Jackson's Cold-Call Script That Built 17 STR Properties

Quick Summary

Jackson joined Ryan's group in November 2024, right after Hurricane Helene flooded Tampa properties, and built his cold-calling business from scratch. He spent mornings pulling 25 to 30 leads a day from Google Maps, True People Search, and PropWire, then called from early afternoon into the evening, tracking everyone across three Google Sheets.

His group has since moved off spreadsheets onto a CRM, and Jackson is chasing 50 properties while running a seven-boat rental business on the side. If you're building your own short-term rental portfolio, BNBCalc can help you run the numbers on the next one.

Key Points

• Jackson joined Ryan and Jeremy's group in November 2024, right after Hurricane Helene flooded properties around Tampa Bay.
• He generated 25 to 30 leads a day from Google Maps, True People Search, and PropWire, then cold called from early afternoon into the evening.
• His opening line, "how thrilled are you with your current property manager," got most owners complaining about their manager within seconds.
• He ran three separate Google Sheets: new leads, follow-up, and closed deals, treating it like a sales pipeline from his old software job.
• Jackson peaked at 20 properties, then dropped to 17 or 18 after letting a difficult owner go and losing another property to a sale.
• He also runs a seven-boat rental business on a subscription model while chasing 50 STR properties by the end of the year.
• Ryan's group hired its first sales rep and moved off spreadsheets onto a CRM for automated messaging and remarketing.

Full Transcript

Listen to the full episode on Apple Podcasts, Spotify, or YouTube.

Ryan: I'm your co-host, Ryan Shapiro. Jeremy isn't here today, so I'll be taking on more of the co-hosting and property management podcast segments. And today with me I have our good buddy, Jackson. Welcome, Jackson, and thank you for joining the pod today.

Jackson: Thanks, man. Happy to be here.

Ryan: So Jackson, tell us a little bit about yourself, what we brought you on today for. I've been working with Jackson for quite a long time, but love his story, so I really wanted to bring him on this show. I think there's a lot of people that will relate to it. So without further ado, why don't you tell us a little bit about yourself and what you're working on?

Jackson: Absolutely, man. Thanks, Ryan. From Tampa Bay, Florida, currently still living here. I run the business out of here, we're all local. It's a good time, man.

Pretty much, my start, I met Jeremy through his Instagram page with all of his boat rental content, because originally I came from the boat rental world, boat charters and stuff like that. I had no intention of getting into Airbnbs or anything like that. I was just kind of looking for some advice on how to run the business. I saw his page and I saw it was running so effortless, and he had a guy running it from the dock. I'm like, d*mn, I want that life. So I started reaching out to him, DMing him, like, hey man, we'd love to jump on a call, buy a coffee or lunch or whatever. Eventually he's like, all right man, you've been consistent enough, let's do it.

So we jump on a call and he gives me some super valuable insights with my boat rental business. He has his business on a lake in North Carolina and he lives full time in New York City. I'm like, I want to be able to do that, that's an awesome life. Pretty much halfway near the end of the call, he's like, you know man, I really think you should get into Airbnb. And I'm like, Airbnb? What are you talking about, dude? I don't know anything about that, I'm in this boat world. And he goes, well, there's a slow season to boating, in Florida it gets kind of cold. I'm like, yeah, it gets to like 50, 60 degrees, but it's not terrible. But there is a slow season.

He's like, well, with these Airbnbs, man, you can become a co-host. And I'm like, dude, what's a co-host? And he's like, you could be like a short-term rental property manager where you get a good percentage of the revenue that the house makes by pretty much managing the property, like talking to the guests, making sure the cleaners show up, changing air filters once every six months, whatever. And I'm like, really? That's not like arbitrage or whatever, right? And he's like, no, you don't have to have any money put into the house. You're literally just reaching out to owners and asking them, hey, how thrilled are you with your current property manager? Or have you ever considered Airbnb or anything like that? I'm like, that's pretty sick.

So before the boat rental business, I was in software sales, so I knew how to cold call and generate business from nothing. I started to jump on the leads, started creating leads from what the group taught me, Ryan mainly, and Jeremy taught me to reach out to bigger property managers that don't have the individual boutique mom and pop kind of service that smaller people that live here can do.

