Boost Your Bookings: Strategies to Fill Calendar Gaps
2 Sept 2024 · 31 min
Sean Wilkinson, co-founder of Host Share, explains how the platform lets short-term rental hosts trade last-minute vacant nights for travel. Hosts average $340/night in savings and can earn up to $20,000/year from empty dates. The platform is free for a year, then $395 annually.
Questions this episode answers
50% off the first three months using code BOOSTLY at stayfi.com/boostly.
About $340 per night (average reported).
Up to $20,000 a year in value by utilizing last‑minute vacancies (as stated).
Host Share cites ~7–10 million short‑term rentals worldwide and an approximate 60% vacancy factor (implying ~4–6 million rentals may be empty on any given night).
Three weeks (21 nights) of free travel per year for members.
Chapters
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Hi, welcome back to the Boostly podcast. This is the podcast that gives hosts the tools, the tactics, the training and most importantly, the confidence for you to go out there and get more direct bookings we do a Behind the well behind the services kind of podcast on this where we dive into services that you need to know about as a host. These services will help you in some way. Sometimes they'll help you with direct booking, sometimes they'll help you with other things. And today is one of those services which is really interesting and is going to help you with filling gaps or getting value for the gaps within your calendar. As a host, I'm not going to go much further into that. I'm going to let our special guest explain exactly what I mean by that. But let me welcome, we've got Sean Wilkinson, he is the co founder from Host Share and he's going to show us exactly what Host Cheer is today on this podcast. So welcome along Sean. Thank you for joining me.
Hey Liam. Hey, thanks so much for having me, man. Appreciate it.
Thank you for being here. Sean. First question is what can people expect from the next sort of 20, 25 minutes over this podcast? What would you like them to remember?
Well, the main thing I would like them to remember is that, you know, as, as a short term rental owner and a host, you're always going to experience vacancy, you know, any time or any year throughout a calendar year. And so main thing that we do is we allow you to trade those vacancies for vacations all by utilizing last minute vacancy. So that's, that's kind of the goal. You know, you get about between. On average our people are getting around $340 a night in savings when they go to travel and an average of about it would be between. I mean you can get all the way up to $20,000 a year in value just by utilizing those last minute vacancies.
It sounds cool. I love this. When I saw it on the, on the website, you know the idea of doing it because we all travel, right? As hosts, we all travel and most of the time we're traveling to other hosts. I certainly try and stay in more short term rentals than hotels most of the time. Depends absolutely on the place. But ultimately it's a really cool concept. So why is this important to you? What, what really?
When did you pick up on this.
Problem and why are you trying to solve it across the industry?
Yeah, well, the main, main thing that we realized was, you know, I'm actually not sure on this number, but between 7 and 10 million short term rentals, you know, worldwide and across that whole, you know, across them all, it's about a 60% vacancy factor. You know, you look at any given year, which was like which is crazy to me. You know, I, I knew we were experiencing that on our own places between you know, midweek and off season. But then to realize that this, that means that every night like there's between, you know, 4 and 6 million short term rentals sitting empty and I was, you know, it was kind of shocking to realize that there was that much waste happening and how much that really if you were able to figure out how to fill some of that, the value that that could bring hosts. And so um, so yeah, we, you know, the goal is just to enrich lives of hosts by, by utilizing waste. You know, that's kind of the, the like mission of the, of the company and. Cause there's, there's inevitably gonna be waste in, in short term rentals. You're always gonna experience some vacancy. And so now this is just a way that you can, you can trade some of that vacancy for, for vacation nights and you know, staying at other people's properties.
So yeah, it makes sense, right? You know, there's nights do go to waste. This natural byproduct of, you know, we're never going to be 100% occupied. And if you are, you're probably too cheap if, if that's the case or yeah, might have a midstay booking or something like that. But ultimately we all have vacancies from time to time, don't we? So take me back. How long has the company been. Been around for? And take me back as in how did it get created? I mentioned you're the co founder was, was this. A few people came together. Take me back through that.
