How to Turn One Property Into Multiple Paydays with Tim Hubbard

Welcome to the Smart Real Estate Coach Podcast, your source for actionable, real-life, practical investing advice. Each week we help you make a quantum leap somewhere in your business, your finances, and/or your life. Subscribe, leave a rating and review, and learn more at smartrealestatecoachpodcast.com. Hey, welcome back to the Smart Real Estate Coach Podcast, where we help everyday people create 3 paydays in every deal, cash now, cash monthly, cash flow, and long-term wealth. I'm Chris Prefontaine. I'm your host. And today we're diving into a chat about short-term rentals. And the reason I wanted to do that, we're pivoting the podcast, and I'm going to say this probably every week here to get you tuned in, to very, very pointedly working on the creative side of things, what we do. So I'm not going to cloud you with a bunch of shiny objects. I'm going to stay focused. And when I heard about what my next guest has done. Tim Hubbard lives in South America and runs a pretty sizable portfolio himself for short-term rentals, but he's also, he's super seasoned global entrepreneur, you could say. And he's an educator and he helps others do the same with short-term rentals, but he's also the founder of Corzly. That's C-O-R-Z-L-Y, where he has owners like you and I across 40 different cities. And he does like, I'll call it, you'll hear in the interview, I call it like a done-for-you. So if you have a property and you do it, you go on the short-term route, whether you're doing that full-time or whether you use that as part of a vacation house and whether you have a portfolio of rentals now, you just want to turn one or two of them into it, all of that he helps you with. And that's pretty cool to have someone who's done this now over a decade helping you with your short-term rentals. That's pretty cool. So, but if nothing else, take some of the resources that he shares with you here as you hear our conversation and use that to kind of improve, ratchet up, add profit centers to what you're already doing. Okay, Tim, that was a little backdrop. Welcome to the show, buddy.

Yeah, thanks for having me, Chris.

Yeah, you bet. I, as I said in the intro, just being in Brazil and running, I think, everything, I'd love to start off with a little, believe it or not, a little definition first of what the short-term rental market means to you, only because there could be a brand new listener going, what the heck are they talking about? And then we'll dive into how you do that from where you do it. Is that okay?

Yeah, sounds good. Yeah. What the short-term rental market means to me, I mean, there's quite a range in the short-term rental market. Short-term rentals have been around for Forever. I mean, as an alternative to staying in a hotel and before Airbnb and people were vacationing and staying in bed and breakfast and those types of homes. So you could consider those short-term rentals. I think today's definition for most people is Airbnb. People just use it, they just use the name Airbnb now, but that's everything from an inner city urban apartment to a luxury oceanfront mansion. And there's all kinds of reasons that people stay in short-term rentals. You know, a lot of it's vacation, but now a lot of it's just as an alternative option to staying in a hotel. So it's kind of all in between.

So do they, is it, I'll use the word a must if you're, you know, the listener's going, all right, well, I want to do my first property, right? Is it a must to be linked to like the Airbnb or the VRBO? Like talk about that a little bit.

You would be doing yourself a disservice if you were not linked to it. I mean, the reality is they spend millions and millions of dollars advertising properties on your behalf, and so the more listing sites you can have exposure on, the more people potentially will see your property, the more potential you have for revenue. So yeah, we always recommend being on all the primary sites for sure.

Awesome. And let's talk about a few things. Well, first, let's talk about your company, Cordially, if I'm saying it properly. What else do you guys do? Does that just run your stuff? Does it also coach and help these guys who are listening? Talk about that a little bit. Yeah.

So it started, it was modeled after the way I've managed my own portfolio. So I've been investing specifically in short-term rentals for the last 11 years. It started off other real estate assets before that. And somewhere along that journey, I moved from the US to South America, and I've been down here the last 8 or 9 years. And so for the first few years of running my portfolio remotely, it was really just figuring out how to run it remotely, you know?

Yeah.

And there's a lot of pieces to that, and our industry's changed a lot. Like there's all kinds of new software programs. I mean, it's really easier to do today than it ever has been. And so it was sort of born out of my personal portfolio. And along that way, I also started a podcast, Short-Term Rental Riches, and a lot of people were reaching out and just saying, hey, can you help us with our property? And our team had gotten big enough to where we had extra capacity, you could say. And so we started working with other owners and investors managing their properties the same way we do. We work with an on-the-ground team, but our company Coresley essentially handles all the core operations, which is everything from marketing the property to guest communication, to revenue management, to, you know, on-the-ground coordination, essentially the whole core process.

I love it because I'm thinking like when I looked at your information, we're transitioning as we speak to more like niched into what we do, right? For guests come on and I looked at your stuff and I'm like, okay, this is cool because they can still buy however the heck they want. In our world, it's owner financing, sub-to, and lease purchase. And then they can go and do this with you. So if I'm tracking with you, they can do one or many. I imagine there's no limit to properties and then have you guys handle kind of like a done-for-you.

