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Liam
Welcome to the Boostly podcast. This is the podcast that gives hosts the tools, the tactics, the training, and most of all the confidence to go out there and get more direct bookings. We do a spotlight series on this podcast where we interview services and people that you need to know about if you're in hospitality. And today I'm joined by Guy. He is the founder of Vacation Rental License. This service helps short term rental hosts cut through all of the red tape and get a property licensed without the stress. And we're going to dive into exactly what that means. But this is going to be a practical and useful conversation if you're working in vacation rentals. So do listen to the end for all the tips and the tricks. So welcome along. Guy. Thank you for joining me today.
Guy
Super happy to be here. Thank you so much for having me.
Liam
Thank you. And to get started, what do you want people to take from this episode?
Guy
Yeah, so I guess at the core I think vacation rentals is an awesome business. You know, especially post Covid, I think it started to explode and people started making a passive income with it and it got really popular since then. What do I want people to take out of this? Before getting into this world and buying a property, look, look at the red tape. Like you said, go on the city websites, make phone calls, just make sure that your property is zoned for short term rentals because you'd be surprised, there are many, many areas in the states where they're cracking down on them. So we on our end, we try to help circumvent certain issues. But there are areas in the states where you can find really good vacation rentals and not have any of the issues of getting the license. So if there's one thing I'd like people to take is just do your due diligence, spend five to ten minutes just researching. Before you buy a property, find out if you could get a short term rental license. You don't have to get it yourself, just find out that it's eligible for one.
Liam
And what we talk about today obviously is concerning, particularly the United States. But when it comes down to anybody, wherever you are in the world, different license regulations, all this stuff is the biggest threat to our hospitality industry, I'd say at the moment. And so wherever you are in the world, please do listen to this, pick up some tips and the sort of thing that can come along because ultimately it can be different from town to province to state to county, depending on where you are in the world. You know, I mean, all these things can be different. So for those who haven't heard of it before, what is vacation rental license particularly how does it help hosts and, and yeah, go from there. Give us from the, the top down.
Guy
Yeah. So vacation rental license as a company is pretty self explanatory. There are different words for this license. Some call it a short term rental license, but essentially what it is, it's just same way that a, a liquor store. If you were to open up a liquor store, you would need a liquor license. And there are different types of licenses that you could get when opening up a liquor store. You still need to get a license when you're opening up a business. So the Airbnb is the same thing. When you're opening up an Airbnb or property management company as well, you need to get licensed. So vacation rental licenses aim is to help streamline that process. It could be pretty tedious depending on where you're at. So for example, South Florida Market, super. You know there a lot of regulations, so it could take three months to get the license. There's a lot of paperwork. So essentially that's what it is. We help short term rental owners, property management companies, investors get these licenses.
Liam
Yeah. And it's a big, big help because ultimately there's so much to do as a host. Right. You've got to be thinking about marketing, thinking about how to furnish, how to do the interior design. You're worried about what gift packs we're going to give to the guests. There's literally so much to this and we wear so many hats in our business as short term rental hosts that anything you can outsource or try and reduce that stress, depending on obviously the size and budget. Ultimately I always find it's easier to outsource the stuff because ultimately then I've got the bandwidth to focus on the stuff that only I can, I can do. How did all this start, Ben? What made you decide to build this particular business?
Guy
So I was working at, for a property management company in South Florida. They had a portfolio of about 20 to 30 single family homes. And they just kind of thrust me into this licensing world like hey, you know, figure this out. We're getting violations. So where I'm at is Hollywood, Florida. That's where most of their properties were located. And Hollywood, Florida was booming right after Covid and they started cracking down, developing their ordinances and zoning regulations around short term rentals. This is an interesting story actually. So I got thrust into this and they said, hey, we're getting fined by the city $1,000 a day for every day that we're not licensed. We need to get this license asap. And it's a long, tedious process. So I'm like, okay, well, how do you do it? So they're like, just go on the city's website. I don't know if you've ever been on any government website. They don't really reveal much information. It's hard to get through to people. It's hard to get direct answers.
Liam
So I'm glad local government with that, it's all government websites everywhere, isn't it? It's just, I don't know how it can be so hard to get in touch with people.
