The Great AI Debate: Direct Bookings, Websites, and the Future of Search with Richard Vaughton and Mark Simpson
AI is changing the way travelers search, compare, and book vacation rentals. But what does that mean for direct bookings, local brands, and the websites operators have spent years building?
In this episode, Alex & Annie are joined by Richard Vaughton of Yes Consulting and Mark Simpson of Boostly for The Great AI Debate. After taking this conversation to the stage at the Host Planet Roadshow in London, Richard and Mark continue the discussion around what AI could mean for vacation rental marketing, website strategy, and guest acquisition.
Richard argues that AI will reshape websites, search, and distribution in ways the industry has not fully prepared for yet. Mark makes the case that strong website infrastructure, brand strategy, PMS connectivity, and niche positioning still matter, especially for operators who want to grow direct bookings.
Together, they explore whether AI search will create new opportunities for independent vacation rental companies or make it even harder to compete with OTAs.
Episode Chapters:
05:29 - How AI is changing the future of vacation rental websites
07:10 - The debate between WordPress websites and AI-built websites
10:00 - Why website design alone is not enough to drive direct bookings
28:25 - How Airbnb, Vrbo, Booking.com, and Expedia continue to shape guest behavior
36:29 - Why broad search terms are becoming harder for local operators to compete for
18:00 - How AI search could make niche positioning more important
21:53 - The growing role of TikTok, creators, and social media in travel discovery
46:03 - Why brand trust still matters in an AI-driven search environment
48:22 - How PMS data, integrations, and distribution may evolve
53:22 - What vacation rental operators should be thinking about now as search changes
As guest behavior shifts, vacation rental operators are being pushed to think more carefully about how people find them, what makes their brand memorable, and how they can stay visible beyond the major booking platforms.
Connect with Richard:
LinkedIn: https://www.linkedin.com/in/richardvaughton/
Website: https://yes.consulting/
Connect with Mark:
LinkedIn: https://www.linkedin.com/in/mrmarksimpson/
Website: https://boostly.co.uk/
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#vacationrentals #shorttermrentals #ai
01:36 - Sponsor Spotlight: Monarch Collective
05:29 - How AI is changing the future of vacation rental websites
07:10 - The debate between WordPress websites and AI-built websites
10:00 - Why website design alone is not enough to drive direct bookings
18:00 - How AI search could make niche positioning more important
21:53 - The growing role of TikTok, creators, and social media in travel discovery
26:34 - Sponsor Spotlight: BookingPal
28:25 - How Airbnb, Vrbo, Booking.com, and Expedia continue to shape guest behavior
36:29 - Why broad search terms are becoming harder for local operators to compete for
44:18 - Sponsor Spotlight: Hospitable
46:03 - Why brand trust still matters in an AI-driven search environment
48:22 - How PMS data, integrations, and distribution may evolve
53:22 - What vacation rental operators should be thinking about now as search changes
Richard Vaughton
I don't think this is a really great opportunity for people to go out there and five code their own websites. I would actually say use a WordPress website rather than do that.
Alex Husner
I went to ChatGPT and I said, show me a three-bedroom condo in Myrtle Beach available June 5th to the 10th. And the options that I got, I got from Expedia, nothing else. No other vacation rental local companies showing up.
Annie Holcombe
Are the different models working differently? Because Alex did hers on ChatGPT. I did mine on Claude. Claude gave me direct booking sites and OTAs, but put the direct booking sites first.
Richard Vaughton
This has to be about making money for the large language models. There's no point in them being in business unless they can milk us all.
Mark Simpson
Only 0.05% of the people on this planet actually pay for AI platforms. So if you're feeling a bit overwhelmed with everything that we're talking about and you're paying that $20 a month, you're ahead of a lot of people right now.
Alex Husner
We'll start the show in just a minute. But first, a word from our premier brand sponsor. If you own a vacation rental management company, this one is for you. A lot of owners have thought about selling someday. Maybe not today, maybe not even this year, but eventually. And when that thought comes up, two questions usually stop people in their tracks. What is my business actually worth? And what happens to the people, the homeowners, the reputation, and the brand that I spent years building? That's exactly why we want you to know about Monarch Collective. Monarch is built for local vacation rental brands that want to grow without losing what made them special in the first place. When Monarch comes into a new market, the local brand stays. And not just the name on the website. The team stays, the homeowner relationships stay, the reputation you earned in your own backyard stays.
Sponsor Spotlight: Monarch Collective
Alex Husner
But now there's a much bigger platform behind it. You get paid for what you built and the parts of the business that drain so many owners. Finance, accounting, HR, legal, backend operations, they come off your plate. And instead of doing everything alone, you get the support and horsepower to keep growing. You can keep running the business as long as you want. You can step back when you're ready. There's not one version of what this has to look like. And here's the best part you don't have to be ready to sell to have the conversation. Even if you're just curious, Monarch will sit down with you, free and no strings attached, to help you understand what your business could be worth. No pressure to sell, no pressure to sell to them, just a real conversation with people who understand this industry and respect what local operators have built. So if you've ever wondered what your company could be worth, go find out. Visit Gomonarch.com/slash partnerships. Welcome to Alex Nanny, the real woman of Vacation Rentals. I'm Alex. And I'm Annie. And we are here today for the great AI debate. And we have two very, very, very well known, respected STR legends with us. So we're super excited. We have Sir Richard Vaughton of Yes Consulting and Mark Simpson of Boosley. So good to see you both.
Mark Simpson
Thank you for having me. Thank you for bringing me on with Richard. It's a pleasure.
Richard Vaughton
Yeah, thanks. Uh both of you.
Annie Holcombe
Thanks for staying up late. We appreciate that. Although the sun is still up where Richard is, and I guess setting where Mark is, because we found out he's way up north. So before we get started, why don't we do some quick introductions again? I think most people know who you are, but just some quick introductions. Mark, I'll let you go first.