Am I tracking? Correct. That's exactly the idea.

Yeah. And what would it, in general, if you can quantify it, what would it cost someone to do like a property with you? How is that structured? Is that something you can pinpoint or does it depend?

It depends a little bit on the amount of properties someone has when they join us and also like the average daily rate, but it's anywhere between 5% and 10%.

Okay.

Roughly.

So if I bought a property tomorrow, I literally could connect with you guys and go, hey, here it is. And you guys would analyze it for me and then spit back like pro forma type numbers, I'm assuming.

Well, we really get started with someone after they already have a property, so they've already decided to run it as a short-term rental. We can certainly talk with folks if We're sort of questioning that, but once they have the property, then we take everything from there. So the reality today, it's just there are way more professional operators because there has to be like, there's way more supply than there's ever been, and guest expectations are a lot higher than they've been in the past. And so there's a pretty big difference between professional operators and someone trying to figure out everything on their own. And so we take that part away. We leave all the ownership under our partners. So the listings that we create, the property, the reviews, those are all owned by our partner. They could leave at any time if they wanted to, but we handle the whole operation underneath that.

It doesn't matter if you're brand new to real estate or if you've been doing this for several years or a whole bunch of years. I learned the hard way back during the crash that doing creative deals is Much better. It's a much better path in real estate in general than, let's call it, the old way. Getting paid once, using banks, signing personally. 3 paydays, getting paid 3 times on a deal. It's better. 3 ways, not 1. Money now, money over time, and money long-term. And I don't care if you're in an up, down, sideways market, it doesn't matter. You can and should operate with the utmost confidence. There's literally nothing I love more than helping people create systems and simple systems and processes to become massively successful with our 3 Payday System, and doing so in literally any market, and doing it geographically literally anywhere. So if you've been learning and learning and listening and studying and not taking action, I'm telling you after going through it myself, it's costing you tens of thousands if not hundreds of thousands of dollars by not taking action on the 3 paydays the way you should be getting paid. Many of the people that were brand new just like you that joined our community have fast-tracked their startup. No. I mean, wouldn't that be ideal? If you said, okay, should I go fast or slow? Should I take action now or later? It's costing you too much money to wait. Each one of you are at a point in your life, I'm sure, where you want things to be easier. You want things to be better for you and your family. You probably realize that you not only want more, but you deserve more in this life. So, to be able to give your family everything they want, build a legacy for you personally too, and to have time freedom to start enjoying life. And frankly, whatever else you're seeking. And for some of you, now's the time, for example, to just focus on security. Maybe it's building a big solid bank account for retirement. We take these things super, super seriously, and it's my life's biggest reward to help you achieve them. I want to give you a free discovery session with our team. It's free. It's 15 or 20 minutes. You have zero to lose and everything to gain, and to understand how you might fit into the 3 Paydays system. That we've done now in over 80 markets as of this filming. Go to smartrealestatecoachpodcast.com/discovery for a free call with our team. smartrealestatecoachpodcast.com/discovery. Because it's not whether or not you can do it or whether or not you fit. You can do it. It's whether or not you'll take action and do what it takes, and we can guide you through that process. smartrealestatecoachpodcast.com/discovery. We'll see you soon. That's pretty cool. I'd imagine that you guys have, well, let me ask you, what, what are some crazy lessons maybe stand out in your mind from, uh, you said 8 or 9 years ago you hit South America, but like even in the last 3 years, 4 years, what has changed and has it been harder or easier? You mentioned both a little bit and alluding to it.

Well, COVID was an interesting time. You know, that was, uh, definitely, but we learned a lot, a lot of really valuable lessons there. You know, what happened during COVID is a lot of people weren't traveling internationally anymore. They were driving to destinations and prices dropped because less people were traveling in general. And so we had a lot of locals staying at our properties, my personal portfolio, you know, and there's reasons that locals will book your property. You know what I mean? It's usually to do something they don't want to do on their own property. And so we learned a lot of lessons there around just protecting properties and having a lot of good things in place.

Wait, that's interesting, Tim. So let me unpack that one. So I wouldn't have thought it, but super common sense now that you say it. So they would go there and maybe have a party or whatever?

Yeah, pretty much have a party. So we've got lots of ways of handling that now. Of course, we have security cameras today. But we also have like really dialed in all of our policies. We can get damage waivers and deposits set up and just really, I mean, on the backend of Coorsly, we have 120+ SOPs essentially for all these little things that we've encountered over the years. So we've had our fair share of parties, but it's nice. It's reassuring for our partners joining today that we've already gone through that. I tell a lot of people, like, we kind of went through bootcamp with some of my properties. I learned there are more budget-friendly places as well. So yeah, we've learned a lot. We've implemented all the best systems that we can find, but that part of the industry's changing really quickly too in terms of technology. So we're just at the forefront.

