Maximizing Last-Minute Bookings with Whimstay | Featuring Alex Alioto

Welcome to the Boostly Podcast. This is the podcast that gives you the tools, the tactics, the training and most importantly, the confidence to go out there and get yourselves more direct bookings. We do a mini series on this podcast which dives into a software or service that you should know about as a host. Today's episode we are featuring whimsday. We've got Alex from whimsday. He is the CEO, co founder and also the head of growth for the company. And this is something that you need to know about particularly. I mean it is hopefully going to be all over at some stage. But if you're in the US and you're now a UK listener, you need to listen up to this because this is such an opportunity for you. So welcome along. Alex, thank you for joining me today.

Liam, what's going on man? Nice to be here. Thank you very much.

Well, it's nice to see. I think we had a brief interaction at the Short Stay Summit last year in the UK and I know you get to go to some of the awesome events, so it's great to have you here on the podcast.

Lovely to be in here. Thank you very much. Mark's a good friend of mine. I love what boos Lee does. I wish that the audience could have heard the conversation you and I had off air about the art of swearing. They're going to miss out on that one, but I think they'll get some nuggets on this, so we'll see.

And also the. What is it? The Dungeness crabs.

Oh, Dungeness crab, yes. Anyone who's listening, come to San Francisco, get Dungeness crab. If you're in Norwich, get Cromer crab. Right, exactly, exactly. That we have, we have, we've promoted crabs and swearing. That's what we do.

Local seafood, swearing and crabs is what we talk about. So anyway, let's, let's dive in. First of all, where are you in the world and can you give us a bit of information, background? What, what is whimsday?

Yeah, dude. So I'm in San Francisco actually. A little, a little fishing village across the Golden Gate Bridge called Sausalito, California. Beautiful little place my wife and I live, but we are a San Francisco area based, our company is a San Francisco based, Silicon Valley based tech company in the short term rental space. And what we do is really simple. We are an ota. I know that Boostly is a, is a direct booking site so I'd love to, to kind of address the sort of OTA versus direct thing at Some point. I think that's actually really a cool conversation to have. But we're an ota, but we're, we specialize in something. We help posts and property managers filled their unsold gap nights, weekdays last minute, so expiring inventory, weekdays shopping, shoulder season, all the kind of gooky stuff that, that other OTAs have a hard time picking up. That's what we do. And we do it pretty well.

And especially at the moment, I mean as we record this for many hosts in the Northern hemisphere, it's off season for many hosts, depending on if you offer winter travel or more traditional seasonal travel, summer. But when it comes down to it, there's always those dates that you don't sell as a host that ultimately that's the difference between maximizing your revenue to not maximize it. So any service which helps that we're definitely interested in. And it's funny you should ask about the, the OTA versus direct bookings. And this is something which not many people know, which we do. We say to people, hey, OTAs really serve their purpose, you know, but it's, it's kind of known why to be on the ota, you know, like to, to do specific things and also for the early, early step in the journey, often it's necessary right at the start there. It's just we don't want people to become too. Some people think it's the only way. And that's where we come in.

Yeah, yeah, yeah. No, I, I think it's right. I mean, I. So here's, here's an interesting little piece of data. So we're a data driven company. So data is kind of where we live and it is showing us going outside our, our little ecosystem that direct bookings actually help the industry as a whole, including OTAs. And here's the reason why. Reason why is because if you do look at kind of the gap between hotels and short term rentals right now, a lot of that gap is based on hospitality, convenience and those types of things, right? So because our, if you're a short term rental, your value is there, right? The space is there, the experience piece, which is very important, particularly to this younger next gen traveler that's there. So what's not there? Well, a lot of times the sort of the hospitality that you can find in a hotel or even the convenience. So what we find is if a host is focusing on getting a direct booking by upping their hospitality game, that only helps everybody.

Right?

That's. I always mess this one up. But the rising tide with the Boats go, all the boats go up, right? Yeah, yeah, I butchered that. But you get the idea.

And also, just in general, the better your hospitality, the more likely it is that people are going to come back. That can only be good for revenue in general. Can't.

