
Radical Hospitality Show · 2026-08-20 · 38 min
Key moments - from our scoring
Substance score
55 / 100
Five dimensions, 20 points each
Tim Hubbard founded Coursely to help short-term rental owners and managers streamline operations across more than 50 cities worldwide. Operating as a virtual-first company, Coursely doesn't replace traditional property management but partners with owners who maintain their own ground teams (housekeeping, maintenance) while Coursely handles guest experience, listing optimization, revenue management, and operational coordination. The company breaks its services into four main teams: guest experience (handling communication across platforms like Airbnb), listing optimization, revenue management using tools like PriceLabs, and an internal development team building custom integrations. Tim emphasizes that AI's real opportunity in short-term rentals lies not in flashy automation claims, but in handling repetitive operational tasks - early check-in requests, lost-item coordination, turnover management - where AI currently struggles with multi-layer decision-making. Coursely uses Host Away for property management, integrates with Conduit for AI-powered guest communication, and builds custom tools like "Smoothly" to bridge gaps between disconnected platforms. The company's competitive advantage stems from managing tens of thousands of reservations across diverse markets, allowing them to offer scalable expertise, dynamic cleaning checklists informed by guest feedback, and professional consistency that individual owners can't achieve. Tim still invests personally (recently acquiring in Orlando), focusing on unique properties rather than competitive markets.
Coursely operates as a back-office partner rather than taking over listings; property owners retain their brand and all revenue goes directly to them, while Coursely handles guest communication, revenue management, listing optimization, and operational coordination. Coursely also charges lower fees because owners maintain their own ground teams instead of Coursely hiring and managing cleaners and maintenance staff.
Coursely uses Conduit as its primary AI-powered guest communication platform, integrated with Host Away and other property management systems. However, AI currently handles only simple queries (WiFi passwords, check-in codes); Coursely builds custom automation on top of Conduit for complex tasks like early check-in requests because existing tools can't manage multi-layer decisions like checking property availability, owner preferences, pricing rules, and payment processing.
Coursely coordinates all cleaning and turnover communication through Breezeway and its internal tool called "Smoothly," which creates dynamic checklists updated by guest feedback, maintenance notes, and reviews. This ensures cleaners have all relevant information without Coursely needing to hire and manage local housekeeping teams.
Tim recently acquired a property in Orlando despite its competitive market, focusing on unique properties with larger lots that differentiate from cookie-cutter vacation rentals. He emphasizes that market selection matters less than operational excellence - two identical properties in the same market can have vastly different revenue potential based on reviews and operations.
Coursely organizes into four teams: guest experience, listing optimization, revenue management, and development (software engineers). Team members are distributed across Eastern Europe, Pakistan, South Africa, Philippines, and South America to hire the best available talent rather than being constrained by geography, allowing competitive pricing without geographic overhead.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains useful operational advice specific to short-term rental management (dynamic checklists, AI automation for guest requests, review-driven operations), but much of the content is relatively straightforward or already familiar to STR operators. The discussion of Coursely's service offering and Tim's business model takes up significant time without dense new insights. Several tangential stories (Colombia project, Orlando property) dilute focus.
You've got to have good reviews...if you're not getting good reviews, we can do everything we can on our end...the difference between two identical properties in the same market, the difference in their revenue potential is just pretty, pretty vast.
we've built a lot of integrations on top of it just to help us make sure that nothing gets overlooked...we need a way to make sure it's doing the job it's supposed to, that there are no errors
Tim's core insights - reviews drive revenue, operations matter more than aesthetics, AI works for simple queries but not complex tasks - are sensible but not particularly novel. The idea of building custom tools to bridge software gaps is practical but incremental. The discussion of remote team structure and distributed hiring is increasingly common. Little here contradicts conventional wisdom or offers counterintuitive angles on the STR space.
AI never forgets anything, you know, so if we've got a really good knowledge base on a property...a human receptionist that's just not going to click
the challenge is there are all different tools like Host Away...they're still not the best when it comes to revenue management or they're not the best when it comes to AI technology
Tim Hubbard is a legitimate practitioner with 16 years in real estate and 11 years in STRs, operating properties across 50+ cities and building a service business. He has hands-on experience and real skin in the game. However, he functions partly as a podcast guest and educator rather than purely as an operator solving novel problems at scale. His recent focus on Coursely's software and service delivery rather than investment limits his current edge.