Mark Simpson
Yeah, so thanks for having me. I think this is number three or four on the podcast. So it's an absolute pleasure to be back. Uh founder of Boostly, I've been in this game for quite a while. Uh Boosley's been going for 10 years this year, which is great, but I've been in hospitality since I was I was born. My whole shtick and the thing that I'm trying to help do is help hosts with getting more bookings, more direct bookings, showing that they can do this this game without relying on the online travel agents. And for the last 10 years, we've we've helped over 2,000 hosts all around the world, and we've generated over a a billion dollars in bookings, which is epic. So really happy. Uh really like this debate. Me and Richard have been doing this this debate now, it seems like a long time over the last month. So I'm excited to to run it again.
Richard Vaughton
And Richard? Lovely to be on with uh with you all again. And uh yeah, Mark and I have been doing this for a few weeks now. Uh so yeah, I'm uh founder of uh Yes Consulting. I've been doing this for a very long time. It started at the end of the last century, so you can see how daddies had a couple of management companies, exited those, owned a tech business, exited that, and I now work with uh some really excellent management companies on growth and exit and MA work. Uh and I'm a board advisor to some tech businesses, one of which is uh Boom, uh the first AI PMS. So that's a bit of a background on me. What I would like to say is that I think Mark and I are converging on thoughts, interestingly enough, over a period of time. So don't expect warfare.
Alex Husner
Well, don't turn off the episode. We don't want anybody to be dismayed by that. But um, and the the reason for this episode is that we were at the Host Planet Road Show, which was right after um the Short Stay Summit in London last month. And this was the end of the day session, and there was a lot of energy, and they played hype songs as you guys ran up on the stage and Richard banged on his chest, and it was just a lot of fun. But I think you probably actually feel more similar, as you said, that than different on some of these things. But the reality is, you know, AI has changed a lot as far as marketing is concerned and vacation rentals. And I think a lot of the changes that are coming, they have not come yet. I think they, you know, in theory, the things that you're able to do are there. But have managers really adopted
How AI is changing the future of vacation rental websites
Alex Husner
them, you know, into their older tech stacks? I I don't believe so to for uh for the largest extent. But uh, Richard, to kick us off, just kind of give our audience a high level of what your position was in that session as it relates to AI and direct bookings.
Richard Vaughton
Yeah, it it's still the same position. I'm not going to dispute the fact that I'm a fervent believer in the fact that uh AI is uh entering the web space um very quickly right now. And there are a raft of very good companies actually providing these services. My gripe really has come down to the 32 million websites or 400 million websites, whatever number it is that are running on WordPress. Um, and having been somebody who's run companies that sold WordPress websites, has built WordPress websites, actually still has a WordPress website, which is driving me crazy right now. They've had the day essentially. They're too clunky, they're too clumsy, they're not developed to their general purpose. Uh so I see AI uh and it's um and its development moving forward, not just providing websites, but providing intelligence and data connectivity, reducing costs, flattening costs, uh, and making everybody's opportunity for let's say it, direct bookings easier. So that was that was why I was beating my chest on stage. I will say Mark had the best line of the uh of the whole show, I think. And when he revealed that I ran naked on Talkie Beach. But
The debate between WordPress websites and AI-built websites
Richard Vaughton
that was his closing line.
Annie Holcombe
Well, now I'm really sad I didn't get to witness this in person. So I guess um, so to go off of what Richard set up for you, Mark, what is your stance on it and maybe share with us what you said?
Alex Husner
Yeah, I think you have to tell that story because it was definitely a good one.
Mark Simpson
Uh okay, so we'll start with the story. So um what Richard doesn't know about me is I've got a very good memory. And when you tell me something, it gets etched in there. And and uh we were doing a clubhouse um 24-hour room uh five years ago. So when Clubhouse was really popular, we we did it. And one of the questions that I asked Richard amongst the other panelists on that clubhouse was what's one thing that nobody knows about you and D he he recoiled and it was uh about him running naked on the beach at nighttime, which obviously in my memory. And when this debate was first muted between James Viley, who organized House Planet, Richard, and I, I I knew that I needed to have something to finish the debate with something that will uh will help sway it in my favour. I dropped, I dropped that uh that bombshell I don't know. It was it was funny, it was good, and I loved it. But coming back to the to what we're talking about, the debate on AI, and it was really good to have this conversation with Richard on stage. And I and I and I'm talking about conferences, I want more conferences to have these like debate styles because it made a really entertaining talk and I learned a lot. And everything that Richard talks about is true. AI is going to disrupt our industry, it's going to disrupt every industry, whether we like it or not. And some verticals in our industry are getting disrupted quicker. PMS is being one, obviously, Boom has done really well with that in becoming the first PMS that is AI built and driven. But when it comes to websites, obviously my business model and the reason why I am here on the WordPress side is that we have built everything on WordPress. And the reason being is you know, 41 or 42% of all websites in the world are powered by WordPress. It's a case of if it's not broke, don't try and fix it. And there's a lot of people who say it is broken. Richard obviously has a lot of very good points about where, from his technical point of view, where it could be broken. But at the end of the day, I spent the last 10 years trying to educate a host about the powers of direct bookings and why they need to do direct bookings. And I've been talking about things like social media, about email, about websites. And we get we get onto the topic of SEO. Um, everybody comes to me and goes, Mark, I want to do SEO, I want to do SEO, I want to become first on Google. And I say, Okay, sound. What does SEO mean? And most people I speak to don't even know what SEO means. And I would talk about AI websites and you know, and and and prompt and et cetera. And it's just, it will affect us, right? And it'll it'll affect us in loads of ways, but not just now. WordPress is still best, in my opinion. I feel like it is one of the the the
Why website design alone is not enough to drive direct bookings
Mark Simpson
expression that I did on a webinar that we did last week, Richard, was if you think about your PMS website as like the walled garden. So you've got your PMS website, it's very basic, it's very, very linear, you can't really do anything. WordPress is like that blank slate, that blank hamper so you can do what you want, you can do all the cool things, have live chat on there, have your all of the things that you want. And and for that, I think that that is why it is number one. And the final thing that I will say about AI websites, and there are some really cool companies like on season, what Boris is doing over in Bulgarian. There's a couple other things that I've seen pop up, but for the most people who are going to try and just build an AI website and say, that's me, that's me done. I've done it in a prompt. AI websites is like looking at a really pretty car. I just imagine the most beautiless car, your favorite car, you just you just look at it, it looks stunning, but it's the most beautiful car that hasn't got an engine. And if your car hasn't got an engine, you can't go from A to B. And and the engine is actually the most important part of a car. And you know, if you haven't got one, you can't drive it. And that is still what these AI websites are. They look pretty, you can prompt one together really simply, but the actual core essentials of it is the engine, and it hasn't got that engine. And so this is why you still need that engine in the background, and that is truthfully what what we've built at Boostly. That's you know, our PMS integrations, that's the things that we've done behind the scenes, and and and that's like sort of my argument on all of this. Um, and and I'm and I'm yet to see an AI website that can do all of the things.
