Winner of The Shortyz 2026 Best Travel Influencers of the Year
Oct. 6, 2026

Beyond Google: Winning the New Vacation Rental Search Journey, with Gil Chan of CraftedStays

The way travelers discover vacation rentals is changing.

Traditional Google search still matters, but discovery is increasingly expanding into tools like ChatGPT, Gemini, and Claude, where travelers can describe the kind of trip they want and receive recommendations based on that intent.

In this episode, Alex & Annie sit down with Gil Chan, Founder and CEO of CraftedStays, to explore what this shift means for vacation rental operators and the direct booking websites they have spent years building.

Gil shares how his experience as a property manager, combined with his background in e-commerce and product development, led him to build CraftedStays around a problem he saw firsthand: vacation rental websites often lack the infrastructure needed to support a seamless, measurable direct booking journey.

The conversation also dives into how AI search is changing website strategy, what CraftedStays has learned from its research into AI visibility, and why content, structured data, reviews, and strong local expertise may become even more important as the search journey evolves.

Episode Chapters:

05:39 - Why direct bookings are still complicated
06:56 - What vacation rental websites can learn from e-commerce
16:52 - Building a website platform that can evolve faster
18:55 - CraftedStays’ relationship with Google and the development of Aria
22:56 - From Google search to conversational travel discovery
28:34 - Reviews, structured data, and helping AI understand your business
32:07 - What CraftedStays learned from 24,000 AI search queries
36:53 - Using AI to create and optimize direct booking landing pages
48:13 - Where independent operators can compete with OTAs in AI search
50:12 - How to audit your visibility across AI search platforms
55:35 - Why there is no “page two” in AI search

Want to dig deeper into AI search?

CraftedStays has created a free AI Search Guide for vacation rental operators that breaks down what property managers should be paying attention to as search continues to evolve.

👉 Explore the guide: https://craftedstays.co/ai-search-for-vacation-rentals/

Connect with Gil:

LinkedIn: https://www.linkedin.com/in/thegilbertchan/

Learn more about CraftedStays:

Website: https://craftedstays.co/alexannie/

✨ Exclusive Offer to Alex & Annie Listeners:

Build a direct booking site designed to get found and convert with CraftedStays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/alexannie/

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/

Reach more direct-booking travelers with Savvy.

List your professionally managed properties for free.

👉 Get started here: https://savvy.com/list

#vacationrentals #shorttermrentals #directbookingwebsite

Send us a message!

05:39 - Why direct bookings are still complicated

06:56 - What vacation rental websites can learn from e-commerce

16:52 - Building a website platform that can evolve faster

18:55 - CraftedStays’ relationship with Google and the development of Aria

22:56 - From Google search to conversational travel discovery

28:34 - Reviews, structured data, and helping AI understand your business

32:07 - What CraftedStays learned from 24,000 AI search queries

36:53 - Using AI to create and optimize direct booking landing pages

48:13 - Where independent operators can compete with OTAs in AI search

50:12 - How to audit your visibility across AI search platforms

55:35 - Why there is no “page two” in AI search

Gil Chan

But we're now moving into this world of conversational search. We're now having conversations about how we want to go about our trip. These chat engines, whether or not that's Gemini, ChatGPT, Claude, they they all have so much information about us.

Annie Holcombe

It just feels like there's no rules of engagement for all of this.

Alex Husner

The rules are they're being written and we don't really have complete access to them, but we do have access to ask as many questions as possible to try and figure things out.

Gil Chan

I think the folks that figure it out are going to win. Because unlike traditional search, there's no page two.