I started with my first short term rental 11 years ago...still operating it
I've been in real estate for 16 years now and I got in at the very beginning...trying to find cash flow properties
The episode includes some concrete numbers (11 years in STRs, 16 years in real estate, 50+ cities, Coursely's team structure across specific regions, Colombia unit cost $60-70K excluding infrastructure, Hostaway valued at $1B). However, many claims lack specifics: no named STR properties, revenue figures, occupancy rates, actual pricing strategies, or performance metrics for individual markets. The AI tool discussion names Conduit and Host Buddy but provides limited data on outcomes.
I started with my first short term rental 11 years ago...Uh, he's the founder and CEO of coursely...remote first company that helps short term rental owners and managers streamline operations across more than 50 cities worldwide
We ended up having more infrastructure than we, we anticipated...I think we were in each unit around like 60 or 70,000
Zeke asks reasonable follow-up questions about team structure, cleaning coordination, software, and markets, but rarely pushes back on Tim's claims or explores tensions. When Tim describes the Colombia project's delays, Zeke sympathizes rather than probing for root causes or lessons. The conversation is pleasant and flows naturally, but lacks sharp interrogation. Zeke does share his own experience (good for rapport) but doesn't use it to challenge Tim's narratives or extract harder truths.
Yeah, development's a whole different thing. I mean, it takes time...not surprised.
So, curious with AI, how are you utilizing AI? Uh, how do you see it changing the industry right now?
Computed from the transcript - who did the talking, and the words that came up most.
Most people think the hard part of a short-term rental is buying it, but the real work starts the day a guest checks in. In this episode of the Radical Hospitality Podcast, Zeke Freeman was with Tim Hubbard, founder and CEO of Corzly and host of the Short Term Rental Riches podcast. Tim got into real estate sixteen years ago chasing financial freedom, bought his first short-term rental in California eleven years ago, and slowly turned a remote operation into a business that now supports owners and managers across more than fifty cities. He runs it all from South Brazil with a team spread across the globe. Tim and Zeke get into what it really takes to operate rentals well, where AI helps and where it still falls short, and the honest lessons from Tim's boutique hotel project in Medellin. It is a practical, grounded conversation about operations, technology, and building hospitality businesses that last.
Transcribed and scored by The B2B Podcast Index.
Speaker A: You've got to have good reviews. You know, it's really clear. Two identical properties in the same market, the difference in their revenue potential is pretty, pretty fast. And so it really does come down to operations and making sure that things aren't overlooked.
Speaker B: Hey everyone. Welcome to another episode of the Radical Hospitality podcast. I'm your host, Zeke Freeman. Today we've got Tim Hubbard. He's a seasoned real estate investor, entrepreneur educator who's built a global business around short term rentals and hospitality operations. Uh, he's the founder and CEO of coursely. Tim leads a remote first company that helps short term rental owners and managers streamline operations across more than 50 cities worldwide. Uh, originally entering real estate through investing, Tim discovered the power of short term rentals to create both financial freedom and location independence. Today he lives in South Brazil and his wife while managing teams and properties and hospitality operations across multiple markets. In addition to growing coorsley, Tim is an educator and mentor through STR Rich's podcast where he teaches entrepreneurs how to build profitable short term rental businesses. Tim's journey combines entrepreneurship, hospitality, real estate, investing, technology systems and the pursuit of freedom through business ownership. Tim, welcome to the show.
Speaker A: Uh, thanks for having me, Zeke. I guess you guys got the long bio version there, but yeah, pleasure to be here.
Speaker B: It's always good to know, just got a little context uh, of uh, who we're chatting with. Yeah, you, you've got a great podcast and so I, I know you're helping a lot of people out there doing short term rentals. It's been fun to listen to a few of those have you on. So today I think you're, you're down in Brazil. How, how did you end up down, down in Brazil through your journey here?
Speaker A: Yeah, yeah, well, I've always loved traveling. You know, I've been in real estate for 16 years now and I got in at the very beginning to, for financial freedom, you know, passive income, going down that, that hole with uh, Robert Kiyosaki and you know, trying to find cash flow properties. So I've always enjoyed traveling and I guess a decade ago I was actually traveling to Columbia a lot and end up moving to Colombia and then discovered Brazil and then really liked Brazil and then so for the last five years or so I've been down here and Brazil is now home based. So love it.
Speaker B: So you're managing properties across 50 different cities. How did you start building up that, your short term rental business? Where did your journey kind of start with that?
