Building Your Dream Team: Proven Strategies for Real Estate Success

Dylan Silver (00:00.643)
Hey folks, welcome back to the show. I’m your host, Dylan Silver. And today on the show I have Ashley Guy, the Femme Investor. Ashley, welcome to the show.

Ashley Guy (00:10.702)
Hi Dylan, thank you so much for having me today.

Dylan Silver (00:13.473)
Absolutely. Right at the top, let’s talk about how you got into the real estate investment space.

Ashley Guy (00:21.538)
I spent about two years looking for a long-term rental. Honestly, I was shopping one day for groceries and some older gentleman came over to me, saw me with my kids and started talking to me telling me that I needed one property for each kid that I had. First time I’d ever heard any type of real estate advice. My parents are very much people that live inside the box. They do what they’re told. They’re the worker bees. Never really dreamt beyond they were supposed to do the status quo.

Dylan Silver (00:36.111)
Hmm.

Ashley Guy (00:50.07)
And so that really intrigued me and we started looking at long-term rentals because at the time they looked like they were a more affordable option. I hadn’t even really heard of short-term rentals. I’m telling you, when I looked at some of these and the returns, I’m not knocking long-term rentals. It just wasn’t what I was excited about. And for me to take a leap of faith into a brand new type of investing where I didn’t know anybody in that space, that was really hard for me. So I really wasn’t sold on it.

And then we had one conversation that completely changed the trajectory of our lives. And that was one of our friends saying, have you ever thought about buying a cabin in the woods? And my response was, why would anybody rent a cabin in the woods? That’s ridiculous. I’m a beach person, not a mountain person. So I didn’t understand at all that that was actually a business model. And we took that conversation, started looking at short-term rentals and

14 days from that conversation, we were in contract on our first short-term rental. And the first goal was to have one property for each kid. And at the time we had five kids. And so we got five properties in our first 13 months of real estate investing. And today we have 11. So we started in 2020, in December of 2020, right in the heart of chaos in America and in the world.

What a better time to just start a brand new business adventure where we were kind of pioneering our own path and it has been pivotal for our entire future. So super blessed for that one conversation that led us here today.

Dylan Silver (02:31.599)
So it sounds like you were initially looking at long-term rentals, but you were saying, you know, this doesn’t seem like the exit strategy long-term. This seems like, how am going to do this long-term? This isn’t it. And so you started looking at other opportunities. Someone mentions cabin in the woods, and you’re like, that’s crazy enough that it might work.

Ashley Guy (02:54.022)
The research really supported it and I could not believe going from making a couple hundred dollars a month as a long-term rental versus making $2,000 a month on a short-term rental at nearly the same purchase price. That was something I could get excited about. Those were returns and you go back to the 2.7 % interest rates, then my risk was minimized.

and we used a 10 % second home loan to purchase. So I minimized my risk as much as possible at that time in order to take that first step. And then we saw very quickly how lucrative that actually was and just continued to buy as many as quickly as possible.

Dylan Silver (03:36.755)
So it started now have the two long terms then first short term is the cabin in the woods and then you’re seeing okay proof of concept Here we go. So at that point in time, are you looking at? Okay, how do we get more of these short-term rentals? Are you thinking let’s see how this goes for a while before we reinvest in a short-term rental another one

Ashley Guy (03:58.19)
I needed about a month and a half of proof before I started looking to purchase the next one. So I saw that very quickly. And this was back in early 21 where you could just have a short-term rental and due to the pandemic, people traveled differently. It didn’t have to be the A plus designs that they are now. So everything rented and it was easier than it is today to be successful in that space.

