The Secrets to Scaling and Selling a Short-Term Rental Business

This week on the Boostly Podcast, we’re diving into the inspiring story of Josh Guest, founder of Guest Homes. Starting at just 20 years old with a handful of properties, Josh scaled his short-term rental business to an impressive 130 units before successfully selling it. In this episode, Josh shares the lessons he learned along the way, from overcoming early challenges to systemizing and scaling his operations. Whether you're just starting out or looking to grow your STR portfolio, this episode is packed with actionable insights and tips for success.

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[00:00:00] Liam: Welcome to the Boostly podcast. This is a podcast that gives hosts the tools, the tactics, the tips, and most importantly, the confidence. So you can go out there and get yourselves more direct bookings. We do a series where we go behind the host and that's exactly what we're doing today. We've got a guest who has got a short term rental business.

[00:00:15] Liam: And particularly today, this guest has not only started his business, scaled his business, but he's now in, in the, uh, he's just sold his business and, uh, going through that at the moment. So this is a really. Good chance for you as a host to learn from somebody who has done this and you can pick up tips, tricks, and all of the good stuff from this podcast.

[00:00:37] Liam: So let me introduce, we've got a special guest. We've got Josh Guest on the, uh, on the line with us. He is from Guest Homes and let's dive into his business. Welcome along, Josh. 

[00:00:49] Josh: Good morning, Liam. Yeah, looking forward to it. 

[00:00:52] Liam: So Josh, for those, I know you've been on this podcast once before, but, um, that was a little while ago now.

[00:00:58] Liam: So can you reintroduce your business? Give us the elevator pitch. 

Josh's Journey: From Three Units to 130

[00:01:03] Josh: Yeah, absolutely. So it started Guest Homes in 2018, um, actually started as a rent to essay business, um, and sort of got into it, um, A bit out of nowhere, actually, because I, I bought an existing rent a service accommodation business, um, which was in Brighton, um, four hours away from where I live, um, which was, uh, definitely lots of learning curves around that side of things, um, which we can dive into a bit later on.

[00:01:32] Josh: And then lots of people then started asking me about managing their properties and where I live locally in Worcester. I thought there's a good market for it here because, uh, there's lots of things going on. And they'd open up a new premier in, uh, quite a cricket club. So if actually there's a good market here, let's give it a go.

[00:01:53] Josh: Opened a couple of units up, they were flying off. Um, and then, and then it just stopped. The traction just started going and, uh. More and more people keep asking me to manage their properties and scaled up from there. 

[00:02:07] Liam: What do you want people to get out of this podcast? Obviously, you've had a lot of experience.

[00:02:11] Liam: What would you like somebody to take away from this podcast? 

[00:02:15] Josh: Yeah. To be honest, just hopefully they can pick up lots of little tips and advice depending on what stage they're at in the business. So we've grown to 130 units before selling a business. Whether you're just getting started and take some bits away from just But again, started or, um, wanting to take advice on how to scale it and exit a business and following you mentioned your, uh, 

[00:02:46] Liam: One of the first lessons there was you, you literally just bought an existing business.

[00:02:49] Liam: So what did you learn in the very early days? What did you feel? That you learned in the early days and what do you wish you'd have learned faster in those early days? 

[00:03:00] Josh: So, well, I got into the industry knowing completely, literally nothing about it. I literally, just some guy basically said he's got these free rental estate properties.

[00:03:11] Josh: I didn't even know the terminology of that. Um, and he literally, basically he showed me his P&L over the last two years. And I was like, well, basically what I'm going to pay him for it. I can get my money back in nine months. How hard can it be? I was like, I've got money just sat there at the moment in stocks and shares getting like 10 percent a year.

[00:03:29] Josh: I was like, well, I can get my money back in nine months and then make that back again the following year. So I was like, it's just a no brainer. So, but the biggest lesson that I probably learned from that was, um, yeah, being four hours away then taking on those properties, then trying to sort all the logistics out within cleaners, um, maintenance issues really know about, and then, um, um, Yeah, any sort of questions from guests?

[00:03:56] Josh: I didn't obviously really know these properties that well because I was just taking it over from someone else. I didn't really know it probably super well, but to try and I had to spend quite a lot of time down in Brighton, which I didn't thought I was traveling. They were staying down there, sorting things out.

Early Lessons: Starting in Brighton and Learning the Hard Way

[00:04:09] Josh: And, and more particularly in Brighton, trying to sort out maintenance or cleaners, um, is quite chaos because it's obviously a busy city, um, and there's not, um, nowhere for anyone to park. So all the trades people don't want to do anything for less than probably a hundred pounds at a time. So. It just changes your life.

[00:04:30] Josh: It's hard to get sorted. So yeah, there was, there was lots of learning curves, but I definitely recommend if anyone's looking to either invest in property or rent USA, um, or even management, just to start off, we try and do it within an hour of where you are. So you can sort of learn the sort of nuts and bolts of things, um, until systemization to scale it.

[00:04:53] Liam: That's really good. And is there anything that you wish you'd have learned faster from way back then? 

[00:04:59] Josh: Not necessarily faster. I think you've got to learn, um, everything else as you go on. But probably just learning more systemization, um, and outsourcing some things. But I think in a way that that's part of the journey.