Exactly. So they'll, they'll either, they'll either come back to you directly or they'll say, oh, I like this vacation rental experience, I'll do this again. And if you look at how travelers, for the most part, how they, they choose their house, their, their lodging, you know, I mean, I think most of the time if they don't have an idea in mind, they go to the ota. So I think the best thing to do from a host perspective is think of the OTA as a traveler acquisition and think of Wednesday's 5% commission as a 5% traveler acquisition tool and then allow yourself the ability to really kind of do what you do best. You know, if I'm, if I've got a place in Norwich, for example, I'm really, I don't off the charts here, but I have no idea what I'm talking about because I've never been there. But for example, Cromer crab, right, that's something that is specific to Norwich. So what you would want to do, in my opinion as a host there is have some, have some Kroma crab in the freezer or something like that. So something that's like a personal localized touch that hotels can't do. So doing those types of things, I think are, are a nice way to pull a direct in. And using the OTA to get that traveler in the first place is an essential way to do it. And I think what Wednesday is doing specifically is we're not fighting against Airbnb and booking and vrbo. That would be dumb. We're complimentary, so you would add us as a complimentary channel. Because if you look at how things are going currently with, with booking windows are shrinking. If you do not have a specific last minute strategy, if you don't, you're just missing out on a massive chunk of occupation and of occupancy. And so that's kind of the idea.

And so how does that look from I guess a guest point of view? Is it just a, is it a site that they go to? What, what does the journey from a guest looks like?

Yeah, it's the same as any other ota. It's an app or a website and you just go in and you find the, and you find the property that you, you go and search for it. It's the exact same way it would work on Airbnb and vrbo. The difference from the traveler's perspective is that they're looking last minute, so they're a little bit more of a spontaneous minded traveler. The host or the property manager is going to be adding a last minute discount in order to get that filled out. So the person, the traveler that's searching is knowing, hey, I'm in London and I want to go to Norwich for three days. It's a Monday and I want to go to Norwich on Wednesday for three days. I'm dropping a lot of Norwich on you, aren't I?

Yeah, yeah, I was gonna say it's good advertising.

But I want to go to Norwich for three days, I go to whimsday and I find what I want to find. And, and that's a booking that probably that host isn't going to get otherwise.

And when it comes down from the host's point of view, obviously, because somebody might look at it, go, well, you know, when I've got last minute, I tend to stick it on my socials or I'll send it to my email list. Where does whimsday come into that kind of journey for the host? Does it, should they be advertising all the time on Wednesday or is it just those, is it those type of bookings that they should put on there? How, how does feature for them?

Just use us as an extra sort of arrow in your quiver.

That's it.

So if you have a last minute strategy that's going to socials, by all means continue to do that. If you've got a last minute strategy that you shoot out emails to your email list, by all means do that. And then on top of that have an OTA and have an OTA that's specializing in filling in your unsold gap, nights, weekdays, etc. So it's just again, I think that the best way to think about us is, you know, the best way to think about your, your revenue is what is my distribution strategy look like? And it can look like a thousand different ways, but I think to have one that's very specific and very intentional is really, really important. One thing that, that, you know, we, that we've looked at is generally in the US people use VRBO for 180 to 90 days out and they use Airbnb for 90 to 30 days out. Well, there was a gap in 30 and under, so that's why we, we chose to do this. So if you look at being a host or A property manager. And I know VRBO is maybe less, less popular than say, booking is in the UK and EU. So let's say that you would use booking for 180 to 90, use Airbnb 90 to 30 and use us for 30 days and under, along with any other tool that you have. And it's just, what it's basically doing is getting you out to as many different travelers as you possibly can. And it's just, it's, you know, if average occupancy right now in the US is 58%, that's the average occupancy. High supply and demand is up, right? Demand is up 10% in the US. I don't know what it is in the UK. I'd have to look at that. But supply is also up about 12%, so that causes a bit of an issue. And so Occupancy is a 58%. Get eyeballs, eyeballs in front of your properties and it's, that's the best option for you.

And just on the most recent stat for UK that I know of is that it was. Travel was up only 6%, but the number of places was up around 15 to 20%. You know, like, so it is, I always say to people because they go, oh, I'm worried about, you know, I'm not going to get bookings. You go, well, actually, year in year, there's more travelers, there's more opportunities than there's ever been before. The trouble is, yes, there's more competition, but all you've got to do is like you say, get the eyeballs, get more seen, market better than your competition and ultimately just provide a little bit more value to, to get people to, to always come back. So when it comes down to whimsday, does it just take the available dates or as a host, do I need to send the dates specifically? How does that work, kind of the operation?

