How Jeremy's Best Friend Andy is Financially Free from Airbnb

Quick Summary

Jeremy and Andy discuss strategies for achieving financial freedom through short-term rental (STR) investments, co-hosting, and value-add real estate projects. It emphasizes taking action, building relationships, and adopting creative finance strategies to overcome barriers to entry in real estate. A focus on scaling investments, optimizing property performance, and maintaining work-life balance is central to the approach.

Key Points

• Use renovations and upgrades to increase property value and cash flow potential.
• Apply the "BRRRR-STR" method (Buy, Rehab, Rent as STR, Refinance, Repeat) to scale investments while minimizing upfront capital.
• Utilize tools like seller financing, subject-to agreements, or HELOCs to acquire properties in a high-interest rate environment. These strategies help overcome challenges like limited bankability and rising borrowing costs.
• Develop strong connections with mentors, clients, and professionals in your market to access new opportunities. Realtors, investors, and property owners can be critical to growing your portfolio and establishing credibility.
• Focus on creating a business model that supports financial independence and aligns with personal goals, such as time for hobbies or travel. A balanced approach can still generate significant cash flow while maintaining quality service and work-life harmony.

Full Transcript

Check out full episodes on:

1. YouTube
2. Spotify
3. Apple Podcasts

Jeremy: We are live with the Short-Term Rental Pros podcast today. I'm super stoked to be here with not only my first mentee ever but actually my childhood best friend as well. I mean, we've been through a lot together—not just in short-term rentals, but also in life. Really, you know, our stories have kind of come up together. So, I'm really, really happy today to hear from Andy Gillespie.

Andy is a realtor and also a short-term rental operator with a portfolio of properties that he manages or co-hosts, as well as ones that he's bought himself. Andy's done a lot of home renovation projects—I call him "Handy Andy" because he's really good at being a value-add investor and leveraging the cash flow from short-term rentals.

We're going to get into his story today, talk about how he got clients, discuss how he identifies lucrative properties, and really dive into the life that short-term rentals have created for him.

So, Andy, thank you so much for joining today!

Andy: Hey man, it's a pleasure. Thank you so much for having me! And yeah, like you said, unfortunately, I've known you for a long, long time—since about second grade.

Jeremy: Hey man, yeah. Well, Andy will give you all the tea on me back to elementary school! But yeah, really, I guess tell everybody your background. I'm sure there's going to be a lot of similarities to my background, so this will be fun. But AO, where are you from, and how did you, you know, get to where you are today?

Andy: Yeah, so for those who don't know, Jeremy and I's story or our connection—we both moved to North Carolina around the same time in second or third grade. I think he was coming from New Jersey, and I was coming from Long Island. We ended up at the same school, and we were basically in school together all the way through college.

We played sports together and even ended up playing on the JV basketball team at UNC together. It seemed like our paths might split a little bit after college—when I was attempting to apply to medical school, and Jeremy was moving to New York and doing other things. But our paths came back together during COVID times. It seemed like everybody from our childhood was coming back into town, and I was seeing a lot more of Jeremy than I had since college ended.

That’s kind of when my STR (short-term rental) journey started. Jeremy had the audacity to join me and my family at our beach house in Oakville and bring a camera. He basically said, 'I'm going to take pictures of your house, and we're going to list it on Airbnb, and we're going to make a ton of money.' If anybody knows Jeremy, he is super rambunctious and can just kind of be a force of nature. So, we let it happen, and that was the initial introduction to short-term rentals for me. From there, we worked together, and it has blossomed into something really good for both of us.

Jeremy: Yeah, and Andy actually helped with boat rentals too early on. I was telling him, 'Yo, these Airbnbs and these houses are crazy, so you’ve got to get into it.'

At the time, AO was—guys, AO is his nickname, childhood nickname, so if I keep saying AO, that's what I call him—Andy was at the time a medical scribe, getting paid... what were you getting paid, like $15 an hour?

Andy: Yeah, so this is a funny story. I was working in the emergency department at UNCC. It was one of those jobs that was a means to an end—something I was trying to get some experience with on my resume to look good for med school. I’d been working there for about a year before COVID started.

When you reach the 1,000 hours worked mark, you're supposed to get a promotion. That promotion was $1 an hour, so it was going to go from $10 to $11 an hour. By no means was I thinking this was going to be a forever job—like I said, it was a means to an end, and money didn’t really matter.

But then, COVID came. They reduced all the bonuses for non-essential staff members, even though we were still working in the hospital while COVID was going down. We were frontline, basically, working every single day in the emergency department. They didn’t approve our $1 an hour bonus for the scribes.

At that point, I was like, 'This is complete BS. I cannot rely on somebody else, especially if anything goes down, to provide for me and my family one day.'

And it just so happened that’s when me and Jeremy kind of reconnected, and we were doing a bunch of work together. It did start with the boat rentals, which was a very fun and pretty lucrative summer for both of us.

I think basically he had started the boat rental business at Ohio Lake first, and I’m not sure how many boats you had at the time when we decided to start at Jordan Lake. But I remember you were doing all the research on the Google Analytics, saying, “If it works at Ohio, why wouldn’t it work at Jordan Lake?” The analytics were honestly even better there.