It's, it's a funny process because I mean, so it was my brother and I that, that initially kind of stumbled upon the, the concept in a, you know, in a roundabout way where we were. So we're both actually, we're both private pilots too. And I, I'm in. Or I was in commercial real estate and he was found founding a internal combustion engine company. And so we, we both had about four, four short term rentals each and but they were for both of us were kind of afterthoughts. And as pilots we realized, you know, we're, we're partnered in on a plane together and we actually have another partner there. And we were realizing man, these assets that people have, the most expensive assets people have sit empty or not being used. Like you know, I mean in, in terms of yachts and than planes like you know, 95% of the year they just sit there, right? And they're just such expensive assets and so that was kind of one thing we started. Like, man, what, you know, how do you utilize some of that waste? And then we, but then we looked at our short term rentals and like, man, you know, we're not the only ones that experience a lot of vacancy at these properties and they just sit there. And you know, we, we knew about things like you know, exchange programs and stuff where you could, you could do a home exchange or you know, like third home home exchange, those sorts of platforms which are awesome, but those, but then they're, they're primarily for, for their primary residents to be able to exchange it kind of a direct exchange with somebody. And, and you're, if you do that with a short term rental, you're going to be giving up revenue nights in the future because it's like, it's further out in the future. So, so that, that was kind of how we came about. All right, well, if it was last minute as an operator, I would trade those nights with another, with another host anytime if I could just have the ability to do the same thing. And, and so, so we, we kind of stumbled upon that. We figured out. All right, let's, let's say everybody, you know, it's three weeks of free travel, which is like if you, if you're on the platform, you automatically get three weeks of free travel and you basically are, are only depending on your price point of your property per night. If you fall above our, our, our median price, right, you'll share less nights than, than 21. So say, say our average is, I think is, our average is $250 a night, $260 a night. And then, so say if you have $1,000 a night property, you might only share about, about six nights a year, but you still get 21 nights of free travel. And if you're below that, then you'll, you'll share more. But it's only if you're vacant, right? It's only if you're vacant last minute and another host wants to come book it. So if you're not vacant, then it's just, we're just kind.
That's cool. That's cool. I like the idea of how it came about. And as you mentioned, you've got short term rentals yourself as part of your portfolio.
Did you say I do? Yeah. That's cool. Yeah, I've got it, got a few.
So this kind of, you understand the industry and you've seen kind of a gap as to what we could be doing with our, with our nights which, which aren't getting used. So I want to dive into how it actually works. But before we do, just to really cover the value add. So as me as a host, one of my worries would be how do I stop people asking for the nights which, which I still might sell because basically how close are those nights would be to advertise?
So it's, it's only a five night window, right. So if, if I was booking for tomorrow I could book up, up to that five night horizon. But, but you can't book up beyond that five night horizon. And then once your property has been, all your nights have been used up. So say you have that thousand dollar a night property and you're only going to share six nights a year, once those nights are used, then it won't be on the platform any longer.
Got it, Got it. And for me as the host, the value add to me is that of course I go traveling. I mean before we hit record, we're talking going down to London for some of the award ceremonies and stuff like that. I'm always looking for good hosts to go and stay with. But of course one of the things is although it is tax deductible, it still costs ultimately, doesn't it? And this is where there's always that way up between maybe a hotel or a short term rental, if it is a short term rental. Of course at Boostly we like to book direct but it's really finding those, those hosts. And of course by having the platform like this, the idea is that I would be able to find a place, go and stay for free for someone who may not have had it booked anyway, but then they can come and stay in one of my places for free. Is that, is that correct? As in not but somebody within the network?