Yeah, that's a really good question. So there's two different ways. So currently the only way that we work right now is via a PMS connection. So we categorize two different things. Professionally managed and what we call RBOs individual hosts. So currently what we do is we work with, with property managers via their pms. They would enable us on their PMS and we're able to consume everything, including their calendar and then we're able to show anything. And if their property is, has availability within that short term window, it shows up on the whimsday app or website. If it's not available, obviously it just doesn't show up. Now what we are currently doing right now because 75% of the market is what we call the RBO, the individual host that makes up a large portion of our industry. So we are building right now, which is going to be ready, we think in the next quarter or so, maybe even less than that. So it should be done by Q1, an RBO portal. So for individual hosts are going to be able to do it and it's all through iCal. So it's the exact same idea. We'll be able to consume the calendar or through the Airbnb link or whatever it is, be able to consume that calendar and then we're going to have the option to, to, to show those, those that way. I want to actually double back on something you said and I think it's just in case this is something that your hosts want to know. I just did a a webinar the other day with Jamie Lane from Air DNA, who's the the head of data for Air DNA, and he mentioned that for the first time in a number of years, the supply numbers are starting to go down. So for your hosts that are a little bit nervous about those supply numbers, they're starting to go down and we imagine this was going to happen because the boost happened post Covid. We think now that that's going to people are starting to kind of figure out they're going to maybe interest rates are going down, start to sell those homes off and that supply will start to even itself out and hopefully get even below that demand number.

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You know, it's interesting that you say that because I was on a podcast earlier on last week and we for the first time I actually said the number of listings dropped by about 30 locally to me and it's worth going on to some of the, the data places you can do. I won't name names but there's lots of these places where you can go and check out the, the data where you can see how many listings roughly there are. Scrape data obviously from your local market and it might be worth tracking. And you can definitely see that post Covid the number just went like this. It was such a peak and then it drops a little bit in the winter months and it actually went even higher the year later which is a surprise considering that was weird. Yeah, it wasn't as there wasn't as many travelers or it didn't feel as though there's many travelers. It definitely wasn't like the staycation boom, was it? But the number of units still went up because people were riding the, the wave of, of, of knowing that there was a lot of money to be made. And I definitely think one of my predictions, I was talking about the predictions for 2025 is that actually we're going to see the lower end of the market that the hosts who are kind of doing this is maybe you know, part time hobby or, or not really necessarily putting in all the amenities that guest needs and getting lower reviews. And I think we're going to see a lot of those lower, less than average stock disappear in the next 12 months because ultimately they won't get a look in. People are always going to go for places which are priced well, great reviews, great locations, all the stuff that you and me, you know, think about day to day and talk about day to day.

Yep. I think, I think the data is actually is actually is that's what the data's saying is going to happen. So I think your prediction is. I think you are a Nostradamus, my friend. I think you're right.

I mean this. Yeah, thank you. I've been called many things, but not Nostradamus.

I got you, man.

But when it comes down to Wednesday, what. Why is this important? Getting those, getting bookings in for people. Last minute. What got you onto this journey of helping people with this?

It was. So my co founder, Ben is very successful tech entrepreneur in the Bay Area. And so he, you know, after his latest sort of sale, he, he bought a couple of homes, bought one in Maui, bought one in Lake Tahoe, and sort of put them on the short term rental market just to kind of see what it was about. And he's got this kind of visa. He's a brilliant businessman. And I don't think it took a brilliant businessman to understand, however, that he was frustrated by the fact that he couldn't sell any of his expiring inventory, that the only option he really had was to put a discount on it. And if you put a discount on something, then really your strategy is kind of hope, right? You're hoping somebody sees your discount somewhere. That's. Hope's not a strategy, as we all kind of know, right? So he was like, well, there has to be a platform, right? Because if you look at any industry, grocery stores, clothing outlets, everything, right, they all have sort of an overstock model. We have in the US a store called Nordstrom. I don't think you guys have Nordstrom, but do you guys have Nordstrom?

We don't. We've got TK Maxx and.

Okay, well, TJ Maxx, TJ Maxx is a perfect example, right? So TJ Maxx is just. You take a department store, department store says, well, these clothes have not sold or they're going out of style or out of season. So let me go put them in TJ Maxx and for 40 off and at least we get something other than nothing, right? So it's like everyone has an overstock model. Hotels have a company called Hotel Tonight, right? It's the exact same model. So that model didn't exist in the short term rental space. And so I think Ben sort of realized that and said, well, that's, that's my next venture. And so he called me and then the rest is history. It was just, it was, it was born out of, you know, necessity is the mother of invention. It was born out of the necessity of an individual host with two properties who said, this is ridiculous, that there's nothing I can do. To sell my last minute stuff. Nothing other than to hope. So there we go.