Guy
Yeah. And that might be a conversation for a different time, but when they don't have competition, government doesn't have competition. So they're not incentivized to make things more efficient. They're not going to be penalized for, for taking five months to get back to you. So what happened there was, I was developing this process for getting these licenses because I was doing it in bulk. I was like, wow, this is really difficult if you just had one property. I think that the Airbnb world is really geared for those types of entrepreneurs who want to make some sort of passive income. They have some extra cash. They want to put it into something that's going to be income producing. So they're not, they're not ready to do the research, get the license, follow up with the city, the county and the state go through all that. So I was like, hey, I wonder if other people need this service. And I was actually at the, at the city, you know, handing in paperwork, physically handing it in. And I remember seeing a guy there that was talking to one of the ladies that I would speak to for the licensing. And he's got his hand on his head like this, and I'm like, oh, he's stressed out about something. And I know what department that lady's in. So she leaves. And I go up to him and I say, hey, are you getting a short term rental license? And he's like, I'm trying. And I was like, oh, no, I know what you're going through. If you need my help, here's my number. I'm not a pushy sales guy. It's not my nature. I just gave him my number. I saw that he was stressed out. I said, if you need help, reach out to me. I'm doing like 15 of these, like this month. So I got a good process for it. I'm confident if I can't get it for you, I'll just give you your money back. No harm, no foul. And then like literally like two days later, he reached out to me and that was my first client. I was like, wow, I'm shocked that, you know, people don't, don't offer this as a service. And I was looking around, didn't seem like I was being offered as a service. And then from there I was like just putting myself out there. I got in touch with a friend of mine who does permit expediting and he was referring people to me. And then eventually I was like, maybe I could do this in other places and started tinkering with that. And then it snowballed from there.
Liam
That's cool. So you found the demand literally in the place where the demand is first of all. And it goes to show that entrepreneurs find a problem and then if you can solve it, you know, put that service out there and you get some traffic. Well, what are some of the biggest mistakes that you see that hosts make when it comes down to like permits and licenses?
Guy
Oh, great question. Biggest mistake is doing work on your property without a permit if you're going. And I don't know, are you aware of what a permit is?
Liam
We don't have quite the same thing here in the uk. I imagine that allows you to under building regs, that you have to have certain things in place to be able to go to the next stage. And if you start, if you start it before planning here in the uk, you're in trouble basically. Right.
Guy
So very similar. So over here, if you were to for example, gut your, the first floor of your house, you want to remodel everything on, add a new bathroom, etc. Change the piping electric. So you need to open permits with the city so that everything is done up to code. The reason why people will sometimes bypass this and just do the work without getting the permits is because again, it comes back to like an issue of dealing with the city. It takes a long time, there's a lot of follow ups, a lot of phone calls. It just, it extends the process and it makes it more costly. So people tend to do it without a permit. The problem with that is that if you're in a jurisdiction where you need to get the short term rental license, chances are they're going to do an inspection on your property to make sure that you're not putting something out there that could potentially harm someone. We don't want a hole in the center of your kitchen that leads to the center of the earth because that could be Dangerous and the city doesn't want to be responsible for that. So incomes, permits, Right. Permits is supposed to save everyone from harm. If you do work on your property without permits and then an inspector comes in because you applied for the short term rental license, he's going to say, hey, what, you're listed as a three bed, two bath. How do you have five bedrooms over here? There's no indication with the city that you did any work. So then not only are you not going to get your short term rental license, but they're also going to give you a hard time with backlogging the permits. You would have to get an after the fact permit. So that is the biggest challenge I would say is do not do the work on your property without getting the permit.
Liam
It makes sense. Right? And here in the uk, I mean if somebody's done something without planning, they can actually force the thing to be taken back down. And like you say, the chance of them retrospectively granting permission is, is a lot slimmer because if somebody's done some wrongdoing, they then have to use that as a case to try and make sure nobody else does it. But this is, this is the thing, because in principle I agree with, as responsible business owners, we want to make everything safe and you know, it's better for everyone. We go and stay in places. Right. But the fundamental is, and you mentioned it before, is that because governments take so long to be able to do some of the things that we need to do and we can't get the, we can't get the license or the permit in, in the time that we need it, it can sometimes make a deal that works, not work if you can't get the time, if the timeline doesn't work, doesn't it? So I guess the solution here is, and you mentioned it in the intro, is that finding areas which are better to purchase the homes in the first place. So if somebody listening to this is thinking about buying a vacation rental, what should they check first when it comes to zoning? Is there areas they should be thinking about over others?