But we saw the opportunity very quickly and we just started pulling funds from left and right and said, this is what we’re going to do. Committed, jumped all in, and we’ve inspired a lot of people along the way sharing our journey, being totally transparent. I mean, you’ve got parents of five young kids that took a gigantic leap of faith, put a lot of money into a property, into a place that they had never been. So I’d never been to…

the Smoky Mountains of Tennessee, have no desire to go there either, bought the property site unseen. Just as like as crazy, you check mark every box of, as crazy as it sounds we committed and we just started replicating that. We would do a lot of research really quickly, understanding the market, what you need to be successful, connecting with real estate agents that were short-term mental focused and can really give us their opinion and some guidance.

And we bought five properties in three different states in 13 months.

Dylan Silver (05:32.899)
Wow. Okay. Let’s talk about that first one in Tennessee. So you buy a site unseen. At this point in time, you’re familiar with long-term, not familiar with short-term other than the research that you’ve done. This person telling you cabin in the woods. Do your research. Buy the cabin in Tennessee. At that point, next steps, I’m imagining you go out there and you make an Airbnb ready, right?

Ashley Guy (05:36.738)
Mm-hmm. Mm-hmm.

Ashley Guy (05:53.878)
I went out there and I changed absolutely nothing. I was like, I refuse to shower in here. I don’t know why anyone would want to do that and left and said, I’ll be totally fine if I never come back. Because it’s not for me, but I understood that it was for other people. And so the second one happened kind of organically because it was actually, it’s a back neighbor to the current cabin, to the first cabin. And I saw it pop up. It was at a great price.

Dylan Silver (06:06.605)
Yeah.

Ashley Guy (06:20.034)
And we knew that we were going to have to switch to do a 15 % investment loan. So it’s going to require more capital than the first one from a percentage standpoint. So I needed to reduce my purchase price. And so I saw this, we actually were in a bidding war because that was the time and we missed out and I couldn’t let it go. I couldn’t let it go. And then about 10 days later, it fell out of contract and our agent said, hey, do you want this? It fell out for inspection. Here’s what’s wrong with it.

it’s yours if you want it. And I was like, sold, wrap it up. That’s what I want. I know exactly where the property’s located. I know the clientele that comes there. And it was a different occupancy size. And so that was really great for us to start diversifying and doing trial and error on different sizes in that market.

Dylan Silver (07:08.847)
You know, this actually speaks to the idea of acquiring properties that are in proximity. I’m a wholesaler by trade. so when I would go look for buyers, one of the things that you would do is just start with people who are in the area. And they might not seem like on surface they may be a real estate investor. But if you tell them, we have this, this is next door to you, are you interested? It’s surprising how many times this happens. And so you get

Effectively, I call this boardwalk and park place when you have the two like a monopoly board next to each other. So you have boardwalk and park place. You’re two cabins in the woods. When I think cabin in the woods, I’m in Texas. And so we see lots of wood cabins. got Jacuzzis. It’s nice interior, but it’s still a cabin. Is this what this is or is this more not that?

Ashley Guy (07:58.582)
a little bit more budget friendly of an experience. They still absolutely had hot tubs and they were surrounded in woods. They were up on the side of a mountain, which was the appeal. Gravel road. One of them is log sided. So it looks like it’s, you know, true log cabin. And that one’s a studio. That was the second one. And the first one was a three bedroom. And that one, the last person had done a shoddy makeover to it.

Dylan Silver (08:00.398)
Okay.

Ashley Guy (08:28.074)
and I bought it, rolled with it, and it still looks the same today. So, it’s a workhorse. I mean, that’s what I was looking for. I wasn’t looking for a vacation home at the time. I just needed something that covered its bills, because that’s what I was so concerned about. And we didn’t really do anything to either of those first couple cabins, because we didn’t have the funds for that, or we allocated the funds to continue to scale.

Dylan Silver (08:34.607)
But it’s written out like a champ, god bless.

Dylan Silver (08:58.649)
So at this point, you have two cabins in the woods. You got the two long-term rentals. And at this point, as far as total time in, it sounds like you’re still newer to being in this position. How long are we talking here? Like a year, two years? How long is this between getting your first long term and now having two short terms and two long terms?