You're absolutely right. And nobody wants to be discounting on some of the, I mean you mentioned booking.com earlier on. Do you know the, the percentage by the time all is said and done? And this is without adding all the additional promotions that they try and sell you. You know, it's minimum 18 of the, the overall total and if you put on one or two of the extra promotions, it can often either discount your portion of, of the income so effectively it's like having higher commission for them or you can opt to have a higher visibility by paying more commission on, on these channels, which you know, a lot of people then do. But like you say, by the time you've discounted, you're then paying huge commissions on, on some of the big named OTAs that ultimately people are left with very little. And this is where you're absolutely right. I've never thought about it before where there isn't really a place where short term rental hoes go to and I suspect that's just as this is still a maturing market, isn't it? Where, where eventually it will be very much something. It's, it's very cool.

We are, to use a baseball term, we are in the first inning of this thing. So this is, this industry is, is, it's brand spanking new. I mean I know that it's been around for a long time and I think in Europe longer than, than it has anywhere else. I think it really picked up steam around 8, 2008, 9, 10, just with the birth of Airbnb. So it's, and it's really just if you look at sort of how it, how it is now, there's you know, with tech stacks sort of being introduced and all sorts of different things. It's really obvious that we are very, that we're very much at the beginning of this which is, which is really great news because there's a really, a lot of, a lot of market share for us to take from hotels. A lot. A lot. Right. And I think, and I think so a lot of room for us to grow as an industry, improve as an industry, defractionalize all that kind of good stuff.

I, I liken it to what we have corner shops. So you know, like 100 years ago there'd be a little independent shop on every corner. And nowadays we're used to the great big, you know, stores, Walmarts and, and you know, the, the big stores that we recognize as brands and short term Rental industry is going to go through that kind of thing where there will be just known brands and there'll be known portals where you go and where you go for the different reasons like you mentioned about the stores and that. So yeah, I think analogy.

That's actually. That's absolutely right. It's a good analogy.

Well I, I really look forward to, to seeing where this goes and what is the future then for, for whimsday. Where would you like to see this going in the next say year, two years and onwards?

Yeah, I mean we're, we're, it's right now is a, is a big time for us. So we're, we're live in the U.S. canada and Mexico. We just went live in Mexico about six months ago and so we are live in those three. I think we've got about 250,000 properties on the platform. Our next move is, is UK and then Europe. So we're in the sort of process of building that out. So by 2025, you know we have. It's, it's so interesting having having a high momentum startup is a very interesting thing because there's a lot that sort of goes with it that you would never really imagine. We feel like we're in a really, really good spot to, to grow into something that, that is going to be indispensable for hosts while maintaining and here's the future of, of how this company is going to work. This company will not work unless our customer service on both of a host side, property manager side and traveler side is grade A. It's the only way. So that is a massive part for us. What does that mean? That means that a host or a property manager, if they've got an issue there's someone or something they can talk to. Okay. So that's a really big part of our, of our next year is how do we scale customer service on both sides of that and then how do we enter the UK and the European market which we've got a full game plan on that as well and those are things that we are very, very confident that we are going to accomplish and if we do that then we think that we are a really solid option for travelers that are spontaneous minded and we are a really fantastic option for hosts to raise their occupancy 20% over the course of a year. And, and so we, we don't think we're going to do it. We know we're going to do it because everything is in front of us. And, and we know this industry is the most Fabulous industry in the world. We really believe that. So that's our future.

Well it's something which I'm excited about for yourself but also for hosts who are listening to this because ultimately we all want to sell those last minute stays and we're all travelers. I mean by, by the sheer fact we in this industry we, we go trav stay at short term rentals. I try and book direct to wherever I can and just it's worth knowing about. If you're a traveler obviously you can go and check out whimsday. If you're a host, what do you want to say to the host listening to this? Where should they, if they're in the UK should they be approaching you now or if they're in Mexico, US like where do you want them to go to? What's the best link?

Yeah and so I'm going to say there's one of two things. You can go right to our website and you can go to list your properties and that'll take you directly to where you need to go. I'll give you my email. My email is aleximstay.com We've got a sales team of about 8 or 9 right now but you can email me and I can, I can get you to the right person. The process to get onboarded is about three minutes really quick and as I mentioned before right now it's just PMS centric but if you are an individual host then let us know, we'll put you in the queue and as soon as we're live in Q1 we can get you on board and then yeah, US Canada, Mexico, good to go. UK we could take you right now just so you know, like we do have UK properties and but they're just open to U S based travelers for right now. So that's how we're opening it up essentially just uk. We have EU as well. Great company Interhome is, is live host and stay Dale Smith, wonderful guy. He's live. Couple other good, good folks are live and, and we'll be live for U S based travelers I think probably for the next few months and then we're going to open up to UK and then eventually EU and open up the entire, the entire continent.