Ryan: Let's backtrack on that, there's so much info. I just want to make sure everybody was following a little bit there. So reaching out to Jeremy, you had a boat rental specifically for people coming on vacation, right? That was the main thing, you were doing boat rentals in Tampa Bay, correct?

Jackson: Yeah. Yep.

Ryan: So you're reaching out to Jeremy because he had a boat rental business out in New York, North Carolina, from my understanding, trying to learn a bit about boat rentals, which is part of Jeremy's whole journey of getting into Airbnb. I'm sure many people have listened to the podcast, but if you haven't, he started doing boat rentals in North Carolina, realized there were these beautiful houses on his lake that he was renting to, and realized, hey, maybe these people also need help with renting out their properties. So he got into, before people even labeled it co-hosting, co-hosting.

So sounds like that's kind of the journey you went through, and then he directed you into that level of co-hosting. You brought up arbitrage, which is huge, people still don't even know what co-hosting is. It's still so new in the industry, that word, that name, but it's synonymous with property management. The slight difference, I would personally say, is co-hosting is like you're helping people on the backend run their listings, where in property management you're doing everything for them and they're looking to step out of it.

So backtracking, you were speaking to Jeremy and then he mentioned that there's a program, I'm assuming, about joining?

Jackson: Yep. Yep.

Ryan: Cool. So let's take it from there and jump into how you started that business a little bit more.

Jackson: Yeah, for sure. No, that's a ton I definitely left out. Jeremy has what seems like all of these waterfront houses on this lake, where he had his boat rental that he converted into co-hosting clients. That's where he was like, I think you'd be great at this, your personality, whatever, we got this group, this community, everybody would help you. I'm like, all right, that could be interesting. I'd never thought about having a second source of income, and I'd already been in hospitality, helping people get on boats and renting boats. So what could be different about it?

Ryan: Yeah. At least it's less of a liability, I'd say as well.

Jackson: Yeah, yeah, yeah. No, but going into it, he introduced me to the group, Ryan and everybody, and got us on coaching calls. Every week Jeremy has a coaching call, and then Ryan does his own for helping people out as well, and they give you everything. They do everything from, what even is co-hosting? What the heck is Airbnb? How does it work? What do you do as a co-host? How do you find new people or market to people? And on top of that, I am the least technologically savvy person on the planet, so I was even surprised I was able to figure out a Google Meet today. But no, they showed us how to set up all the integrations to Airbnb, and all the tools to really make it a seamless operation.

Ryan: Yeah, no, definitely, and you definitely took the rings with that as well, too, you became a natural at it. We'll get more into where you're at and where you started, but my biggest question is, from seeing the success you had, what was that North Star like? What was the driving factor that allowed you to take everything that you learned and just dive straight into it?

Jackson: For sure. I think it was really just, in the boat rental world, not to go too far off, but I think I was just a little bit lost. It was going into the slow season in Florida, I had just freshly quit my software sales job, and I was like, I'm an idiot, I just quit my job, I don't even know what seasonality is, I thought it was just going to get cold here in Florida. And I felt like, what am I doing? I really needed, I had a sales manager, a general sales manager at my old job, telling me what to do, how to be successful. So I felt like I really needed that in a way, like a mentor, or a couple mentors. Joining them really helped me grasp what I really needed to do to be successful, instead of just figuring out everything on my own.

Nah man, if you've got this group behind you, you're going to go ten times faster and you're going to get kicked in the teeth way less. Just seeing what Ryan has, and a lot of other successful people in the group, it's like, holy crap, that's possible, I want that. I want to create a better life for me, for my family, have more time freedom. That's the main goal for sure.

Ryan: Yeah. And me and Jackson go back and forth all the time, where he gets jealous of where I'm at, and I get jealous of where he's at, because I'm like, well, dude, you're kicking yourself in the foot, you're running two businesses at the same time, swimmingly, where I'm still trying to stay afloat with our 30 or so properties that we manage. So it's always a fun back and forth that we chat about, you're doing great, no, you're doing great, but it's like an F you, you're doing good, in the most positive manner. So I think that keeps it competitive as well too.

