Achieve The Highest ROI: Vacation & Short-Term Rentals | Raising Private Money with Jay Conner

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How can you manage a short-term rental property from anywhere in the world?

Avery Carl is an Author, Podcast Host, Real Estate Investor, and CEO/Founder of The Short Term Shop.

She was named one of the Wall Street Journal’s Top100 and Newsweek’s Top 500 agents in 2020 and her team, The Short Term Shop, was named to the Wall Street Journal Top 50 Teams in 2021.

Avery and her team at The ShortTerm Shop focus exclusively on VacationRental and Short-Term Rental clients.

She has sold over $300 million in short-term/Vacation Rentals in 2021 and over $750million since her start in 2017.

An investor herself, with a portfolio of over 50 properties, Avery specializes in connecting with investors with short-term rentals with the highest ROI potential and then training them to manage their short-term rentals from their smartphones from anywhere in the world.


0:01 – Raising Private Money with Jay Conner

0:13 – Today’s guest: Avery Carl

3:56 – Short-Term Rentals vs. Long-Term Properties

6:41 – Find The Right Market For Your Short-Term Rentals Investments

10:58 – How To Properly Invest In Short-Term Rental Properties

15:47 – Do The Math Of Your Short-Term Rentals Cash Flow:

17:52 -Connect with Avery Carl:

21:11 – How To Manage your Short-term Rentals Remotely


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What is Private Money? Real Estate Investing with Jay Conner

Jay Conner is a proven real estate investment leader. He maximizes creative methods to buy and sell properties with profits averaging $67,000 per deal without using his own money or credit.

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Achieve The Highest ROI: Vacation & Short-Term Rentals | Raising Private Money with Jay Conner

Jay Conner


Well, hello and welcome to another amazing episode of Raising Private Money. I’m Jay Conner, your host, also known as the Private Money Authority, and I’m so excited about the guests that we have on the show with us here today. My guest is an author, a podcast host, and a real estate investor herself, and she is also the CEO and founder of the company that’s called The Short Term Shop. Now, she was named one of the Wall Street Journal’s, Top 100 and New Week’s, Top 500 real Estate agents in 2020. And her team, the short-term Shop, was also named to the Wall Street Journal Top 50 teams in 2021. Now, she and her team at the short-term shop focus exclusively on vacation rental and short-term rental clients. She has sold over 300 million in short-term vacation rentals in 2021 and listen to this over $750 million since they start in 2017. Now she knows what she’s talking about because not only is she a real estate agent and realtor, but she is an investor herself. She has a portfolio of over 50 properties. She specializes in connecting with investors with short-term rentals, with the highest return on investment potential, and then she trains them to manage their short-term rentals from their smartphones from anywhere in the world. My guest is Avery Carl, and she’s coming up on the show right after this.

Jay Conner


Well Avery, welcome to the show. It’s so exciting to have you on here to talk about your real estate investing success, and short-term rentals, and you really got my curiosity up on how you manage all that stuff, you know, from your smartphone. So welcome Avery.

Avery Carl


Hey, thanks so much for having me.

Jay Conner


Absolutely excited to have you. So you know, you and I were talking before the show, your PO portfolio does not just consist only of short-term rentals, but you have an array of different types of properties. Tell me about that.

Avery Carl


Yeah, yeah, so I actually need to update my one sheet. It still says 50, but I’ve got 220 now and I take a little bit of a different approach to investing in short-term rentals than a lot of other influencers in that space. So to me, like a lot of people will say, you know, know Short-term rentals are the only way to go. They make the most money, it’s the only thing you need to invest in. Everything else is a waste of time. I don’t agree with that. Yes, short-term rentals do cash flow very, very heavy in some cases between three and five times more than a traditional single-family long-term depending on where the property is and what market it’s in. But for me, short-term rentals should be treated as more of like a cash-flow turbocharger as a part of any real estate investing portfolio, especially for beginners. So especially if you’re trying to get some cash flow rolling to build your portfolio, if your first few investments are short-term rentals, you can get that cash flow rolling in faster so that you can then scale your portfolio more quickly than if you start with traditional long-term. So my strategy was to use short-term. So five of my first six investments were short-term and I’ve just rolled all of that income from those into long-term in multi-family.

Jay Conner


So if short-term rentals create so much more of a cash flow, positive cash flow, and are more profitable, why would you not want that to be the majority of your portfolio?