Ashley Guy (09:19.054)
So we never committed to the long-term game. So we didn’t purchase any of the long-terms, so it was two years of searching for long-terms, no pulling the trigger. Then December 2020, we closed on the three bedroom. And then February 21, we closed on the one bedroom.

Dylan Silver (09:21.667)
Okay.

Dylan Silver (09:38.849)
Okay, okay. So at this point in time, you got the two short terms right next to each other. They’re both doing well. It’s also like peak COVID. So it’s interesting time to a person, right? Especially, especially I don’t know how things were in Tennessee specifically, but that’s still East Coast. So I’m in Texas. So things might have opened up a bit, but I East Coast was a little different. So from there, you’re seeing proof of concept, you’re seeing this and it’s going well.

What’s the thought process and are you thinking, okay, how do we get as many of these as possible and what was the next steps looking like from there?

Ashley Guy (10:12.686)
I’ve always wanted to own a beach house. Go on vacation every year and my parents would take us to the same beach, Holden Beach in North Carolina every year. That’s where I up, went for 25 plus years. And I always, you we’d rent somebody’s house. And it was back in the day when we didn’t call it VRBO. We would use the property management companies that were local. And you’d be like, who owns this? Is it a doctor? Is it a lawyer? Is it this?

really wealthy person, like you must be extremely wealthy to own a beach house. And then we were thinking, wait a minute, we know how to make this thing cover its expenses and then we can own the beach house. And so we pivoted to the beach at that point. And that was in July of 21 that we bought our first beach house in Gulf Shores, Alabama. So that was our first thought.

Dylan Silver (11:10.319)
Okay.

Ashley Guy (11:12.526)
And how to kind of get there, so let me take you back because one of the things I think I’ve mastered is what I call like your order of operations for loans. Because there’s a very specific order in how you have to purchase based on when you file taxes. And a lot of people don’t know that. So I’m really passionate about educating people on if you are looking to scale, what order to do that. So in the end of 2020, the first one, we purchased with a second home loan.

And despite its name, second home, you can have nine second home loans according to the government. So knowing that I could do that one time, it automatically qualified me for the investment loan. So I knew that I was automatically qualified for the 15 % down loan next. So I did that. And then I filed taxes in April of 21 and re-qualified.

because now I had a little bit of rental income, I could offset the debt that I took in, and I was able to re-qualify for a 10 % down loan again. And so that’s when we purchased the beach house with just 10 % down. And so we really just tried to minimize our risk. And I know that comes out an ugly interest rate, but the goal was kind of different because at the time interest rates were ugly was still 4.5%.

Dylan Silver (12:39.375)
Yeah.

Ashley Guy (12:40.814)
So it was still tolerable. But that’s how we got to scale financially.

Dylan Silver (12:44.247)
And so you.

Okay, so at this point, you’re realizing I maybe I’m developing a niche here with understanding you call order of operations, where when how to utilize tax strategy to your benefit, you’re seeing that there’s ways where you can acquire more property and how am going to find the capital to purchase these properties. So you have your two cabins in the woods, you have the beach home. And I’m imagining at this point, you’re like, wow, this is really like my dream. So I have the beach home over here.

I have the cabins that are renting it out. They’re pretty much hands off. let’s talk and let’s pivot for a bit here. Cabins are in Tennessee. You’re in Alabama and this is where the beach home is. And so how are you managing the cabins in Tennessee while living in Alabama?

Ashley Guy (13:19.875)
Mm-hmm.

Ashley Guy (13:32.974)
So I did not live in Alabama when I bought here. I lived in Ohio. So I moved from Columbus, Ohio to Gulf Shores two years ago. And that was simply because this stream that we built allowed us to then now live permanently by the beach. So I was remotely managing and I self-manage all of my properties from Ohio utilizing the softwares at the time.

that either were newly developed or were continuing to improve. And that allowed me to run a really, really smooth operation, but I had to have great cleaners. Your cleaners are your eyes and ears, and they’re in the heart of the business. And so that was a struggle to get those established, get your boots on the ground group perfect in order to make sure that you could run it effectively from offsite. So that’s.