Speaker

My name is Chris Petsy. Our company is called Seacoast 2 Summit Vacation Rentals. We manage over 100 listings. We've been working with Crafted Space for a little over two years now. When we were looking at our Google Analytics and seeing how little SEO value our URL actually had and how many keywords were not ranking at all, a lot of that has to do with content, but the website also has to be set up for conversion, and we were just we're not working with the site that made that possible. When we were looking for a new website provider, we were looking for somebody that understood the industry intimately, but also understood e-commerce and how SEO, AEO worked from the development side. So we weren't looking for a canned solution. We wanted very industry specific. And that's what we got with Crafted Stays. The experience that our guests get now with Crafted Stays on our website is much more fine-tuned and direct to what they actually want to see. The website allows them to get to where they want to go very quickly, but it also creates stickiness. And so that experience is helpful for brand recognition as well as seamlessness to booking an actual property. I think the Crafted Stays team understands what property managers actually need because they're owners themselves. They go through these same experiences that we do. And so they can speak to the industry. What we've seen with Craft Estays in the direct booking space year over year from this past month is a 40% increase in the number of direct bookings. That's a 300% increase in booking value, which I thought was really, really impressive. And there's lots of variables to that. But the credit has to go to craft estates because people, once they get to the site, need to have a seamless experience to book. And so those results, to me, speak really highly of the performance of the site and is a good indicator that's helping drive direct bookings, which is the whole point. I 100% recommend crafted stays to other folks in the industry. I talk about them all the time. They're one of the best parts of our business. It's the highest efficient use of your time to just have a site that's ready-made for vacation rental managers.

Alex Husner

Whether you manage 20 properties or 200, go to craftedstays.co slash Alex Annie to schedule a test drive. They'll connect your PMS and show you what your own properties could look like on the platform. This is a quick, no commitment call to show you what's possible. Now let's get back to the show. Welcome to Alex and Annie, the real woman of vacation rentals. I'm Alex and I'm Annie. And we are joined today by Gil Chan, who is the CEO and founder of Crafted Stays. Gil, so good to see you.

Gil Chan

It's so good to be here.

Annie Holcombe

I am so excited about this. I feel like I get to see a different side of Gil. We're in a group together that like talks business and stuff monthly. And so I've watched him kind of ruminate over ideas and all this stuff. But I think what's interesting is that we didn't know you until about two years ago. And a lot of people didn't know you, but you've been in the business for a while. So why don't you give people a little bit about your background and then kind of your journey to where you are today?

Gil Chan

Yeah. So I'm, I think first and foremost, I'm a property manager myself. We have a couple properties out in Tennessee and in Missouri. Uh, and we started kind of in the early kind of days of the pandemic when there was that big goal rush period there. And we ended up kind of getting into this space in direct bookings was mainly because we were heavily reliant on Airbnb. I think we're like 95% reliant on Airbnb at the time. We were hitting our metric, which is phenomenal. But just having all most of our business being run by the platform was just not a great place to be. And in my day job, I was in tech. Uh, I've been product director for the last 15 years, um, most predominantly six years in e-commerce. So that's where a lot of my background comes from. And when I wanted to kind of build our own direct booking website, we didn't have many different options. So we were trying to get out of that 95% Airbnb rate, and we were looking at different options. We either had what the PMS offered, or if we wanted anything better, we would have to go ahead and hire a bunch of developers and have them build us a WordPress website. To me, that felt a bit odd because it coming from the the e-commerce industry, if you wanted to build an e an an online store, you wouldn't go hire a bunch of developers and do that. You would sign up for a Shopify account, you'll add your products to it, and by the middle of the afternoons, you'll all have one of the highest converting websites out there. And there wasn't anything like that, or at least what we found in hospitality. So I ended up coding the first version of what Craft the Stays is today. It was terrible. Like it was nothing like what it is today. But I shared it around with a bunch of my mastermind peers, and they collectively convinced me to go all in. And I did. And I left my W-2, hired the best engineers I've had a chance to work with. And yeah, we've been helping property managers of kind of varying sizes. And the very beginning, three years back, we were helping smaller property managers, folks that had maybe a handful of doors, and now we're helping folks that have 20, 60, 100 plus properties. Right now we're talking to a property manager that has 650 doors and supporting their platform. So things have evolved quite a bit, and we've we've learned a ton along the

Why direct bookings are still complicated

Gil Chan

way.

Alex Husner

Yeah, it's such a good point how you to compare it to Shopify, because you're right. There's not just an easy way to spin up a website in this industry, and it is, it's a it's a long, lengthy process and expensive. And you know, there's some really great websites that are out there, but I think the industry, we've really complicated things to an extent that maybe they had to be that complicated out of necessity. I mean, the the APIs and the property management systems and everything else have made it difficult for property managers to be able to get their inventory out there, which leads to why the OTAs have been so successful for the ones that are not able to do that, you know, in a meaningful way. But when we first met you, it was actually at VR Nation in April of 2025. And we were walking around, we asked everybody what the biggest problem was in vacation rentals, and you said direct bookings. Immediately we thought, okay, you know, we we talk a lot about direct bookings on this show and and you know, the balance between that and OTAs. And that's always kind of been a thorough line of of our content on here. And we thought, okay, we need to learn more about what you do. But why do you think direct bookings is as complicated of a topic as it as it is? I mean, like for what you're building, you've built an easy website, everything else, but the rest of the whole direct booking flywheel is still very complicated for most property managers. Why do you

What vacation rental websites can learn from e-commerce

Alex Husner

think that is?