Avery Carl


So that’s a really good question and I have the answer to that is twofold. So short-term rentals are not as passive as long-term rentals. So even though you’re able to do all of it on your own without the use of a local property manager, there are lots and lots of apps which we can get into later that make it doable from your phone, from anywhere. It’s still managing systems, so you’re still having to pay attention to things like you’re still gonna have to answer guest questions. Now you can do that from the beach drinking a margarita, but you’re still gonna have to do it, right? So it’s still management, whereas long terms can be more passive, multi-family can be more passive. You’re putting that with a property manager and moving on. But in terms of my actual portfolio, so of 220 doors, eight of ’em are short-term rentals.

Avery Carl


But if you look at them from a dollar value perspective, it’s actually much more balanced than it seems like it is when you look at a number of doors. Because my average price for a short-term rental is like five, 600,000 whereas my average price per door for a long-term is somewhere around 90,000. So in the short term, we buy only in true vacation rental markets like Destin in Florida, and the Smokey Mountains in Tennessee. So those are just more expensive per door than you know, an apartment building would be. And then also, you know, I started investing before covid, and at the time that Covid happened in 2020, we had I think five short-term and maybe like 25 long terms. And when that first shutdown happened we were like, Oh crap, there go the short terms, the other shoes finally dropped, the short-term is going outta the toilet, but at least we have all these long terms that can carry our short terms until we get this all figured out.

Avery Carl


What actually ended up happening was the opposite. So the short-term boomed after Covid because everybody was tired of being cooped up in their houses and they went on vacation drivable vacations we actually had to worry about our long terms because we had to worry about the eviction moratoriums, which we never saw coming. So whichever way that Covid pendulum had swung, we were in good shape because we had a diversified portfolio and not just all on one thing. So that was a really good lesson for me in, you know, having been prepared for whatever comes, I think it really is just a good idea to have a good diverse portfolio and not go all in on one asset class.

Jay Conner


Well, that makes a lot of sense. I mean it’s back to the principle of you know, not putting all your eggs in one basket but having a diverse portfolio as well. So that’s interesting you said that you focus on luxury properties or true vacation destination properties for your short-term rentals. I hear other people saying, you know, any town that’s got a hotel, then there can be a demand for short-term rentals. So tell me why do you focus exclusively on high-end luxury properties for short-term rental?

Avery Carl


So in terms of where they are, are they luxury compared to a lot of my long terms? Oh yeah. But in terms of the market that they’re in, they’re not necessarily luxury. They’re very like standard, middle-of-the-road, nice, cute, clean places to stay, but not necessarily luxury. So like in Dustin, I have a four-bedroom beach house, three blocks from the beach. Now I paid, it was a foreclosure, I would’ve paid about six, I paid about six 50 for that. Had to do quite a bit of rehab, which made it worth about a million when we were finished with it. But a luxury property in Dustin is 10 million. So it just kind of depends on the market, what you’re, you know, what you’re comparing to. So for me, the reason we focus on the markets is that we focus on because there’s not a lot of hotel presence and it’s a normal thing for tourists who go to these markets to stay in short-term rentals like cabins, condos, beach houses, things like that, rather than hotels.

Avery Carl


And that’s been the normal thing since before Airbnb existed, since before the internet existed in some cases, like my grandmother has been renting vacation rentals in destined since 1937. There have been vacation rentals in the Smokey Mountains. Everybody started coming and staying in cabins in the Smokeys in the sixties. So we try to stick to markets like that where the whole short-term rental asset class predates Airbnb. So we’re not going in and buying places in like the middle of a subdivision and Nashville, Tennessee and trying to turn that into a short-term rental, making the neighbors mad who are trying to like raise their kids in a quiet neighborhood. And now all of a sudden there’s a short-term rental in there. We stick to markets where it’s the normal thing, there’s not a lot of hotel presence and they’re very mature and established. So they’ve been through X amount of, of Nat natural disasters, they’ve been through wars, they’ve been through economic downturns, they’ve been through every kind of president we’ve had in the past 50 years. So we stick to those types of markets because they’re the most proven and you don’t have to worry about the volatility with regulations as much.

Jay Conner


So how do you research those markets to actually get those answers?

Avery Carl


That is a really great question. So there are lots and lots of data tools out there now. Air DNA is one, and RABU is another. There’s one called S STR Insights that is a really good one that kind of helps you choose markets, but it’s really easier than that. Like when I started investing in these types of things, there weren’t really, there weren’t those data sources yet. So I just thought, well where did I go with my family when I was a kid where we stayed in a house, like a privately owned place rather than a hotel? I grew up in Mississippi, so you know, we went on weekend vacations to Pigeon for, or Gatlinburg or to Dustin or 30 a Florida or Gulf Shores, all of those places we stayed in a cabin in the mountains or a condo or a beach house. And so that’s kind of how we started with, all right, this, I know this is the type of market we want to look in.