There was only one other boat rental company, and they weren’t doing weekend rentals. So, you basically were like, “Let’s start at Jordan Lake,” and I was going to be the full operator of this operation at Jordan Lake.

I was hands-on, putting boats in the water, meeting with all the renters, and doing some minimal bookkeeping. I did that for the whole summer while we were also kind of getting into some co-hosting and that type of stuff, which I think you’ve shared quite a bit about on the show—kind of your start as well.

Jeremy: Yeah, so when Andy and I, we were pretty much playing tennis every day. COVID hit in March of 2020, I went back home to North Carolina, and we just started playing tennis. Obviously, we’ve been really close friends for a long time, but, you know, I had been living in New York, and he was working a medical job in Chapel Hill.

So, there wasn’t a lot to talk about from a business standpoint. But once we started playing, I was kind of like, “Wow, this is crazy.” You know, I had the experience initially with the boats as well as the first properties I managed.

I’m like, “Dude, these things are making a lot of money, and wait a minute…” You know, I’m pretty nosy—I ask questions, and I can be kind of a brute, pretty forceful. But when Andy’s telling me all the stories about how, “Oh, next week I’m supposed to get a $1 a week raise promotion,” and then that week goes by, and he’s like, “They took it back. Never mind. They’re making us work more because they need more shifts. A lot of people are quitting, and there are a lot more people physically at the hospital. However, now we’re actually getting paid less.”

I was like, “Dude, come on, man. We gotta—All right, check it.”

Andy: It was eye-opening for me too. I think it’s really good to have those types of conversations with somebody like you, who’s so open about numbers and talking about money and things of that nature. If I had only surrounded myself with people who were aspiring med school students, it wouldn’t have even crossed their mind that that was weird.

But when you’re like, “Wow, dude, come on, man. They’re taking away your $1 an hour raise? How freaking disrespectful is that?” I think that was eye-opening for me to a certain extent too.

For me, I had always had aspirations to be an orthopedic surgeon, to work in the sports field. I was always very connected to sports. And, you know, when I think about it.

Jeremy: And he’s very athletic. Andy—Andy can dunk.

Andy: Uh, thank you, Jeremy.

Jeremy: He’s an athlete, just in case you guys didn’t know. He was always more athletic than me. He was an All-Region High School football player, and he was, you know, a really good basketball player as well. So, it made sense that you wanted to work in sports medicine.

Andy: But yeah, so I guess when I think back on it, a lot of my aspirations to do that were: A) because it’s, you know, sports-related, but B) those are the highest-paying jobs in, you know, the medical fields. It’s going to be your super niche or your surgeon that needs to go to four extra years of residency.

And so, when I think about it, it wasn’t like... it was a dream of mine, but it wasn’t something that I was dead set on—like I wouldn’t be happy if I was doing anything else, for example. So, when Jeremy came around, it wasn’t hard for me to be convinced to pivot into something else. And I think it’s opened up so many more doors for me too.

Jeremy: Got it. So, you initially... that first property, uh, for you, was like taking an asset— you know, a friends-and-family property. Which is actually funny, that specific property, because, I mean, your family bought that house in foreclosure, in distress, in, what, 2013 or 2014? And I remember us literally going up there and sleeping on the floor.

The fans all had, like, birds in them. Like, it was completely in distress. There were holes in the walls. It was a POS. It had—you could look out and see the ocean, so it definitely, you know, had potential. But we literally slept on the floor. There wasn’t any HVAC at the time, so we had to open the windows, and, you know, bugs were flying through.

And so, really, like, I feel like we got, you know, experience. And, you know, I’ll give a shout-out to Phil there being like, ‘Hey, you guys want to enjoy this? We’ve got work to do.’”

Andy: Yes.

Jeremy: We gotta, we gotta get our hands dirty. And so, really, you kind of helped renovate that property. And your family just used it for personal enjoyment, but you also kind of let friends use it, and you charged your... I mean, Andy was telling me, like, how much they charged their friends. And I was like, ‘This is too low.’

Like, obviously, you know, I love coming—don’t get me wrong, I love that I can come and hang out—but, like, you know, you could definitely... you know, you should, if you’re already renting it to friends, like, you guys don’t use it all the time. Yeah, rent it out the other weeks you don’t use it and get a premium for it.”

So, yeah, I literally took my camera and invited myself over to their beach house. And, uh, I don’t remember if I made their listing or you made it, but whatever—we got that one up. So, that was your first one.

And then, at about that time, I was showing Andy, like, “Yo, check out how much these boats are making. So, check out how much the houses are making, but, like, the boats...”

And, you know, we’re both just right out of school. Like, we had very little, you know, money to invest. And the math on the boats was, at that time, like, really... I mean, just feel free. I mean, COVID was crazy for boat rentals.

Like, I mean, right now there’s still obviously opportunity, but COVID—like, if you think Airbnb was crazy and good during COVID—like, boats were just on another level. Like, how much could we rent out the boats at that lake, uh, each day in the summer?

