Social Media Secrets: Boost Your Real Estate Career Like Ashleigh

Dylan Silver (00:00.782)
Hey folks, welcome back to the show. Today on the show I have Ashleigh Gillespie in Denver, Colorado and she is the National Director of Sales for Savvy STR Agents. Ashleigh, welcome to the show.

Ashleigh Gillespie (00:15.915)
Thanks so much for having me, Dylan.

Dylan Silver (00:17.888)
Absolutely. I’m a little jealous because you’re in Denver and I always see, especially now that the college football team is such a big deal, all the beautiful landscapes you have out there in Denver, Colorado. Are you taking advantage of that?

Ashleigh Gillespie (00:21.515)
you

Ashleigh Gillespie (00:29.685)
Yeah, absolutely. I do call myself a fair weather hiker, so I don’t go out too much this time of year. We just had a big soft hail storm, so the start of hail season is here, and I’m super excited for the warmer weather to get here so I can get back out on the trails.

Dylan Silver (00:48.544)
I am very jealous. kind of have a bipolar sense of where I want to live in the country. I’m like, do I want to live in Fort Lauderdale or do I want to live in a place like Denver, Colorado? Which one do I want? And I can’t pick, so I’m kind of in the middle in Texas. But Ashleigh, how did you get into the real estate space?

Ashleigh Gillespie (00:57.815)
Ha

Ashleigh Gillespie (01:08.908)
Yeah, am I?

journey into real estate was not very intentional. I actually took my first real estate course in college in Southern California. My first class ever. I thought it was the most boring thing. I was like, I’m never going to get into real estate. This is terrible. And then I transferred schools to one in Boston. And if you know anything about the education requirements there, it’s much lower. It was only 40 hours to get my license. And I had a friend that was helping me buy a house.

He convinced me to get into real estate. I was like, well, it’s only one really long weekend to get into sales, so I might as well try it out. So I got in while I was going to college, graduated college, and I was like, well, you make a lot more money with real estate than with a degree. So here I am.

Dylan Silver (01:55.288)
Yeah, that’s how it happens. I do see that trend as well. I went to school in Boston briefly at Northeastern. Which school were you at in Boston? Get out of here. Well, you graduated. I didn’t, but I still have love for Boston. And when I was there, they were winning so many championships. It was a really cool city to be a part of. And so have a lot of love and affinity for Boston. So you’re now active in the real estate space.

Ashleigh Gillespie (02:03.307)
That’s where I went! Woohoo, go Huskies!

Ashleigh Gillespie (02:15.414)
Yeah.

Dylan Silver (02:24.266)
in Boston, talk about the first year, the first couple deals.

Ashleigh Gillespie (02:29.729)
Yeah, luckily I was really stuck in that place a lot of agents are where you don’t know what you don’t know and that can be a good thing and a bad thing. For me, it was a great thing. I walked into a real estate office and I signed up and I said, well, what do I do now? Somebody handed me a book of Tom Ferry scripts and they said, do you know how to go to the white pages? I said, sure. And they said, here’s the scripts, just go call people. And I said, okay. I didn’t say like, what’s the do not call list or you what do I do if somebody

mad at me I just started calling and I learned all about calling expired listings for sale by owners I was cold calling and I got into real estate in 2014 so home prices were really just starting to recover from that initial crash in 08 09 and I found a lot of luck with old expired so people had tried to sell and just couldn’t get what they needed out of the property were finally at a place with their equity that when I called it was time to go and it

It was a great niche, I learned a lot. It was just a really hard grind.

Dylan Silver (03:34.368)
It is a hard grind, especially being young. don’t know, were you in a sense very familiar with the business maybe from family or friends or was it totally new to you?

Ashleigh Gillespie (03:45.01)
I was very new in terms of real estate. I had bought my first home before that. It was a foreclosure. It was all pink and outdated. So I had lived in it while we fixed it up and sold it for a profit. And that got me kind of hooked on like what real estate can do. So I was on my third house personally by the time I got licensed.

Dylan Silver (04:07.118)
Okay, so you were in the game, but just not for other people. You weren’t listing other homes. So at this point in time, you’re still in school or you’ve graduated.

Ashleigh Gillespie (04:17.617)
I was selling homes for about a year by the time I graduated.