Avery Carl


And so let’s stick to that. And then once you’ve kind of discovered that kind of market, there are tons of other ones you can think of across the country. Myrtle Beach, South Carolina, Broken Bow, Oklahoma, I already said Gulf Shores a western North Carolina Mountains like Maggie Valley, places like that. So there’s lots of these types of markets, lots of data online that you can use nowadays. But you know, back in the day when there wasn’t that, I just kind of thought, well where, where did I go when I was a kid where we didn’t stay in a hotel?

Jay Conner


Well, that makes a lot of sense. I mean one of my and Carol Joy’s favorite places to go in Gatlinburg Pigeon Forge. In fact, we actually had our honeymoon up the mountain from Maggie Valley, so I know what you’re talking about. So once you have determined, okay, here’s a market that you want to invest in with short-term rentals, how do you go about analyzing what’s the most you should pay for that property analyzing, would this make a good short-term rental property? I mean, I can answer that very, very clearly, just investing in a single family house that I’m wanting to flip, but I’ve never done a short-term rental myself other than three condos over on the beach. So how do you go about analyzing the opportunity?

 Avery Carl


That’s a really good question. So where a lot of investors make their mistake, and it’s not gonna sound like a mistake when I first say it, but I’m gonna swing back around to where it makes sense. So a lot of investors will just say, Oh, what’s the rental history on this? Cuz if you’re buying a place like in Panama City Beach, Florida, basically all the real estate in Panama City Beach is vacation rentals. So pretty much everything’s gonna have rental history, but to me, rental history means nothing because it’s not actual data, it is one random data point. So it’s what one random person, host, or manager has been able to do with one random property that could be underperforming or overperforming. And you don’t really know because you’re not, you’re just looking at this one data point, so you have nothing else to compare it to.

Avery Carl


So you wanna make sure that you’re using market-wide data and you’re using data that is comparing apples to apples. So what I mean by that is if you are gonna be managing self-managing using Airbnb and VRBO, then you wanna be looking at data of properties that are on Airbnb in VRBO, you don’t wanna be looking at data from properties that are on like Uncle Ricky’s cabin that doesn’t use those websites because it’s gonna be different. So you wanna make sure it’s market-wide and comparing apples to apples. So there are a few websites where you can get that kind of data. One of them is Air DNA, which Air DNA does have a subscription fee per market. And what it is, is it’s a data scrape of all the properties that were on Airbnb and VRBO for the past few years. And it shows you all of the gross annual incomes, the average price per night, and average occupancy rates of everything across the market by the number of bedrooms.

Avery Carl


So you’re looking at averages of all the four bedrooms in the market, not just one random four-bedroom that you happen to be looking at. There’s another one called Rabu that does basically the same thing. Their algorithms do work a little bit differently, so they’re, you’re not gonna get the same numbers on each platform, but you know, use an average when you’re analyzing. And then there’s another one, there’s a tool called Price Labs that you’ll need when you buy the property that helps you dynamically price your property, like for holidays, and different events that might be in town. It’s like constantly analyzing other people’s prices and historical pricing to make sure you’re getting the highest price per night. But there’s a function within that tool called the market dashboard that you pay a little extra for and it’ll show you just the 30-day snapshot of the performance in the market.

Avery Carl


So that’s pretty good too. So you wanna use those three data sources? There are a few other ones too that are pretty good. And then there are some things also though that data can’t tell you. So if a property’s performing badly, the data’s just gonna show you the performance, it’s not gonna tell you why. So a property could be performing badly because maybe it looks like junk in the pictures, maybe the paint’s peeling off, maybe the pictures are blurry, maybe they’re dark, maybe it just looks like really not a professionally done listing. So people are steering away from it. While it might actually be a pretty good property, because of the way it’s presented, people aren’t booking it. So in conjunction with the data, we use what we at the short-term shop call the enemy method, where it’s basically you’re kind of running comps on your competition.