Speaker A: Yeah, so I started with my first short term rental 11 years ago. I'm from California originally and so that's where my very first one is and still is there today, still operating it. But the numbers kind of changed in California back in the day and I was looking for better investment options. And so I, I headed out some different states, did quite a lot of research, ultimately landed in Tennessee where I acquired quite a few short term rentals, uh, then expanded to Oklahoma City. Not your, not your typical vacation rental places, but as we know, people are staying in short term rentals for, for lots of different reasons. And so it worked well and I started a podcast along the way. Uh, you ment it briefly there. It's called Short Term Rental Riches. After I moved to South America, a lot of friends were just asking like, hey, how are you managing, you know, all of your short term rentals remotely and still growing your portfolio? And this was kind of back in the day when managing a property virtually especially short term rental, was like, you know, like a new idea. People were like, I don't know, that sounds really difficult. And so the podcast was really a way to answer those questions in short form. They're like quick, actionable episodes. And it was just talking about my own portfolio and what I was doing. But then a lot of people started reaching out on the podcast and they said, hey, can, can you help with my property or can you help with my property? And, and my team had gotten big enough to where we had extra capacity. You know, we, we could handle more reservations, we could uh, communicate with more guests. And so pretty organically I guess we turned that into a business and today we operate Coorsley and we're completely virtual, which is why we're in so many different places. And our whole mission is to handle the core operation behind our short term rentals.
Speaker B: Nice. So I run a virtual architecture team as well. I think there's a lot of advantages that people don't, you know, quite understand. There's also some challenges that you know, you have to deal with. Building a virtual team, what does that look like for you as you built out your team and what, what are, what is your team composed of to handle your short term rental business?
Speaker A: Yeah, good question. We're really broken into four groups. Uh, at ah, Coorsley we have our, our guest experience team. So there are reception, communicate with our guests, you know, make sure everyone's happy. Also talk with the travel agencies like Airbnb. We have our listing team. They're the ones that help us create all of our listings, make sure they're optimized. Make sure they're on all the platforms where they should be so that people can actually find them. Uh, we have a revenue management team which put, puts the right prices at the right time in the right places. And, and now we, we have a development team which is, is really exciting. So we have our own developers on board and we're, we're, we've always used a lot of different software. I love software. I used to work for a software company and I'm always like trying to use the next gadget, you know. So that was part of my, um, my process for managing my rentals was just taking advantage of technology. And now today, because it's so much easier to build, we've really incorporated that and we're, we're trying to fill holes where we saw them exist in the market. Um, so yeah, I guess that's, that's what it's like on the back end. And we are spread out all over the place. So we've got team members in Eastern Europe and Pakistan and South Africa and Philippines, South America. And why we're so spread out, I guess, I don't know. We used to hire everyone out of the Philippines because it was like when you were looking for a virtual assistant or virtual help, that was one of the most common places to look. But now, I mean you run a virtual architectural firm. That's amazing things virtual today, you know. And so we've really branched out and you know, our, our positions at Corsley, we're just looking for the best talent we can find. And that's sort of led to having people in lots of different places.
Speaker B: Yeah. Uh, do you still feel like when you're in a market, do you guys have any on the ground presence to even to kick off or start, or do you bring out a client completely remote? What are the things that you have to, that fill in the gaps for on the ground that you're either partnering with or going out and doing? Like what, what, what does that look like?
Speaker A: Yeah, great question. So we call our customer relationships a partnership because there are a couple pieces they're doing, we're handling all the rest. So we handle the core operation, you know, that setting up the listings, the guest communication, the uh, revenue management, uh, all those types of things, software setup. But we're not actually hiring their on the ground team. And so when people started joining us, you know, I've always had my own on the ground team that helped me manage my properties. And when people came to us and said, hey, can you help us manage our properties? A lot of them already had their uh, their team in place. You know, they had their housekeeping team and they had their maintenance and so we simply just took over communication and we have a lot of processes in place that you know, maybe they didn't, you know, and things that we've learned from managing a lot, a lot of reservations. And so today we partner with our, our customers and they either have their, or they go out and find one and we take over the management. Yeah, we charge a discounted management fee because of that. You know, it's not for everyone. There's some people that don't want to handle anything but it's, it works out really well for a lot of people. And you know, finding a housekeeper today for short term rentals I think there's, there's more options than there ever has been because short term rentals are just more, more of a, they have more of a place in the market I guess in the real estate market today.