Dylan Silver (04:22.816)
Okay, wow, so that must have been a balancing act.

Ashleigh Gillespie (04:26.379)
Yeah, it was. I’ve always found school to be, I’m learning based, so school’s always something I enjoyed and not too much of a challenge for me. And that’s something that’s worked well in real estate for me too, right? We’re always learning.

Dylan Silver (04:35.062)
Okay, that’s good.

Dylan Silver (04:40.182)
Yeah, I’ve noticed this. Yesterday I was speaking with a guest who was a nurse. She has a PhD. She was a commercial realtor and a bunch of others. And so it was like a spaghetti line of different initials and things. And I was like, wow, this is a very accomplished person. But you see a lot of that. And so from there, Ashleigh, talk about scaling. What was the next couple of years like? And and how did you end up as the national director of sales over at savvy STR agents?

Ashleigh Gillespie (04:52.779)
Hahaha

Ashleigh Gillespie (04:58.603)
Yes.

Ashleigh Gillespie (05:10.017)
Yeah, I did probably the thing that you should never do, which was relocate when I was two years into the business. So I was in Boston. It wasn’t where I was from. I loved things about Boston, but I hated being so far away from my family who was all in Colorado and California. And I made the decision that we were going to move. had two young kids, wanted them to have a different upbringing. So we moved to Colorado, came to Denver and restarted completely from scratch. I had no one really left in the

area that I knew. Everybody had moved away, had no sphere of influence to rely on, and had to start all over again.

Dylan Silver (05:48.168)
tough. I can relate to that. I’m in Texas kind of by accident but now that I’m here in Texas I love Texas and I feel like I would never want to move elsewhere unless it was a Colorado or Fort Lauderdale like I’ve previously said. But those first couple years in Denver were you basically building out your network or did was it a

Ashleigh Gillespie (06:04.34)
Yeah.

Dylan Silver (06:16.588)
divine intervention, you hit the ground running. How did that work?

Ashleigh Gillespie (06:18.388)
Yeah.

Yeah, so I said to myself, well, you’ve done this once before. You can do it again. And so I started with my cold calling, my expireds, my for sale by owners, and I had some success there. But the grind the second time around was a lot harder. So I was like, you know what? There’s got to be another way. And I started to do more social media and more agent networking. Specifically, I started with videos and I just those took off social media videos in about 20.

2016-2017 just started flying and I ended up getting a great network a great sphere I was getting a lot of agent referrals and that was the key to rebuilding a new business in Colorado

Dylan Silver (07:03.662)
So how many people where you were in Denver were doing what you were doing being active because of course we see it now on social media but back then I don’t know who is active on Denver social media.

Ashleigh Gillespie (07:16.523)
Yeah, it felt like not many. You know, at the time, there’s so many people saying it was time to start doing video, but TikTok wasn’t around. Instagram didn’t have reels. You still had to upload things to Facebook in landscape mode. Like there was YouTube, but no one had really cracked that code yet. So it was just really interesting to be in that space at that time.

Dylan Silver (07:40.376)
Yeah, there was a gentleman who I was talking to who moved from Chicago to Northwest Arkansas and became the relocation expert for people who are considering moving. And so I put it in YouTube, sure enough, first thing that comes up and he’s one of the top brokers in Northwest Arkansas. And so he said, I had people who told me I was going to move to another area of the country.

Ashleigh Gillespie (07:50.923)
Love that.

Dylan Silver (08:08.75)
But then I saw your videos and now I’m moving to Arkansas. He said that was a lot of pressure.

Ashleigh Gillespie (08:12.341)
Wow, yeah, no kidding. That’s cool.

Dylan Silver (08:17.302)
So for you Ashleigh, when you’re building up that following, I’m imagining you’re getting listings and you’re feeling like, okay, this is going well, how did that scale for you?

Ashleigh Gillespie (08:28.981)
Yeah, so social media, the great thing about it is it’s very scalable. You take down a lot of the resistance from when you’re cold calling, they don’t trust you at all and you have to fight so hard to get in the door. And even once you’re in the door, they still can be resistant and you have to continuously push that sale, push the closing. Social media, they come to you and they don’t want to talk to anybody else. And so it makes your conversations faster. There’s less follow up involved. And I was able to scale up very quickly.

to a lot of sales and I ended up getting asked to become a real estate coach with a Keller Williams office here in Denver. I took that position and really more out of a favor to a friend thinking I would hate doing it and ended up loving it so much that I put out into the universe that I was open to being a coach on a more on a higher level for more advanced agents and ended up as

director of sales for a residential team here in Denver.