Avery Carl


So you’re looking on Airbnb and VRBO, zooming in to the neighborhood of the property that you’re looking at and plan to buy and you’re looking, looking at your enemies or your neighbors. But the enemy method’s way more fun to say and you’re looking for, okay, do I have this property next door to me that looks terrible in the pictures and doesn’t look pro, and people aren’t booking it well, they’re gonna be getting, you can look at their calendar, you can open up their calendar and look at it, see what their prices per night are. Well, you know your property’s gonna look better than that because you’re gonna have pro photos and you’re gonna do things right, you’re gonna manage it well. So you know you’re gonna be getting a little higher price per night than them because you’re going to have a pro-looking listing. Or if you’ve got one next door to you that’s offering like a private jet, private chef, private chauffeur, if you open up their calendar, you know you’re probably gonna get less of a price per night than those guys cuz you’re probably not offering all of those things. So you’re looking at the data from all those websites to kind of give yourself a range and then you are looking using the enemy method on Airbnb and VRBO to kind of figure out what that real-life scenario looks like.

Jay Conner


So when you get all of that data, those different data points, et cetera, how do you come up with the maximum offer that you can pay or you’re willing to pay for a property?

Avery Carl


That is a really good question. Such a good question in the fact that I actually built a calculator around short-term rental investing on my website. It’s the And what you’re looking at is you wanna get what your monthly, you wanna look at the price, you start with the asking price and do the math figure out from maybe get an estimate from your mortgage broker, hey, this is what the, what the mortgage payment’s gonna be. And then you’re looking at your gross annual income, which you’re getting from these data sources. Like you, you’re coming up with that range and coming up with a conservative estimate and you’re working backward from there to see what your cash flow will be over the course of a month. And, with short-term rentals, you kind of have to start with analyzing monthly but then extrapolate that over a year because it’s different than long-term.

Avery Carl


So if long terms the rent is what the rent is all year, every month, No, nothing’s changing because they have a lease, but with short-term rentals it’s seasonal, and also their price is dynamically based on oh 4th of July, well that’s gonna be a lot more expensive than a random Tuesday in January. So the monthly isn’t always gonna look great depending on what month you’re looking at, you kind of have to look at it on an annual basis. But anyway, back to what I was saying, figure out what your monthly payment’s gonna be, figure out what your utilities, your cleaning fees are gonna be and work backward from there to figure out what your cash-on-cash return and monthly cash flow are.

Jay Conner


So give out that again the calculator that you’ve created is that your website? Your website is and then slash what comes after your website?

Avery Carl


Cash dash flow dash calculator, cash flow calculator with dashes in between.

Jay Conner


Okay, very good. So your company, , what services does the short-term shop provide your clients and customers?

Avery Carl


Great question. So when I started investing, we were probably on our second short-term rental purchase and it was a cabin in the smokes and I kind of realized there weren’t really any real estate agents who could answer even our basic questions about like, Oh, how do I find a cleaner for this thing? How much do you think this will make? So I got my license bridged that gap and became that agent starting what would eventually become the short-term shop. Our first office was in the Smokey Mountains. We now have offices in 15 markets across eight states, all in the top vacation rental markets. And what we do is, so we are real estate agents, but if you buy a property with us, then we’ll teach you everything you need to know about managing it remotely. So we’ll teach you how to set up your Airbnb V B O listings, we’ll teach you how to use the property management software that you’ll need to kind of streamline everything and make it easy for you all the way down to helping you find your local boots on the ground like cleaners, handymen, et cetera. And we do all that while you’re under contract on the property. So by the time the closing date rolls around, you already have a pretty good idea of what you’re doing so you can kind of hit the ground running with making money on it.

Jay Conner


That’s awesome. So what are some of those 15 markets that you have present with the short-term shop?

Avery Carl


All right, so we are in the Smokey Mountains in Tennessee then we are in four markets in North Carolina. So we’re in the southwestern part of the state, which covers basically everything from Asheville all the way down to like Bryson City. We’re also in the high country of North Carolina, so that’s like Boone Banner, elk-blowing rock for people who aren’t familiar. I know you are Jay.

Jay Conner


Oh my land, I was, I was just there last week.

Avery Carl


Yeah, yeah. Then we’re also in the Outer Banks and then we have what we call our Carolina Beach market, which just basically covers all the rest of the North Carolina beaches that are not part of the outer banks. We are in Myrtle Beach, South Carolina, Blue Ridge, Georgia, Gulf Shores, Alabama, Galveston and Crystal Beach, Texas, the hill country of Texas, and Broken Bow, Oklahoma. And then we are in three markets in Florida. So our biggest one is the Emerald Coast, so that’s destined for Panama City Beach, 30 a Pensacola, basically everything from Panama City all the way to the Alabama state line. And then our Gulf Shores agent picks up from there. Then we are just east of the Emerald Coast in what’s called the Forgotten Coast, which a lot of people don’t know about because it is technically forgotten, aptly named. And that’s Cape Sandblast, St. George Island, Port St. Joe, and Mexico Beach. And then last but not least, we’re in what we call the Disney Market outside Orlando in Kissimmee and Davenport, Florida.