Speaker B: Yeah, we kind of looked at this when we were looking to hire a management company on our short term rental and it does seem like there's different slices of management, um, groups and there's also probably different tiers of fees depending on how engaged you want to be as a, as an owner or not. You know, we are, for example, you know, we're close to our short term rental but we also have, you know, other focus areas of business. And so when we first started we just wanted to be, you know, hands off but we can still run over and deal with management, you know, maintenance issues. Mhm. And so we didn't want to pay, you know, some, some management companies, you know, are like this kind of 20, 30% tier. We didn't feel like we needed that level. And then on the other end there was companies like Vacasa that seem like, you know, there's less engaged but also completely remote. And then there's some that was kind of in, in between and handled guests, communications, maybe cleaning, had their own cleaners. We kind of landed a little bit in between with the first management group before we took it over. But it's, it's interesting. You know there's not kind of a one size fits all in, in property management. What, what, what's kind of yalls like expertise and specialty like when you're looking for an ideal client and what are the things that it's kind of the competitive advantage of? Of courseley. And if someone's looking to work with you guys?
Speaker A: Yeah, well, there's quite a few things. I mean as you know, there's a lot that goes into a short term rental operation. You know, there's, there's a lot of pieces and the more properties you add, the more all of those tasks, you know, the more of them there are. So we really like working with, with owners with small portfolios or property managers. And what we found is, and you know, I was in the same position myself as when I was getting started. It didn't make financial sense for me to go out and hire a full time revenue manager or you know, to hire five full time receptionists to make sure I had 24, 7 coverage and there was someone there in case someone else got sick. And I wasn't asking people to work, you know, 14 hour shifts or be on call all week. And so like to have a team. And the other thing is, you know, we go out and hire a virtual assistant, which is, it, uh, can definitely work, but there are challenges and one of them is that we sort of expect, you know, someone joining us to be an expert at all the different pieces of a short term rental. And there's a lot of different pieces. You know, revenue management, for example, is completely different than talking to guests. But then we have all the different policies and all the different listing sites and there's just a ton of things that happen on the background. So we take that away. You know, if someone still wants to be the owner of their listing. You know, a lot of traditional management companies own your listings like Vacasa and, and if they don't do a good job, you're kind of just locked in there, you know. And so we're different. We work on behalf of our partners, properties, all the money goes to them. It also means that like a property manager keeps their image and keeps their brand and Coorsley handles that core operation on the back end, which allows them to focus on what they probably got in the business in the first place for which is, you know, growing, growing their portfolio. And so yeah, we bring the organization, we bring the expertise for managing, you know, tens of thousands of, of reservations, all the SOPs, no one has to hire anyone and we just make it, we make it a lot easier.
Speaker B: How do you deal with cleaning on the ground? Are you guys coordinating those or is that.
Speaker A: We do, yeah, yeah, we'll, we'll handle all the coordination and we've got a lot of pieces in place for that. You know, first thing is just making sure the cleaner knows about it. So uh, we've got, you know, we use Breezeway right now, but we've also Built a cool tool internally. We call it smoothly and it's to make sure the whole turnover goes smoothly and it does some, some nice things like you know, we're tracking ah, all of the communication that comes in for a reservation or for property. And so if a guest mentions something, whether it's during the, during the stay, whether it's in a public review, whether it's in their private feedback, if a housekeeper had mentioned something before like during a turnover, all that information is getting tracked and we incorporate it in, in each checklist. So we have a checklist for every turnover. We highly, highly suggest photos. You know we have all those basic sort of elements that you can put in, in a turnover checklist. Uh, but we have a really good follow up program. You know we're really transparent with all the reviews. So if good reviews are coming through we pass those over. If a uh, not so good review or something that needs to be changed comes over then we incorporate that in the future checklist. So it's, it's, it's dynamic so we're never really overlooking anything.
Speaker B: So you mentioned you've got developers coming in. I'm assuming that software developers, not like land developers or you mentioned you're, you're doing smoothly what that seems like to be a core part of what you guys do. Some, some of the software integration in your, in your company. What, what type of software components or technology are you guys integrating in?
Speaker A: Well we, you know we still use what we found to be the industry leading tools, you know so our, we use Hostway for our PMS and we use tools like Price Labs and Breezeway. We use some AI tools for, for guest reception. But the challenge is there are all different tools like Host Away, you know, was just valued at a billion dollars but they're still not the best when it comes to revenue management or they're not the best when it comes to AI technology for short term rentals. And so we've gone what we've found um, has been the best but because all those programs are separate it makes a little more complicated and not everything's connected really well. For example we have a lot of AI automations that we've put in regarding operational, you know, turnover tasks. Maybe a guest left something at the property, for example. Like all of these tasks happen frequently, you know, maybe not with one individual property but at some point in time like someone's going to leave something at your property, you know and you're going to need to message them, um, to figure out how to get it back and to go through that process. And so that requires two tools right now in the industry. You know, of course we have our human team, but we're working towards using AI to automate as much as we possibly can. And so, I guess, long story short, we're using our developers to bridge the gap between a lot of tools that exist. We have a central hub where all of our partners go and they can see everything without logging into multiple tools. But it's also helping us to create things that don't exist. Like, you know, having a dynamic checklist for a housekeeper doesn't exist in Breezeway, it doesn't exist in Turno or some of the other options. And so we're, we're bridging everything together, but then we're filling some holes where, where we've identified them.