Andy: Yeah, man, I mean, it varied, but you’d have weekdays at $350 a day, and then you would have your weekends at $500 to $600. And then, uh, holidays... I mean, shoot, I think there were times where we peaked at, like, $1,000 or $1,100 for a boat rental for a day. And, you know.

Jeremy: We would do, like, two half-days—like, two half-days at $500 or $550. So, it’d be, like, a thousand bucks a day, per boat.

Andy: And, uh, I mean, we only had... I guess we had two operating pretty much the whole summer. And then, um, a third that I think we might have gotten out a couple of times.

But, I mean, being that it was just me running it, I mean, two was a good amount for, you know, a first summer. I mean, I basically learned how to trailer that boat the first day I was taking it out to a renter. So, you know, a little bit of a learning curve, but I got really good at it by the end.

But, yeah, no, they were crushing it. And I saw how well they were doing at Ohio, and I thought it would be cool to get involved. And I was in the area anyway, for... I was still scribing at the time, just every once in a while. So that was it.

Jeremy: Got it. But I like to give numbers on the podcast, just because I’m a numbers guy, and I think people like it. But I think—yeah, I could probably look it up and probably should have had it prepared—but I think that, like, those two boats really, uh, I think they probably both made, like, $35,000, $30,000 apiece.

Yeah, uh, that summer. And, you know, that summer was, like, three months. You know, we didn’t run those from, like, April to November—it was really just the peak season there. So, you know, pretty, pretty solid.

Again, for a one-man shop to do, I don’t know, let’s say, like, $75,000 in, I don’t know, 100 days. Yeah, like, so $700 bucks a day on average—pretty, pretty solid. And then, you know, you took your cut and what you did.

And also, obviously, what I’ve been doing is, then you invested that into growing your portfolio. So, tell me about that first investment you made.

Andy: Yeah, so my first investment was buying a duplex in Downtown Wilmington. Obviously, we had those... I had connections with the Oakville area—my family had been coming down here for years. I wanted to be nearby, but I was also a huge fan of the Downtown Wilmington area.

Running some numbers, you know, I found that they cash flow super well. At that point in time, anything was cash flowing, though. The interest rates were so low, you could literally analyze any property, and it would most likely cash flow at least a little bit.

But for me, I was looking for somewhere that I could move because, at the time, I was living at my parents’ house. I could move into it and also rent the other side. So, it was a bit of a house hack, but it was set up as a duplex, so it worked out just perfectly.

I put a good amount of my own money, time, and effort into renovating this unit. It was $210,000 a side, so $420K total for this duplex. I utilized a first-time home buyer loan, and I think we put in $20,000 in renovations on each side. That honestly might even be high—I literally did everything myself, with the exception of the countertops, and we had some people come in and put in LVP flooring in the kitchen.

Everything else, I did myself. I was grinding in here, sleeping on the floors. It was pretty much still COVID at that time, so I didn’t mind. I didn’t have FOMO from seeing people in bars or anything like that—I was just chilling here, working on the house.

I sanded and refinished all the floors. And, yeah, then I got the next-door unit furnished before I officially furnished the side that I was technically going to live on. I got it renting on Airbnb, and it’s done about $4,000 to $5,000 a month consistently for three years.

Jeremy: So, and you’ve also—again, I’m the numbers guy here—and I mean, Andy showed me this deal at the time and got my feedback on it. But your mortgage on both sides is like $800—like $800 a piece or something like that?

Andy: Yeah, exactly. I think at this point, it’s $900 for the Airbnb side and just above $1,000 on my side. That might be because we added some wind-and-hail insurance or some sort of other insurance, but the principal and interest are ridiculously low—it’s like $500 or $600 a month.

So, yeah, it’s ridiculous. This could cash flow with any sort of exit strategy that you wanted to do. I could rent this out; I could mid-term; I could short-term—anything would cash flow.

It was a great deal at the time, and, you know, I think this just goes to show that I didn’t have all the expertise at the time. But just getting into the game... now in hindsight, I’m thinking, 'Wow, I mean, this was an absolute home run deal.' But all the nerves and, you know, getting into it in the beginning—it’s all worth it. And I think just taking action is so important.

Jeremy: Exactly. And so, you also rent out—so, just to give the context—and I know a lot about Andy here, so, you know, I didn’t prep him to give this to me. So, if I’m wrong, Andy, correct me. But there’s two sides. Both sides are two beds, one and a half bathrooms.

The side you live on—you also rent out that other room, and you rent that out at about, like, $800 a month.

Andy: Yeah, so initially, when I first finished, I was still living at home. So, I actually rented out both bedrooms in here. I didn’t even live here for the first year and a little bit that I had this house.

Jeremy: Slept on the floor, lived with my parents. Like, no—we both did what it took early on, for sure, just to keep every cent we could possibly keep in order to grow.

Andy: It didn’t make sense for me to move here at that time and pay the mortgage myself, even if it was just on one side. So, I rented out both rooms, I think at $700 a piece—so $1,400 a month on just my side as a long-term rental, basically just renting to friends who lived in the area and were also in a similar stage of life post-college.