Richard Vaughton
I think uh picking up on your last point about uh all the PMS connectivity and the API integrations and the fact you can bring data from PMSs into websites to populate them and create a booking engine, that is certainly the most powerful part of the whole discussion at the moment. But if you go back to your car analogy, and I said this uh on a previous episode, is that you all probably won't remember, but uh in the 1950s, um East German car called a Trabant, known to all its followers as a Trabi, uh, was the most popular car throughout the whole of Eastern Europe and sold millions and millions of these. And to this day they still run, but they didn't have a fuel gauge on them, they didn't have a speedometer, they were falling apart, they rusted to death. But people actually produced all sorts of um extras on these Trabans. So they give them um they give them a speedo, they give them a fuel gauge, they try and bolt in a V8 engine to them, they try and give them new brakes and new exhaust pipes and give them green bumpers. But it was still a Trabant at heart. It was not a Tesla. Okay, um, this is where WordPress sits. It sits as something that was that it was invented in 2003, I think, actually, which is a lot more recent than a Trabant, but let's face it, the internet only exploded around about the year 2000 anyway, so we weren't gonna have these things before that. You have a very poor architecture and infrastructure, which has been around for a long time. I know somebody's gonna say WordPress 7's just being launched and it's gonna revolutionize everything. I don't I don't believe it. The really important bit is the is what Mark is saying. It's the booking engine, it's the integration. All those other parts of the website can be created through AI tools very, very quickly, very, very elegantly. I will agree with Mark on on one point here, and I think this is an this is a industry challenge, is that I've created my own websites on AI and I've used Lovable, I've used Anti-Gravity, I've used Redlet, and they are beautiful websites. But I have to stay on top of those websites all the time because I've integrated APIs to them for various purposes and for various things, and and they're not a hundred percent reliable, and and I know what I'm actually doing to a great degree. So I don't think this is a really great opportunity for people to go out there and find code their own websites. I would actually say go to Mark and use a WordPress website rather than do that, okay. What is coming, however, is a big change, and and and it's the big change that I'm talking about. I'm not talking about everything that exists right now, and there are great companies like Boris's on season and Crafted Stays and uh stai and and others, but they're doing amazing things with the data and the intelligence, the SEO, the connectivity to the PMS and all sorts of things. So we're in that transition point at the moment. And I interestingly, I got shown a slide this afternoon from a discussion I was having, and it was quite terrifying because it showed 3.2 million people actually are professionals using AI for coding, and they actually are software developers and high-level coders as well. There is somewhere in the region of 18 million people doing bytecoding and a little bit of software development and touching on these types of things, and then there's about 7 billion people not doing anything with AI at all. So I'm talking about this very top level at the moment, and and that's why we're all sitting here talking. It it's it's a word we're all using, but in general, the population doesn't know very much about it. So there's a huge space fill for WordPress websites. I'd just rather have a Tesla than a trap.
Alex Husner
Yeah, and a lot of things to unpack there. So I want to go back to one comment, Mark, that you made that I think is is really important. And actually, uh, if Terry White is listening, I know he smiled when uh you said that because we had him on our show several years ago and he said, get your website out of your PMS. And I could cannot agree with that, you know. Until recently, I couldn't agree with it more because to this point, most of the PMSs that have a website builder, it's extremely basic, doesn't let your property pages be indexed by Google. You have very little flexibility as far as content that you can add. Um, but there are, and actually Boom is one of them, the website generator that we have now is is far more complex than or advanced than most PMSs have been in the past. But that aside, for the most part, would never recommend just going with whatever the PMS gets you if you want to be serious about direct bookings. But I think where I see it from property managers that I speak to, and I come from a world, you know, years ago that we had uh a website that generated multi-million dollars a year of 95% direct bookings. So I mean, like we were heavy, heavy on brand, heavy on marketing, um, internally built. So a lot of things going on within that website. I don't think I would recommend to anybody these days to be 95% direct. That was a different era. But you know, the OTAs every year are taking more and more business from direct booking side. And it's like when you look at the mix of bookings from a property management company that's established, been in a market for a long time. Direct, if they are established, has is typically still the highest amount of volume that they have. But Airbnb and Verbo have really, you know, had caught up over the last couple of years. And I think a big part of that is not just because of AI, but I I think it's because people have finally gotten to that point that we were all worried about, that they have really owned the space of when you think about booking a vacation rental, you're gonna go to one of those two channels. And part of that is because of the trust that they've they've built. And when you look at websites within our space, a lot of them don't really look trustworthy. I mean, they they a lot of them were built many years ago and they don't, they haven't kept up as far as the UX of where Virgo and Airbnb has, and those they
How AI search could make niche positioning more important
Alex Husner
really establish brands, and that's really where trust originates from. So, my my question in all this is uh Mark, I'll throw this one to you. Where does brand come into play now? Like how important is brand as far as building a direct booking uh company?
