Scaling to 100+ Rentals: The Grit & Growth of Tennis Pro Ashley Freeman

March 19, 2025 00:30:36
Scaling to 100+ Rentals: The Grit & Growth of Tennis Pro Ashley Freeman
The Short Term Show
Scaling to 100+ Rentals: The Grit & Growth of Tennis Pro Ashley Freeman

Mar 19 2025 | 00:30:36

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Show Notes

On this week's episode of The Short Term Show, Avery is joined by Ashley Freeman, a former tennis pro turned short-term rental powerhouse. Ashley shares how she transitioned from teaching tennis to managing over 100 properties in a college town, leveraging local knowledge and relationships for success. She dives into the pros and cons of investing in college town rentals, how her athletic background shaped her business mindset, and why adaptability and competitive edge are key in the short-term rental industry. 

 

How to connect with Ashley:

@Velvet_ditch_villas on Instagram

 

How to connect with Avery:

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

www.strquestions.com

Follow Avery Carl on Instagram 

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Join the Short Term Shop Facebook group!

Check out the Short Term Shop on Youtube

 

 

For more information on how to get into short term rentals, read Avery’s Book, Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties

 - https://amzn.to/3Adg6PA

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Episode Transcript

[00:00:05] Speaker A: Welcome to the Short Term Show. The show about short term rentals and long term wealth with real property owners hosting real properties who are crushing it in the vacation and short term rental space. And here's your host, Avery Carle. [00:00:29] Speaker B: Hey y'all. Welcome back to another episode of the Short Term Show. Today I have the very distinct pleasure of interviewing another Mississippian, which doesn't happen too often, but Ashley has a really cool story. She is doing short term rentals in a college town, which I think is my second favorite type of market to do short term rentals after vacation market. So anyway, I'll let Ashley tell her story. So welcome to the show. Ashley Freeman, owner of Velvet Ditch Vill. How's it going, Ashley? [00:01:00] Speaker C: Hey, Avery. It's going great. I'm super stoked to be here. I've been a huge fan of yours for quite some time. So this is like a dream day for me. So thanks for having me. [00:01:12] Speaker B: Well, awesome. Thank you so much for coming on. I'm really interested to hear your story. So start off just by telling our listeners a little bit about your. And I feel like my accent that has gone away over the years is coming back a little trying talking to you, so. [00:01:29] Speaker C: Oh, I know, I know. And I don't feel like I have a thick accent, but you know, it's cute. So sorry, sorry. I was really. I'll try to tone my mind down. [00:01:40] Speaker B: No, don't. But I just feel like people are going to be like, Avery doesn't normally talk like that. And now she's talking like that. She's being. [00:01:47] Speaker C: Takes one person to just bring it out of you again. Yes. So, yeah, so like many people, this was, you know, big fat accident for me. I, several years ago was a tennis pro here in Oxford and went through a divorce. It was very unexpected. I had a four year old at the time and you know, I just, I didn't know how I was going to make ends meet. Lucky for me, I do live in a college town. Ole Miss is here. And Airbnb was just hitting the market, just kind of gearing up. And so I had this five bedroom, beautiful house on some acreage and I thought, what the heck, I'm just going to go for it and see what happens. And that ended up doing really well. We brought in a little over 25,000 the first year, just, just through busy season. So I thought, oh my gosh, you know, this is amazing for me as a single mom needing some extra income. So I. That's how I first got started. Several years later, I Added a small cottage on the farm. So we live on a little redneck petting zoo. But it's great. It's. I love it. Oxford's amazing. There's an energy here that just cannot be explained unless you've come to visit and, you know, and just get it. [00:03:17] Speaker B: Awesome. So let's, I want to hear, you know, more about this. So you started with one and now you have how many? [00:03:27] Speaker C: We are sitting right over a hundred properties at the moment. And so that was less than three years ago. Started with the, the homestead, which is my farmhouse. And after it did so well, I built the cottage that did really well. I thought, you have got to have a game plan. I don't want to teach tennis forever. My daughter, as she was getting older, it was not as easy to work with the schedule. You know, she was getting out of school, I was getting know, going on to the courts. So that just wasn't going to work well. So I needed to come up with a backup plan. And since both properties were doing so well, I kind of brainstormed with my brother, who's been a huge mentor of mine, and we came up with this game plan to just arbitrage several units. So I had a friend that was looking to, you know, lease his unit that was near the square, which is a really popular, popular place here in Oxford. And so I did the arbitrage model and leased his place, furnished it, picked up another arbitrage model really close to the square. And I just put my, my journey on Facebook and the social media world and people started following me and just asking me like, hey, what are you doing? We have a condo in Oxford, like manage ours. And I just went from having two places to 35 in less than a year, doing it all on my own. I recruited a friend of mine who was really close to me in