And, yes, so that worked out great. This side was cash flowing about $400 to $500 a month, and the other side was cash flowing $2,500 to $3,500 a month. That’s kind of how it all started. And since then, I’ve moved—I have moved in here, yeah.

Jeremy: Okay, so that duplex strategy. So, you initially, you know, started with boats, co-hosting, duplex strategy. What was your next move? How did you scale from there?

Andy: Yeah, so I think co-hosting was a big... you know, it was kind of a priority at that point. After I deployed the little bit of capital that I had into my own property, I was pretty much broke again.

So, co-hosting was the obvious next strategy to generate some more cash flow. I started marketing to people in Wilmington as well as back in the Triangle. I remember, you know, I had been somewhat involved in talking to some of your first co-hosting clients on Ohio and just being, you know, somebody—a facilitator in the area.

And then I used that experience from working with you and your clients to then market to people in Wilmington. That’s how I got my first co-host deal down here. It was basically a mutual friend, and they had an extra house they were looking to rent out. They had just moved, and I pitched them on Airbnb.

In this area, it’s kind of a no-brainer—it’s basically double the potential income for them, and it’s still hands-off. Especially if people are moving from a house that they’ve been living in and they want to get new furniture, it’s also a lot easier to just utilize some of the things that they already have in the house. And, you know, I pitched them on pretty much all the benefits that co-hosting has to offer.

Jeremy: Yeah, I think one thing that was interesting that we did early on—because, you know, we first got my first co-host, then you got your first co-host—so we didn’t have, like, an expansive portfolio like we have today. But we kind of used each other’s listings to, you know, make ourselves appear more credible.

So, when we would go to someone, we wouldn’t say, 'Oh, I only have one property,' you know, one listing. We would add each other. You know, we would add each other to each other. So we’d say, 'Oh, no, we have our beach division, and we have our lake division.'

Andy: Yeah, exactly.

Jeremy: We have our Triangle division.

Andy: Yeah, there was a point in time there where we were kind of almost sharing a PMS, or I had your properties also on my PMS. And then your side of it just kept on growing and growing and growing, and I was like, 'Okay, I might need to split this up or get his off of mine quick.'

Jeremy: You were probably getting a lot of notifications.

Andy: Yeah, definitely.

Jeremy: I went balls to the wall.

Andy: Yeah, you did.

Jeremy: Andy’s had a more tapered approach versus me.

Andy: Yeah, and I think that’s another important note for anybody listening. I feel like everyone can kind of grow at their own pace and focus on the areas that they want to focus on more.

You were expanding the co-hosting very rapidly. On the other hand, I’m kind of selecting and only marketing via word of mouth. So, I wasn’t expanding as fast as you on the co-hosting side. I think that’s just important for people to know—it’s like you don’t necessarily need to go completely gangbusters. I mean, you can do it at your own pace but still have a pretty good little portfolio of listings.

Jeremy: Got it. So, right now, we’re at the beach condo or the beach house, the duplex, the one in Downtown Wilmington. Then you picked up one in the Triangle region of North Carolina, and then you kind of got a 'mac daddy' property at the beach that you took over from another property manager.

This is something that I’ve talked about on previous episodes—I talked about it with Mike Riley of STR Secrets, and I just talked about it with Jetstream. You took a property that was like a Vacasa property, one that was very poorly managed.

Andy: That’s right.

Jeremy: You took it over. So, can you walk us through how that happened?

Andy: Yeah, so this homeowner had their property managed by a local beach company. There are all sorts of beach realty or beach property management companies that are local or semi-local and have local operators in the area. For years, I think they were pleased with their service.

Then Vacasa came down and bought the contracts—not all of them, but a pretty large portion of these smaller, beach-style realty companies. From what they were telling me on our initial introductory calls, they just couldn’t get a hold of somebody.

They used to have a local office. Now those people were basically fired or moved into other areas of the company, and they couldn’t get a hold of anybody. They didn’t feel like it was a personable management experience.

And so, when I basically reached out to them to say, 'Hey, I know you guys—it sounds like you guys are not happy with your current situation...'

"I'm local. I have a smaller portfolio of properties, and, you know, I can offer something that these other, bigger corporations can't. I don't think that that is something Vasa necessarily took into account when making these big acquisitions.

This isn't the same as a long-term rental lease acquisition, where the homeowners don't really care. Some of them are pretty hands-on, and that was the case here. These homeowners are pretty hands-on with their property, so they want somebody who they can get in contact with, who they can meet in person.

We can kind of do like a hybrid strategy—implement what they want to and implement my management skills. So that was kind of what happened there. I can see that being a big way for people to target co-hosting properties.

Jeremy: And I say it's a really good place to be in the vacation rental management game. Less properties is an advantage in many ways with this boutique vacation rental management.

You know what Vacasa did—they tried to swallow and buy up everybody. It is hard to offer that personalized service when you've got 20,000 properties.

Andy: Exactly.

Jeremy: When you've got 10, you know, seven, 10, 20, 25, you can offer that service. When you get to, like, 100, it becomes more difficult.