Mark Simpson
Yeah, it is a very good point. Loads of good things that you made. Uh, one thing I just want to quickly piggyback on to what Richard said is only 0.05% of the people on this planet actually pay for AI platform. So basically that $20 for Chat GPT plus or for uh $20 on Claude. So you're right. So many people are not using this tool. There's a very, very small minority who are. And if if you're feeling a bit overwhelmed with everything that we're talking about and you're paying that $20 a month, you're ahead of a lot of people right now. So that's number one. Number two, there's a massive argument at the moment that not just brand, but your but your niche of your avatar that you appeal to is more important now than ever. When I wrote the book that's behind me, the book direct playbook, there's a chapter in there about focusing on on your niche. Like bury yourself so far down in a niche, there's not room for anybody else. And I was speaking with Gil from Crafted's Days, is as Richard mentioned, and Gil's going down this really big GEO, uh, which is obviously the AI version of SEO uh phenomena at the moment. He's obviously based out of San Francisco, near Silicon Valley. He knows the people at Google really well. He goes to all their meetings and he's going really in on this topic. And he actually said to me that at the moment, if you really want to appear on these large language model searches, so when someone puts on ChatGPT, plus best place to go on vacation in X or best management company to work with in Y, the thing that's really going to help you stand out is by really narrowing down on a niche. So the brand obviously plays into that, but the the the avatar, the ideal guest or the ideal homeowner that you want to be working with, or the guest that you want to appeal, that's now more important than ever. And it's easy to say, well, I appeal to families or I appeal to solo travelers or I appeal to whatever, but you've got to go like steps down now that that ladder of that niche. And the more that you can go down that rabbit hole of that niche, whatever you're gonna fall into, the more likelihood that you are going to appeal higher on these searches when people are putting it in. Because I don't know if you've you've done this, and I've definitely done this, but I haven't done a Google search in 2026. I don't know about the three of you. And now, if I want something, so for example, uh, I'm going to America this summer. I wanted a a new pair of uh sliders, I call them flip-flops, whatever, whatever you guys call them over America. And I went on to Perplexy, which is the tool that I use probably more than anything else. And I put in exactly what I was looking for, right? I didn't just put Sandals UK men. I just put in like the size, the style, what I wanted, what I didn't want. I went really down on that niche, and obviously something came up. And I feel like for vacation rentals, people are gonna be booking the same. I want to be going to uh Myrtle Beach on the on the 1st of September. It's got me, it's got my wife, it's got my four kids. I want to be somewhere close to the beach, not too far away. I don't want it to be a hotel room, I want it to be a vacation rental, it needs to have parking. These are the sort of things that people are gonna be asking. And this all comes around your avatar, your niche and who you're appealing to. So I think now more than ever, it's really important, yes, for brand, but B for your niche and for your avatar. And if you haven't done this exercise before, it's my one top tip for 2026 is to do that niche, do that exercise because it will massively help you for the rest of this year and moving forward as search, as AI becomes more impactful to these
The growing role of TikTok, creators, and social media in travel discovery
Mark Simpson
9 billion people, whatever Richard said, of people who are not properly using it yet because they they soon are when app. Gets caught up on this when Siri gets better, when Alexa gets better, and when people start using these search tools that Google give them now instead of doing the traditional old school SEO.
Annie Holcombe
I have a question, direct booking. I mean, obviously we, you know, that's we all try to like help people make sure that they're available for direct booking, but I was looking at something yesterday um related to TikTok booking. So like TikTok has the path now where you can do booking, but it goes through the OTA. So that's a challenge. But on that, I had lunch with a local um operator today, and they operate in a branded hotel/slash vacation rental resort. And so they are stuck dealing with brand standards that they have to deal with. But vacation rentals, the whole point of booking a vacation rental is the uniqueness of it. So, yes, while their standards you can, you know, you can assess to it because they have the hotel, the vacation rentals want this description. The challenge that this group is having is that their mandate from the brand, the higher up, the vast majority of the product is hotels. They're not let giving them the leeway to be able to be descriptive with their vacation rental product. So what would be your suggestion, somebody that's in a hybrid space? Because I feel like this is where vacation rentals are going to be able to surpass hotels in a lot of destinations because they're going to be able to tell a full story. But like this particular group, they can't really tell a story. So, like, what is a what is somebody that's operating in a hybrid space to do with this? Do you have any thoughts on that?
