How Jon Street Builds Profitable Short-Term Rentals Through Guest Experience and Repeat Bookings

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In this episode, Jon Street shares his journey into real estate investing and how he built a successful short-term rental business in Myrtle Beach. He explains how his first major investment—his own home—sparked his interest in real estate and eventually led him to vacation rentals. Jon discusses how choosing the right location plays a critical role in profitability and how he identifies strong rental opportunities in a competitive market.

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Investor Fuel Show Transcript:

Cody Crabb (00:00)
what?

Jon Street (00:00)
Yeah, people,

I don’t know, lot of people that owners, they mail it in and they just don’t understand. They don’t have that customer service mindset. They’re just trying to squeeze out a dollar and it hurts them in the long run.

Well, I I personally have a vacation down there for 20 some years. So, you know, I, you know, I put myself in the, in the client’s shoes and what, what they’re doing is they’re making memories with their families.

Cody Crabb (00:16)
Mmm.

Welcome back to the Real Estate Pros podcast. I’m Cody Crabb with Investor Fuel. Today we are joined by Jon Street. Jon’s gonna give us some great advice here. We’ve been chatting a little bit. Jon, thanks so much for joining us.

Jon Street (01:45)
Glad to be here.

Cody Crabb (01:46)
So Jon, give me the quick version of your real estate journey. How did you even get interested in it in the first place?

Jon Street (01:52)
Well, I think someone said once that by real estate, they’re not making any more of it. So I’ve kind of taken that to heart.

Cody Crabb (01:57)
I like that.

Yeah, I like that. So what started you? What made you want to ⁓ do your first deal? Were you investing in anything else and that just came up?

Jon Street (02:13)
Well, you for most people, their first major real estate investment is their own home. And, you know, over the years I was able to, you know, pay my home off. And then I was, you know, I liked it so much in the appreciation on, you know, a physical property like that. I was like, how can I get a passive income? So I’ve been murder.

Cody Crabb (02:18)
Sure,

Jon Street (02:35)
vacationing in, know, Myrtle Beach for the last, you know, 20 something years. So I ended up investing down in Myrtle Beach in condos and then renting them out through Airbnb, Vrbo and direct rentals. and

Cody Crabb (02:50)
Gotcha. is it all,

is it exclusively short-term rentals right now?

Jon Street (02:54)
Yes, we do look for snowbirds in the off season, like three or four months, which, know, like if someone from New York or Canada or somebody wants to get away, that’s awesome. That’s a wonderful option for us. And those rates vary depending on the season.

Cody Crabb (03:11)
Yeah, that makes sense, that makes sense. All right, so this very first deal in the condo complex, I’m curious, so how many units is it? Two units.

Jon Street (03:20)
We

have two units in two different locations.

Cody Crabb (03:26)
Gotcha, okay. So this first deal, looking for that first deal, where did you go to, what did it look like? Where did you go to find it? Was it a good mix of coincidence and good luck or was it one of those you just tripped into it kind of things?

Jon Street (03:41)
No, we definitely were looking. I had some issues in my personal life and I had to liquidate a condo that I owned. But I don’t have those complications anymore. So I wanted to get back into it. the thing with real estate, as everyone knows, also another thing is location, location, location. That is hugely important. So if you’re going to have rentals, you have to kind of, you know,

see what your budget and your financing can put you, the closer to the beach you are, the better. It’s because you can command higher rates. So the

Cody Crabb (04:15)
Sure. Yeah, I mean,

I’m no expert, but I feel like that, yeah, that tracks. That seems right. Cool, yeah. Well, okay, so what types of borrowers have you worked with thus far? Is it your own capital or how has that worked so far?

Jon Street (04:23)
Yes.

It’s been my own capital, getting loans. One condo is paid off and the other one is still has a mortgage, but we’re working.

Cody Crabb (04:45)
Gotcha,

gotcha, okay. So, ⁓ yeah, yeah, Okay, so just out of curiosity, what’s been the hardest part about the short-term rentals specifically? I mean, you said you’re vacationing there. How far are you from the actual units?

Jon Street (04:47)
with other people’s money.

Well, I live in New York, upstate New York. ⁓

Cody Crabb (05:53)
⁓ Well, yeah,

that’s pretty far. That’s pretty far. what’s been the biggest challenge for you in the way of short-term rentals?

Jon Street (06:00)
The ongoing expenses outside of the mortgage would probably be the biggest challenge with HOA fees and most recently the ever rising insurance costs for flood insurance due to insurance companies really taking some hits over some hurricanes in the past years.

Cody Crabb (06:19)
that makes

sense. Yeah. Cause yet on the coast, that’s pretty much, I mean, you can’t really get around that. So that makes a lot of sense. and, and he, luckily you haven’t had any issues with actual hurricanes hitting. I’m hoping that’s, that would be, that’d be a lot more.