However, I kind of want to preface this with the lifestyle aspect of what you're doing. Sitting at that 10-property mark—you’re cash flowing a good bit. You're profiting. You're providing good service. If the owner wants to send you a message, text you, and give you a note on something, you can respond to it yourself.

It’s not overwhelming; you're not getting too many of those a day. But, you could live a pretty damn good lifestyle. So tell us about that—kind of like, you know, what’s your 'why' and why have you crafted the business that you have?

Andy: Yeah, I think, you know, I am a pretty big lifestyle guy. I do enjoy the idea of being able to go surf in the middle of the day or, you know, play basketball or travel. By no means am I saying that I'm just content with exactly where I’m at.

I think I’m always looking to grow and always looking for ways to increase my cash flow and increase my net worth.

Jeremy: You're under contract on another house right now.

Andy: I am, I am. Yep, that’s the next move. But yeah, for me, I mean, that was really the 'why'—the ability to... and I think it’s actually funny. When I bought this duplex that we were just talking about, and I’m living at my parents’ house and I’m cash flowing, we were kind of joking around: 'Oh look, we reached—or you reached—financial freedom.'

I’m like, 'Heck yeah, dude, I guess I did.' You know, I don’t have to worry about my bills at this house, and I’m cash flowing. I could basically—I mean, if I wanted to continue to live off $3,000 a month for the rest of my life, I guess I could.

That’s one way to describe financial freedom. But obviously, we weren’t done there.

Yeah, so I am under contract on another house. That’s kind of the next move. I’m looking to probably do a midterm rental on this side of Dock Street. That’s the goal.

Jeremy: Oh, wow. You wanna move out? Or so this new house is for you?

Andy: Yeah, yeah. Well, I’m going to move into it. It needs a lot of work, so I’m gonna kind of do a live-in rehab. Handy Andy is gonna come back, and, um, yeah, gonna live there and renovate it.

Then I think we’ll just completely short-term rental it in a year and then move into. Probably, yeah, yeah. And then, uh, likely move into... uh, I don’t know. We’ll see what happens after that.

Jeremy: But, um, you’re gonna—you’re gonna—you’re gonna add value. So, essentially, you’re gonna kind of like live-in flip.

And I want to—just for example, that first property you bought, that duplex—you bought it for 410 grand. You worked on it yourself for a couple of months. It’s not that much, you know—it’s like, what, two years? Three? Or three years later?

What do you think? Uh, I think you recently—I remember you asked me about a HELOC, like, kind of to give you the rundown on how that works. Did you go through with the HELOC? And what did they value the property at?

Andy: Yeah, I did go through with the HELOC. So, I have that line of credit, which I’m hoping to use for some of the rehabs on this next project.

But I just did it on one side because, weirdly enough, this duplex was actually deeded as two separate properties. So, I just, uh, had one side appraised and got a HELOC on it. And it appraised at 328…

Jeremy: So if you multiply that by two, yeah, now you’ve got a $656,000 asset. You initially bought it for 410. So Andy’s net worth has gone up a quarter million dollars in... so he’s made the cash flow. He’s quote-unquote—when we say financial freedom—like, I’m gonna admit, we kind of laugh.

We laugh—it’s a joke, you know. Not that financial freedom is a joke, but just, like, the concept and everything we see on social media—it obviously gets, you know, thrown out there a lot…

Andy: Just an overused buzzword. But I do love cash freedom. Yes.

Jeremy: Yeah, so AO’s got that financial freedom, you know—the monthly cash flow that, you know, pays for his bills. He’s able to save some in order to, you know, invest in real estate.

He’s also creatively using the equity he has in his first property. So, again, guys, it went from 410 grand. He put a low down payment on one side and had to put a higher down payment—had to use more of the boat money than he probably wanted to use on the other because, you know, unfortunately, they deeded it as two separate lots.

But you used the equity—the equity gain from that property—pulled a home equity line of credit against it to now, uh, do the down payment or the improvements on this new property.

And then what you’re going to do is you’re going to improve it, you’re going to increase the equity value, and just keep rinsing and repeating, right?

Andy: Exactly. And that’s—you know, I’m a big proponent of doing value-add to STR. It’s almost like a BRRRR-STR strategy, where you buy, rehab, then short-term rental, then refinance.

But I, yeah, I think that’s a huge—it’s a huge opportunity to get into a property. And then you can basically, uh, end up having no cash into the deal if you structure it right after you, uh, do these renovations and then refinance.

Jeremy: And then do the next deal.

Andy: Exactly. So it’s definitely—especially when you’re doing it my way—I have to be very selective on what deals I’m taking on. Because, you know, I’m not the most... I don’t know the word for it, but bankable or loanable person in the world.

I’m also, you know, like... I don’t—I’ve never had a W2, except for in the hospital, which I don’t think would ever qualify me for a loan. But I have to be—

Jeremy: It helped for that first—you were able to get, like, an initial loan, and you’ve done some, like, DSCR stuff…

Andy: Exactly. DSCR stuff, yeah. And that’s something else that I think is going to be huge in the next year or two. And something that I’m really focusing on is trying to be a master at finding creative finance deals. I think that’s going to be the name of the game here in the next year or two.

