area, you know, Phoenix, and there's a lot of other industry there. Same thing with Sarasota. It's still such a vacation destination. So I didn't know, cause I'm not from out West.

I'm from the Southeast. I'm from North Mississippi. I don't know anything about Arizona. You know, a lot of people who live in Montana, Wyoming, Colorado, come down to Arizona for the winter time. These are things that I just didn't know because I don't I didn't grow up in that region. Same thing with Sarasota and Bradenton and Clearwater and all like that whole kind of big Tampa metro.

Yeah, it's a big urban area, but that's where a lot of people go to the beach on the barrier islands out there too. So I've opened my eyes to what I call vacation-ish markets that are kind of Metro, but are very tourism driven as well. So what's the difference between long-term markets for you and short-term markets? I know that there is a difference.

Can you describe those? Yeah, sure. So for me, my personal preference in my portfolio already said short-term rentals, I like vacation markets, beach, mountain, lake, desert, national park type markets. For me with my long-terms, I like small to medium metro areas. So like Chattanooga, Tennessee, Birmingham, Alabama,

we've got a few in the Midwest in Ohio. So areas that are like growing a little bit, I wouldn't say the Ohio one is, but areas that things are pretty stable. Things are kind of growing, but they're not like the Austin level yet, or not like the Charlotte where they're on those lists of all the hot spots of places to move yet. Because that makes all the investors jump in these lists. So I like to find those a little bit more under the radar. You're seeing some growth in the economy, but nothing too crazy. Southeastern and Midwestern cities. What's been your biggest challenge that you've had?

In terms of the growth or like you want to hear a horror story? Whatever it may be. Give me one of each. OK, OK. So in terms of growth, like it's always just, you know, wish I would have had the capital 10 years ago that I have today to, you know, the best time to buy real estate was always yesterday. In terms of growth, I feel like we've not done everything right, but we haven't like made any major screw ups, like, oh my God, we chose the wrong market or, uh, but we have had a few horror stories and I feel like, or I know, I don't feel like if you buy enough real estate and own it for long enough,

you're going to get a non-performer at some point. You can do everything right and still have some property that doesn't work. So for me, that property was an apartment building in the Midwest. And I think this is really important for other investors to hear because a lot of times they say people buy cheap properties just because they're cheap. They choose cheap markets just because they're cheap. Makes sense. Seems logical, right?

They look at markets and the cash on cash return is really high all the way across the board and they're like, this great, I found this treasure trove. Why are all the other investors not jumping on this? Well, there may be a reason for that. Yes. And usually that reason is because it's not desirable real estate. And I don't mean like wrong side of the tracks. I just mean it's in an area that's not growing or if it's a short term rental market because it's not desirable real estate. And I don't mean like wrong side of the tracks. I just mean it's in an area that's not growing

or if it's a short-term rental market, it's in an area where there's not a lot of tourism. So for me, it was a long-term and an area that wasn't really growing. And we've still got five or six apartment buildings there, but this particular one, the mistake that I made in these areas that aren't growing, there's a reason they're cheap

because people aren't moving there. So they're not appreciating. You're not getting that appreciation that you're getting in some of the hotter areas of the U S. So, you know, a lot of people move into Texas. A lot of people move into Tennessee, Florida, cause no income tax. Um, this particular area not happening, but the cash on cash return looked good across the whole market.

So we're like, sweet, we'll jump in and this one property going fine, owned it two or three years. And then the bigger apartment complex across the whole market. So we're like, sweet, we'll jump in. And this one property going fine, owned it two or three years. And then the bigger apartment complex across the street starts looking a little crappy and it starts looking worse. And then it's like miscreants, drug dealers, things like that coming across the streets are as eventually that property is condemned by the city. I don't know what that owner did or why he just kind of quit. But that property is condemned by the city.

Nobody is allowed to live there. Of course, people are living there and all that crime is coming across the street to our place. Our tenants don't feel safe. People are breaking into our units, units that we've already rehabbed by the way, how many, how many, how many doors did you have in that building? That one was 12.

