Boost Your Bookings - Strategies To Fill Calendar Gaps

Sean Wilkinson, co-founder of Host Share, explains how the platform lets short-term rental hosts trade vacant nights for travel instead of losing the booking. The five-night window and quick Airbnb import make it simple to list, taking just three to five minutes to set up.
Questions this video answers
Around $340 per night.
Up to $20,000 a year in value.
Between 7 and 10 million short‑term rentals worldwide, with about a 60% vacancy factor (implying roughly 4–6 million rentals empty at any time).
Three weeks (21 nights) of free travel credit as the platform’s example.
Around $250–$260 per night (median/average used for sharing calculations).
Chapters
You know, how you do anything is how you do everything. And, and so, and that's one that keeps me in check more than you know, that 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.
Having a blast. Gonna get it on the Bruce Lee podcast. Bruce Lee, like so hard on the T is loose leaf making up those rhymes. Don't write it, just do it loosely. If you want my respect, you're better, but direct. Here are the words in the podcast. That's what comes next.
Hi, welcome back to the Boostly podcast. This is the podcast that gives host 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 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 Share is today on this podcast. So welcome along. Sean, thank you for joining me.
Hey Liam. Hey, thanks so much for having me, man.
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 the 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 and 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 vac.
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 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, so yeah we, you know, the goal is just to, 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 because there's, there's inevitably going to be waste in, in short term rentals you're always going to experience some vacancy. And so now this is just a way that you can, you can trade some of that vacancy for vacation nights and staying at other people's properties.
Take me back. How long has the company been around for? And take me back as in how did it get created? I mentioned you're the co founder was this. A few people came together. Take me back through that.
It's a funny process because it was my brother and I that initially kind of stumbled upon the concept in a roundabout way where we were. So we're both actually, we're both private pilots too. And I'm in or I was in commercial real estate and he was found founding an engine, 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 partnered in on a plane together and we actually have another partner there and we're realizing and these assets that people have, the most expensive assets people have sit empty or not being used like you know, I mean in terms of yachts and then 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, 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, you could do a, 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, for your primary residence 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, gets 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, and then, so say if you have a thousand dollar 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 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 of going off law of averages.
How do I stop people asking for the nights which, which I still might sell? Because basically how close are those nights? Would yeah. Advertise.
So it's, it's only a five night window. Right. So if, if I was booking for tomorrow, I could look 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 dollars 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.
How does it work for the hosts listening to this? If somebody listens to this, wants to sign up, what is the process? Do they have to list all of their places individually? Is there a lot of work involved? What does that process? Talk us through that?
And when we, when we got started in, in the development, one thing that we were really keen on is just making it as simple of a process to sign up. You know, there, there was a couple things that like, we just, we spent a lot more time on them than I had expected to. You know, we, we brought on a develop development team as partners too, and which was, you know, which was a. 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, to dive in and get this thing, get, get this, this platforms up, up and 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 and it scrapes all their, all their information from their website from, and brings it into to profile on host share. And they basically just have to, they have to confirm a few details. They do a, you know, Persona ID verification. And then depending on if they're there, there's a few things we have to do to make sure that 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 via the ICS calendar and then now it can communicate to all their PMS systems and Airbnb. And it's just very simple. It takes probably three to five minutes to get your property up and running on host share.
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, in.
Short term rental, however, I would say, I mean, there's a, there's a couple things that I, that I just, if, if I'm just like thinking to myself, but like in, you know, one, one would be, you know, how you do anything is how you do everything. And, and so, and that's one that keeps me in check more than, you know, that 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 gonna, if I'm gonna commit to it and, and it, 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, I look forward to seeing you guys be successful and seeing you at the events and, and all of that, all that cool stuff. And yeah, thank you again. I look forward to seeing you on the next Boostly podcast. Bye for now.
Having a blast. Gonna get it on the Boostly podcast. Bruce Lee like Bruce Lee. Cause it's so hard and the tea is loose leaf Making up those rhymes don't write it, just do it loosely.
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