Speaker B: So, curious with AI, how are you utilizing AI? Uh, how do you see it changing the industry right now? Like, what are the opportunities that are really helping short term rentals? All right, guys, I've got one quick favor to ask. If you've been enjoying radical hospitality, if these conversations have inspired you, encourage you, or help you think bigger about what it means to create spaces that truly serve people, would you hit the subscribe button? It's a small thing, but it makes a huge difference for our show and for our team. We're working hard to bring some of the most thoughtful entrepreneurs, builders and visionaries in, um, hospitality people creating meaningful spaces all over the world. And your subscription helps us keep getting better every single week. And if you're someone who's dreaming about building a hospitality project of your own, that's what we do at Root Architecture. Every single day. We help clients design and bring those spaces to life. You can book a discovery call with me or someone on our team@therooteam.com. thanks so much for being a part of this journey. This really means a lot to me. Subscribe, stay with us, and let's keep building. Cool stuff that serves you.
Speaker A: Yeah, I think tons of opportunity with AI and I know there's a lot of tools out there. You know, it seems like every week there's a new one that promises you can turn it on. And you know, your business is going to be automated. We have to be really careful.
Speaker B: Right.
Speaker A: We don't get second chances when it comes to a guest experience usually. And so what we found is that a lot of the AI, uh, tools out there today do a good job at responding to simple questions like, you know, what's your WI fi password? Or, you know, what, what's the address. You know, I can't find my check in instructions or I don't what's my door code? You know, even though we've sent it several times. And so those basic type questions AI can do a really good job at, but where it's not doing a great job yet is in more detailed operational tasks. You know, take like uh, an early check in request for example. Let's someone and we know most guests request early check ins or maybe they request a late checkout. Right. There's quite a few components that go into that. Right. First of all we need to make sure that the property is clean. You know, if as us as a, as a manager helping lots of different owners, we also need to make sure that that's something the owner of the property is okay with. So that's the first place we check. Then uh, we make sure that the property's clean. But then maybe we charge for early check ins, you know, but we only charge for early check ins if it happens to be like three hours in advance or more. Then we need to know how much to charge and then we need to send a payment link to. So some of these like multi layer tasks is where we found that AI is just not there. Like there is no tool that you can turn on and automate. So we've built a lot of that on the back end. But the beautiful thing about that is like those tasks are the same. You know, we manage properties of all different sizes and shapes, you know, small and big. And the way someone asks for an early check in is the same. Like you know, the processes we need to check are the same. And so I think there's a ton of opportunity with AI for us to uh, continue automating a lot of these tasks that are normal, that are core to the, to the short term rental operation. And that's our mission as to continue doing that and to be able to offer really competitive prices. So someone doesn't have to figure this out on their own, but also make the guest experience better. And so that's ultimately one of the really big pushes with AI is make the guest experience better. Because if that's better then we get better reviews and we get more visibility and then our property earns more money. And a couple just quick ways that we see that happening today is AI never forgets anything, you know, so if we, we've got a really good knowledge base on a property, you um, know every little detail that comes up we're going to remember, we're going to remember if A guest was there two years ago where, you know, a human receptionist that's just not going to click unless there's, there's something there. It also gives us a way to be really professional and consistent with our messaging. You know, so as someone grows their portfolio, you have multiple people working on reception, but they don't all respond exactly the same way or maybe with the exact same tone. But with AI we can, we can have a central tone. So yeah, they're a little, a little bit there. But we're really excited about AI, uh, because it's making the operation more efficient. It's uh, making the guest experience better as long as it's used in the right ways.
Speaker B: Now are, are you using AI with any specific tools that people should be thinking about or are those like built in custom tools?
Speaker A: Yeah, both. So we've, we've tried a few. We used to use Bestie, I think it was called. We use Conduit right now. But we also have a lot like we maxed Conduit out after like three months. You know, we're, we're like on a direct Slack channel with their team and, and it's like we just keep maxing them out on things, you know, so we've built a lot of integrations on top of it just to help us make sure that nothing gets overlooked. I think that's one of the really important pieces with AI too is like we need a way to make sure it's doing the job it's supposed to, that there are no errors and that certain types of messages that maybe shouldn't be going to, you know, and in AI right now are automatically going to one of our team members. So we have lots of escalations and things set in there to automatically route messages depending on the type of message.