Guy
Yeah, it's interesting you say that. So I have had so many people call my company and say, hey, you know, we're investors, we want to look into different areas. And they'd call me and say, hey, can you do the research for me? And I said, yeah, sure, you know, the potential client over here, I'm going to do anything, anything you ask me. So they'll call me. And eventually what I found out was that didn't necessarily convert to more business and I want to do that research because, you know, it's good for people to know, like I don't mind doing it. It takes me about an hour to get like a clear, a clear answer for them of whether or not they can or cannot get a short term rental license. The problem that I found was that people started taking advantage and would just shoot me a list of like 15 properties. Hey, do research. And I'm not in the business of doing free research. You know, I'm in the business of getting you a short term rental license. So what I, what I implemented was a research fee. Usually it's like 100, 150 bucks. And it's really just so that you know, I'm not, my company is not going to get abused with doing free research if you decide to move forward. Like if we do the research and the research comes back and says, hey, you can get this license, this is the process, this is how long we estimate it would take. And you say, hey, that sounds great, like let's go for it, then I'll credit you back the, the charge and put it towards the, towards the license. I don't want to make money from doing research. That's not the business.
Liam
You can't say fairer than that. I mean ultimately so many property managers here are probably completely simplifies from a property manager point of view. Obviously we can sometimes research places and, and you sometimes just get sent the links to the online portals and, and like you say, there can be so much research that hours and hours of work goes in that ultimately if you're crediting them back, if they become a client, that's all. That's, that's brilliant, isn't it? Because at the end of the day they've got skin in the game and you know, they're serious. It's not just a whim, which is so cool. And that research would identify then the length of time it could take, which then they can build into their plans as to, you know, the development plans and stuff like that. Is that right?
Guy
Well, the research is basically a paper trail from the city that says whether or not you can or cannot get a license. It doesn't include, for example, like cost of licenses. That would be a lot more in depth. We also have another service, it's like a DIY where we basically break down everything for you. Instead of us doing it, it's like a packet or say, okay, click here, then go here and input this. So yeah, that's, yeah, that's basically it.
Liam
That's cool. And so I love any businesses like this, which are solving real problems to help, you know, people out there, help investors, and basically make hospitality a better place, one that we can operate with confidence in. What has been the biggest challenge, building this business so far for you or for the company?
Guy
Yeah, that's a great question. It has been a long road, I would say navigating the landscape in different areas. So I'll give you an example. When we get a client who has multiple units and let's say they're in an area that's not so friendly towards short term rentals, we want to help this client because we know that their businesses, if they can't, if they can't get in compliance, then their business basically goes under. And we want to help out as much as we can. So we need to find ways to work around the issues that they're going to get with the city. So I'll give you real life example that I'm dealing with right now. And this happens every once in a while. But essentially they're in a zone where they allow short term rentals, but they only allow what's called a home sharing license, which means that you have to live on the property while you're renting it out. You can't really have a business doing that. It limits you to like one single unit. So now what do you do? Right, we have to find ways in order to get maybe a different license or maybe we can change the address so we find out different ways of doing this. One of the things that we did was figuring out, okay, fine, we could put the house under this person's name who's part of the company and change their address. Lot of loopholes to get to that point. Depends how dedicated the client is. If they're willing to go through that, change a driver's license to match that, that address, we would do it for them. You know, it just, it depends on how far they're willing to go. So that's been the biggest hurdle for us is kind of like navigating these, these difficult cities. You'd be surprised. Like Los Angeles also, you think that they would be friendly towards vacation rentals. People want to be in Los Angeles. I think that has what to do with like hotel lobbying, but maybe a conversation for a different time. Again, Los Angeles also only allows home sharing licenses, so people are forced to find creative ways out. That creativity is probably the hardest thing for me because I want to make sure A that they're in compliance and, and B, that it's a smooth sailing process. For them it's not like, oh, now we have to do this. And we didn't foresee that. That's been the biggest hurdle.