That’s how I started setting it up and I, it’s weird now living in a state where my properties are five minutes away. I don’t like that, but we’ll talk about that when we get to a little bit further down this timeline.

Dylan Silver (14:43.907)
Let’s talk a bit here about cleaners and finding the right people. Now, 2025, I’ve spoken with some people who are involved in all different types of short-term rental businesses. I would call it service providers to that space. Then, I don’t know what was in the space, and for sure there was lots of service providers. I don’t know if it is exactly where it is today. Was it as simple as you just go onto an app and you can find cleaners back then?

Or was it a little bit more challenging? were the apps not particularly helpful as far as consistency?

Ashley Guy (15:18.03)
We never used apps. would either, so one of our strategies was to message other hosts. We would look at their reviews and if they were bad cleaning reviews, we’d ask who their cleaner was, because I wanna not work with those groups. And then if they were great, I’d also wanna know who they were working with. The other thing that we would pursue was Facebook groups. The local Facebook groups, your locals are gonna tell you, your mom and pop, they’re gonna tell you who to avoid.

Man, if you let the locals give you an opinion, they’re gonna give it to you. So that was really pivotal for us to get some feedback of, hey, here’s who to use, here not to, who not to use.

Dylan Silver (15:52.196)
Yeah

Dylan Silver (16:02.393)
So then you get your team, have your two rentals, you have the beach home. How do we scale from there from three properties to 11 and under, you know, four years from there?

Ashley Guy (16:14.456)
So we actually refinanced the first one, took it from a 2.7, I think, to around a five, pulled all the money that we put in there and used that as a down payment. We also did a 401k loan from my husband’s W-2. And that was one of the secrets I felt like that kind of got unlocked for us. I work with a really great lender who helped me strategize all the next moves.

and some of the things that I just didn’t know, like the 401k loan. So that was really great for us to say, we can pay ourselves back, but we know that we’re gonna leverage it and put it into something that is gonna make money and be an appreciating asset and check all the boxes. So that was helpful. We also brought in partners. So that was a big step for us.

Dylan Silver (17:08.495)
What year did the partners come in? 21, okay, so right at that time. you, in hearing this and getting a picture of it, a better picture of it now, you’re seeing proof of concept, you get the second one a month later, and so you’re saying, how do we expand? Let’s bring in partners. A lot of people, they don’t get this till years later, like 10 years later. And so you figure it out right away. And so at that point, did that feel to you actually like, wow, this is, you know,

Ashley Guy (17:10.286)
21.

Yeah.

Dylan Silver (17:35.777)
a big journey that I don’t know how to navigate or was it like second nature to you like I’ve done this before let’s go get these partners and it’ll be a value add for both of us.

Ashley Guy (17:44.968)
I live by the motto commit and figure it out later. So I still, I mean, I thought I wasn’t even a year in, I was hardly six months in and was, but I had enough proof of concept that other people wanted a piece of it. And so my first partner was actually my parents. So it wasn’t that I went out and got somebody I didn’t know or an angel investor, but my dad has always wanted to just take a risk, but he just wasn’t

raised that way, didn’t have enough confidence to believe in taking such big risks, because my dad is a savior. So he works for a large bank.

Dylan Silver (18:19.843)
What did dad do for work?

Dylan Silver (18:25.251)
Okay, so bank guy, I can imagine sometimes banks and real estate. It’s like the banks don’t want to own the real estate. Everybody in real estate knows that the banks don’t want to hold the real estate. So bank guy, dad comes in, he’s like, Hey, I trust you. Here we go. You do the first deal with dad. And then from there, did you expand to maybe more distant family and then from their friends and people seeing the deals that you’re doing and say, how do we be a part of this?

Ashley Guy (18:32.11)
Yes. Yes.