Speaker B: Yeah. So is Conduit a, like, is that primarily a guest communication platform where it's picking up and making recommendations?
Speaker A: Yeah, Conduits started specifically in the short term rental industry. They, they've since branched out to become a communication platform trying to serve lots of different industries. So they, they integrate with a lot of the, you know, most common property management softwares like Guesty and Hostaway and those types of tools. So that's the one we've been using. I, I think the writing's on the wall and, and we're, we're already on our way to replacing Conduit and just probably building it out on our own. But there are some, what's the other tool that Host Buddy is another one. I hear quite often that people seem to be pretty, pretty happy with. So quite a few tools out there today.
Speaker B: Yeah. And then you came in it from the investor side. Are you still investing and is there certain markets that you like or are working well still in 2026?
Speaker A: Yeah, let's see. So I haven't been as active, you know, looking for new properties. I, I did actually acquire property in Orlando this year, which most people are probably thinking like, why would you buy a property in Orlando? It's the, you know, the most competitive short term rental space, you know, maybe in the US but it's interesting, I think the property is interesting and it's unique. You know, it's, it's, it has a larger lot where most short term rentals in Orlando, they're like the same, you know, they are, you know, they've got a pool, they've, you know, they're basically cookie cutter homes. And so I think there's quite a bit of opportunity with that property. But it was also sort of a personal decision because we, it's sort of like our mid place between my family and Brazil. So it's a good, it's a good stopover place and, and we like Florida. So aside from that, I've been investing in Medellin, Colombia for the last like four years. We built a small boutique hotel project. Well, we have eight units today. The license is for 20. It's taken a really long time and so I'm kind of backing out of that one. I also haven't spent as much time there, but it is up and operating. Amazing, amazing location. A little different, you know, doing a development project internationally. There's definitely been some learning lessons there. But outside of those two things, I would say, Zeke, I. There are properties I have that I am planning on exchanging. You know, they have a lot of equity but I, you know, they're both long term or short term rentals. But we've just been so focused on coarsely recently. Honestly I haven't spent a lot of time so.
Speaker B: Yeah, yeah, you know, I mean I, I think it's good like you know, to have a core focused business and I always look at real estate as a place that, you know, we're you know, parking long term wealth and building long term wealth and it's, I think it's good to kind of do both alongside. So that's what we do on the architecture. But I think it's also, you know, helpful when you can speak to your clients and say, you know, here's what we've done and experience and learn A lot of what I tend to focus with on radical hospitality. Since we're kind of involved in this niche of boutique hotels and outdoor hospitality. Um, we're doing a lot of micro resorts. It is that space so you know, good, bad or ugly, and sometimes they're, you know, things don't work. But I'd love to hear more about that Columbia project and you know, how that's started as much you'd be willing to share about what it is and how, you know. Yeah.
Speaker A: So I was living pretty much full time in, in Colombia for, for quite a few years and I love real estate and so naturally I just, you know, was looking for opportunities and I had acquired a property there in 2017. I think it was like a personal residence. So that was the first place I got. And then a buddy came up with another opportunity. I was looking for a lot to build, build a home. Actually I wanted to build my own house there. And uh, this lot came up that was pretty good size, like a little over two acres, pristine location, amazing view, you know, relatively good price. And it already had a license for a, uh, commercial license to build, uh, in an area that's surrounded by like nice subdivisions, which is pretty unique. And so we both went in together to purchase the lot and it was big enough to where we both were going to build our own homes and then like basically divide the lot in two so we could have some rentals to support, you know, the property, pay for everything, make a little extra money and then, and then have, you know, somewhat of our, our dream homes there. And so we, we went through all the architectural plans and then city's plans or the city changed, you know, our, our permitting, they basically weren't allowing us to build individual homes there anymore. And so we went through quite a long process of getting a new license. Ultimately we couldn't build the homes, but we could build 20 units. And again, an amazing location and, and the license also allows for a restaurant. So we went down that road, started construction last year we finished about eight units. Uh, we ran in a couple other pauses along the way. You know, neighbors that wanted to shut the project down, even though it was fully permitted and legal and everything like that. And in the meantime I was spending more and more time in Brazil, which is pretty much home based now. And so I kind of just became disconnected from the project a little bit last time I was there. Yeah, we're up and running. My partner lives there full time and he wants to continue to build it out. But I'm actually looking to sell my, my 50%. So, yeah, it was a good, good learning lesson. I had it gone quicker, you know, I, I would still be fully involved with it, but we were really delayed like a couple years. And during those years just, you know, my life changed a little bit. So that's where we're at today.