Liam
I can completely see how it's the biggest hurdle. And also, I mean I, I know friends of mine, Dina from Keys to Kelowna, based in Kelowna in Canada, her local district basically said no stays under 30 days and it just suddenly came in and, and this is a real threat to our industry and I, I think there is local councils and, and districts and who have like you say potential hotel lobbying or things where their kind of perspective over short term rentals is that actually it is bad for their local community. But I was looking at statistics not long ago and actually if somebody comes and stays in a short term rental, although they, unlike a hotel where in a hotel they stay in the hotel, they probably eat in the hotel, they're probably only there one night, they're probably, or a couple of nights and things like that, in a short term rental they're often bringing more than one person. That's why they're in a short term rental. In, in a lot of cases they're not solo traveler. Along with not being a solo traveler, they'll need to consume more so they'll be spending more money locally, you know, grocery stores, perhaps restaurants, perhaps activities and days out. And that the amount of money that short term rentals puts into a local economy is, is bigger than number of people going through a hotel. So ultimately it's something where I, I'm firmly on board with more regulation providing us the right kind of regulation. At the end of the day, nobody wants somebody operating illegally or, or if, if there was a fire or somebody gets hurt at one of these properties, do you know what I mean? Like nobody wants to, to see that sort of stuff happen and it's bad for everybody, you know, for, for the press if, if that happens. But ultimately that needs to be a level playing field, doesn't it? And it feels a little bit unfair where, if your business is based in this location versus, you know, this location two states over, that is just not an even playing field. Which is why it's so important for people to reach out to yourself guy and to, you know, talk to you about vacation rental licenses. So flipping that question around, what's been the biggest wow moment so far since starting this, this venture, biggest wow moment.
Guy
Is how many people are willing to go forward with my service. And to be completely frank with you, when I have a phone call with a client, I try to be as transparent as Possible in order to avoid confusion down the road. And I tell them, listen, I want you to know I'm not able to wave some sort of magic wand and immediately get you a license. I'm not doing anything special. I might have a process, I might have a team, but, you know, essentially, you can do the same research. You can find out how to get this license. We. Which maybe do it faster, maybe make less mistakes. And, you know, I kind of love this because I'm a big fan of delegation and people see value in the service, even though I tell them, you know, I'm not. I'm not doing anything that you cannot do. This is something that you could do the research. You could find out how to get it yourself. You don't have to pay me to do it.
Liam
Right.
Guy
You could do it yourself. So I would say the biggest wow moment is probably, like, how much people trust my company to get them the license, even though they could probably do it themselves. It's nice. It's actually nice to see because I'm a big fan of delegation and I like to see. And I think that that's like the Airbnb kind of the Airbnb owner that ICP is a guy who's like, I want this thing to run itself, right? You have the cleaners come in. They're probably on a schedule. You don't need to tell them when to go in. They have a shared calendar. You probably have auto locking mechanisms that generate new locks. Each guest. So I'm a big fan of automation, a big fan of delegation, and I like streamlined processes. So it's nice to be part of this community, honestly.
Liam
And it's credit to you, Guy. I mean, ultimately, you obviously know what you're talking about and people. It's what I call the old Star wars story, or if anybody's read Donald Miller story brand. Everybody wants a guide to guide them through a difficult situation so they can learn and grow themselves. And that's. That's why people are happy to, you know, sort of contract work to great people and great businesses, which is why we love these podcasts where we get to be introduced to businesses like yours and people like you. So what is with all these changes happening in this regulation coming in and licensing? Is there any advice for kind of just staying ahead of the curve of stuff which may change in the future? And in your opinion, is this something we're just going to see more of? Is this just going to become, like, part and parcel of what we have to deal with more often?
Guy
Yeah, unfortunately, it Seems to be trending that way. I had a conversation with a client who had many multi unit buildings in Chicago and he was telling me that he knows for a fact that the, the hotel lobbyists are trying to shut down Airbnbs. So maybe we need some sort of a movement to counteract that. It does seem to be trending that way where they're coming out with more regulations. I wouldn't say they're getting friendlier towards Airbnbs. How to stay on top of it One neat little trick I noticed is the zone or area that you're in, the city usually has some sort of like a newsletter that they send out. So maybe subscribe to their newsletter. They're not there, they're not going to put out more than one a week. And anytime that you see the newsletter come in, just scan it, see if it has anything to do with like a new ordinance about short term rentals. And then if you see it there, read through the ordinance. They're, they're a bit intimidating to look at, but ultimately you just read through it. If it doesn't make sense to you and it's written in gibberish, plug it into some sort of AI chatgpt and say make sense of this and you'll probably figure it out. But yeah, stay on top of the, of the local regulations by, by subscribing to newsletters.