the teaching world and we just went face first into the. The wild, wild west of Airbnb. So it was. I didn't know what I signed up for, but it ended up being the greatest gift ever. I just absolutely love what I do now. So, yeah, that's how everything started. [00:05:28] Speaker D: Fear not saturation. When you are the cream of the crop, you will rise to the top. Come learn from me. The best in the business. Voted 19 time World's Greatest Landlord. Luke Cash Flow [email protected] where you will learn to be the best in your field and the world's greatest landlord. We are teaching all the best practices in the world of vacation rentals and we would love for you to join [email protected] that what a great story and. [00:06:09] Speaker B: I have a lot of questions, but first I'm going to start with so you're 100 and something units. Are you doing a true property management model where you're doing like a percentage or are you arbitraging those like a master model? [00:06:22] Speaker C: We do a true property management model. So I do own several, I own four and then we are still hanging on to my brother and I still have several, seven actually arbitrage units that do really well only because we know the folks. You know, a lot of that doesn't work anymore just because leases are so high, especially in the college town. People are getting so much money for long term rentals here. But we actually know the folks and they, they really love having us in their units. We're easy to deal with. We're not college kids that tear stuff up. So it works for us. I know it doesn't work a lot of places, but. And then the majority of, of the other units are all property managed. [00:07:06] Speaker B: So I think this is a really good example what you're doing of being able to be successful in a market because you have a competitive edge. Meaning, you know, you, you live here, you understand who comes to Oxford and why. I think that, you know, if somebody from Seattle said, oh, I think I want to try Oxford, Mississippi because I heard Ashley on the short term show podcast, they probably would not be as successful as somebody who lives there and has these relationships with people that you have to get these better rates. So, so I really wanted to kind of shine a light on that because so many people are like, where should I invest? Let me look up the best places to invest lists and then they just pick based on these lists. But they don't really have any connection to or knowledge of the areas and then they're not as successful as they could be. Maybe somewhere that they're a little more familiar with just because, you know, some data companies said, oh yeah, invest here because it's cheap. [00:08:02] Speaker C: Right? No, I 100% agree. If I had not planted roots here and plug myself into the community and built this reputation of, you know, there's so many people and parents and kids that knew me, they trusted me with their business. And also these folks that are coming in that, that are from, you know, Seattle and other parts of the world, if they do buy here, it's very important to get connected with somebody that truly knows, you know, the area, the people that have the connections. You know, we have a person for everything. But I Also genuinely care about how successful our owners are. You know, I know how hard it was for me to get established in this business. It changed my life and so I really, it's, it's super important for me to, for my owners to have that same success. So yes, to answer your question, so important to know boots on the ground and have eyes and ears here. [00:09:09] Speaker B: I want to ask you another question about being a tennis pro. So how do you think being a tennis pro has influenced your ability to be a successful short term rental host? [00:09:22] Speaker C: This is a loaded question. As you grew up too in the sports world everything was performance based. So I just naturally have this competitive side of me. I don't like to lose, I can't stand to fail. And so it gave me this really gritty attitude when going into this market and being able to have my owners backs and really compete because it is. We've seen our numbers increase from 1500 to we're almost, you know, probably sitting at closer to 4,000 units now. And so my ability to just get in there and get gritty, be competitive while keeping a level head when it comes to business is really important. But also the leadership skills that it takes to run a team, you know and the way we empower my team to lead with service and so I think it's taught me so many important lessons. [00:10:34] Speaker B: I totally agree and that's. I'm huge. I don't think anyone's going to be surprised by this about having my kids in athletics and being serious about it. And it's not because I think my kids are the greatest athletes in the world, although they're pretty good but. Or that I'm trying to, you know that I think that they're going to play college or professional or anything like that. Some moms at the four year old t ball games and they're like, we just think it would be great for him to be a, a professional baseball player and see the world. And I'm like girl, I don't know about that. Like first of all he's got to learn how to hit it and he's four anyway. But so nothing. Those are not, that's not why I'm very, very passionate about my kids finding a sport that they really like and being serious about it but because it builds grit. So I don't care if they play college or do whatever if they want to. Great. But it really does teach you how to work hard and you know that stuff hurts. Like you know, you right. Cross country is very painful. I ran cross country all through junior high and high school. And it's. I