Jeremy: I asked Andy what episode of the pod he liked the most, and that was the one he said—the one with Ryan Bakey. Yeah, I guess it makes sense now.

Andy: Yeah, definitely, definitely. No, there’s a ton of value in that episode. And, you know, I feel like I’ve just ingested a lot of information and a lot of, uh, knowledge from different people online about creative finance in general. It just makes a whole lot of sense in this financial environment that we are in, in the world—with interest rates where they’re at and people struggling to, you know, find affordable housing.

Maybe people got in with interest rates at 2.5% and need to move and/or can’t afford their mortgage payment anymore. You can do subject-to. You can do seller finance. As a non-great loanable person, that’s something that I’m going to be trying to put a lot of effort into.

Jeremy: And they don’t need to know that. They don’t—that’s the thing. With subject-to and creative finance, it doesn’t really matter, you know, your bankability.

"So, okay, I’m excited to hear about your, you know, subject-to, creative finance pursuit. But tell us—so you did this, you know, you got—you built your co-hosting business, got the cash flow, you’ve been gaining equity through ownership. But you also got your real estate license, and you also, you know, sold your first property to, uh, to an investor.

Andy: To Jeremy…

Jeremy: I don’t know—I don’t know who—I don’t know who, uh, who fell for your, uh, fell for your antics. But, yeah, tell us. So, I guess, how has been the—you know, adding that to your arsenal? What’s—you know, what was the thought that went into that, and how has that helped you?

Andy: Yeah, definitely. You know, I think part of getting into this business and wanting to do short-term rentals and co-hosting is, you know, creating a life or, you know, sources of income that are not your typical office job.

You can create more time for yourself and time freedom.

Jeremy: That midday surf—you gotta wait till the temperature is perfect before you go out there.

Andy: Exactly, exactly.

Jeremy: And the surf conditions—the waves are as high as—Andy watches the wave cameras.

Andy: Oh, yeah. wblivesurf.com—shout out.

But, yeah, with that, you know, it seemed like an obvious vertical integration for me to get my real estate license. And I had a good amount of time to, you know, work with clients during the day. You don’t need to be on your phone or computer 24 hours a day when you’re co-hosting.

So, I mean, that was a—it was a pretty obvious next step for me. And something I always wanted to do was to be able to, you know, provide some value for other people that were in the same situation as me two years ago, for example.

Or somebody who wanted to get into their first house. Or somebody who has been an investor for a long time but doesn’t really know the STR game that well. To kind of come in as a, quote-unquote, real estate investor before getting a real estate license, I think, is pretty invaluable.

And, you know, I think there are a lot of things that I learned over the last couple of years that a lot of real estate agents don’t focus on or just don’t know.

So, and that being said, Jeremy and I worked together on a property not too long ago. And, you know, to have me in the local area while he’s up in New York, and also be able to run numbers and kind of visualize floor plans, is very helpful for people who, you know, have an agent that understands the game.

So that—that was kind of the idea.

Jeremy: Yeah, if anyone listening to this is an out-of-state investor looking to get into North Carolina, hit up Andy, you know.

I mean, Andy was—yeah, for that transaction I did, uh, I think about five months ago—you know, really, like, I didn’t go to it before I got it under contract. Like, Andy went there, took the videos, he measured the floor plans.

He knows, you know—he knows how to look at things like I do, which is really important. And that’s why I always say, like, vet your Realtors. Because there’s a lot of Realtors who, you know, 'Of course I know short-term rentals. Like, you know, my friend has an Airbnb.'

But they don’t really know. You know, they’re like—I think a prime example of that is, like, in Wilmington. Like, if you hit up a Realtor, they’re probably like, 'Oh, you need, like, a waterfront property. You know, like, you’ve got to be on the beach. You’ve got to be, you know, on the water. Downtown is sketchy.

You know, like, Downtown Wilmington is scary. Nobody wants to travel there.'

But Andy knows how to do the research. He knows how—you know, he identified a property with—it was very important to have, like, a private backyard because he looked at the comp set, and he knew in Wilmington that being downtown, in order to beat the competition, you want to have a private, fenced-in backyard.

So, like, those little details are what allow you to get that $5,000 a month. You know, just simplifying things—'Oh, you need to be waterfront or not waterfront, or this close to X or this close to Y.' That’s simplifying.

You’ve got to know the little details. You’ve got to think about it like an investor, which is what Andy does. It’s like, 'All right, if someone’s coming here, what do they want? What’s the experience they’re looking for?'

Uh, I’m sure when you craft a midterm rental—which is, you know, what you might initially do—you’re going to know how to think about it like a short-term rental investor and create the experience that is needed to attract the type of guest that you want.

So, that being said, if you’re looking at North Carolina—especially the beach, uh, definitely the beach area—or even the Triangle, Andy’s good. But wherever you’re looking for a Realtor, you’ve got to vet them.

You can’t just go with the Realtor who claims to be a short-term rental expert. That’s just—you’re going to set yourself up for disaster.