Liam
I think that's great advice and guy, you took the words right out my mouth. For anyone watching on the YouTube instead of listening to the audio, you can see a great big smile on me because as soon as you say AI, that's exactly. You could easily set up a zap to filter all that information for you, couldn't you? And ultimately it's just good to stay ahead using those newsletters. So great piece of advice. So if hosts listening today wanted your help with licensing, how do they get started? Where do they need to go? What links or where should they go and find all your information and connect with you?
Guy
Yep. Vacation rental license.com, there's, there should be a get started button over there. You fill out a form, our team will reach out to you, find out exactly what you need. It's again, I try to be as fair as possible. I want it set up to be as fair as possible. We have a, a zero risk guarantee. If we can't get you the license for whatever reason due to, you know, a fault of ours, like we did faulty research and you just are not zoned, we'll refund you 100% of the money. I don't want to take that. I want to take your money. If I. If I'm not going to give you anything, I will caveat that if you give us a property and you don't tell us that you have a hole leading to the center of the earth and we start doing work, I wouldn't say that the guarantee applies over there, but I try to be as fair as possible. That's how you could find me. Just vacation rental license.com, not yet on the social medias, but we'll work on that.
Liam
We'll probably get there one day, no worries at all. And of course, if you listen to this on the podcast, when safe to do so you can click the link in the show notes and that'll take you straight over to Guy's website. So that leaves us with the final question, which we love to ask all of our guests, especially entrepreneurs and people who start their own businesses, if there was a quote or a mantra which guides how you work or live, what would it be and why?
Guy
Oh. Huh. Okay, I said it yesterday. Ready for this? It's pretty short. Perfection is the enemy of good.
Liam
I like it.
Guy
Yeah, If I can explain that for a second is you don't want to get into analysis paralysis. You just want to start doing and then tweaking from there. Just, just do it now. Just get the idea done. Have a good plan of action. Don't perfect that plan of action. Just go in because you don't know the unknowns, don't know the other variables that are out there that you could never figure out until you just dive in. So come up with a good plan, not a perfect plan, and then start perfecting from there because you're not going to go in with a perfect plan.
Liam
I think that's brilliant and very true. And the more work I do in business or the more things I produce, the more I realize that perfection. One, you never achieve it anyway. And. And two, it is just more about the quicker you can start that feedback loop, the better, isn't it? The quicker you get something out there and you do something, the quicker you get more information to then do the next thing. So yeah, I love that quote. And thank you so much, Guy, for coming on the Boostly podcast, sharing this with us and basically just giving us an option for where we can reach out to you, but also just an understanding that these licenses are here to stay with us. Don't worry too much about the stuff you can't change. Focus on getting the right people, the right information around you to be able to still push forward and create a successful hospitality business. And this is the fun of what we do, right? So everybody on the podcast listens to this. Go and check out vacation rental license.com or in the show notes. And we thank you for listening to this episode on the Boostly podcast. If you have not already come over to our YouTube channel, you can go to YouTube, type in UK and you can come and subscribe to that channel where you get to see us on the video and you'll get to see your faces and there's also some bonus content and some extra direct booking guides on there. Thank you very much. We'll see you again. Bye for now.
Guy
Thank you. Liam.
Liam
Having a blast. Gonna get it on the Bruce Lee podcast. Bruce Lee like Bruce Lee because it's so hard and the T is loose leaf making up those rhymes. Don't write it, just do it loosely.
The Boostly Podcast: Episode Summary
Episode Title:
How to Get a Vacation Rental License (Without the Stress or Fines) – Expert Tips for STR Hosts
Release Date:
June 15, 2025
Hosts:
Mark Simpson & Liam Carolan
Liam Carolan opens the episode by highlighting the critical role that licensing and regulations play in the hospitality industry, particularly for short-term rental (STR) hosts. He emphasizes the variability of licensing requirements across different regions and underscores the importance of understanding local laws to avoid operational disruptions.