think for girls it was 2.3 miles maybe, or maybe like a full 5k. I can't remember. No, I think it was 2 and a half. So anyway, you know, that first mile is extremely painful because, you know you're not anywhere close to being finished. Things are starting to hurt. It's. You're, you can't breathe. It's Mississippi. So, you know, the atmosphere weighs a thousand pounds on you. [00:12:09] Speaker C: Oh, my gosh. [00:12:10] Speaker B: Yeah, yeah. But you, you learn to keep going and that it's okay to hurt a little bit and that you're not going to die and you don't stop. And what I do see out of people who, not all people who weren't involved in athletics growing up, but people quit very easily, more easily, I think, than people who did play serious athletics. Because you understand that hurting doesn't mean it's time to stop. Right? [00:12:34] Speaker C: Right. [00:12:35] Speaker B: Well, another thing that I wanted to ask you on the actual tennis pro side, so you have, you have clients that you're teaching how to play tennis, and I would imagine that, you know, that's, that's a bit of a service industry vibe, and you're dealing with people with different levels of experience, different personality types. Maybe you've got a couple, like, quitter types, or maybe you got some people who care way too much and they're being way too competitive on learning how to play tennis. So how do you feel like dealing with a bunch of different personalities has translated over to helping you in the short term rental world? [00:13:07] Speaker C: Wow. You know, it's. You have to adjust quickly and be able to really be very nimble on your. Your feet and toes and just be able to roll with the punches and, and get used to adversity and, and learning how to deal with the big personalities and then the people that, you know, want to have a big opinion about what you do. And so this, how I lead with my mindset around this is, is the same. And I don't think it'll ever change. It doesn't matter if you make a million bucks or if you're the janitor. I'm always going to approach people with respect and love. And, you know, if somebody comes at me with an attitude because they're not happy, I'm going to, you know, listen and listen with, you know, genuine intention and, and lead with a heart of service, like, how can I truly serve you in a way that's going to help you? And I think if you just approach it in that way doesn't matter what attitude, you know, you're dealing with. It's a lot easier to soften the blows from the big attitudes to the small attitudes. But also people. That's all people are looking for these days. You know, it's just to feel special and to know, hey, she's got my back, you know, and so it truly has helped in that way. And I used to be really offended when people did not like the service that we were providing. I took it very personally. And so, you know, that's another thing I had to kind of grow out of. Like, not everyone's going to be happy. You're not going to be perfect. You're not. You know, there. There will be people that don't like you, and that's a. Okay. But I'm. My standards about how I treat other people are going to remain the same and be consistent across the board. [00:15:10] Speaker B: Yeah. And it will. I think that if it doesn't. If you don't take it just a little bit personally, if somebody isn't happy with you or chooses another vendor over you, then, you know, you don't care enough. Because I know it's been 10 years of, of owning real estate and being a host and being a real estate agent. Oh, my gosh, if. If I see one of our clients that we helped listed their property with another agent or bought a property with another agent, that ruins my day, sometimes ruins several days. And, you know, I always ask, always call them and say, you know, hey, what happened? Why? What. What could we have done to keep your business? And it's like, it sucks. And I don't think that, you know, people on the other side of that. So whether it's, you know, people who chose another property manager or what have you, they don't understand how that sucks. And they'll switch, like, on a whim, like you could. It's always the ones you don't think will do it, too. It's the ones that you invited to Thanksgiving when they didn't have anywhere to go. And then, you know, somebody bought them a beer at a bar and they went and listed with them. [00:16:14] Speaker C: So I think that's your competitive side, too, because, you know, like, in your heart, you know, you're the one that's going to be able to take care of them and serve them the best. And so the fact that they didn't trust you, like, what the heck? You know, just like, man, come on. But. So I take it really personally and. But I. I think that's. If you don't if you don't care, I mean, something's, something's not right, you know. [00:16:39] Speaker B: Yes, I, I totally agree with that, that you do have to, if you, if it doesn't ruin your day when your client goes elsewhere, then you're not doing it right. But I want to switch back to Oxford. So Oxford, Mississippi, for those who don't know Ole Miss is there one of the two SEC schools in Mississippi. The other one is Starkville, where I grew up. And so I want to hear a little bit more about this. So in a college town like this, you, you manage, I would imagine, a number of different size properties. What have you found is kind of the magic number bedroom count in a community like this. Because for me, when I think about it, I've never done it, I've never invested in an SEC college town, but I think I would. But like you mentioned earlier, like Starkville is really expensive for a small town in north Mississippi. But anyway, when I think about who my, my guest avatar