A) You should know how to run the numbers and analyze deals yourself. B) But if you don’t want to, like, you know, fly out there and tour a million properties, you need to vet your Realtor.

So, super important. Uh, again, super, super just tangible tip for those out there. But Andy, so what are you excited about for the future?

Andy: Yeah, wow. I’m excited to continue growing as a person and growing cash flow. I’m excited about opportunities that are going to present themselves here, like we just said, in the creative financing world.

And, you know, me as an agent—I hope to help more people get into the game and kind of be that person that people look to in my market here in North Carolina as the expert in short-term rentals.

I think to be able to provide, you know, from the brokerage perspective—helping people get into a house—to having the management background where I, you know, I could potentially manage somebody’s house that I sell them and continue to grow my personal portfolio—those are the goals and what I’m super excited for.

Obviously, the immediate next step is this property I’m under contract on right now. It’s literally just at the inspection before I got home, so it’s all looking okay, moving along nicely while under contract. But, um…

Jeremy: Did you go into the crawl space?

Andy: Dude, this crawl space had a very, very small access, and the inspector couldn’t actually even fit into it. But he was able to sneak a long camera down there, and we were looking at it together.

And it—it all looked good. So, no problems there. But, yeah, I’m looking forward to this. This house has a pretty big pool in the backyard and a pool house.

Jeremy: Oh, really? Andy hasn’t actually showed me this house.

Andy: I know! I’m excited. I’m excited for you to see it.

Jeremy: So, I guess—you’ve gotten some confidence this time. You don’t even—uh, don’t even need—doesn’t even need— It’s when, uh, what’s it like? The quote in The Karate Kid, when it’s like…

Andy: 'The apprentice becomes the master.'?

Jeremy: Yeah, he has become the master. Yeah, he doesn’t even—Andy doesn’t even need to send me deals anymore. He knows how to. And that—that just shows, you know, how much he’s grown.

It’s been really, really rewarding personally to, you know, see your friend—Andy’s my childhood best friend and, you know, still my best friend to this day—so to see, you know, the kind of life that he’s created.

And also, you know, Andy has—you know, one thing with his financial freedom is he doesn’t just spend his time in real estate and surfing. He really gives his time to other people. He’s like a family man, and, you know, great relationships with his—you know, I’d really say he’s the connector of, like, a lot of my high school friends.

You know, Andy’s been able to—for me, it’s like, I’m doing all these things, you know. It’s hard for me to, like, maintain relationships with every person that I’ve met in my past. But, like, Andy has.

And, like, I can easily catch up—I feel like I can catch up with, like, 200 of my past friends through Andy. So, again, super, super valuable. When you have your time, give it to other people. Maintain relationships. Build new relationships. Grow your portfolio.

So, it’s been beautiful to watch everything you’ve done.

Andy: Thank you so much. That means a lot. And, you know, to throw it back at you—to see your growth and where you’ve come and to be on your damn podcast, it’s—it’s awesome, man. It’s awesome. You’ve, uh—I think you inspire a lot of our friends from home and even throughout your journey.

I mean, I think it was maybe middle school when we were trading stocks on a stock game. You were the one killing it, always the one saying, 'I’m gonna make a whole lot of money one day,' all this type of stuff.

And, you know, at the time, everyone’s like, 'Oh, Jeremy, I can’t believe he’s saying that. He’s so annoying.'

But now, it’s like, 'Hey, look, here he is. He’s doing it big.' So, that’s been a pleasure to watch too, and also so fun to be a part of the journey—from boat rentals to, you know, co-hosting—all of it. I have—I have you to thank for a lot of it, too.

Jeremy: Don’t—don’t say that. You know, I—I appreciate that, and I’m excited. And we’re going to have Andy back because, you know, we’re not done yet. You know, we’re not done. It’s just the beginning.

I really feel like we’re in the first inning. I wanted your opinion on, uh, barrel saunas. Do you have an opinion on barrel saunas?

Andy: I love the sauna. I think it’s my favorite—my favorite thing right now. I have not gotten a barrel sauna yet. I think at the first opportunity I get, I’m going to implement it at one of my properties so that I can use it when the guests are gone.

Jeremy: Yeah, that’s—again, Andy weighs that aspect of time pretty high. Whereas I’m like, 'I will never go into any of these things.' Uh, but I’m adding hot tubs to, like, every property, guys.

A big part of this game and crushing it in 2023—like, yeah, when Andy started a couple of years ago, that first duplex he did—frankly, it would be hard to mess it up.

I mean, obviously, to hit, like, an absolute home run like he did, he put in the work. You know, he renovated the house. He gained a quarter million in equity. Like, that wasn’t just because the market went up that much—that was, you know, Andy putting value into the property.

But that being said, in, like, 2023, you should continuously be leveling up your portfolio as well as just, you know, doing everything the right way from the get-go.

And I’m adding hot tubs to every single one of my properties. Uh, that doesn’t—you know, that makes—I have apartments, but, like, I’m not going to add a hot tub to an apartment. You know, there’d be no way to put it. But for all the houses, we’re adding hot tubs. You know, I’m taking—I’m not letting that cash sit in the bank account. Like, it’s—it’s getting deployed.