Mark Simpson
Like I say, it's these type of vacation rentals slash ex hotels that are being like converted, they're getting really, really popular in in the States at the moment. And I feel like again, the the hard thing for the person that you are talking to as well is that it's pro is owned by a brand. So they've obviously got these brand guidelines that they have to fit in. So they're sort of stuck between a rock and a hard place. So these people obviously they have to work alongside what the brand guidelines say that they have to do. But talking about social media, social media, TikTok in particular, is gonna make a massive play for this pie of online travel agency bookings, vacation rentals. And what this person you're talking to, this hotel hybrid owner can start doing, is basically working with people that are on TikTok, people that are content creators, and really starting to sell that story online, obviously still fitting within all of the things that they have to do. But one of the things that uh these large language models are going to start doing more and more and more, and they've started to do this. TikTokers, um, the sources that Gemini or the sources that chat or the sources that Claude get their sources from, TikTok has jumped up in where they get it from. I think it's jumped up by about a couple four or five percent. So if they can just get a ton of people to work with them, content creators, you know, whoever, influencers, whatever you want to talk about it, they get a ton of them to post content about the property, obviously fitting within the guidelines and obviously then talking about exactly what they want to be talking about, then that will actually help them with their visibility and how they how they show up on these large language searches as well. Plus, as well, when you work with a content creator, you are being exposed to their audience. Doesn't matter whether they've got a thousand followers or 10,000 followers, it all helps. And if you want to see an example of this in play at a larger scale, Virgin Cruises, I believe it was a couple of weeks ago, they put on a cruise and they filled it full of TikTokers, right? And they did this cruise somewhere in the Bahamas. And at the end of the cruise, they they compiled all of the reach that they had. It was in its, you know, eight, nine figures in reach. The amount of traffic going up to the website for Virgin Cruises went up 61% because of these TikTokers that they were working with. And it's it's just going to show that social is going to become probably one of our next biggest OTAs, and we just don't even realize it. And if you want to see somebody who talked about this really well, much better than I have just then, Ben Wolf on LinkedIn. He talks about this so eloquently and really, really well, and is definitely a good resource to be tapping in for that. So that's what I would do with um the person you're speaking to.
Alex Husner
We'll be back in just a minute. But first, a word from our premier brand sponsor.
Speaker 4
My name is Sally Lockard. I'm the head of sales and marketing at Hoseva. We have been working with my BookingPow since about 2019. Hosiva is a full-service property manager and software company.
Sponsor Spotlight: BookingPal
Speaker 4
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How Airbnb, Vrbo, Booking.com, and Expedia continue to shape guest behavior
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Alex Husner
Okay, so I'm gonna tie a couple things together there from the follow-up I had, but then also what Annie just asked kind of plays into it too, and your response, Mark. I mean, as far as brands go, and actually, Richard, you said this at the A debate that was live, that, you know, back in the early 2000s, there were, what did you say, like 42 e-commerce brands or something like that, or 200 e-commerce brands, which that still sounds small to this point, but now there are, you know, three or four, right? I mean, like when you're going to buy something, you're going to Amazon. Does there exist a world in which, I mean, when I will need something that I know Amazon has, I'm going to go to Amazon because I know I can get it very quickly. Going to ChatGPT is actually going to take a lot longer because it's going to deliver those results, but then I have to go look and decide if that's really what I want. So when you apply that thinking to vacation rentals, I feel like the ball is kind of in the court of the verbos and the OTA and the Airbnbs of the world. Because yes, you could go to Chat GPT and ask for the best vacation rental in 30A with the criteria that you want. But do you know that it's really pulling all the best listings, right? Because we know right now that most websites are not equipped to be able to do that. So what does the other side of this world look like? Is it brand focused or is it we just we're gonna go to one source instead of two or three or seven? Like, and Richard, I'll throw that one to you.
Richard Vaughton
Yeah, I I think I actually said there was something like uh 500 e-commerce businesses, then we ended up Okay, sorry, my not good with that. You must be wherever you were listening. So uh it was um we ended up with seven essentially, and we know them all Google, Facebook, Apple, and all the rest of them. And and that's the way that the world has transitioned over the last 30 years, it follows the investment in money. Airbnb has been successful, they had a really good business model and it had a huge amount of money pumped into it to to buy the business, and now it's uh it's guest-facing as opposed to supply facing. What you've just asked is a really, really complex question because up until now, what's happened is that uh bookings have been made down large OTA channels, and that was like 54%, I think it was, certainly UK-wide uh last year. I think it's gone up 10% uh uh over the last two years because they're spending a lot of money, they're getting more bigger brands, they're getting more dominant. One thing people never talk about is the app. If you've got an app on your phone, you've got a booking.com app, you use the booking.com app. They're not paying anything for search at that point in time, you're going directly to them. So the more apps they get on your phone, the more brands they get on your phone, the more traffic they're gonna get. Amazon is seamless. It's a product, it's not a service industry. 2015, Amazon were talking to one of us in our management company, saying they wanted to get into short-term rentals and accommodation. After about three hours discussion with them, they realized this would be a really, really bad idea that they even started thinking about getting into service, particularly in accommodation. Too many moving parts, bad reputation, not enough margin in it, that sort of stuff. I actually think we're gonna we're seeing something completely different. We're having a conversation around about websites. Okay. First of all, if you get traffic to your website, it's gonna have to convert. And that's why I think AI websites are going to be better. But this is a very small part of what's happening. I'd love to say that direct booking's not going to increase. And I'd like to say it's gonna happen for everybody. But as you know, I've scraped 28,000 websites recently. Pretty much 27,500 of them are absolutely dreadful and they're never gonna get a direct booking. They are PMS websites with poor templates, they're not popular, there's no SEO, they don't look trustworthy, they don't really care. Because all the bookings come from OTMs. So we're gonna have a handful, and uh like Marx customers, the people who actually invest really heavily in making their business worthwhile. The more effort you put in, the more likely you are to actually get direct bookings. But it is going to get harder, and it's gonna get harder because of these larger language models. Booking, Airbnb, VRBO, XP DR, everybody else pumped mountains of money into Google. Google is billions every year on advertising revenue from them. So just today, I don't know if you saw somebody posted that TripAdvisor lost 40 million um visitors last year in 2025 to its website. Why are they losing it? Well, they say they're losing it because of large language models and the way that everybody's moving to social media and everything else to actually generate interest. And that's happening in lots of places right now. So we have e-commerce now bolted into large language models. We have booking.com and Expedia already in the booking channel. I don't see that going away, I see that increasing. So if you're a manager with a hundred properties, you really should be working very, very hard at your brand. You should be spending an awful lot of time, and I completely agree with Mark here, you have to go niche, you have to go deep, and you have to focus on your properties as well. You know, if you're gonna go really, really deep, then you need consistency, you need properties that cover a single spectrum. You need to be the master of your own local territory. And I think the ones who do that well will still maintain, let's call it 50% of their bookings. I mean, I know some hundred percent, you know, people have got 70, 80 percent, but they work really, really hard at it. So it's gonna be a minority, and you can do it if you put the effort in. The really big companies, and as you know, we got three of them in the UK. We've got Sykes Travel Chapter, we got Waze, they've all got 20,000 properties apiece. They are micro OTAs, they actually command enormous traffic right now. So these very large companies have scale, they also use the OTAs to a degree, but they can game them better than anybody else. So we got the experts who are gonna do work really, really hard at brand direct booking. We've got massive companies, and in the States, you've got Casagon for Casa and these types of companies who can command much bigger direct bookings. And now we've got a we've got a real challenge with large language models coming in, all and TikTok and social media bolting in direct opportunity for bookings. And my biggest problem with these is who actually controls the biggest supplies with the biggest tech with the deepest pockets? Well, it's Airbnb and it's booking.com and it's Expedia, and they're just they're all they're doing is they're removing their affiliate programs because that's dead. They're removing their influencers. By the way, Mark, who would go on a cruise ship with hundreds and hundreds of TikTokers?