Gil Chan

I think part of it is that there's like there's a lack of underlying infrastructure that's to support it all. Uh, if you kind of look back in the last 10, 15 years and you look at even the biggest vacation rental websites out there, what are they built on? They're probably built on WordPress. Um, and if you're built on WordPress, if you want to get data in or out, or if you want to be able to connect to it, you're gonna have to use plugins. So nothing was natively ever built for this industry. I share this analogy quite a bit, but the e-commerce industry and the hospitality industry is actually not that different from a from a digital marketing perspective there. You have in our space in hospitality, you have the big OTAs, you have the Airbnb VRBOs, um, Airbnb kind of being the most predominant ones specifically in short-term rentals. But if you look at the e-commerce industry, you have Amazon. And Amazon that is that big mammoth that that it's the Goliath in in the space there. And about 15, 15, 17 years back, that's when kind of like Shopify started to kind of build their own thing. They were trying to help independent operators be able to create their own stores, and nothing like that ever existed before. And if you kind of like read back on Toby, the founder of Shopify, he started because he wanted to start his own e-commerce industry or business. And he wanted to build his own store and he had to figure out, oh, I had to do payments, I had to do tax, I have to be able to do checkout, I have to have a product catalog. And there wasn't anything. So he ended up building his own and then sharing it with others, which is quite synonymous to kind of what we're doing here. In rather than having Amazon, we have Airbnb as kind of the big Goliath there. And for us, we're trying to like figure out what that underlying infrastructure is, how should we be building? And I see that there's a lot of similarities, even then in how we do marketing today. Like today, for instance, we still can't do card abandonment really easily. I I don't understand why that is such a hard thing for hospitality to tackle. And a lot of it has to do with like, we just don't have the underlying infrastructure again to be able to support something like that. But if you look at e-commerce, if you can be a small brand with two people working out of a garage, and if someone left something in your car, you started a Shopify store, you can send them an email and saying, hey, you left something behind. Here's a coupon code for 5% off for you to use. But in hospitality, like unless you're a big brand, no one's doing that stuff.

Annie Holcombe

Do you think that that has to do with calendar syncing, though? Like I always feel like that whenever that has come up as a conversation, it's like, well, if it's sitting in the cart, then it's blocking a calendar and the calendar like PMSs don't function that way of like a hold. I mean, am I am I wrong?

Gil Chan

Or I had to think it has to do with a little bit more on like how do you make sure that your data is getting into the email service provider that you're using and making sure that checkout is thoroughly read because at least in the smaller property manager space, you'll have a lot of times where you may be having your website maybe on a WordPress site and then you're checking out on a very different surface. You might be checking out on a guesty website or the hostaway one. So you have a very disconnected system where your website doesn't talk to your checkout system, which makes conversion tracking really, really difficult. So if you're trying to do any sort of card abandonment, you need to know if someone actually abandoned the card. And if you if you don't do that, then it's really hard. So like we actually had to reverse engineer everything from the ground up where we try to use native checkouts as much as possible. So like every guesty user, even host away, we can even like have our own native checkout. And we integrate directly back into the PMS where we can support guesty pay, for instance, or if you're using Stripe, it goes all back in there. So your rules for 50% up front and 50% seven days prior to stay, that continues to hold true. But now you get Google Analytics built in, you know which traffic sources are going to your site, where they're dropping off. You can tell whether or not an influence is actually driving conversion and not just traffic there. Um, and then you can start to do fun stuff like card abandonment because you now have full funnel view on your entire pipeline.