Key Quote:
"Different license regulations, all this stuff is the biggest threat to our hospitality industry..."
— Liam Carolan [02:00]
Guy, the founder of Vacation Rental License, elaborates on the nature of his business. He explains that obtaining a vacation rental license is akin to securing a business permit, such as a liquor license for a store. The process can be tedious and time-consuming, especially in regions with strict regulations like South Florida, where it can take up to three months to obtain a license.
Key Quote:
"Airbnb is the same thing. When you're opening up an Airbnb or property management company as well, you need to get licensed."
— Guy [03:00]
Guy shares his personal journey, detailing how his experiences working at a property management company in South Florida exposed him to the complexities of licensing. Faced with hefty fines for operating without a license, he recognized a significant gap in the market for streamlined licensing services. This insight led him to establish Vacation Rental License, aiming to alleviate the bureaucratic hurdles for STR hosts.
Key Quote:
"I saw that he was stressed out... if you need help, reach out to me."
— Guy [06:00]
The conversation shifts to the prevalent mistakes hosts make concerning permits and licenses. Guy identifies the most significant error as undertaking property modifications without obtaining the necessary permits. Such oversights can lead to failed license applications and potential legal repercussions.
Key Quote:
"Do not do the work on your property without getting the permit."
— Guy [09:00]
Liam and Guy discuss the importance of choosing the right location for purchasing vacation rentals. Guy advises hosts to conduct thorough research on zoning laws and eligibility for short-term rental licenses before investing in a property. He also shares his approach to handling bulk property licensing and the challenges associated with areas that have restrictive regulations.
Key Quote:
"Spend five to ten minutes just researching. Before you buy a property, find out if you could get a short term rental license."
— Guy [01:00]
Guy delves into the challenges faced while expanding his business, particularly in navigating diverse and often stringent regulations across different cities. He provides an example of dealing with Los Angeles, where only home-sharing licenses are permitted, forcing creative solutions to comply with local laws.
Key Quote:
"Navigating these difficult cities... creativity is probably the hardest thing for me."
— Guy [15:00]
As regulations evolve, Guy emphasizes the necessity for STR hosts to stay informed about new laws. He recommends subscribing to local government newsletters and utilizing tools like AI to interpret complex ordinances. The discussion also touches on the increasing trend of stricter regulations influenced by hotel lobbying and community concerns.
Key Quote:
"Subscribe to their newsletter. They're not going to put out more than one a week."
— Guy [21:39]
Guy expresses his appreciation for the trust clients place in his services, despite the fact that hosts could potentially navigate the licensing process independently. He attributes this trust to his transparent approach and dedication to simplifying the licensing journey for his clients.
Key Quote:
"People trust my company to get them the license, even though they could probably do it themselves."
— Guy [19:00]
Concluding the episode, Guy shares his guiding mantra: "Perfection is the enemy of good." He advises STR hosts to avoid analysis paralysis by implementing actionable plans and iterating based on real-world feedback. This philosophy underscores the importance of proactive decision-making and continuous improvement in business operations.
Key Quote:
"Perfection is the enemy of good. Just do it now. Just get the idea done."
— Guy [24:47]
This episode of The Boostly Podcast offers invaluable insights for short-term rental hosts navigating the complexities of licensing and permits. With expert guidance from Guy, listeners gain a comprehensive understanding of the licensing process, common pitfalls, and strategic approaches to ensure compliance and operational success. The emphasis on due diligence, proactive research, and leveraging specialized services underscores the importance of informed decision-making in the hospitality industry.
Key Takeaways:
For hosts seeking assistance with securing a vacation rental license, visit VacationRentalLicense.com to get started with a streamlined and risk-free process.
Connect with The Boostly Podcast:
Follow Us for More Insights: Subscribe to our YouTube channel for engaging video content, bonus materials, and additional direct booking guides to enhance your hospitality business.
Thank you for tuning into this episode of The Boostly Podcast. Empower your hospitality business with the knowledge and strategies shared here, and stay ahead in the dynamic world of short-term rentals.