Annie Holcombe
Mark would.
Alex Husner
True.
Annie Holcombe
Probably Annie and I would, I don't know. I definitely would not, but I don't not a crazy.
Alex Husner
Can I ask one follow-up question to that? Because I think this is an important thing to touch on too. So as you were saying that, I just I went to Chat GPT and I said, uh, show me a three-bedroom condo in Myrtle Beach available June 5th to the 10th. And the options that I got, I got from Expedia, three different cards of actually their condo hotels, more actually hotels that showed up. Beyond that, below was four listings for actual condos, all from Virbo.
Why broad search terms are becoming harder for local operators to compete for
Alex Husner
Nothing else, no other vacation rental direct, like local companies showing up. So what do we need to do, Mark, as local vacation rental companies, to make sure that our sites are showing up in these results?
Mark Simpson
See, that is still a pretty, in my opinion, a vague LLM search. I feel like what's gonna happen more further down the line is that because the way that these models are going, they're gonna know everything about us, especially like the way that we give them more access to things. So I don't know about your what if you use Claude or chat, you can now do things where you can connect it up. So you can connect it up to your Gmail, so it's gonna know everything about you, it's gonna learn loads about you. So at the point where you will go, listen, I'm going to Myrtle Beach, it will already know about, you know, it's you know about my wife Laura, it'll know about my four kids, it'll know what I like, what I don't like, it'll know what car we drive, it'll we'll, you know, we'll be able to figure all of that out. It's just like we talk about SEO at the very start. With with SEO, if you want to try and rank well on a traditional Google search or Bing search, there's no chance you are ever going to become visible if someone puts in uh a condo for for for rent in in Myrtle Beach because Air Verbo, Expedia, Airbnb Booking.com, they've got so much money in deep pockets that they will make sure that either rank organically or B will will be there in the paid. And paid on Chat GPT is something that is coming, so paid ads, right? So I don't think that we can get involved in that, but we can a hundred percent get involved in that next level down as what I was talking about earlier about about the niche. So when people are searching for it and they're they're trying to go a bit deeper, uh you can appear on that search, you can get involved in that mix. And I know it is happening because we've seen it. We've seen it from the people that are coming onto our websites from LLMs. We know that people that are are talking about this in the in the Boostly community as well as other forums. And one thing about Chat GPT and Gemini and these and these large language models, I don't know if you've ever recognized it with your companies, if anybody's found you via these channels, or I've definitely noticed it at Boostly, for example. When somebody runs a search, let's just say, for example, uh website design for my short-term rentals, right? And they've they come to us from Chat GPT because they tell us when they book a call of us, they say, hey, I found you on ChatGPT. Because they trust these models more than a generic Google search, it is modern day influencer marketing, where they're pretty much sold because they've done all the research to that point with this Chat GPT, just chatting to it. And so when they book a call of us and they get on, they say, Listen, I know everything about you, you know, I know all the things that you've done, I know what you do, I've seen all everything because I chatted to Chat GPT. This call is literally a case of just, you know, making sure I get the best price. These are large language model searches at a modern-day influencer marketing. And if you can do it right, not focusing on the vague search, but get involved in the deeper down searches, again, focusing on your niche. I feel like there is an opportunity. It's not all doom and gloom for direct bookings. And I and I've and I've got a massive, massive faith in what we're talking about can still be a thing where we can we can still play a part and we can boost our own direct bookings if we do this right. But my worry is a lot of people are gonna just get lost, confused, overwhelmed, and just go, I'll just leave it on uh go ahead and get on airbnb and booking.com. So that's what we can do.
Annie Holcombe
I have a question. So I did I use Claude. That's who my Claudity is my guy. So I go to Claude, I typed in, just I said, um, you know, can you find me a three-bedroom condo, Panama City Beach, Florida on Ocean for July 1st through 6th? It gives me first four direct booking sites worth checking out. So it gave me some direct booking, and then it gave me two OTA searches after. And then it said, you know, quick tip, you need to make sure you check availability directly with these people because it's this is not real time. So I'm curious, are the different models working differently? Because, you know, she did it, Alex did hers on Chat GPT. I did mine on Claude. Claude gave me direct booking sites and OTAs, but put the direct booking sites first. So what do you I mean, what do you think caused that to happen?