[00:05:21] Josh: And also, if you do that too early on, you probably end up overspending on systemization or end up overspending on staff. So it's in my view, it's actually good to learn. 

[00:05:33] Liam: You're certainly younger than me, but what age were you when you started this business? 

[00:05:38] Josh: Yes, I was 20 years old when I started.

[00:05:42] Liam: Amazing. And a very brave thing to do, but also a very savvy thing to do because you say you looked at the PNL and just went, Hey, I can make money here. So talk us through how you went from those first few units. What was kind of like the next stage? Did it just happen gradually? I mean, you mentioned that you've sold the business at 130 units and you mentioned, I think it was four rent to rent units you started with.

[00:06:04] Liam: So what happened in the middle?

[00:06:07] Josh: Yeah, so, um, like I said, I kind of came back to Worcester, uh, and I had like a bit of a brainstorm moment. I said, like, actually, now we need to, we need to actually scale this business. Like, this is a great opportunity here. Um, so it's kind of like starting from scratch again, because technically these, these first, um, Free units, I never, I never found, um, so I never had to go and speak to agents, landlords, etc.

Building Momentum: From Struggles to Scaling Locally

[00:06:33] Josh: Because obviously I just bought an existing business. So it's fortunate in that side, but then I was basically starting from scratch, so I needed to go and Network, speaking to agents, speaking to some director, landlords, et cetera, trying to find some more, um, rent service accommodations. And that's what I'm looking down initially, um, because I thought I was going to initially scale up.

[00:06:55] Josh: So I started to look, look around for options to try and do that. Um, but I've had quite hard and it took, it did take me three to six months of hard graft of doing lots of viewings. Um, With either letting agents or, um, trying to do direct to vendor viewings as well. Um, and I kept getting lots of no's and I thought it would have been easier to start off with.

[00:07:19] Josh: Because I technically had a track record of these three units even so obviously they didn't know what it was because it's in a complete different area. Basically, everyone's treating me as a new start business still. So I was like, this is actually harder than I thought. Um, but yeah, I did lots and lots of lots of viewings and then eventually, uh, I got a yes and then I got another yes and then they got another yes and then suddenly within like a two or three month period, um, Just then the traction just really hit and it just like, just drove off.

[00:07:52] Josh: And then some of the people were like, actually, cause some of the direct vendor clients, they were like, actually, I want a piece of that, but I don't want to manage it. So could you just manage it for me? Um, and then I was sort of just connecting with other investors in the area. And they were like, Oh, I know my friend as well.

[00:08:06] Josh: He's got a property or she's got a property and passed me their details. And then it just sort of just snowballed effect. Um, just flowing off from that. 

Secrets to Scaling: Networking and Gaining Traction

[00:08:13] Liam: How do we get in touch with you, Josh? If somebody is listening to this going to know, Josh, sounds like he's got a lot of experience. I want to reach out to him.

[00:08:20] Liam: Is there is a way to do so? Is the way to check out, um, Guest Homes and host and say? 

[00:08:26] Josh: Yeah, absolutely. So, yeah, well, if you get Guest Homes websites, love. So just go on to www.guesthomes.co.uk You wanna reach out to myself personally, then just drop me a, um, uh, a message on Instagram or Facebook. So, on Facebook it's just Josh Guest, um, Instagram's, Josh guest.

[00:08:48] Josh: Um, it's pretty easy to find me on there or LinkedIn or anything. Um, any questions about scaling, starting or exiting? Um, yeah, just reach out to me and drop me a message. 

Advice for New Hosts: Starting Local and Staying Persistent

[00:08:58] Liam: That's cool. And to finish, what's the plan for the future? 

[00:09:05] Josh: Um. Never know where, where, where it will take me, but, um, yeah, there's, there's Lots of stuff going on, um, for a complete different podcast.

[00:09:16] Josh: Um, we also have our, our own, uh, linen business as well. So we have a linen hire business, um, which is called guest linen. So, um, we, we at the moment we're, we're facilitating within an hour to an hour and a half of Worcestershire. So that's all the way up to sort of Birmingham, the whole of the Cotswolds down towards Bristol, Bath area.

The Future: Expanding with Guest Linen and New Ventures

[00:09:37] Josh: Um, so, so we get it. Be scaling that up. Um, and that's supposed to be a completely different podcast on its own. Um And yeah, uh, I'm going to take obviously a long think about it, uh, over the next sort of 12 months. I'm going to continue with obviously working with hosting stay as well, continue growing out their portfolio of properties.

[00:09:59] Josh: Um, so I'm really looking forward to that. Um, and then see what, see where my journey takes me. 

[00:10:05] Liam: Yeah. Well, you've certainly earned some, some time to ponder that question. And if anyone's listening and you need linen higher in those areas, obviously, you know, who to contact as well. So thank you so much, Josh, for, for coming on to the Boostly podcast.

[00:10:18] Liam: If you're listening to this and you've got even one piece of value from it, and maybe another host, a friend share this podcast with them. If you want to podcast with them, If you want to continue the chat on a social media channel, you can come to our free Facebook page. Just go onto Facebook and search the hospitality community.

[00:10:37] Liam: It's a free, uh, community where you can come and join and we can talk about anything you've heard on this podcast or we can talk about direct bookings. We can talk about whatever you like really, but we'll see