Jon Street (06:32)
They, you

know, there’s, well, it’s been really light the last few years, but, know, I mean, they come through, you might, know, you got to worry about storm surges and, water coming up, but, you know, my units are close to the beach, but not on the beach. So, you know, I haven’t had an issue like that.

Cody Crabb (06:41)
Yeah.

There you go, that’s way to do

it. That’s good, that’s good. All right, so as far as short-term rentals, I’m just kind of curious, because in real estate, you can go different ways. You kind of pick a lane when you’re starting out. I’m curious, what made you want to do short-term rentals instead of long-term rentals?

Jon Street (07:08)
I think you can generate more revenue.

Cody Crabb (07:10)
Yeah, I mean in a literal sense that’s definitely true. So as far like, you work with a property management company? Do you work with an individual? How do you work that since you live so far away?

Jon Street (07:20)
Well, we kind of have a multiple prong strategy. We went with Vrbo. We think their approach is just easier, better than Airbnb. Vrbo, they take care of a lot of the administrative stuff, taxes, things like that, which is nice. But what we tend to do is once we get a Vrbo client and then they come in,

then we try to move them into a direct rentals to get repeat customers and we’ve had a lot of success doing that and then our margins go up.

Cody Crabb (07:50)
Mmm.

Yeah, sure, because you don’t have to give them a cut. That’s great. That’s smart. So what are some ways that you’ve done that? What are some tricks that you’ve used to get them to books directly with you instead of through the apps?

Jon Street (08:00)
Right.

⁓

customer service communication, follow-up, reminders. And, you know, and, and mostly, you know, I’m at, I’m actually, my partner is my, my mother and she lives in, she lives near Myrtle beach in the area. she’s local and it really, she’s really the mastermind. She, she’s, know, that grandma that everybody likes. And she, you know, she, she gives them, you know, puts things in the condo for

Cody Crabb (08:22)
that’s good.

Jon Street (08:36)
people like, you know, depending on what they like, you know, a bottle of wine, complimentary bottle of wine for people and guests is worth every penny because you’re going to get repeat people because people don’t get customer service in this world and anything. And when they see it, it’s such a refreshing thing for them that you’ve got some loyal customers and some repeat business.

Cody Crabb (08:56)
Yeah, every definitely

every time I get some kind of benefit in something I think it’s a trap somehow nowadays because it’s like that if I saw that I’d be like I have to pay for that. There’s no way this is basically a mini bar in an Airbnb because I’m so I wouldn’t trust it. But that’s no that’s true. That’s having something complimentary is like a great way to end it really like how much does it cost really like if you if you throw some extra here’s a pair of slippers to take home with you like that it’s that’s such a nice little thing you can do that costs almost nothing that is like that would be a memorable thing.

Jon Street (09:05)
Right.

Cody Crabb (09:25)
forever, that they got some slippers to take home or they got something like that. I think that can really make a difference, especially if they want to book directly with you. Because you’re trying to get them to book with you specifically, that’s a good way to do that, I think. Yeah, keep going.

Jon Street (09:37)
Correct.

important point to

build on top of that. It’s super important to respond quickly when there’s an issue. People, you you get all kinds of different individuals in there. Some are more technically savvy than others. If there’s a problem with television, if there’s a problem with TV, if there’s a problem with air conditioning or anything, the faster you respond and overcome those obstacles for them is immensely important because people are, they spend a lot of money to go vacation.

and they don’t want, they’re not there for issues.

Cody Crabb (10:46)
Sure, yeah, I’m thinking in my head, if I’m on vacation and I have a limited time there and the AC is broken, I’m gonna be furious. I can’t get that figured out on my vacation. So that makes a lot of sense. You gotta be a little more responsive than you would say in a long-term rental, because you’re only gonna be around them for a little amount of time, and you have this window to, yeah, and you’ve got this little window to make sure you make a good impression, and yeah, that makes a lot of sense.

Jon Street (11:07)
Typically a week. You know, we have a minimum of three days. Right.

Cody Crabb (11:16)
What’s something that you’ve done with your investment that’s kind of been a big, a change that you made that ended up being like, I’m really glad we made that change kind of thing?

Jon Street (11:29)
Hmm. ⁓

Well, I guess with the newest condo that we purchased, we revamped it. It needed a facelift. mean, as far as changes go, it had good bones, as they say, but it was dark, dark walls and stuff like that. So basically, it’s amazing what a fresh coat of paint and some new carpet and things like that. Just…

Sprucing it up a little bit, know, new furniture, new, you know, lamps and stuff like that, new mattresses. Some of these rentals are notorious for the worst mattresses. Just, you know, those kind of things.