Speaker B: Yeah, you know, development's a whole different thing. I mean, it takes time. It's, you know, uh, it's not something like a, uh, short term rental that you can either go buy and put on or even a single family. So not. Sorry, sorry that it didn't like pan out the way you wanted, but also not surprised. You know, it takes time.
Speaker A: Yeah, yeah. Fortunately, you know, we have enough units up and running. They cover all the costs and you know, and they are beautiful units. They're like, they all have.
Speaker B: What kind of units did you guys.
Speaker A: So our designs actually have three different layouts. The first date we did are like individual cabana type properties, but they're all raised up on, on big columns and amaz views. They have big porches with a private Jacuzzi. They're one bedrooms. But they also have a good amount of space. Like they have full kitchens, they have full laundry. And so in Medellin, a lot of people end up spending months there, you know, or they go there and then they want to go back. And so they're really built to accommodate someone that would spend weeks or months there, but also a great place for someone looking for just, uh, a couple nights. And then the other two designs were two six unit buildings, so they're still fully approved today. We just haven't got into them yet. And then there's great spots for a restaurant. My partner happens to have another hotel project that's already up and running. He's got a really nice restaurant that's up and running, so that's kind of his forte. On the restaurant side, what's the name of the development?
Speaker B: Somebody wanted to pull it up or check it out.
Speaker A: Vista. Yeah, Hotel Vista.
Speaker B: In, in Colombia or just.
Speaker A: Yep.
Speaker B: Yeah.
Speaker A: Ah, we need to. I, I don't think we do actually.
Speaker B: Okay. I was like, I'm not fighting it.
Speaker A: Yeah.
Speaker B: I feel it's got a couple, like one shot of it and looks like it's got some cool canvas, um, designs on it.
Speaker A: Yeah.
Speaker B: What were, you know, with the overall, like, cost per unit was on, um, what you guys did on these things?
Speaker A: We, we ended up having more infrastructure than we, we anticipated. So there's a natural spring on the lot and there was a lot of water drainage and stuff we had to do. And we also have a rather large reception building that we put in place, you know, that has a backup, um, generator and like electrical room and laundry and reception and bathrooms and everything. I think we were in each unit around like 60 or 70,000, you know, not including the land costs or the infrastructure or the reception building.
Speaker B: Yeah. If you were to do it again, what would you do different?
Speaker A: You know, at the, at the time? So I had first I have a partner there that's lived there full time, already has another project, already worked with the architect that helped us and nothing but great things to say about the architect. Like he already had some other successful projects and he also managed the construction. And so from the very beginning it was sort of like a hands off type of project I should say. After we found out we couldn't put our houses there, it became like a, you know, a hands off project. And so I'm really fortunate that I have my partner and then also had the architect that managed the project. I guess. You know, I would, I me personally invest in another country now I would be a little more cautious just on the permitting process and not just assume that because there's a license, you know, that everything is gonna, was, would go as planned. You know, that that whole process is, is quite a bit different there than I think it is in, in the United States and I still don't fully understand it and so I probably wouldn't do another one internationally.
Speaker B: Yeah, we we kind of started on the path. So a lot of our, our team is down in the Dominican Republic and the uh, my business partner on our hotel, a uh, coffee farm down there and he's been working on this coffee farm for, for a long time. Beautiful property. Our, our team helped do the master plan. He's an architect as well, so he kind of led that within our team and you know, went down the path initially of uh, doing this as a development that we were going to kind of work on together, bring our investor groups in and not being for so for not speaking the language to not understanding the local politics. It seems really good on the surface how cheaply you can build in foreign countries and the quality of construction. I went down there and walked through some properties that uh, he'd been involved in and you know, beautiful construction, fraction of the price of what it cost us to build here. But as we got down the path there's just so much involvement in a hospitality project that you've just got to be able to engage and be able to get in, in control and for, for me not speaking the language, I never got to that comfort level of hey, I could go in and you know, if a contractor, you know, wasn't performing right, be able to correct that, that situation. The same thing with permitting it not being, not that permitting the US is straightforward but at least you know, there is a set of rules and understanding and you know, you can push and drive through. You know, there's a little bit more of, you know, bribery and things like that that just kind of happen. Which honestly is like the US like we might be better off with some of our permit officers if we could just bribe them to actually do their job. That's not the worst system in the world. But yeah. So you know, I, I kind of had some, you know, step backs on that and then we, we chose to actually step back the same partners and, and work on a project here locally while he's continued on on, on that development down there. So you know, I, I, I, I love Central America and you know, to vacation down there. I'd love to do something in Costa Rica, you know, because they're just fun but they're also uh, you know, as not local and not understanding certain local politics, especially language, you know that has, that has made me nervous. Seems like. Do you speak Spanish? Well and are you?