Yeah, it's someone within that network. So it's not a direct exchange, but yeah, so it opens up, you know, where you can, you know, say like you and your family didn't have any plans this weekend. You could say hey, let's look at the coolest place we can find within a two hour radius, you know, and let's just go, let's go and go and explore. And, and that's how we've noticed, you know, a lot of posts are actually that's how most people are using it, right? Is there, there's been a little bit of this practical use like where they're you know, going somewhere and they're just like wait till last minute to book something and, and that's great. And you know, as we get more and More properties that will become more and more of a, of an option. Right? Because now if you have 500 listings in Miami, more than likely one of those is going to be, you know, vacant that the few days before you go. But, but right now kind of how people are using it is like, well, you know, we have access to this. Let's, let's find the coolest spot and you know, take the family and go. And, and so it's been really see how these hosts that maybe not weren't, weren't going to plan on traveling as much are now, you know, have access to, to 10 more weekends a year of, you know, they can go make, make memories as a family. And, and it's, it's really amazing to see the, you know, because it, it, it's really tricky, you know, when you're, when you're trying to start a network effect like this. You know, it's because it really is a network effect that you have to get started because you need properties. It's that chicken before the egg, you know, like you need the properties to get the people. And then, you know, and then, and then it's interesting to see how people use it because you don't, you don't fully understand how people will. When you're building a product, you know, we start building the, the program and platform and you know, and it's like, are people going to, how are people going to use this? Because you just won't know until you do. And so, so it's just, it's been, it's been really interesting to see how, how people are using it. And what's really cool though to see is when a host get someone to come at their, to their property. We were curious how that would be. You know, you're, you're hosting another host for, for free and there, mind you, there are cleaning fees, so we still do charge a cleaning fee. So you're not, you're not losing money. But that goes directly to the host, not to us. And just to see that, that interaction between the host traveling and the, you know, the host, because it was like, is this going to be a, a point attention, you know, like where, you know, you're, you're hosting for free, but it's been like the complete opposite. The hosts are like always really excited to see, you know, to see how it works. They're very inviting and they're, and then it prompts them to want to go and actually get value for it and, and make trips, you know, so that's cool.
That's cool. And I think networking is, is such a big thing. I mean just in any industry, but especially in hospitality, one of the things when I get hosts come and stay with me, there is that moment of go, oh, is this going to be a bit of a cringe guest? Because hosts can, can be your best friends or your worst enemy, can't they? Depending on how critical or how nice they want to be. I know when I go and stay with another host, any private feedback I give privately and any, you know, any good feedback, I make sure it's public. And that's the great thing about this is assumingly you can still get a review from people and you can use that as, I mean, for me personally, I get people to review me on Facebook or on Google. Yeah. And this is great leverage for more bookings for people to see in the future. So you've already not only got a place where you can then go and you know, potentially book with another host as well, but actually you're getting a review for what would have been an empty night if you're utilizing it well. And I guess as well you can check out how that host is hosting. You can pick up ideas, you can be inspired by, by what they're doing, which is, which is cool. Right? That's how we all, we all grow. So. Absolutely. How does it work for, for the hosts listening to this? If somebody listens to this, wants to sign up, what is the process? Do they, do they have to list all of their places, like individually? Is there a lot of work involved? What does that process talk us through that?
When we got started in the development, one thing that we were really keen on is just making it as simple of a process to sign up. There was a couple things that we spent a lot more time on them than I had expected to. You know, we, we, we brought on a develop development team as partners too and which was, you know, which was because my brother and I aren't from the, you know, aren't aren't in that world. And so, so we found some strategic partners that we were able to bring in and they, they were able to dive in and get this thing, get this, this platforms up and running. And one of the main things that we, that we started on was just a very simple, you know, you, you, when you sign up, you just put your Airbnb link in. It scrapes all their, all their information from their website from and, and brings it into to profile on host share and they basically just have to, I, they have to confirm a few details they do a, you know, Persona ID verification and then depending on, on if they're, there's a few things we have to do to make sure that they, they are qualified to host that property. We don't want people, you know, to falsely be putting in properties that they can't host and then they just have to import their calendar and export it, you know, via like the ICS calendar. And, and then now, now it can communicate to all their PMS systems and Airbnb and, and it's just very simple. Like it takes probably three to five minutes to get your property up and running on Host Share this episode of.