How do you like, I gotta think it's, uh, all over the place with respect to reviews because of what you said earlier with all the competition out there. I know you can't control it, but how do you, yeah, I guess how do you control it? But, or can you, can you control it?

Yeah. Reviews are all about expectations and meeting or exceeding expectations. And so there's lots of ways to make sure that that's set up properly. It starts with the listing. and advertising everything exactly how it is. If there's something that's not good about your property, people are going to find out about it when they check into your property. So we have to be really transparent and then having really good guest communication. So our whole guest experience team, the job is to make sure that we've answered all the questions someone might have so they don't even need to ask them. And when it comes to reviews, That's really the important piece aside from just making sure you have a clean, well-maintained property. I think that the number one reason for bad reviews is generally it wasn't cleaned well enough.

Yeah, I've had it. Yeah.

Yeah.

Yeah. Meaning where I stayed.

Yeah.

That's probably a repeat one that I've experienced as a consumer. Yeah. What are some, I'll call it hacks if they're doing it on their own, right? And they go, well, I don't, I don't necessarily need Tim's company, but what are some hacks that you've learned profitability-wise? Like, we've tweaked this, like in our world, it's over the years, over 2, 3 decades now, I'm like, well, we've probably eked out all these little profits that add up to a whole bunch of money. So what comes to mind when I ask that?

Yeah, there's quite a few things. I mean, the interesting thing with short-term rentals is that you can look in most every market and you're going to find that The worst performing property is earning like 3 times less than the top performing property with most things being equal, same amenities, same location. And a big piece of that is the reviews. So you just have to have good reviews. If you don't get good reviews, it hurts your visibility and then your property can't do well. So making sure that you have the operation in is really essential. But with that in place, Then revenue management becomes a big piece. The amount that we can charge for a property depends on how many similar properties are in the market. It depends on whether there's an event going on or how far in advance people generally book. And so there's all these policies and ways that you can adjust your nightly price that make you one of the prime properties to rent at that moment. And there's tools for that. So like someone could sign up for a dynamic pricing tool. There's one called PriceLabs, there's one called Wheelhouse. These can plug into your listings, help you adjust for all those things and make sure that your pricing's competitive. So that's a quick hack. I think those tools in themselves have gotten so complicated now that You, uh, you can turn them on and you're going to be way better off than you would be just like creating the static property. But there's also like, you know, a few other steps you can take to get them fully dialed in.

So prior to, let's say, let's ask this prior to that, like you got the property prior to that, how, if there is a way, how do they pick like the best in their area? Right. Because we're all in different areas. Like I'm in a super vacation area in Newport, Rhode Island, but not everybody is. So how do they pick the best property and how do they know that their area's quote unquote suitable?

Yeah, good question. There's a lot of data today. So basically every Airbnb, VRBO that's on the market, there's data that's been scraped for it and compiled and you can run analysis. There's a tool called airdna.co. They're the industry leader in this space. And so you can sign up for an inexpensive subscription with them. You could look up Rhode Island, for example, and you could see how many short-term rentals are there and also how that supply has been changing over the years. And so my sort of quick tip for anyone like looking to see if their market makes sense or maybe they like another market is to look at that supply, see how many new units have been added, and then to look at both the average occupancy and the average daily rate for those properties over like the last 3 years. And if the supply's been going up and the average occupancy and ADR, which would equal your total revenue for the property, isn't going down, then you're at least in a market that's sustaining all new supply. Yeah.

Yeah. Really cool. What am I not asking you for a listener that is either in the mode of short-term or they want to enter? Like anything that comes to mind that I'm not hitting you on? Because I think there's so much to unpack here.

Yeah, I mean, it depends. I mean, I think that's a good place to start. Like, you know, a lot of my properties were long-term rentals before I turned them into short-term rentals. And so if you're an investor out there and your main purpose with all your real estate is like just to earn as much money as possible, then you really have to consider those options. A lot of people in the short-term rental space also use their short-term rentals for for vacation, you know? Yeah. So assuming it doesn't have a personal piece into it, then running the numbers is a really good place to start because if you have a portfolio of properties and they could be earning 5 or 10% or 15 or 20% more on a year-over-year basis, then it has a really big impact. And there's also some some potential tax benefits on the short-term rental side of things that don't exist on the long-term side of things. Because depending on how much time you spend on your property, you could materially participate is the way the IRS would describe it. And it doesn't require you to be a real estate professional to take deductions against other income if you materially participate. So there's also a lot of like potential tax benefits for someone looking to get into the space as well.