Jackson: Yeah. Big time, man, big time. And it's great having a group where it's like, me and Ryan, I feel like we're more sales oriented, we've come from that background. So it's a good, bittersweet, like, oh, freaking Ryan's at like 30 properties, it's like cake for him. I'm at whatever, 17, 18 now, but it's really cool to have a goal, and a friendly, not battle, but a friendly, like, oh, I want to be where Ryan is at.

Ryan: Yeah, exactly. See, so, no, but it's cool to see what other people can do. And it's a great example to have, if you're doing anything in life, any business, you're that small fish in the big sea. How did that guy get to XYZ revenue and whatever? He couldn't have done it alone, he had to have learned it from somebody that's there doing it themselves, you know?

Jackson: Definitely.

Ryan: And so you mentioned, you're at about 17 properties at the current moment. Walk me through your journey, you joined the group, we talked about all that, you started ripping dials. You could talk a little bit into how we structured it, what we recommended doing. But walk me through how long you've been at it, and where you started, and where you're at today.

Jackson: For sure, man. Back when I joined it was like November of '24. I remember we had just got hit by this storm here in Tampa, Hurricane Helene, and all the properties around here flooded. It was like the absolute worst time to start prospecting, like, hey, how's your Airbnb doing, bro? It's underwater. That's it.

I quit my job, I've got this boat rental thing I'm trying to make happen, I've got this property stuff, and Ryan and Jeremy were like, hey man, you've got to start from somewhere, just start making some leads. I knew I could sell, but I just didn't know how to get started. So we found some of these other big property managers, and every day, Monday through Friday, what I would start doing is like 8, 9 a.m. in the morning, I'd jump on Google Maps, True People Search, PropWire, and then some of the bigger property managers. I'd start making leads every day from like 8 to 9 a.m. till maybe about 1 or 2 in the afternoon, and I'm just rocking it, making about, I don't know, 25, 30 leads every day.

I have a Google sheet, new leads every day, I'd be filming them, boop, boop, boop, boop, boop, making new leads. Then I'd have a second Google sheet called follow-up, anybody that answered the phone, even if they're like, F you, don't ever call me again, you've got to call them next week, check on them, see how they're doing. And on the third sheet I would have just closed leads. Just thinking from my old job, like, we've got to have a pipeline, the goal is to move the leads along the pipeline.

Then once I'd finish making leads in the morning, around 2, 3, 4, 5, 6, 7 p.m. at night, I would just start calling. We came up with a good script, and it was kind of positioned on how we thought they were going to react, because it was really low hanging fruit. This owner's Airbnb listing with these bigger property managers was on average like a three, four, four and a half star. It was never a flawless execution of service that the owner was facing with that manager.

So I'd ring him up and I'd be like, hey, hey John. Hey man, what's up? It's Jack just over here, Tampa Bay Stays Property Management. I'm looking at your property, is that still you at 123 Main Street? Yeah, why are you calling me, what's going on, what do you know? And I'm like, well, I just came across your beautiful property, I love that pool in the backyard, man, saltwater pool. Your property on the XYZ Property Manager website, and I was just really looking to see how thrilled you were with them. And I would just shut up. And then, dude, like nine times out of 10, they would be like, oh, man, like these guys suck.

Ryan: I promise we do, but we'll figure it out, we're going to just keep going because it's just take two on here. But I have to have a quick pause because a delivery showed up at my house, of course.

But where we're at, we're talking about the script, which, before jumping back into the end of it, Jackson was the king of coming up with that: how thrilled are you with your current management. And I still run with that today because it's just such a good line, because odds are, you're obviously calling the low hanging fruit of some degree, but odds are nobody's thrilled with some large corporate company that is treating them just like another number.

Jackson: Yeah, man.

Ryan: It opens up the door right away.

Jackson: Yeah.

Ryan: For them to just be like, yeah, they're all right. You're forcing the over exaggeration, bringing in the wording that they're not going to come back and say, they're fantastic, they're this. Sometimes they do, but you're kind of twisting it in a way that's going to make them come back and say, yeah, they're all right, because nobody's thrilled about them.

Jackson: Yeah. So that's exactly how I position it, because like I said, eight, nine times out of 10, they're like, oh, you know how XYZ is, or, oh, they suck, or they're okay. Or, we just signed on and they haven't gotten us any bookings, just stuff like that. So I'm like, oh, really? Sorry to hear that, man. I just think your property deserves so much more potential, I just think you're missing some bookings. Would you have like 10, 15 Friday morning or afternoon for a quick call? And then that was it.