I’m under contract on a property right now, you know. So, I’m, you know, keep—keep going, and—and I’m trying to add, you know, really nowadays: great pictures, great management, but more and better amenities than the competition.

So, I’m checking the hot tub box right now. But the next one I’m eyeing and trying to figure out, like, the logistics, as well as the ROI potential, is the barrel sauna.

Andy: Yeah, so that’s—that’s why I, yeah, I—I, uh, I’m definitely gonna have to, you know, uh, talk to you a little bit about making some of these additions to mine as well.

Jeremy: That’s—yeah, your back—your backyard’s at Dock Street. You can—

Andy: It is. It is. Uh, but I think, as we speak, I think there’s somebody sitting out there on my beautiful Adirondack chairs. So, clearly, they’re enjoying it.

Jeremy: But, yeah, I didn’t say the front yard. I said the backyard. Andy’s got two fenced-in backyards, which are, I think, somewhat bare bones. I think you got, like, a picnic table back there.

Andy: They are, yeah. We just did a very simple—we basically just put a big, like, 4x4 post and created a little perimeter, infilled it with some gravel—pretty gravel—and put some Adirondack chairs and a grill.

It—it was super simple. And it was something that we just needed to just basically DIY because, you know, we’d already deployed a lot of cash.

Jeremy: Cheap as possible.

Andy: Cheap as possible. And it worked for what it was. There’s string lights, which are great—obviously, like you say, the best ROI you can do. But, yeah, there’s room for improvement here, and then also pretty much at—you know, there’s room for improvement in a lot of different ways.

And to be able to continue to improve like you are—I think that’s something that I really need to, you know, step on the gas and do some of those things. And, yeah, I’m excited for you to see this new property. And I’ll keep—keep you updated, and maybe we can—we can do this again when that’s all completed. It’s a—it’s gonna be a good one.

Jeremy: Awesome. Well, yeah, everybody, Andy will be back, so stay tuned for that. Andy, where can they find you if they want to reach out, you know, want help buying a house, or just want to follow your journey? Where can they find you?

Andy: Yeah, my Instagram is Surreal Estate, and that is, uh, Surreal Estate Management—that’s my property management company. I’m with Better Realty brokerage based out of Durham.

Jeremy: Shout out—shout out Better Realty."

Andy: Yeah, we’ve had a fellow Better Realty—Better Properties, Better—Better Everything—guest on a couple weeks ago.

Jeremy: Devin. De—I had Devin on earlier, so you guys should watch that episode. Devin is—and Better is also my landlord. So, talk about relationship building, technically I'm actually—Andy didn't start working with them until recently, but Andy's also technically one of my landlords for arbitrage.

So, I don't know, a little bit, you know—again, relationship building is super key. People say, 'Why wouldn't your landlord screw you over?' Well, I'd hope Andy wouldn't want to hurt his old pal.

Andy: Yeah, and even if I'm not involved in that on a daily operational level, it's still nice to know that you have somebody, you know, that has your back and can kind of be somebody on your side within our company too.

So, obviously, I want to see you succeed. I want to see everybody succeed. We can all do it together.

Jeremy: So, exactly. Relationships—I mean, obviously, we go back to childhood, but just focusing on relationship building is a huge tip. But also, yeah, what is your—I’d like to ask everybody—what is your biggest pro tip for someone listening?

Andy: Yeah, I think, I mean... I want to say it's more important that you take action than what you take action on. That’s kind of a key one for me. Because when we talk about this duplex deal, you know, I didn’t have to be a complete master at everything at the time. Looking back, it seems like I was a genius.

And I think that that is the case for a lot of people. Obviously, you can ingest as much information as possible and listen to podcasts for years, but you kind of get stuck in that analysis paralysis.

Just getting out there and taking action—whether it's, I mean, there are so many different avenues that you can get involved in here. Co-host, you can arbitrage, you can buy a property. But just go ahead and get into it and get your feet wet.

Yeah, and I would say join—work, like, you know—build community and relationships with those who are going to—I don't want to say put a gun to your head and make you take action, but—

Andy: No, no, that’s a very good point. It's important that you take action, and you're more likely to take action if you're surrounding yourself with people that are also doing it. That was a big, big thing with me—kind of being alongside Jeremy with his journey and him supporting me on my journey and giving me tips here and there."

Jeremy: Yeah, I’m sorry if I was a little aggressive with the action, you know. I was very forceful with Andy on…

Andy: Yeah, honestly, I didn’t have a choice. It’s easy for me to say take action—I actually didn’t have a choice. He had cocked the gun back.

Jeremy: Yeah, this is all figuratively. Andy does like to—you know, he’s a hobbyist with guns as well. Maybe a bit literally. Not literally. Not literally. But, yeah. Okay, I digress. Let’s get back to the podcast.

Andy: Please digress.

Jeremy: Awesome. Well, AO, love you, brother. Appreciate you coming on today. And, as always, everybody, stay tuned to the next episode of the Short-Term Rental Pros Podcast.

Andy: Hey, thanks for having me, man. Look forward to coming back soon.