I definitely didn't know that. This is interesting. That's why I asked the question the way I did, that what am I not hitting on? Talk about how they can reach you, Tim, so I don't forget that, because I'll get blabbing here and then we're almost wrapping it up. How do they get you? Anything you want to share for links or anything?

Yeah, sure. Our company is called Corzly, C-O-R-Z-L-Y.com. You can, there's a link there. You can chat with our team. We can look at your properties, see if it makes a good fit. I also have a podcast I've been hosting the last 6+ years. It's called Short-Term Rental Riches. Quick actionable episodes. I've talked about literally everything that has to do with short-term rentals. And so if someone's curious, there's a lot of good content on there and it's on all the normal podcasts, YouTube outlets.

Nice. I love it. Let's write it down, right guys? Tim, it's been awesome. I, again, when I looked at him, like for selfish reasons, I want to brainstorm with Tim a little bit and see what's going on here. So I love it. Hopefully we can chat on your show someday and And super appreciate you coming on. Thanks much.

Yeah, thanks for having me.

Okay, guys, that wraps up our time together with Mr. Tim Hubbard. If you got value from today, make sure you subscribe so you don't miss any of the next episodes coming up, because we're going to again fine-tune this very, very niche and very focused view. If you're ready to start structuring deals with all 3 paydays, sometimes 4, head over to smartrealestatecoach.com and let me help you Take the next step. I would tell you guys, I know you hear different links we throw out, but if you haven't done the basics with us, I would just suggest you go there next. For example, you know about the event coming up in September in Rhode Island? That is the 3 Paydays Live 2026. So that's easy, 3 Paydays Live you can go to. But if you haven't looked at, for example, our apprentice program yet, this is something that we started, I think we're going on 2 years now. Having been at this for so long, we included this entry as an apprentice to kind of have you look under the hood, so to speak. Have you look behind the green curtain and what's going on with Smart Real Estate Coach? Because I'll tell you that nobody's doing what we're doing. Nobody. That's a pretty bold statement. Go over to 3, the numeric number 3, 3paydaysapprentice.com. And when you go there, use the coupon code podcast. And that'll get you 50% off. Uh, there is zero reason for you not to jump on that. And if you're not ready to look into that further and kind of fast forward what you're doing into '26 and '27, take advantage of our freestyle. Go to 3paydaysbooks.com. Again, that's the number 3, 3paydaysbooks.com/podcast. We're going to ship you out some free books. They're yours. There's no cost for shipping. They're all yours. We'll see you next week on the next amazing show. And we have just a plethora of cool guests coming up for you. Can't wait to be back with you. All right guys, super cool announcement. On the 27th through the 29th of September, we have our 3 Paydays Live. I'm talking no gurus there, no fluff, just a proven system that builds wealth. Literally join us on this 3-day event, guys. It's in person. There'll be no virtual. We're going to show you literally step-by-step how deals are constructed, how we negotiate and solve challenges for sellers, and how we close those deals without banks or credit. Super important when I came out of the crash. You'll see real deals, real numbers, and exactly how the 3 Paydays model creates multiple streams of income from just one deal. I'm talking averages of $45,000 to $350,000 per deal, all 3 paydays. Just one or handful of these can change your year, guys, and certainly create a total breakthrough by the year 2027 for you. You're going to leave this event super clear and confident about how to speak with sellers, how to structure offers that are win-win, and how to think through deals literally in real time. We've made some really cool adjustments this year too. We've built in hands-on workshop learning experiences and extended the Q&A after each section, and some other really cool experiences so you can actually do deals when you leave— not just conceptually understand it, but do deals. And lastly, we've removed all outside speakers, back to our roots. Just the family team. You're gonna hear from people who've recently closed deals and how they made it happen, and that's important because association with others and proximity really, really matters and can and will change your trajectory. If you're serious about totally replacing your income or adding a really cool supplemental income and building some long-term wealth, this is where it becomes real, guys. 3 Paydays Live, it's led by our family team and our coaches, all who are in the trenches every single day, every single week Again, no outside speakers selling you stuff. None. Just go to 3paydayslive.com/podcast to learn more and to claim your spot. We'll see you there. All right. Thanks for tuning in to the Smart Real Estate Coach Podcast. If you got value from today's episode, guys, be sure to subscribe so you never miss a future episode. It literally takes one nugget to access some of the things we're doing. And we talk in the amount of the size rather than paydays, it's an opportunity cost that you can't let go. So don't miss an episode. And for goodness' sake, share it with someone who needs to hear it. If you're ready to find your best path for getting started on your real estate investing journey in general, head over to smartrealestatecoach.com/getstarted. We're going to help you take the guesswork out of your next steps. See you in the next episode.