Dylan Silver (09:32.974)
Hmm, I think the coaching space is very interesting and honestly Ashleigh I feel Strongly that a lot of people are Not able to capitalize on it because it feels like such a draw on their time and that Coaching in the real estate space is actually like ripe for innovation because there’s so many people myself included who would love to have real estate coaching but there’s

Ashleigh Gillespie (09:53.942)
Yeah.

Dylan Silver (10:00.686)
in a sense that the people that you want to coach you sometimes don’t have the time or maybe it’s simply a financial matter. You know, it’s either a nominal fee or it can be quite costly. And so I just have this sense that it’s just ripe for innovation that these people, myself included, who are looking for coaching, it’s going to be a expanding space.

Ashleigh Gillespie (10:05.622)
Mm-hmm.

Ashleigh Gillespie (10:23.287)
Absolutely, I would agree with that. And I think it’s been so difficult to navigate, especially when you’re new, how do you tell that a coach is going to be worth the money? Even if it’s not a huge investment, right? Some coaches are 500 bucks a month, some are eight grand a month. How do you know that that’s going to be worth it? And that’s scary. Yes.

Dylan Silver (10:41.986)
Yeah, it’s a leap of faith. It’s a leap of faith. I mean, I can say in my experience, I did not come from real estate, did not know a single person. Like it was actually the opposite of real estate, I would say. At that point in time, I was, you know, working in restaurants, then I ended up selling cars and was working for a Nissan dealership where it was very, very long hours in San Antonio. And I just felt like it was literally impossible.

Ashleigh Gillespie (11:06.956)
Mm-hmm.

Dylan Silver (11:09.954)
it was literally impossible to go learn anything when you’re working six days a week, 12, 14 hours a day. to me, it was quite literally a leap of faith. And I wish that it would have been easier at the time, but I just knew that I wanted to get in the spaces willing to do anything in order to grow and to break in. But pivoting a bit here, Ashleigh, so at this point in time, you’re a coach, you’re active, and you’re doing well in Denver. You’ve got the social media presence, you’ve scaled.

Ashleigh Gillespie (11:20.238)
yeah.

Dylan Silver (11:38.818)
people are coming to you so you don’t have to be actively seeking out listings and so on and so forth. What were the next couple of steps like for you and how did you end up with savvy STR agents?

Ashleigh Gillespie (11:53.494)
Yes, so.

Really a couple of big flunders. I had a year where I was just losing a few listings that I thought I had in the bag and it kind of checked my confidence a little bit. COVID had happened so real estate was hustling and bustling here. It was insane and I was really struggling with my residential buyers especially because they were very emotional. It was definitely difficult right to lose out six, seven times before you finally get a house under contract. Sometimes waving those inspections and

you’re hoping that you’re doing the best you can to help people and to help guide them. But sometimes they look at you and they’re like, am I making a good decision? And you’re like, I don’t know. Do you like the house? Like, that’s kind of what matters, right? You live in it, not me. And that was really difficult. I’m not much of a feelings person. And so people being so emotional was a struggle. I went to list a house and it was a potential flip. The investor offer

we got was so good that I decided to match it and drop any commissions so my sellers could net more. And so I picked up a flip just in time for the interest rates to flip on their heads. What was that in 2022? So I closed and just about a week later they announced that interest rates are going up. So I’m doing work on this flip. I’m trying to get it done in time, watching interest rates go up every single day and the market shift what felt like overnight.

And I had a hard money loan out I had never used hard money before and it was definitely a leap of faith that didn’t work out I had to sell it for a loss and this is where I got into short-term rentals because I Knew that I was looking at a loss And I was trying my best to navigate some sort of pivot that would help me something else I can do and Short-term rental was the one that I was like I can cash flow this and still afford the pay

Ashleigh Gillespie (13:54.73)
Payments on this crazy high refi But Denver has such strict STR regulations that I actually could not get a permit for it and I had to sell for a loss But it was one of those things where you your eyes open up and you’re like, wait a minute though If I could have cash flowed that where else are you able to buy a short-term rental? What numbers are other people doing? I had really just not even paid any attention to it So that’s what got me into the space and into looking

out what is even the potential of the short-term rental and Airbnb markets.