So nothing like dire, but also not what you want. So eventually, you know, we're cleaning this thing up. We're cleaning this thing up. And after about a year and a half, maybe two years of trying to like keep the people from across the street, from breaking in, from selling drugs, from doing all these things, we're like, OK, the return on our energy is no longer there. The police do not care about your landlord problems. They have better things to worry about.

They didn't care. We just could not keep this building from getting broken into. The police do not care about your landlord problems. They have better things to worry about. They didn't care. We just could not keep this building from getting broken into. It got to the point where we had ring cameras on the outside that when the motion sensor would trip, we would hit the button to make the siren go off to make them think somebody was coming. And it's just like, why are we doing this? Why do we have this?

Why are we spending our time watching this ring camera and hitting the button and yelling at people to leave? So we're like, you know what? We're done with this one. It's time to sell it. This is a dog. So we go to sell it. Well, you know, three or four years later,

it hasn't appreciated. The market's also shifted to be a buyer's market and we're having to sell it, had to unload it for less than what we paid for it because we chose a market where nothing appreciates. And I used to argue with people all the time on the internet like a stupid little newbie internet troll. Be like, no, no appreciation. That's that could change in a minute. That's stupid. You want cash flow only cash flow only. And now I had to take my medicine and learn like no it's not all cash flow you do

need that appreciation so if you ever need to sell it you don't have to sell it for less because that really that was a situation where it wasn't like we underwrote it wrong or we did anything wrong it was kind of outside of our control. I spent a lifetime in business and in sales you know what I've seen far too often? Struggling. Struggling to close deals. Struggling to gain trust. Struggling to create consistent and predictable income. That's a problem I'm here to help you solve. Because success, it starts with a simple truth. It's not about you, it's about them. That's why I created the Consistent Predictable Income CPI Inner Circle. A system designed to give you the tools to thrive.

Master teach to sell. And finally, eliminate uncertainty in your business. Inside you'll learn how to overcome doubt and build trust that leads to sales. How to spot hidden opportunities, influence meetings and get hired fast, how to master hiring and find top tier talent without the guesswork, how to inspire, lead and gain influence so people follow you with confidence. Just think about that. Listen, there's a formula to success and I'm handing it to you. No more trial and error.

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So you have to pay attention to that. And for a while I didn't. And now whenever I see lists with, oh, this is the cheapest property in the country, this is where you can get the highest cash flow. I think there was a best places to invest in short terminals list rentals list that came out last week and they were like Detroit number one. I'm like guys come on let's let's think about the capex here. So anyway that's my horror story buying a cheap property just because it was cheap and learning the hard way why you don't do that. One of the concerns I don't have personally I've not done short-term rentals. I've always

done buy and hold long-term type stuff and one of the things that I'm ignorant to, I'm not ignorant to it, I have an awareness of it, but I don't have the experience in it. And so I share that with you because one of my concerns that I have personally is, well, what happens if laws change or municipalities say, you can do this and then suddenly now you can't? Do you think that most of that has already been sort of sorted through through time and it's not likely to make changes that would make it a challenge for you? Or do you think that that's still a potential problem? In certain markets, it's absolutely still a huge problem.

So again, that's why I choose markets that the entire economy would collapse if there were no short-term rentals for guests to come stay in. That's why I stay out of Metro markets because Metro markets don't need the tax income from short-term rentals like a Nashville. For example, they've got tons of other industry coming in. All these other corporate headquarters are coming in the people who live there. Their income does not depend on tourism. It depends on other things.

So markets that aren't dependent on tourism, I'm not in for that exact reason, because there's no reason for them to to protect it. And then the other piece of it that I heard you say is with few hotels. You want a few hotels. Yeah. So like the fewer the fewer hotels that they have have, but that can be a little bit of a challenge to find those markets, right? But you gave us some examples. I mean, they certainly exist.