Alex Husner

Yeah. And I think it's a super important topic of like, you know, that's the biggest trust signal of non-trust, I would say, when you're on a website and when you go to check out whether it's a vacation rental or something else you're buying, and now you're taken to a completely different domain and a site that looks totally different. Like, I don't buy anything when that happens. Like, you know, and I think consumers are, you know, they've become a lot more savvy to know this looks kind of sketchy. Like I you just sold me on one thing and now it looks like I'm dealing with a totally different company. And, you know, beyond the inability to track, which that's a huge part of it, but just the experience that somebody has, it just doesn't look professional, I don't think. Um, and it just it really puts up a red flag in in somebody's mind. But I also think, too, part of why card abandonment has been complicated is the PMSs, several of them kind of bid off more than they could chew, I would say, and like to try to be able to do that. And they have the best ability to because they have the most amount of data, as long as the website's talking back to them too. But in most cases, PMSs were not meant to be email marketing platforms and their capabilities to send emails that are effective and actually going to convert to get somebody to go back and and book that property. You know, it's you're very, very limited in terms of what you can actually do. And I was just working with a company that I did an audit of their whole direct booking strategy, and that was one of the things that we found was the email that gets sent from their PMS once they've left that page and didn't check out. It's you know, it's very bland. I mean, it shows the property name, this is the price, and then you click over, you would think you would be linking back to that property to book it. Nope, it just goes to their view all properties. So now you have to go and try and find it again. And it's like, you know, it's like you tried, but like that, that's not the it's not the effort, isn't what counts at the end of the day. It's the conversions. So I think there's a there's a mix of things there, but I I love that you guys have built something where it is a full ecosystem from start to finish. And do you offer those types of services as far as card abandonment abandonment? Because I know you kind of you do draw a line in the sand as far as some of the other digital marketing components that you try and stay more on website, but where does that one fall?

Gil Chan

Yeah, the way I see it is that like, yes, we do offer some services, but we pretty much try to focus and really be that domain expertise on kind of the website side of things, and more so lately on the AEO side as well, too. But we try to partner with the right folks on making sure that they have the connections. Whether or not that's another email service provider like MailChimp, Clavio, Go High Level. Um, there's a new one, Lasso, that we're working with as well too. Yeah, Orly. Um, but we're also working with like Switchback and the Sta Fi team as well too. So like these are the common kind of email service providers that we see on our industry, and we're looking at others as well too. But what we're trying not to do is like become like an email marketer ourselves. Like we don't have a team dedicated on that, but we want to make sure that the pipe is there so that if you're, for instance, working with a switchback team and they have a full campaign being built out for you, that everything's just gonna work seamlessly. Or if you have your own in-house marketing team or a CMO, perhaps, and you want if you're already already using GoHigh Level or MailChimp or Clavio, that you can be able to pipe all those things in there and focus on building out your campaign and not necessarily figuring out, oh, this person, did they actually abandon the card? How do I make the pop-up appear? How do I make sure that all the pages are being read properly, all that? Like we don't want our property managers or or the CMO teams that we're working with to have to worry about those things.

Annie Holcombe

I wanted to go back kind of say two years. So when we first met you, and I said this kind of loosely, you know, that you see it feels like you popped on the scene like out of nowhere, but I know you didn't. I mean, you were obviously working on stuff for a while. You said you were, you know, a host yourself, but you've grown tremendously and a lot of it has been word of mouth. And so, like looking back at the beginning, what were you hearing from property managers that helped you adapt and kind of make sure that you were tooling the right, the right system for people, the right answer for people? And what were property managers sharing about you that you think helped that growth?

Gil Chan

I think first off, like I come from a product background. So when I hear a problem, like my brain immediately wants to solve that problem and to kind of solve that there. And any good product managers out there, like if anyone's listening here that's a good product manager, they know that the best thing to do is get in front of your customers. So, one thing that I did was I actually did not hire a CSM person for the longest time. That was probably painful. Like I probably should have hired someone earlier. But that allowed me to interview every single one of our property managers. For the first 160 property managers that we worked with, I talked to them very first hand. I onboarded them, I helped them build their websites, I figured out what they need. And I'm still pretty hands-on myself to even to the state. I work with some of a lot of our clients on the onboarding, but also as we're thinking about new strategies at well, as well too. And I think that that allowed me to really create that kind of high quality bar there. I think we've done 892 product releases since September of last year. So over the last 12-month cycle, we've released a ton, a ton. And that's comes from just all the feedback that we hear from our customers there. So I think that that kind of led us to a lot of the successes uh led us to getting pretty good strong word of mouth just from our clients.