Cody Crabb (12:09)
And which is so funny cuz why

like what it’s really how much are you actually saving by getting a cheap mattress? You’re not just kidding. Just get a good one. Yeah, I know what you mean Yeah, I’ve definitely run into that before like I’ve got I’ve rented an Airbnb or something and been like are you kidding me with this like

what?

Jon Street (12:25)
Yeah, people,

I don’t know, lot of people that owners, they mail it in and they just don’t understand. They don’t have that customer service mindset. They’re just trying to squeeze out a dollar and it hurts them in the long run.

Cody Crabb (12:36)
Yeah, well that’s extra funny to me because you’re in short-term rentals and you would think that that means you can kind of get away with more because they’re only there for a little while. But what you’re really saying is like, no, you only have a little while to make it a really good impression because you want them to come back. So I think that’s a really good point. Making something unforgettable in a short-term rental is probably way more important than just your typical landlord down the street. So that’s true.

Jon Street (12:42)
Mm-hmm.

Well, I I personally have a vacation down there for 20 some years. So, you know, I, you know, I put myself in the, in the client’s shoes and what, what they’re doing is they’re making memories with their families.

Cody Crabb (13:12)
Mmm.

Jon Street (13:19)
And if, if they have positive, you know, experiences and that’s really what you’re providing is this experience. Then they’re going to come back and we’ve had a great success with it. We’ve had people, we’ve had people come back three, four, five times. We have people.

like, hey, can we, we want to buy now in the area because of us. So I go, well, stay at our unit. Why you looking?

Cody Crabb (13:40)
Wow. There you go. Yeah. Yeah. Wow. That’s

great. See, and that’s, I think that’s the, like, I mean, I’ve stayed in, I’ve stayed at many different places like Airbnb’s and stuff back when it was a little more cost effective to stay at Airbnb. But, but, in those days, I do remember, you know, I’ve had pretty much the gamut of situations, like someone’s basement versus like an actual, they’re trying to make like a short-term rental. And the one that really sticks out to me was we were in Seattle.

And this lady was like, you know, how are you? Who’s who are you bringing and what’s going on? They were she’s asking us some questions. And I mentioned that our our like one year old son was coming with us. And she said, OK, I’ll get a I’ll have a pack and play for you there. And I was like, that’s nice. Thank you. And when we got there, she had bought it just for us. And I was like, OK, that’s amazing, actually. And that’s the only time I’ve ever repeated a rental like that is when I when I had something like that. And I’m not going say that’s exactly the only reason why. But like

that definitely helped. was like, she really cares about this and it’s not a huge expense. yeah, think really the summary is like, if you look after the little things, you can really start to make a big impression.

Jon Street (14:54)
It’s so much easier to get repeat business instead of trying to find new clients.

Cody Crabb (14:59)
Yeah, yeah, you already know who they are, yeah.

Jon Street (15:02)
Well, no, well, no, they’re they’re coming back because they want to be back. We’re not we’re not even trying needing to find them. So you book up so much faster. It’s less work. You know, it’s. I mean, we’ve done the exact I think we did buy a pack and play for a family. We did that as well, actually. It’s funny. We put in I mean, we had some older an older couple come in and they asked about like a handrail in the shower.

Cody Crabb (15:13)
Yeah, yeah, why do more work when you don’t have to? I agree with you.

Jon Street (15:31)
So we had that installed. People remember that if you care for them, they look at you like you’re a friend, you’re an extended family member. And that’s the kind of reaction we’ve had from customers.

Cody Crabb (15:42)
Seriously, yeah.

Hmm, that’s good, that’s really good piece of advice. I think like, if you think about like, that’s also an investment because it’s not, you don’t have to take it down even. Like you could, that could just be a thing that’s there now and then congratulations, anyone else that asks about that, you can say, yep, we’ve already got that. So it’s just, yeah, there you go. Yeah, that’s a great way to look at it. Well, cool, okay, so another question I wanted to ask you about was, you know, have you, okay, let’s see.

Jon Street (15:54)
Correct.

Correct. And it’s all a write-up anyway.

Cody Crabb (16:47)
Okay, so we talked a little before about you maybe wanting to expand and get into more properties. Tell me what you’re hoping you can do going forward with real estate and what your plan is.

Jon Street (17:01)
Well, you know, as far as, you know, bigger dreams, you know, I’ve always kind of talked, joked about, you know, instead of having a unit in, in, in these complexes, because like, let’s say, one of the, one of the property locations is Arcadian Dunes in Myrtle beach. And it’s, it’s very nice. They have, you know, tennis court, there’s, there’s a restaurant bar, two pools. It’s, it’s, it’s nice for families. And we’ve been, I’ve been going there for 26 years and it’s nice for one of our units. Well, they have like.

12 units in a building, to have the entire building would be amazing to me. And that’s my building.