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That's cool. That sounds really good. I mean, one of the things you mentioned earlier on is getting more hosts at the moment. Where is the majority of your hosts? Is it, is it just us based at the moment or are you looking for people all over? If our audience is based literally all, all Over So let them know where you're looking for and hosts from, from any area where you want them to.
Sign up for sure. So we, we're in. Currently we've got people signed up in about 40 countries, but, but we're only live currently in the United States. We plan to, to strategically start to launch in these areas that are starting to get more and more hosts, you know, because again, you kind of have to get this wait list and had a, have a little bit of a critical mass to then go and launch. I do think that we'll launch a. And this, this isn't for sure, so I probably won't even say much about it. But if there's a free model to, to Oshare that might be launched sooner to, to everywhere and then that will be able to kind of create that waiting list and until there's a critical mass to where we can do a full rollout and each country kind of has as it makes sense. And so right now we, we're only live in the States, but we've only been live for about a month because, because Hosher is only a year old as of this month. And so.
Amazing. That's amazing. I mean, just to take an idea to make it into reality is, is I, I'm always inspired from that as, as an entrepreneur, you know, I, I always look at that and just go, hey, if this was an idea year ago, six months ago, 10 years ago, wherever it was and now it's actually real, then it's like being a magician in a way, isn't it? You know, you've created something out of nothing there, which is cool. What would you say is some of the things in the future you mentioned one there. Is there anything else you're kind of excited about, either for host share or just in general about the hospitality communities, man.
I mean, our, our community of people. Like you said, hosts are kind of like, I mean they're, they're usually great, but sometimes they can be the most, you know, give you the most critiques. And, and so, you know, the way we're building our platform, we're really wanting to make it a really positive interaction between hosts and, you know, you're getting a place for free. So we have what's called like a share pledge. When you, when you sign up, you're seeing these like, you know, you're treating this property like, like, like it's your own. You know, like these are, these are things that, that, that we want our hosts to, to abide by on the platform and, and so they're, they're agreeing to all these things that, that they're just saying, you know, we, we want to be the ideal guest for these people. And then, you know, there's, there's a way to give a, you know, feedback and you know, and, and, but it's not like public to, you know, to anybody. It's just, it's just a way to better, you know, better hosts. And, and so it's a really cool community of people. And like I said, I mean that, that idea that you're potentially adding, you know, up to 10 weekends a year of, of memories to these, you know, to hosts that they might not have otherwise had or, you know, you're giving them the, I guess, you know, not, not putting the financial pressure on those days.
Right.
That's pretty cool. I mean we're, we're really just, it's just really fun to, to see some of those, some of those trips take place and I think that some, some really lifelong memories, you know, that, that people are going to make. So that's really exciting.
I think that it's one of those things as well where I meet so many hosts. I mean, I went and stayed in a cabin in the north of the state where I am, and the lady who met said, no, I went away last weekend. That's why we couldn't have people come that weekend. It's my first trip away for 20 years. And I was like, how do people host without going away and enjoying themselves? Because I think it's really important to remember that people are making memories, especially for the hosts that are listening to this, who host for leisure. I know there's, myself included to do some sort of midterm and some corporate stays, work stays, things like that. But ultimately there's a lot of people who travel for leisure and it is about creating those memories. These are things which last a lifetime, you know, and we should be doing it as well as hosts. We should be getting those trips away. One question I'd have for you though, Sean, would be, what would stop me from going to like the best place on the books versus my, and don't get me wrong, my places are nice, but they, you know, they're not like high end luxury. So how do you balance that kind of equation?