would be if I were to do that, like is it, you know, affluent alumni that maybe it's two to four older couples coming in or are these going to be, you know, the college K from Alabama coming over for the Ole Miss game and they're going to tear my place up. So I want to hear, you know, what you think the magic bedroom count is and what your guest avatar is for these properties. [00:17:59] Speaker C: Yes, we are sitting right at the magic number of two to four guests. I love a small property. If I could invest, you know, put all my eggs in one basket, I would go all in on two bedroom, two bath properties. They just turn so often here. That being said, you know, we have 15, 15 to 20 really big weekends here that will draw in the amount of guests you need for a four or five bedroom. So on those weekends we do see big numbers. So those, those weekends generate lots of income for these folks. Obviously the smaller units aren't going to generate as much income, but they're going to do it more consistently on a regular basis and they still will draw in a gigantic amount. It's, it's insane. We're looking at two bedroom properties around the square generating anywhere from between two to $3,500 a night for a huge Florida game or a Georgia game. I mean, it will blow your mind brains to think about how much income is, you know, is, is seen on these big weekends. But yes, to answer your question, the smaller units are bread and butter. Just because we see so much turnover. It is the parents that are coming in town, they Might bring a couple friends but just with it being a university town, our avatar is, you know, parents and friends visiting and this episode. [00:19:45] Speaker D: Is brought to you by Short Term rental listing advice. Join this Facebook group and post your listing to get advice from other hosts, including myself on how you can improve your listing or just post your property so you can show off. Join [email protected] that's strange listing advice.com from the hardest working gal in real estate, Avery Carle. We now have a new book, Smarter Short Term Rentals available wherever books are sold. Build a dynamic real estate business and out host the competition that Smarter Short Term Rentals the book. [00:20:35] Speaker B: Okay, and also my other question, I think all the listeners other question here would be okay, so we know football games that we know. I mean and Ole Miss has turned out some serious football players and Mississippi State, we got Dak. [00:20:52] Speaker C: There's a few others out there. [00:20:54] Speaker B: Yeah, but yes, so obviously football, but let's talk about not football season. So when it's not football season, not graduation, are you renting? What, what does that look like? Because I think when people think college towns are like, okay, football season, graduation and then what else is there? [00:21:14] Speaker C: Yeah, we do see a lot of, you know, with, with Ole Miss, the admissions, they keep upping the percentage of kids that they're allowing to come to the university. So with that you see tons of visits, parents visit days, orientation days. We used to be very flat and dead in the months of January, February and then also obviously end of November, December. But we're starting to see that, you know, there's, there's really never a dull moment. There's always people coming in to visit, whether it be a festival that we don't, there's a quilting festival, there's you know, literature festivals. There's, there's usually always something going on. The bigger events are also, they're always going to bring in top dollar. But there's, there's people traveling to Oxford year round now. It's not like a beach community. [00:22:16] Speaker B: Right. [00:22:16] Speaker C: Or the mountains, you know, but you're still going to see a trickle. We've quadrupled our revenue almost every single month. This since it's been over a year. We, we changed some things in our processing systems and we've quadrupled our bookings, but also our revenue just by tweaking a few things. But yeah, the traffic here is non stop. You just have to plug in and know what's going on and you know, cater to those people on social media. And email blasts and things of that nature. [00:22:54] Speaker B: I have another question regarding summer. So I know when I was going to UT in the summertime, I was always scrambling to find somewhere to stay for the summer because I did not want to go back to Starkville. I want to stay in Austin summer. So do you get or do you even offer like summer accommodations for students? Because looking back, that would have been such a clutch and my parents were paying my rent back then anyway, so that would have been such a clutch thing to not have to, like, find somebody's house, to have to, like, sleep on the couch for the summer, which is what I did. [00:23:30] Speaker C: Right. [00:23:33] Speaker B: Yeah. Do you, do you see any of those kind of bookings that something you would consider. You want to kind of stay away from the college kids, which is totally. [00:23:40] Speaker C: We absolutely will absolutely open our doors to college kids for, you know, the summer months if the price is right. Now we know how much we can get if we put, you know, a traveler that's coming in two to three times. So we have a number that, you know, our goal number that we want to reach every month, even during the summer months. So as long as they're willing to pay top dollar to stay there and they've signed all the waivers, hey, bring it on. You know, we're, we're happy to open our doors for. And it makes it easy for us just to have somebody in there for two to three months. But yeah, yeah, yeah, as long as they don't, you know, do keg stands in