Ashley Guy (18:48.832)
No, so we just have two partners. One is my parents and then one is a longtime friend of my husband. And my parents, we have two properties with. They bought a beach house here as well. And so that’s really great. They have a place to stay when they come see us. So there’s some of that, you know, emotional ROI in that as well. And it’s convenient. But for them, it’s the same. It was the same thing.

Dylan Silver (18:51.48)
Okay.

Ashley Guy (19:17.688)
They rented beach houses from other people for a long time. And then now they have their own slice of that. Like that is so cool. There’s so many people that can’t say that. And then on the flip side, this is what I love is all those memories that we hold as a family, we create for other families now. And it like makes me want to get emotional because it’s so full circle and it’s such a blessing to, you know, give back to what everyone that let us rent their.

Dylan Silver (19:20.239)
Mmm.

Dylan Silver (19:26.543)
Cool.

Ashley Guy (19:47.384)
how escape to us as kids.

Dylan Silver (19:49.615)
Okay, so now it seems like a whirlwind, but actually to you, this is just how you go. You’re like, I’m gonna dive in. you’re two and a half years in, and you basically go from just, really being on the outside looking in, which is how a lot of people stay for long periods of time, to then getting two properties, I call it Boardwalk and Park Place in the woods in Tennessee. Then you have the beach home, you get a second beach home, scale it up, and so now you’re rolling, right?

And so at this point, you’re not even three years into this and you’re doing well. We haven’t even gotten to talk about the managing 25 plus properties and owning a short term rental cleaning business. How did that come about? Or were you doing these things beforehand?

Ashley Guy (20:17.198)
Yes.

Ashley Guy (20:35.19)
No, I didn’t do any of that until we moved here. So I was in network marketing for 11 years prior in Ohio. And then my husband was a registered nurse. We knew that we didn’t want to live a traditional life and we couldn’t figure out those first steps and short-term rental helped propel us into the right direction of taking Leaps of Faith. And we relocated our family in March of 23 from Ohio to Gulf Shores.

And it was at that time that I got licensed for real estate to be able to sell here. You know, for several years I was consulting, helping people choose short-term rentals to purchase, but not as a real estate agent. And so the plan was when we moved here to start a management company, to start a cleaning company, and for me to sell real estate. And we can fully service properties that we own, but we can help others along the way.

Dylan Silver (21:30.541)
Yeah.

Ashley Guy (21:31.402)
and the management company grew organically extremely fast. It’s like anything else, if you’ve got a good recommendation, you’re gonna share it. And we started with one and that person told somebody else and then the next person was happy and they told somebody else and it became this domino that grew very quickly. We’ve been in the property management space for about 18 months now and for us to not advertise any of…

Dylan Silver (21:40.164)
Hmm.

Ashley Guy (21:58.966)
our services or for any of these properties, like that’s really, it’s really humbling that a lot of people trust us with their property, not only for maintenance, but then to cover their bottom line. That’s a big, big job. And then we couldn’t, yeah, it’s a lot of pressure.

Dylan Silver (22:10.817)
It is a big job. It’s huge. Those next guests are depending. I I certainly know. And then these Airbnb’s, know, people can leave it in any kind of condition, right? And so you have to come in and kind of get it ready for the next people. And so this actually has me thinking, because I just got my license in Texas, in Dallas, real estate license, actually two weeks ago.

Ashley Guy (22:17.486)
you

Dylan Silver (22:35.311)
First a question on that was the test hard the test up here was so hard I didn’t think I passed I passed it on the first try, but I was like I don’t think I passed that it was so hard was a test hard for you Yeah

Ashley Guy (22:43.826)
It was so hard. It was so hard and I felt like they didn’t teach us any of that. None of the practice questions were right. But same thing, I walked out of there going, I have no idea and she hands me a paper and it says pass and I’m like, you’re joking, right? Because I did not think I did well. So, all right, congratulations.

Dylan Silver (22:48.203)
It was so hard.