Dylan Silver (14:29.696)
On a personal note, did you have fix and flips or rental properties at that time or was it you had a homestead and you were an active real estate agent but you weren’t actively investing for yourself?

Ashleigh Gillespie (14:41.771)
Yeah, so I’d continuously actively invested. I had had some long-term rentals in Southern California that had worked out fine, but I was never happy with the cash flow. I had a property manager. I’d picked it up at a good price, but it still was just such a nominal amount of cash flow that I almost thought maybe I’d be better off sticking this in the stock market or sticking it in fix and flips where that cash turns around faster. I’ve done, I’d done a few fix and flips. I had a condo that had been a great success.

not too far behind the one that flopped. But sometimes those are the ones where you learn the most. The ones that you mess up real bad.

Dylan Silver (15:20.642)
Yeah, it’s an education. I’m not the hugest proponent of a traditional education, although I love people who are able to succeed with it, just for me personally, I didn’t jive with it, but I think education in the real world sense, like you doing the fix and flips, those will teach you so much, especially when you don’t necessarily come out on top.

Ashleigh Gillespie (15:41.643)
so much.

Dylan Silver (15:46.254)
Some people fight through it and are successful and continue to do that and other people pivot as it seems you have. So from that point in time, you’re seeing that this short-term rental space is a potential cash cow for lack of a better word. And you’re seeing, well, how do I get further involved in this?

Ashleigh Gillespie (15:46.678)
Yeah.

Ashleigh Gillespie (16:06.133)
Yeah, so the next step was definitely like most people and like you said seeking some education Where are the trusted people in this space and it’s really difficult because when you first start talking to you know, like bill faith kenny bedwell these big short-term rental influencers and they say the numbers that they’re doing and they’re too good you’re like No, there’s no way you guys are doing this because you’re selling me a course and then you get into the software platforms like air dna that’s polling the actual occupancy rates and

the actual nightly rates of these Airbnbs and you’re looking at the numbers like this is insane. The question then becomes how do you scale something short term rental wise? It’s very different. The management is different. It’s way more hands on. It is not my favorite for people that are looking for passive income. And so that can be pretty daunting to say like this is going to take work. I can’t just set it, forget it and you can get property.

managers for it, but obviously that cuts into your profit. there’s some question about is that worth it? Are they getting me the best revenue possible? You know, these large property management companies for short term rentals, we’ve seen the data support that they’re getting much lower returns than some of the local, know, locally owned property management companies. And so it’s a whole different world. You come from long term rentals and you think that you must have a pretty good understanding and it’s a

whole new education.

Dylan Silver (17:37.568)
It is an entirely different world. I was talking with a gentleman in Miami who all he does is service provider to the Airbnb space. He doesn’t do the cleaning. He manages the communications with people. And then I believe he also facilitates bookings on other short term spaces. And he’s like all over the country and in the Dominican Republic, Ghana and Belize.

Ashleigh Gillespie (17:39.915)
You

Ashleigh Gillespie (18:04.936)
Wow.

Dylan Silver (18:04.95)
And I said, wow, that’s a business that’s even out there. And yeah, it is. I mean, there’s so much way to expand in this. you know, to your point, Ashleigh, it is daunting, right? Like in my mind, if you want to be on Airbnb, it’s yeah, for the ROI that you could see, but also I tend to think you have to love to host people. You have to love to be a host.

Ashleigh Gillespie (18:08.852)
yes.

Ashleigh Gillespie (18:29.121)
Sure.

I think that can be part of it. was actually recently chatting with somebody that was like, think I want to sell my property because I hate being a property manager. And I think that that’s a fair assessment. And at the same time, like we don’t always love every facet of things that we do. This is a people business, but real estate is also a people business. So there’s a component of frustration. And if you really don’t do well with communicating with people, probably not the space for you, or maybe you need to offload it to a property manager.

co-host something like that to do that portion of it.