That's a great question. What's really neat is if you're, you know, if you're, if you're on the look, looking for these properties, right? Because they, their, their subscriptions are renewing all year round, right? So like it's not like, everyone's subscription is on January 1st. It's, it's every day. There's, there's new renewals happening. And so those, those really nice properties more than likely are only going to be up for a shorter amount of time. Right? Because as they renew now, people are going to see that and go and book it. Right. And, but as a, as, as somebody looking out for those properties and like, willing to go, you know, at the, at the drop of the hat kind of thing, you're able to, that's where you're able to really get a significant amount of value, you know, because you're, because you're finding those deals and you're able to just go and like I said, like, you could get, you could get four to $5,000 worth of value or, you know, there, there's properties that are, you know, 15 to $2,000 on the proc. You know, on the platform, you go stay at Those properties for 21 nights a year and get, you know, significant value. And so that's what's really neat. But we don't, of course, we don't like, limit it because we want more properties, right. Where people give some more, more options. So, so even if those aren't available, it's like, okay, well, like, what's the, you know, what's the next, you know, 3, 400. I mean, the average money people are saving on, on per night so far has been around $340 a night. And some of those stays are, you know, they're maybe saving $600 in a stay and some of them are saving like, you know, $2,600. And, and so it's just, it's, you know, it's kind of like you just find what, what makes sense and, and, and go and you have those 21 nights no matter what.
Yeah, I like it as a concept overall. I just, I like the idea that especially within hospitality, the community is very good and it's an opportunity thinking with marketing and direct bookings, it's an opportunity where presumably the hosts get to talk to each other once they know the host is coming to stay, I presume. Is that right?
Absolutely, yeah.
Awesome. So as me, as a host, I'd be saying, look, you know, you know this game, you come to stay, you know, are you active on social media? If so, do you mind just when you're there tagging yourself in, doing a little picture, doing this stuff, and this is great ways to promote obviously to other people's audiences, to their friends and family and stuff like that, but again then when you go and stay in somebody else's, you can do the same for them. And as a community, if we all do this for helping each other for, you know, you get a free stay, you, you create some cool memories, it's only costing you a cleaning fee. You know, to do a little bit of social media push for them is fantastic. And that's how we can get more people to discover our stuff. Right? How we can get more people to come and stay with us.
And on that, on that same note, one of the main, I guess avatars or people that we're, we're marketing towards is, is management companies to, to allow their owners to be, you know, to support Hosh share to their owners so their owners can go and utilize it. And what's neat about that as a manage management company is that you're able to kind of create this almost a free marketing I mean because now you're able to of course market, hey, you know, we support our owners to be on hoshare and they get three weeks of free travel. Now your owners don't feel that pressure to come back to their property. You know, that's not the only free property they can go to now. They can go anywhere in the world for free and just paying the cleaning fee. But then there's also this side of, you know, when other hosts come to your properties, you've got a captive audience there, you know, that you're able to say, you know, this is what we do as a management company. And you know, and, and if, you know, if they're interested in utilizing those tools and, and bringing them on as a management management company, it's a, it's an interesting way to, to grow your management as well.
Yeah, it's a great thought. And of course if there's hosts out there who do training or you know, you can collect emails from people so these people might book with you for, you know, a paid stay in the future. You can. Yeah, you know, there's, there's add on products that they might decide to do if you have experiences that they decide to take when they're staying with. You know, there's all this stuff that ultimately it would have been an empty night. Right? So yeah, yeah, it's a really cool concept. One question I do want to squeeze in is because this idea of creating a concept from start to, you know, to reality, what advice would you give to somebody listening to this podcast who is looking, they've got an idea and they're looking to start it, is there Any advice, you'd go back to the start and tell yourself, I said this.
On the last one, last podcast I did. But the biggest thing for us was just, you know, not being afraid to give up whatever you have to to the right people to get them on board. And, you know, getting the right people involved is so key because if you try to do it all yourself, it's, it's, you know, it becomes a lot less likely to, to come to fruition. And so, so if you have an idea, go find the people that, that, that fill the gaps that you don't and, you know, and just, and get them on board, you know, and give up what you have to, because a, a smaller piece of a bigger pie is going to be better than, you know, than nothing. Right? And so, so that, that'd be, I guess, the biggest advice I would have, you know, for someone in that. And I mean, same, you know, my, my background's in real estate too. And so that was, that was the same thing. It was, you know, I can't do this deal on my own. How, you know, how do I make that happen? Get a partner? You know, I've got, you know, if I, if I've got the time and I've got the drive, I don't need the money. But if you've got the money, you don't need the time and the drive, you know, so, so that was, that was kind of my, my thought process early on, and, and that's kind of how it transitioned into this venture.