Speaker A: I do, yeah. I think it's, it's you know, the last years in, in Brazil I probably have more of like a uh, port, Portanol they call it, you know, Portuguese Spanish. M. But yeah, ah, comfortable enough at least to get, get involved with, with projects in Spanish.
Speaker B: Yeah. Have you seen many people or helped any clients buy short term rentals either in Colombia or Brazil?
Speaker A: I haven't personally helped anyone, you know, maybe connected a few people. I, I have a lot of, a lot of my friends in, in Colombia are naturally real estate guys too. And so like we have real esteem real estate meetups and stuff like that. But yeah, I usually just gave a few tips and referred them. You know, like actually finding a property in South America versus the United States is quite different too. You know, it's a bit of the wild wild west where there is no centralized mls. You know, there's some websites that show listings but you know, you might find the same listing on multiple websites for multiple different prices and you know, you really have to do your due diligence and I guess my number one recommendation is like make sure you a good lawyer that does uh, speak your language and, and understands everything if you're planning on acquiring something.
Speaker B: Yeah, yeah, yeah, we we Again like we've, we've looked a few times and you know, have not have gotten cold feet as we've gotten close down, uh, there seems to be, you know, just something easier about investing in your backyard and vacationing, you know, where you might want to vacation. Yeah, yeah. And which seems a little bit what you're doing in Orlando. You know, it's nice having a place that, you know, you can go to. I think a lot of people get into short term rentals for the ability to be able to sometimes utilize it. Mhm.
Speaker A: For sure.
Speaker B: Yeah. Well, as, as you are moving ahead with Coorsley, what's kind of next in, in your radar? What, what are you excited about and working on these days?
Speaker A: I've never, I'm really excited about the technology side. I mean we, we meet regularly with our team and we can just move so quickly today, you know, where we're using some sort of tool and we're like, hey, we could do this better. And then next week we've already made the tool, you know, and we're using it live with, with properties and it's having better results. So I think that's what, what I'm most excited about. And you know, my partner and I, I actually met my partner in Columbia, he built a, a boutique hotel there years ago.
Speaker B: Oh, cool.
Speaker A: And we partnered up with Coorsley about three years ago and like we both understand the industry just really, really well and being able to have the perspective, helping owners in dozens of different cities, it's just a truly, truly unique perspective. And so like we know what the issues and the challenges are and, and we get to try to build things to make them all easier and, and to make everyone' and, and optimize their properties at the same time. So yeah, I'd say that's what we're most excited about.
Speaker B: Thanks. And, and what do you see in 2026? Which, which of uh, your kind of portfolio of properties, which ones are, are performing well? What are the things that are helping them perform well?
Speaker A: You've got to have good reviews. You know, it's really clear uh, like if, if you're not getting good reviews, we can do everything we can on our end, you know, list the property perfectly, price. But if you know something's getting dropped there at, at the property, the doorknobs loose and it never gets fixed that, you know, the difference between two identical properties in the same market, the difference in their revenue potential is just pretty, pretty vast. And so it really does come down to operations and making sure that things aren't overlooked. I think, you know, my personal portfolio, a lot of them are in urban areas because I had acquired properties that were previously long term rentals and I converted them into short term rentals. A lot of people jumped on that bandwagon as well. And so there's been a lot more supply increase there and you know, revenues have dropped down. So I think the, the urban, more commodity type properties have definitely it's, it's more competitive. And so we see, you know, a lot of the properties that are, you know, more of like an experience type property, like the boutique resort, micro resort stuff you guys are doing. There can be a lot of opportunity there. Just gotta make sure the operations in place because you can make a beautiful, beautiful property. But if it's not ran well, then you know, it's kind of a, kind of a waste.
Speaker B: Yeah, nice. Well, if people want to get in touch with you, Tim, what are the best ways to connect?
Speaker A: Yeah, my podcast is Short Term Rental Riches. It's on all the normal outlets there, also on YouTube and our website is coorsley.com, c o, r, Z, L Y. Uh, there's a little partner with us button there if anyone's interested. I would love to chat with you personally and see if your properties, your portfolio make a good fit.
Speaker B: Awesome. All right, well, thanks for hopping on. Good to get to know you a little bit, Tim.
Speaker A: Yep, same here. Pleasure to be here.
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