Dylan Silver (19:04.46)
Airbnb is very communication intensive. Even when I go book it for myself, I’m like, I’m weeks out from this and so much communication. You know, it’s like if you go book a upscale hotel, you’ll get a confirmation email and that’ll be about it. You know, there’s no multiple weeks out communicating with the host. How do I enter? You know, Wi-Fi, when am I leaving pets, you know, so there’s a lot that goes into Airbnb. And so,

Ashleigh Gillespie (19:11.319)
Mm-hmm.

Ashleigh Gillespie (19:29.257)
yeah.

Dylan Silver (19:32.792)
you know as someone on the outside looking in I didn’t even know that you know there was all these different roles within the space so what’s your role as the national director of sales at Savvy STR agents?

Ashleigh Gillespie (19:47.798)
Yeah, so we are an extremely busy team across the country here. We’re in almost every single market and our agents are short-term rental experts. They own short-term rentals, they manage short-term rentals, and they help people buy and sell short-term rentals. One of the things that we run into a lot is people needing education around that Airbnb space. How do they identify a good property? What’s a realistic idea of returns and what market do you buy in?

When people buy long-term rentals, they tend to gravitate towards purchasing nearby because it’s a little less stressful to manage a property that’s nearby. With short-term rentals, it’s less common. You usually want to go buy where the returns are, which might be a vacation city that you don’t live in. And you really need a local expert that’s going to help you understand that, that you can lean on, that has the vendor list, that can connect you to a property manager. Otherwise, you know, people think of it as, it’s real estate.

I’ll just contact my buddy and ask him if he knows somebody there. And they end up with agents that don’t understand the short-term rental space or don’t have the vendor list. They don’t know how to run a pro forma and they buy these properties that are poorly performing. And so that’s another piece of our business is helping people sell these poorly performing short-term rentals to then get them into an actual profitable property.

Dylan Silver (21:12.472)
So many questions. I, let’s say I’m first time looking at purchasing a short-term rental. Would I be reaching out to your team, Ashleigh, to find me a short-term rental or would I be reaching out for guidance or both?

Ashleigh Gillespie (21:13.943)
You

Ashleigh Gillespie (21:26.645)
Both. So we actually have a process where we do a market discovery call. We have a client care specialist, Scott, who will chat with you about your current experience with STRs, what you might already know or not know, what expectations you might have. And we’ll ask if there’s a market you’ve already identified you’re interested in. But from there, Scott will actually pair you with three different agents and three different markets that he believes would be a good fit for you. You can then talk to all three agents, hear what they think about their market and what

whether it’s a good fit for you. And a lot of our investors will actually work with three agents at a time until the right property comes up. And so that’s a very unique team angle that you can work with multiple agents at the same time in different locations. And that’s all free. We just only charge a commission upon closing. So you don’t have to pay upfront. There’s no retainer fees. And we’re helping you understand the market, helping you identify the market, getting you paired up with somebody who’s going to help you under right properties.

So our process, we send you properties. We’ve already identified what their revenue projections are. We help you understand what value adds. Maybe you need to add some great design. Maybe it needs some amenities. We help you with budgeting that and then we negotiate you a great deal. Help you go through the contract phase like any transaction you buy the house. We’ve got great lenders that can do DSCR loans, no down payment loans.

or back down in 6 % interest rates too. And then you can also do conventional financing for it. So we get everything you need start to finish and then you are up and running but you’re not abandoned. We’re still available to help you if you have a cleaner that didn’t show up to a job or you you need help with something. Our agents are there for you long after that transaction closes.

Dylan Silver (23:20.238)
This is so novel and new. I’m thinking of it like a broker on steroids for short-term rental. And also what a niche that has been carved out here. Cause I can’t imagine there’s that. I mean, maybe there are, but I don’t know about them. And if I’m thinking, Hey, where do I go? I want an agent to help me in the short-term rental space. I don’t really know who do I call? You know, call Ashleigh, call savvy STR agents.

Ashleigh Gillespie (23:47.766)
Yeah, exactly. And that’s exactly what we’re trying to do. We’re trying to help agents. We know that they want their clients to find a good deal. And the problem has really been a lack of education in the real estate space around whether or not you should be helping your clients with a short term rental if you don’t understand that space at all. And we’ve seen agents that unfortunately have put clients into homes that are not possible. The regulations do not allow it. And now these clients are sitting on homes that they can’t rent out, they can’t cash

They’re selling at a loss a year later. So it’s really important that if you are an agent that doesn’t understand the short-term rental space that you partner with us. We love having referral partners to work with us and we are always happy to help educate your clients and get them into a profitable home so that you still look like a hero in their eyes.