Cody Crabb (17:35)
Yeah, yeah, well of course, yeah. That eliminates a lot

of potential issues. It’s all just in one spot. You don’t have to go run back and forth and stuff. Yeah, I agree, that’s a huge deal. So what roadblocks are you seeing? Just on a ground level, what’s your kind of general, if I’m gonna do that, then what’s my plan kind of thing?

Jon Street (17:59)
Well,

I mean, there’s a lot of opportunities out there and, you know, you’re looking at different ways to do it. like, how can I get another unit with, with, you know, but not overextend your budgets because that’s how people get in trouble. As I think the Dave Ramsey got in trouble doing that. It went early in his career. He bought all this stuff and then they, hit something and then it, it fell like dominoes and that’s not, that’s, I want to avoid that. So I’ll go a little slower, more pragmatic.

Cody Crabb (18:17)
That’s ironic.

Yeah, sure.

Sure.

Jon Street (18:28)
I mean, you know, there’s a unit, there’s, you know, there’s actually a unit down there that has 10 occupied, full-time occupied apartments. And they’re asking like 1.6. I think that’s beyond my financing, unless I had other investors in that. And then it gets a lot more complicated. You know, I just, I’m a, my thinking is slow and steady and, you know, don’t overextend. Make sure you have emergency funds.

Cody Crabb (18:38)
Hmm.

Of course, yeah.

Jon Street (18:56)
things like that because things will break. Unexpected things will happen. You could have assessments.

Cody Crabb (19:00)
And would say probably, I

don’t know for sure. Again, I’m not a genius on this, but I’m assuming it happens a lot more in short-term rentals because it’s…

Jon Street (19:08)
Well, you know,

some guests are better than others. But but most the most recently, most recently we, you know, we had that cold snap in the country and it dipped all the way down to us. And we had a we had pipes burst because they froze in Myrtle Beach. Now, I’m in New York. I didn’t have that problem, but in Myrtle Beach, it did. And that was that was like a fourteen hundred dollar, you know, got to fix it now because we have people coming in a week.

Cody Crabb (19:11)
Right, exactly,

Mmm.

Wow. Yeah, sure.

Yeah,

yeah, yeah.

Jon Street (19:36)
So that’s so, you you need that emergency fund. need to make sure you’re not overextended so that you don’t get in position where you have to take the shortcuts and hurt yourself in the long run.

Cody Crabb (19:48)
Okay, yeah, I think that’s really good advice. Okay, so if someone wants to get in touch with you, or if they want to rent those lovely, lovely places out there, or just kind of have questions for you, how can they get in touch with you?

Jon Street (20:02)
Well, they can, the easiest way to do it is to go to our website. We have a website that has pictures and explains everything about the condos and how to book them. It’s the website is condorentalmyrtlebeach.com

Cody Crabb (20:18)
Easy to remember, love it. And if someone wants to reach out to you directly, is there a different way to do that? Maybe like a LinkedIn or something.

Jon Street (20:24)
I’m Jon Street on LinkedIn. I have a cowboy hat on, I didn’t pull that up. Let see.

Cody Crabb (20:27)
Yeah, okay.

It’s fine. I’m sure if they’ll look for Cowboy Jon Street, I’m sure they will find Cowboy Jon Street.

Jon Street (20:42)
What is my,

⁓ here I can, I can put a link in here for you. It’s basically, you know, cause I also started a photography business recently. So it’s a Jon street dash photo on LinkedIn.

Cody Crabb (20:54)
Gotcha,

okay cool. Well that’s great. Jon, thank you so much. think this is kind of interesting dive into the short term world. And I think that you’ve got some really good advice in here. One last question before we end. Let’s say you’re in front of a bunch of people who are either interested in investing or they’re investing for the very first time. I hand you the mic. What is the one thing that you’re gonna tell them that you think is gonna save their life or like.

Keep them from making a horrible mistake. Would you say take it slow and take it easy? That’s what you seem to be like, that’s my big thing. Is that what you’d say? Yeah.

Jon Street (21:28)
Yes. ⁓

You need to work with reputable people. have realtors that I bought a condo from 20 years ago in Myrtle Beach area and I’m personal friends with them today. And that makes a big deal because if you’re dealing with like a reputable real estate agents that know the area, know the neighborhoods and know the market, they can guide you.

for whatever goals an individual may have, and you’ll avoid a lot of expensive issues.

Cody Crabb (21:59)
Yeah. Jon, thank you so much. I appreciate you joining me today. Thanks so much. You’ve given a lot of great advice and we’ll talk to you next time. Well, no, we’re not going to talk to you next time. Let me say that again. I’m not going to talk to you next time. All right, Jon, thank you so much for joining us today. If you’re not subscribed to the podcast, please go ahead and do that. And listeners, thanks so much for joining us and we’ll see you next time on the next episode of Real Estate Pros.

Jon Street (22:21)
I did.