Richard Vaughton
Uh I mean, I think it's gonna be one of those answers that no one's gonna really know unless you are these are the algorithms, but I want to pour a bit of cold water on this compensation. This is a reiteration of 25 years of American corporate dominance in technology and online travel. You know, in the year 2000, we all built websites and we all had direct bookings in like January 2005. We would get a thousand bookings in January direct, not one single OTA. We dominated search because we did all the things that actually Mark's been talking about. We were actually on our game and we did incredibly, incredibly well. It only took three or four years before that went down to 50% because we'd had the homeway roll up, we had all the big investments, we had all the VR BO owners direct, holiday lendings, all the acquisitions across the globe, and money was poured into rolling up and aggregating inventory. And you know, we landed at where we are right now with VOTA, you're talking about direct bookings, beginning to increasingly dominate the space. Don't think the large language models are not going to act the same way that Google did when they went everything, it's a level playing field. Then they introduced ads, Google ads. And then we had all the all the blue lines. And how long is it taking before you don't actually see any organic listings anymore because you've got all the sponsored ads and they got all the photographs of the sponsored ads? This has got to be the same. This has to be about making money for the large language models. But there's no point in them being in business unless they can milk us all.
Annie Holcombe
So yeah. I don't think anybody that doesn't think that already is is is missing it. But I I yeah. I mean, I think we all know it's all about it's all about the it's capitalism at the end of the day, you know. It's like everybody's gonna get their piece.
Richard Vaughton
That's what will win. And I think we have to come back to what Mark has been saying again, is is if you really want to be in control of your business, you really have to invest time and effort and money in it. And I can tell you, it's only gonna be 10% of the industry that are gonna actually make this difference to their own business, and then the 10% will have capital value at the end of their life when they've got too old and they want to sell their business. Right now, I remember buying four or five companies at the end of uh 2019 for an American company, and it was kind of really the first time I've witnessed a PL where they actually had two lines on it. One said marketing and the other said OTAs. Previous to that, they'd all put into the same pot. That was a marketing pot. But no, no, we have to split it out because we've had to uplift all the prices to the guests, and the price differential is one of the powerpoints in our favour, of course, because we've got direct opportunities. So big companies will win this game, but those who actually put the effort in on their brand, their niche, their SEO, their GEO, everything, their rebookings, their tech make beautiful. a full company.
Alex Husner
We'll be back in just a minute. But first, a word from our premier brand sponsor.
Speaker 6
My name is Eli Stoughton. I am the owner operator of Lahaina Studio. I have three vacation rentals in Lahaina, Maui, Hawaii, and I've been using Hospitable for over seven years now. I
Sponsor Spotlight: Hospitable
Speaker 6
would say I realized pretty early on in my hosting career that managing everything manually wasn't going to be sustainable over the long term. When I started using Hospitable, the primary tasks that I was able to automate were the automated messaging and the AI messaging where Hospitable will draft a response using my previous messages and my knowledge hub and everything that I've set up there. Oftentimes I find myself just getting a message from a guest, opening up Hospitable, seeing that they've already drafted a perfect reply for me and just hitting send. And it also saves me a lot of time when it comes to dynamic pricing. If I had to manage all of my pricing manually for multiple properties, that would take a long time to get that in sync. Hospitable has had a massive impact in how I run my business because I don't know if I would have scaled my business up over time had it not been for the fact that I had software that could help me do it. Having Hospitable save me a bunch of time per week, opens up a lot of possibilities and it also opens up more time for me to spend with my family and you can go on a trip and not have to worry about that your business is going to run into so many pitfalls because if everything is automated as much as possible, all you have to do is sort of oversee everything. My experience working with a hospitable team is great. They're very involved in the community forum that they've set up and you get direct responses from the founder and CEO or from the other team members. And I found that you don't often have that kind of level of communication from most companies. I highly recommend Hospitable to other hosts out there who are looking to grow their business, take their time back. I recommend that you drop in on one of the Hospitable town halls, that you join the hospitable community and see what this team and this company
Why brand trust still matters in an AI-driven search environment
Speaker 6
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Speaker
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Alex Husner
Things change and are changing faster day by day right now, but it's like you know some of those core tenants of just true good marketing still stand the test of time. And if you build a relationship with a company and you've had a good experience and you know that they have great selection, they're going to take care of you, you're going to go back to them. You know, I mean that but you have to make sure that people know that even if they booked an Airbnb and they found you somehow that they're going to get back to you for the next time. And I think that's really where a lot of brands struggle is they're they're not they're doing the first part. They're providing the great hospitality but they're not doing that next step of what the marketing actually is that's going to get those guests back into the funnel.
Richard Vaughton
Yeah and we always we never really differentiate between urban and vacation rentals. I mean I'd love to be always talking about vacation rentals there are so many urban companies and they are completely dominated by OTAs. It's many it's worth actually having a website website on many occasions for these things. You know whereas vacation rentals still has a really good chance you know if you put the effort in.
Alex Husner
Well and we had a a conversation very early on in the show and Mark this might have been an episode that you were on I think we had it a few few times but we talked about what is the difference between a vacation rental versus a short term rental. And Annie said a vacation rental can be a short term rental but it doesn't mean that a short term rental is a vacation rental. The people listening to this are like this is just a bunch of riddles you know but but that that's that's the truth. You know I mean it doesn't have to be a vacation rental short term rental could be uh an apartment in an urban area that people are not going there for vacation purposes. So uh the semantics and things and and really when you look back on it over the past five years, what we talked about and we used to have proudly our shirts we are not Airbnb. Like unfortunately that is what has happened. I mean like you know not that we are but I think the you know worldwide traveling base has just completely associated Airbnb and then Verbo underneath that as the main brands of where you go to to search this inventory. And there's
How PMS data, integrations, and distribution may evolve
Alex Husner
the trust factor and then there's the quantity of inventory that I don't want to go to one shoe store to search for my flip-flops like Mark I want to go to Amazon where I can see a lot of different options. So it's it's the same premise of e-commerce it's just it's hitting us in in different ways now.