Jay Conner


Oh, that’s great. So anyone that’s interested in investing in an Airbnb or short-term rental or VRBO or whatever, then you and your short-term is like done for you. The one place to go where you can help them find an investment property and teach them how to manage it. That’s fantastic, Avery.

Avery Carl


Yeah, and we also have a mortgage arm called the Mortgage Shop, so we can help you finance it too.

Jay Conner


Wow, that’s great. That’s great. But

Avery Carl


That’s not raising private money though.

Jay Conner


There you go. There you go. Well, hey look, I say forge many relationships as you can. So you know, you teased us up front and you teased us one more time. So now you gotta answer the question, how can someone manage their short-term rental from anywhere?

Avery Carl


Really good question. So it’s really just a mindset shift. So you need two people to start off. You can build everyone else out from there. You need a good cleaner, you need a good handy person. And then you need property management software, of which there is a lot we use Hospitable, that’s the one that I use. It’s really easy to use and it automates a lot of the communication with guests. So it automatically sends them their check-in instructions the day before, check-in, automatically sends them their checkout instructions the day before checkout sends them. Ours automatically sends them a few days before they get there. Our digital guidebook, which says, teaches them you know everything they need to know about the property, how to work the thermostat, how far away the nearest grocery store is, all of the restaurants that deliver to that property, and what the wifi password is.

Avery Carl


Just anything you would need to know about living in the property for a few days, we’ll be in that guidebook. So you need that, then you need a pricing tool. But in terms of the mindset thing, so a lot of people are like, Oh, what if there’s, what if something happens? What if something breaks and I need to get over there fast so you don’t need to get over there? If a toilet breaks in my house in Tennessee, I’m gonna do the same exact thing as if a toilet breaks behind me in my office in Florida, I’m gonna call somebody causes what am I gonna do? Am I gonna go fix the toilet myself? I don’t know how to fix the toilet, so I’m gonna call somebody whether it’s 10 feet from me or whether it’s several hundred miles from me. So it’s really just a shift of like, okay, the task is the same. I’m making a phone call, I just have to be comfortable with it, I’m not standing over this person watching them do that. And it’s from there, it’s like you really just build out from your cleaner and your handy person. So as you need more specialized vendors, like maybe an HVAC technician or a roofer or a plumber, those two people will typically have the recommendation to give you, but you just start there.

Jay Conner


That’s awesome. Well, I can see what you mean, Avery. I mean it is a mind shift. I mean right here in my single-family investments, it doesn’t matter. I mean, I’m not, like you say, I’m not going over there to do the repairs myself. Somebody I’m gonna send somebody else or somebody on my team is gonna send them. So you’ve got your mind wrapped around what I call the magic of being a 3D person, which is dictated, delegated, and disappears.

Avery Carl


I like that. Disappear part

Jay Conner


And get out of your own way. Well, this is great Avery, and such fantastic information. One more time, tell everyone the best way to get in contact with you because I know we’ve got some listers that want to

Avery Carl


Yeah, yeah. So definitely follow us on Instagram. It’s at the short-term shop. Or if you wanna work with us in any of our markets or sign up for our masterclass, you would just go to the short term and you can click Get Connected to an Agent. You can schedule a meeting with me. We do actually like an open q and every Thursday that you can get a link to on the website or just shoot us an email, and we’ll get you set up with whatever you need in terms of what we can offer you.

Jay Conner


That’s awesome. Thank you so much, Avery. And so there you have it. Be sure and connect with Avery, Carl, and her team at www the short term Avery, thank you so much.

Avery Carl


Yeah, thank you so much for having me, Jay.

Jay Conner


You betcha. Well, there you have at another episode of Raising Private Money. I’m Jay Conner, The Private Money Authority, wishing you all the best, and here’s to taking your real estate investing business to the next level. We’ll see you right here on the next episode of Raising Private Money. And in the meantime, I need your help. Think of someone that you would love to share this episode with. Be sure and share the episode. And if you happen to be watching us on YouTube, be sure and click that bell so you don’t miss out on any other upcoming amazing shows. Be sure to follow us. And with that, we’ll see you right here on the next Raising Private Money show.