Nice, nice. And we've had Dale on recently as well so. Fantastic.

Fabulous dude, isn't he?

Oh very much, very, very inspirational and he is it go goes a million miles now.

He certainly does.

He's a good but so one last question which is how did you come up with the name Whimsday Yeah.

So we had an original name which, which was, you know, Ben and I are kind of hippies and we, and we do yoga and we meditate and so our original name was, was We Must Day, which is a take on Namaste. And we thought to ourselves, well, that's just a stupid name. And we overthought it. No one's going to know what the hell it means. So we got rid of that. Stay on a Wednesday, stay on a whim. It just seemed kind of obvious, right? Let's, let's build a company that, that tells what we do right in the title of our name. I did not, I'm. I, I did not think of it. I think Ben might have thought of it or maybe our head of, our head of marketing, Noel might have thought of it. But whim. Stay. Stay on a whim. There it is.

I like it. I like it. As soon as I saw it. It does. It's exactly what it says on the tin. I mean, and I checked out before, before this podcast. I know Mark put this together and I was like, oh, this is interesting. I went and checked out the website and sure enough, there's a fantastic deal in the next 30 days. I searched places, I mean like in UK. I was just like, hey, let's search Disneyland or whatever, you know what I mean? Or Orlando. And yeah, there is, is some good deals. So even as a traveler, if you're listening to this and you're thinking, hey, let's go and check it out, like Alex says, you can, if you're a host, you can go onto the website, which is wimstay.com you can go, he's giving you the email within this. If you are listening to this and you're driving at the moment and you can't write that down, all you need to do is after the podcast is have a look in the show notes, click the link in there and you'll be able to go straight across the website and, and check it out. So Alex.

And email me too. Alex at whimsday. Really simple. Yeah, I'm happy to reply in chat. It's fun. I like it.

Thank you so much. Well, as, as we like to end these, we love to just have a bit of random question or inspiration. Is there a motto, a mantra or any kind of life lesson that you want to share with. With the people listening?

That's a good one. Well, I, I'll say this, here's something that I have learned about running a business in a startup and I'll Say a startup, which means basically running any business at all. If you're an individual host and you want to start this going, here would be what I would say that I learned. If your timing is right, if your market fit is good, in other words, and if you're a host, then your timing is right. I'll tell you that right now. And your market fit is right because people want to travel to these things. And so you're in good shape. If that's the case and you believe in this thing, then. Then life will. Will maybe throw things at you that will say, I can't do this anymore. Those are, in my opinion, believe this or not, I don't know is what I believe. These are tests, I think. I think if you keep going, if you really believe what you have is right, you will have a successful business. So long as you just keep going. It becomes, after a while, it's just. You just got to keep going. And it's hard, man. This is the hardest thing I've ever done in my entire life. There's simply no question about it, dude. So I think it's not. I don't know if how inspirational it is to say, to say, keep going, you know, it's like, fall down four times, get up five, and it's a.

Truth bomb, you know, like, it's really, really, really is.

I mean, again, this is not very inspirational, but at the end of the day, it's a war of attrition. I mean, if you can get through. If you can get through the stuff, the obstacles, I think that only something like, I think 15% of all, of all startups get past the third year. A lot of that has to do with people just saying, like, I, I can't. I can't do this anymore. And if that's the case, that's fine. But if you feel it and you're like, I want this and this is something I want, keep going. Seriously, keep going, like something will happen. And so that's. That's probably. I don't know, I'm sure everybody says something like that, but no, no, it's cool.

It's cool. And ultimately there's. There's people who need to hear that, and certainly I feel inspired by it. So thank you so much, Alex, to, for sharing that and for sharing about whimsday. There's people on this podcast who will go and check out whimsday. If you are a host and you know somebody else who would yet benefit out of it, go and share this podcast with them. So that's it. From myself. Alex, any last things to say?

It was. That was a really good time, man. Thank you very much. I told you before, I've been dealing with the flu the last two days, and this is the first 15 minutes I didn't feel like I had the flu. So I appreciate that.

Hey, man, you. You wouldn't know it. And thank you so much for doing this, even. Even with the flu. And thanks again for joining us on the Boostie podcast. We'll see you on the next one.