But what I'm hearing you say is fewer hotels and vacation as an industry, that's a prime spot because they would kill themselves if they change the rules. Is that what I understand you saying? Yes. You just, uh, published your second book. Mm hmm. Smarter short-term rentals. Yes.

Tell me a little bit about that book. Sure. So my first one came out back at the end of 2020. It was more of the basics of short-term rentals, how to choose a market, how to analyze, how to choose a property, that type of thing. This one is more the systems and processes to really make sure that you are, it's, well, it says, build a dynamic real estate business and out-host the competition. So just because you buy a nice house in a nice market does not mean you're going to be successful. This is a business. You have to run it like a business. So we talk about systems and processes,

standard operating procedures, hiring VAs to help you scale the actual business running of it so that you can optimize and scale your portfolio in whichever way you choose, whether you wanna buy more short-terms or you wanna go buy long-terms, you gotta have systems, you gotta have processes, you can't just wing it.

How many VAs do you have? Less than you would think. So we have three total across all of our businesses or four total across all of our businesses. Two of them are allocated specifically only to work with me in the short-term shop and the sales side and manage our agents, et cetera. And then we have two who work with us

on our larger real estate portfolio. And then also our education piece of the short-term shop. So those two as a piece of their larger job description, help manage our short-term rentals. So we have eight short-term rentals, everything else is long-term. So part of their job, definitely not, I would say less than half of their jobs

are helping to manage the short-terms. My business is DF. So we have- their jobs are helping to manage the short terms. How many businesses do you have? So we have- I love asking entrepreneurs that question because if you ask me that question, I don't know, like how do you not know how many businesses that you have? It's weird.

Well, it depends on how you divide it up. So we have the short-term shop, which is a real estate sales company, broker by EXPs. That one, we help people buy and sell short term rentals. Then we have the mortgage shop, which is a mortgage company that focuses on short term rental and just general investment products. So you're probably not going to come to us to buy a primary. You could, but that's not our specialty.

Then we have our I kind of think of our long term single family portfolio and our long term apartment building portfolios to separate businesses. And then we have our education piece of the short-term shop. So if you come buy a house with us in any of our markets using one of our agents, we'll put you through what we call our world famous Management Monday for free. Any, I would say eight out of the 10

big short-term rental influencers out there started buying their first property, learning how to do it at Management Monday with us before they became big influencers. But then we also recently started in the last year an education piece for people who maybe are buying in markets that we're not in that still want to learn from us. So just like a true mentorship, we keep it super affordable. So we call that STS Plus or short-term shop plus. So we've got short-term shop plus regular short-term shop mortgage shop, and then the investment business. All right.

You got a lot going on. If I'm interested in maybe I'm an agent that wants to learn more about being a part of your network or maybe I'm a buyer that's interested in being able to purchase short-term rentals or I'm just looking for education just in general. Is there like a one-stop shop that I can get in touch with you? Yeah. Yeah. So we're always hiring agents, whatever markets, like pitch us your market or,

you know, we're always hiring in the markets that we're already in. I would say the best place to do that is on our website. So the shorttermshop.com we've got links to, if you want to buy with us in any of our markets, we've got those links, we've got short term shop plus links, we've got careers links. So there Instagram at the short term shop for the brand. If you want to just follow what I as running this many brands and things do in a day at the Avery Carl. I love it.

Avery, you are amazing. I wish you much continued success and thank you for taking the time to share your insights with us. Yeah. Avery, you are amazing. I wish you much continued success and thank you for taking the time to share your insights with us. Yeah. Thanks so much for having me. It's my pleasure. Viewers and listeners, thank you for tuning in today. Until next time, have the best day of your life. Be grateful, make good choices, go help somebody and check out Avery's stuff at theshorttermrental.com. Did I get that right? Shorttermrental.com? The shorttermshop.com. Ah, damn it! I'm glad, as soon as I said it,

I knew I screwed it up. The shorttermshop.com. God bless you guys. Hey there, No Broke Months listener. I've got some exciting news. We just passed 375,000 downloads for the No Broke Months podcast and I could not have done it without you.

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