Dylan Silver (24:40.814)
My thoughts on the Airbnb space are it’s such an unbelievable expanding space and I think most Americans may not be aware of how global this is. You know if you go to developing countries, you go to Caribbean, if you go to Latin America, they’re everywhere but also colloquially they’ll call them B &B. know, air may be difficult to say, right? So you’ll be in Latin American country, they’ll be B &B, B &B, B &B and I’ve traveled so I’ve seen this.

Ashleigh Gillespie (24:52.471)
True.

Ashleigh Gillespie (25:04.417)
Mm-hmm.

Dylan Silver (25:10.958)
No one has a crystal ball for the future, but what’s your thoughts on, you know, where this is heading?

Ashleigh Gillespie (25:18.251)
Yeah. So the regulation and Airbnb space has been very interesting over the last five years. We had a huge boom in Airbnb during COVID times when you couldn’t really travel on airplanes. Countries were locked down. It was all very difficult. So people turned to staying in large Airbnb’s for their vacations. And there’s this huge boom. Everybody saw this potential for revenue and they just started buying up properties to slap them on Airbnb. And the problem was that that worked only for that specific time.

Now the Airbnb got saturated with subpar homes. There’s no quality control You know, sometimes you stay with a host who’s just awful, right? They give you this huge chore list to do at the end and they charge you a cleaning fee and they still get mad at you at the end because you left like a pack of unopened beers in the fridge and The quality control hasn’t been there So I see the future as being we are probably going to see some type of quality control get implemented with Airbnb some sort of

expectations of hosts and making it a little bit better for the consumers who stay at Airbnb’s to have an idea of what to expect across the board. So I expect we’ll see something along those lines soon. We’ve experienced it in Denver with regulations. You can still Airbnb your personal residence. So if you want to rent out your basement, put a room on Airbnb, you have an ADU, all of that’s allowed. But they went all the way into

No other STRs are allowed and I think we’ll continue to see some cities implementing some restrictions and regulations I don’t know that how many will see do a total ban because it has turned into an issue for some areas like Boulder they’ve had some regulations around short-term rentals and now they just announced that the Sundance Festival is moving from Park City, Utah to Boulder, Colorado and it’s like do we have enough rooms available for the

influx that we’re going to experience? Do we loosen those regulations? So there’s a question about finding balance. We went really far one way and now does it start to retreat to a more balanced area?

Dylan Silver (27:31.246)
Yeah, I I lived in San Antonio the last five years before moving up to DFW Metro at the tail end of last year. And the final four basketball tournament is in, I believe, San Antonio. And I’m reading this thinking, you know, it’s already, you know, kind of congested. Where are all these people gonna go to? And they’re doing so much construct, I mean, so much. If you’re in the San Antonio area, you know, like this is peak construction for the city of San Antonio. They’re adding like a second.

Ashleigh Gillespie (27:48.864)
right?

Dylan Silver (27:59.798)
I guess layer or level on the highway system out there that wraps around the city. There’s whole areas that are like cordoned off. You can’t go there at nighttime. And so I’m thinking, wow, gonna be interesting. But we are coming up on time here, Ashleigh. Where can folks go to get ahold of you?

Ashleigh Gillespie (28:18.859)
Yeah, so we have a website, Savvy.Realtee. That’s a great place to go. You can check us out. You can read more about us. We are all over Facebook as well. If you look up Savvy STR Agents, you will find us. And then you can also find me on Instagram and TikTok at That Realtor. Pretty easy to find.

Dylan Silver (28:41.304)
And I’ll just say this to our listeners, I think the Airbnb space, short-term rentals, whichever avenue you decide to go into, it can be overwhelming. You might not have that trusted resource. And so just to know that that exists out there is comforting and I think a lot of people are not aware. if you’re potentially thinking about it, reach out to savvy STR agents and have a chat with them and…

Take away some of the fear in that process so that you’re with an expert that can guide you down the path.

Ashleigh Gillespie (29:16.328)
Absolutely, we’d love to help.

Dylan Silver (29:18.976)
Ashleigh, thank you for coming on the show.

Ashleigh Gillespie (29:21.643)
Thanks so much Dylan.