And I'd get them on the call, and this sales cycle, it's not like you're going to get a deal in a day, but a quick one would be like a week. A normal one probably be like a month or two, but that's kind of it. And then, whether the people come to town physically, you go show face, shake their hands, or, there's some owners I still haven't met in person and I've had them for like a year or so.

Ryan: Yeah, but it's good. It's an interesting business because you kind of have two clients. You have your homeowner client that really has the keys to everything, and then you got the guest that's coming in, and you kind of have to be the middleman. But I would just suggest having some systems and processes set up in place, some standards for them to follow.

So you're ripping dials back and forth nonstop, reaching out to me and being like, hey, what do I do here? What do we do there? Going through the whole process together. And then before you know it, you're at how many properties in like a year or so?

Jackson: Yeah. We had 20 at one point, like about four or five months ago. I had an absolute insane owner, so I had to let him go. And then one of the properties actually ended up selling. So we're at 17 or 18, but this month is July, and by the end of the month, we just onboarded another one two days ago, and we'll have hopefully three more by the end of the month or beginning to mid-August. So we'll be back at that 20 mark.

We're coming up on Ryan, man. I'm coming up on you.

Ryan: Jackson, try and...

Jackson: Well, I got two more, and two more potential closes this week as well.

Ryan: There you go. I'm trying to stay ahead of him one by one.

Jackson: My goal is to get to 50 by the end of this year, at least.

Ryan: Oh, you got it. Yeah.

So we've been good, we've been putting more processes in place, hired my first sales rep as well too, which is Jackson's buddy. So he's slinging subscriptions for his boat rental business, and also slinging calls for co-hosts, sales plug around here. Which has been fantastic, been excited about it for sure, so hopefully we'll get his first close. And then thankfully we're outside of that Excel spreadsheet world, we've moved into the CRM world of it all, which we're building out for all our people in the group to follow, for more automations, more Claude buildouts, more automated responses, automated messaging to potential clients. We're bringing in some remarketing campaigns to past guests, Google review campaigns, automations.

But it's always fun, me and Jackson chat pretty much once a week. It's probably the best part about being part of our group, just having that guy to call you like, how sh*t's your day going? He's like, awful. How about you? I'm like, terrible. Like you're surviving that. It's never the same, man.

Jackson: Ryan will call me and be like, dude, I just got like five more clients in the last five seconds. I'm like, yeah, dude, I just had some guy fricking back his car into the neighbor's garage. And then I'll be like, yo, dude, I got like two more clients. And Ryan's like, dude, I can't with these fricking people, I'm about to fire them all, I'm firing my VAs, they're all done, that's it, we're done.

Ryan: Exactly, yeah man. But it's fun though, man, it is what it is.

Yeah, so I'll end it off on like two notes. One, Jackson, my favorite thing about your whole story is obviously your age, running two businesses, which is one of my jealous mindsets of him, where I'm like, d*mn, Jackson, you're fricking, how old are you? 20?

Jackson: 24.

Ryan: 24, running two businesses successfully, 17, 18 properties. And then you have, what, how many boats at this point?

Jackson: Seven.

Ryan: Seven boats as well, and counting. If you guys have any questions about the boat rental world, he's got this subscription model, which, if we had enough time for another pod, we could go deep into. But subscription model, crazy, crazy business, seems like he's deep diving into that along with growth in the short-term rental space, which is so cool.

I'll end it off with my last question for you, which is pretty much, if you could go back in time, anything you would change, any advice, anything you'd like to offer to people starting out, what advice would you be giving them?

Jackson: Definitely wouldn't join Jeremy's group. No, I'm just kidding. No, no, no, no. In life, you just don't know what you don't know. So if I could go back, I'd start this a heck of a lot sooner. I would join the group a lot sooner, try to meet Ryan earlier back in the day and just fail fast. That's all about learning what you don't know and just opportunity costs. So you just got to think about, in the moment, what can you do now that in five years you would think, what if I only knew back then, you know what I mean? So no, man, but definitely just starting this sooner and just getting on it, you know what I mean?

Ryan: For sure.