Dylan Silver (22:59.191)
Yeah, I stayed up all night. Thank you. Yeah, because it was I let me get out of here before they find out that I didn’t pass. But I somehow passed. And the machines that I have everything right now is digital. So that was my first time in a very long time taking a test like that. It was incredible. But I digress. So you go and you have the real estate license, property management, getting 25 plus properties, property managing, short term rental cleaning business. I imagine now you really have a niche.

in that area as far as being kind of the short term rental go to person for a lot of people. It’s like, hey, this woman owns these properties. She does it herself. She’s managing other people. She also does the short term cleaning boom, boom, boom. If you’re interested in this space, you should reach out to her. And it was just really organic growth for you.

Ashley Guy (23:51.586)
Absolutely, and what I offered to my real estate clients that I end up almost best friends with every real estate client because I have a genuine interest in their success and my goal You know just kind of like I talked about owning the beach house is just to give back to What helped get me here and I wish I would have had somebody that held my hand a little bit more So I could have made less mistakes and less costly mistakes. So that’s what I offer for my clients I helped them completely get set up

They get my advice whether it’s unsolicited or it’s truly needed or wanted and I want them to be successful. No one’s investing in real estate to just be average or to not do well. And so I really take that on and that has helped grow these businesses too, that they’ll trust me with their properties for cleaning. Or they trust me with their properties for management. Because they know my standard and they know that I have proof of concept that

I keep setting higher rates and higher rates and my revenue is just increasing. So if they want the same, they’re going to follow my steps.

Dylan Silver (24:57.461)
right now focused in Alabama.

Ashley Guy (25:02.026)
Actually, we’re still split. So I have some up in the Smoky Mountains and then I have one in Blue Ridge in Georgia and then I have several down here in Gulf Shores.

Dylan Silver (25:16.527)
and the ones that you manage are spread out like that as well. Okay.

Ashley Guy (25:19.406)
Actually, the ones I manage for other people are all in golf shores, but I still manage all of my properties that are out of state.

Dylan Silver (25:24.046)
Okay.

I think, know, selfishly I’m thinking, hey, how do I do this? I’m a licensed realtor now in Texas. And I’m also thinking, you I know all these investors. I really feel like I know so many people with Airbnb’s. I don’t know if they use the same people or not. Maybe they do, but maybe they’re doing it themselves. I’m thinking, you know, I can’t think of a big name that comes to mind. It’s not like I’ve seen the people at the meetups or the, you know, mastermind groups. I don’t know. So I’m thinking, hey, maybe I should go do this. So

Thank you for bringing this to the audience selfishly. You know, I may go look into this in Dallas and yeah, such an interesting way to expand organically from doing it yourself to then realizing I can get the shore home, multiple people, investors, family, husband’s friend, get the license, and then other people are seeing what you’re doing and just organic growth. that’s, that’s a testament to something’s working.

Ashley Guy (26:21.742)
I I think we’re doing pretty well.

Dylan Silver (26:24.577)
We are. We are coming up on time here. I would really love to have you back to discuss a deep dive into some more short term rental strategies, which you didn’t get to talk on as granularly. But actually, where can folks go to get a hold of you?

Ashley Guy (26:41.27)
Easiest place to find me is on social media. It’s at the FemInvestor, F-E-M-M-E, investor. And TikTok is my primary social media platform of choice. So you’ll find real raw and ugly on there anytime. So I’d love to connect with you. Truly reach out for anything. If you’re looking for guidance on your listing, if you wanna talk about expansion, if you need help connections,

of lenders or cleaners or real estate agents. I’m part of a great real estate team as well. So we are nationwide and you’ll get to work with somebody that is completely focused on short-term rentals. And that’s the Savvy Realty. We’re Savvy STR agents and we’d love to absolutely serve you in this capacity and help you find a very profitable short-term rental.

Ashley Guy (27:36.718)
Dylan this was awesome, we need to do it again.