Definitely. They say if you want to go fast, go alone, but if you want to go far, go together. And that is, yeah, 100%. There's one more question I want to ask, but before I do, I want to throw the mic open. How can we come and sign up to host share?
Yeah, for sure. Well, Liam, I mean, as an operator, you definitely need to be on there. So you just basically go to hostshare Co. So hostshare Co. And first thing you'll do is just go to the right hand corner, click, sign up or what does it say there? Start traveling, I want to say. And then you'll just put your email in, put your password, and then it will create. Now you can search all the properties and if you go to switch to hosting, up in the corner, it will show, you know, ad listing. Now just click that. Click. It's the simplest way is just to add your Airbnb listing and then it'll drag it all in and, and then the prompts will, will easily get you get you on board and you could be traveling, you know, tonight if you wanted to. I will say, though, I don't know when this, this podcast launches, but anybody that signs up still gets a year free on the platform. So you get your three, three weeks before the 17th. So the 17th there is a paywall that comes to play. It's still a no brainer if you're going somewhere last minute because it's only 400 or 395 a year. And you know, if I was thinking about this the other day when I was booking a place because I had to book a place that there wasn't a host share in the area and I was booking it last minute and I was, I was thinking, you know, I went to book and it cost me like 800 or something like that. And I was thinking, wow, if, if I, rather than paying that $800 I just paid for my subscription and a cleaning fee, I'd still be saving money going to this place for two nights and I'd still have 19 more nights to go travel. So that we're trying to figure out how to get in the path of people booking last minute like that. Because then it's just a no brainer, 100%.
Like if anybody's looking to book and you're listening to this right now, like you say, you might as well just sign up and just see if there's a host and share. Sorry, Host chair. Yeah, place in that area. Ultimately it's, you know, it's a no brainer like you say, for that. So. And of course I know you've got your Facebook and Instagram links as well, which we're going to have somewhere around. However you're consuming this media, you can go to click the links in the show notes and that'll take you through to the socials for Host share as well as the website. That website, just one more time is Host Share Co. And you can go and sign up there. So thank you so much for this, Sean. It's been really fun and I think it's a great idea. Like I said, I'd love to see concepts like this come to fruition. Can you leave us with what mantra or what motto has resonated with you either? In business, in life, in short term rental.
However, I would say, I mean, there's a couple things that I, that I just, if, if I'm just like thinking to myself, but like, you know, one, one would be, you know, how you do anything is how you do everything. And so, and that's one that Keeps me in check more than, you know, than I'm say. I, I live by that. It's more like, you know, if I'm going to say yes to something and I'm going to commit and you know, if I don't want to do it half heartedly because so, so it's just that, that idea, like if I'm going to do something, I want it to be done well. And, and so that's, that's one thing that, that's on my mind quite a bit and when I make a decision, it's like, well, can I do this? Well, if I'm going to, if I'm going to commit to it and it helps, it helps keep me in check sometimes.
So I love it, I love it. It's very true. And the more I see successful people, they don't do, you know, thousands and thousands of tasks. What they do is they, they commit in one direction but they give it their all. And, and this is really important. So thank you, Sean. This has been really, really fun. I look forward to seeing you guys be successful and seeing you at the events and all of that, all that cool stuff. Thank you too for listening to this on the Boostly podcast. If you know somebody who can get some value out of this, please do share this podcast with them. If you want to carry on the conversation about direct bookings or about anything you've heard in this podcast, you can do so by joining the free Facebook community, which is called the hospitality community. If you go on Facebook search groups, you'll be able to come and join our free group there. And yeah, thank you again. I look forward to seeing you on the next Boostly podcast. Bye for now.
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