the living room on the couch. [00:24:22] Speaker B: Well, they don't stay with it, you. [00:24:24] Speaker C: Know, or as long as they clean it up really well. Yeah, we're okay with it. [00:24:31] Speaker B: All right, cool. Okay, so what else about running short term rentals in a college town? Do you think our listeners would benefit from hearing that? I haven't asked. [00:24:42] Speaker C: Oh, let's see. This is like any typical Airbnb, you know, location or you're all, you just have to learn how to roll with the punches. You know, for the most part, we don't see anyone coming into our units and thrashing the units. There's always going to be someone that comes in and does something that, you know, you would consider to be, you know, disrespectful. And you just have to learn to roll with it. I mean, it's the wild, wild West. Especially when you get 300,000 Georgia fans in town and they're all celebrating the same thing. You just have to be able to, to have a good attitude about it. Roll with the punches. Regardless of what pops up. You know, every day is different. But that's what's so cool about this business is it's never the same. You've got to be constantly on your toes and you're the firefighter and putting flames out at all, all times. So that's what's fun about it. I love it. [00:25:45] Speaker B: Yeah, it is fun. It sure beats in an office all day. [00:25:48] Speaker C: Oh my gosh, yes. Or out on the tennis courts with I love my babies, but I taught three to eight year olds and so it was just like herding cats, you know, and just always having to be on and be a cheerleader. And yes, you have to be very. [00:26:03] Speaker B: Energetic with the little kids. My kids are 4 and 6 and they're in tennis lessons and their coach is so great because he's so energetic all the time. But I'm kind of like, oh my God, I would not, I can't, I can't. [00:26:14] Speaker C: So I would, I would sit in my car at the courts afterwards, like and not realize it, but just be in the car for 30 minutes just sitting there like a psycho, you know, just decompressing because I don't know what had just happened, you know, because I had so many kids and so much going on and talk about different personalities and the things, the things that come out of their mouth. I do miss, I miss that. But yeah, this business is life changing and it's exciting and if you're passionate about it, it just makes it all the more worthwhile. Yes, it does. [00:26:51] Speaker B: So we are to the final three questions of the show that we ask all of our guests. And the first one is, what advice would you give 20 year old Ashley? [00:27:02] Speaker C: 20 year old Ashley needed to save some of her beer drinking money and invest it, but also just to take the press off myself, you know, I just, you're. This life is too short and I just, I think I had to be perfect at everything I had to do. And so now I just, I've learned to just have faith in the ride and know that, you know, the Lord is working everything out for me and to just relax and knowing that and take, you know, just take that pressure off and enjoy it. It's it, it goes by so fast. [00:27:40] Speaker B: Yes, that it does. Well, good advice. And question number two, what advice would you give a new short term rental investor who's looking to get started today? [00:27:50] Speaker C: You know, definitely know the location that you're investing in. Definitely have boots on the ground. If, if you're going with a property management company, just make sure they know how to play the game, and they're genuinely invested in your well being as a client. You know, I see so many people that are in the getting business, you know, get, get, get, get, get. And it really just needs to be the opposite. It needs to be us in the giving business, like, how can we give to the client? So just make sure that you are choosing wisely when it comes to property management. It takes a lot to be successful in this business, as you know, and there's lots of irons in the fire when it comes to managing well and knowing how to do it. And so just do your knowledge or do your due diligence and make sure you're choosing wisely when it comes to property management. [00:28:48] Speaker B: Also good advice. And last question, what's your favorite book that's impacted your mindset? [00:28:54] Speaker C: Okay, well, I'm not a huge reader. I really want to be when I grow up, but I'm still working on it. But the last book I read is called. It's called YouTube, actually. It's u Squared. It's by Price Pritchard Pritchett, and It's all of 36 pages, but it is power packed. It's like mindset, A high velocity formula for multiplying, multiplying your personal effectiveness and quantum leaps. And it really, it hits hard. It's really good stuff. So if you're like me and only listen to like podcasts and audiobooks, like actually read this really fast. So I would recommend anybody to read it if they're trying to just, you know, get in a great mindset and get fired up about what you do. [00:29:41] Speaker B: All right, that's a good one. We haven't had that recommendation yet. All right, and last, if anybody wants to follow you, check out your property, see what you're doing. How can they do that? [00:29:51] Speaker C: Yes, I. We are at Velvet Ditch Villas on Instagram and Facebook and also TikTok. And then we are launching my personal branding site, which is Ashley Freeman official. So that will be coming soon, but those are the two places that people can check us out. [00:30:13] Speaker B: All right, well, thank you so much for coming on, Ashley. It was a great show. [00:30:17] Speaker C: Thanks, Avery. Take care. [00:30:31] Speaker D: J.

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