Richard Vaughton
Mark can possibly answer this as well for all of you there are a lot of PMS companies out there and I think it's probably 30% of companies that actually use PMS in the United States all those crazy numbers but they actually hold they silo the property information that information goes to the OTAs we're now talking about MCP servers and UCP servers and mass distribution for everybody with an opportunity to create businesses for distribution and that can go into social media and everywhere I'm just curious whether and this will be a this will be a joy is for uh some institution to create a massive opportunity for all those properties within all the PMSs to actually uh seed the inventory at lower rates than the OTAs currently do. So to date they've reinvested all their money of course the OTAs and and seed it out for dividends but I just wonder if there is an opportunity in here through AI technology mass integration to actually see other types of businesses that will give opportunities to to direct bookers.
Alex Husner
That's my question for the evening well that's what we're doing with uh boostly connect we're working on it we've got the 27 integrations taking the data out of these PMSs putting it into a a much bigger idea so definitely one to check out boostlyconnect.com well I mean you think about it like Streamline has stream sharing and I kind of maybe similar to what you're talking about Richard that if you are a streamline user you can pull other streamline users' properties onto your website and I think that was uh very underutilized concept but do you mean to take all the inventory and find other places to have it bookable besides the OTAs as like a as yeah we shouldn't get into a discussion on this because I'm I'm I'm slightly cynical about uh combining inventories between managers and I've actually lived at I'm actually talking about Mark's pulling in inventory from PMS and he's aggregating it giving managers opportunities for booking other properties which which is fine.
Richard Vaughton
What I'm actually talking about is is being able to let's say I am a a coder let's say I'm an entrepreneur and I've got 10 million or 20 million and I say I want inventory from every PMS and I want it all to be going through one source. If all the PMS is put all the inventory into an MCP server for example which gave access to me as an entrepreneur to take all that inventory and then redistribute it myself in my own business model that is actually a challenge to the OTAs because you've got a new player in the game who's got access to all the inventory in real time with pricing and all the information I can tell you part of the problem with it I'm assuming Streamline would probably say well if you want to be in this channel we're going to charge you more money because that's the way they make their money but I just see I just see that there is an opportunity to collate lots of data outside of the OTA silos for it to feed its way into more distribution mechanisms that are not the ones we currently know. So it's a bit of blue sky thinking it's a bit foggy and I've been hoping for many things over the last 25 years and version none of them materialized.
Annie Holcombe
Well maybe this is the one that you'll get Richard. Yeah we're gonna have to have a second part of this because I don't know that we even scratch the surface on the amount of things that we could talk about. It's in almost every conversation I have with anybody whether it's a property manager or it's a tech company I mean I think everybody's trying to wrestle with it but I I did find it interesting of what you shared in the beginning about the the the lack of adoption and the lack of people actually using it is is quite astounding to me because I always felt like I was very contrarian about it in the beginning and kind of nervous and and now I'm you know using it every day. And so I feel like if I've adopted it it's surely there's got to be I have to be like the last the tail end of it. So maybe I'm a little farther advanced in things than I give myself credit for.
Richard Vaughton
Well Mark's got a channel that many many people are in uh a boost AI channel you know and there's a lot of contributions in that there's some really interesting stuff but it you know we've all been out there coding and creating and MVPs and trying to understand what's actually happening. But it it is that 0.001% of people actually do it. So we think it's normal it's not actually normal and I mean managers who actually
What vacation rental operators should be thinking about now as search changes
Richard Vaughton
go what's fine coding first of all and you know are you interested in AI? No I'm just interested to know how clean I can get my toilets on a staff today. Yeah there's a big gap between those two things.
Alex Husner
Well but your point is is spot on and I think hopefully for anybody listening to this makes them and all of us feel a little bit better that even if you're experimenting a little bit with Claude or ChatGPT or whichever model that you're using, you actually are further ahead than than you think. And I think the you know we're all part of a world where we're hearing this all the time. Not everybody is you know but it's like for all of us like we're hearing very high level people talking about this and it's very easy to feel like you're you're never doing enough and you're never going to be able to catch up to where people are but I think you know we're what there's going to be an evening out point and we're all in this together. It's like COVID hopefully a lot better on the other side. Well we will definitely have you guys come back. I think this is the part part one of could be multi-series that we yeah quarterly come back because in three four months from now everything could be completely different. But in the meantime if anybody wants to reach out to both of you gentlemen what's the best way to get in touch Mark start with you yeah LinkedIn uh on this topic would be really cool just go to LinkedIn and just type in Mark Simpson Boosley.
Mark Simpson
And if you want to be on Instagram uh findboosley UK and if you want like a deep dive of what Richard and I talked about in London just send me the word matrix and I'll literally send you all of the notes everything that we talked about everything that I spoke about on my other talks that week so I've got it all literally laid out in these cool little AI notebooks. So yeah just send me the word matrix on Instagram and I'll get all that to you.
Alex Husner
Okay I'm saying matrix right now because I asked you for that you said you had no notes.
Richard Vaughton
You put it together since you said it's you got you gotta you gotta give me this gotta give me some good at marking drive you to Instagram just send me the word matrix goodness gracious okay Richard yeah same as uh same as Mark just uh type in Richard on LinkedIn and hook up to me on LinkedIn I'm more than happy to talk to anybody about short-term rentals which my children find very sad or visit my uh my website uh yes.consulting where you'll find I write an awful lot in a sometimes cynical, hostile and um untenable way for some people but uh it's what I actually believe and think. And I'd like to say I've often been right and I've sometimes been wrong.
Alex Husner
Yeah I wish there was a way to pull old clubhouses from back in the day because I'm pretty sure I mean that's how Annie and I started connecting more that's actually how I first met both of uh you as well that I'm pretty sure there were some old clubhouses back in the day that we were all on but in the archives that this was a great great uh bringing back the band again type of episode. So thank you guys if anybody wants to get in touch with Annie and I you can go to alex and annie podcast dot com. And until the next debate thanks everyone