Alex Husner

Yeah, I mean, that's the best kind of advertising and marketing you can have. Happy clients uh share sharing their experience. So that's great. And you know, one thing that seems very different about what you've built is that it it seems like it's something that's truly built for the future, because this is something that you've built within the last few years versus a very long time ago. And it seems like there's more flexibility as far as where things can continue to go. That you mentioned in one of our calls that if you make a new functionality that somebody has requested that you feel like will benefit everybody, now that's available to everybody instead of them having to be charged if they also ask for it. It's just another rollout of something that that you're doing. And in that too, you've built a relationship with Google that now you're, you know, you're out in California, so you're close to them, but just being close doesn't exactly make that happen. So maybe share a little bit about like kind of your view from the development standpoint of like both the flexibility and then also like what does Google being kind of in your back pocket do for the future of what

Building a website platform that can evolve faster

Alex Husner

you're building?

Gil Chan

Yeah, I think I'll speak to kind of like the platform approach first. Um, there's kind of two ways to think about kind of building out your website. You can one build it on WordPress, it'll be very bespoke, very tailored to you. They may have some custom rules in there. And that's really good if you have a really customizable site that you want to build that has very unique things that you want to offer that no one might want to offer or might be different. But for the most part, a lot of the same flows happen. We want to make sure that our conversion funnel is buttery smooth. We want to make sure that our site loads really smoothly. We want to make sure that on mobile it has the right kind of native feel there. And all of those are universal. And the kind of the way that we take it is rather than building a uh a bespoke where you would have a developer create your WordPress website, we built it on an underlying infrastructure, an underlying platform there. So we have, we built our own templates or canvases, we built our own editor, our own um dashboards, all the front-end pages, everything has been built in-house. And so, like you mentioned, we may be working with a property manager that has like 200 doors. And we may do a test where we'll change the mobile navigation some sort of way. And we'll figure out like, does that actually change positively impact their conversion? Does it negatively impact their conversion? And if it has a positive impact, can we test that a few more times? And if it does hold true, then we'll roll out that change for everybody. And then on top of that, if we have a property manager that we're working with that has maybe custom things that they're looking for or things that are maybe unique, we can then roll that out for not just one property manager, but everybody all at once. So all of our email marketing tools, we were working specifically with property managers that have go high level, and we're trying to figure out how do we integrate this in for them. And when we rolled it out, everybody that was using Go High Level now gets to take advantage of it. So it just allows us to move a lot faster. We're not having to go back and say, oh, now guestia allows us to pull reviews or pull uh house rules. Now we have to go back and update everybody's WordPress instance. We don't have to necessarily worry about those things because we roll out changes altogether. I think that that's probably more important now because we've been seeing a lot of changes on

CraftedStays’ relationship with Google and the development of Aria

Gil Chan

AEO and GEO and the things that you need to optimize for and the how schemas are being marked up and how the what pay what things should be on the pages and how AI crawlers are visiting your website. So we're seeing a lot of those types of changes and we're learning about what's actually happening there. And so we're able to learn really quickly and roll those changes out for everybody all at once. So I think like speed is like our superpower now that was less relevant prior. And then kind of to your to your point, yes, we are part of the Google for startups program there. Um, so it's and uh quite honestly, that's a program that's available to a lot of different startups, but we've been using Google Cloud for the last 15 years. Me and my team have done multiple projects on it. I've known the Google team quite quite well. And we've been able to build a relationship where Google has invited us to their headquarters. We visit every quarter to Google headquarters out in San Francisco. It's it's and it's for us, it's it's it's a train rider way away. So we get to meet the team, we get to see what they're doing, we get to understand what they're investing into. They invited us to Google IO, the conference that was earlier this year, where they introduced UCP. But we get to talk about some of these things a little bit in advance of kind of what they're doing there. Um, they're not telling us things that are gonna be confidential, that's not gonna get out there eventually, but it gives us a slight edge a little bit. And we also use like the Google Gemini APIs as well, too. So earlier this year, we launched a product called ARIA. And ARIA is basically our AI persona. It's it allows you to kind of optimize your website. And that was built alongside Google. Um, so they really helped us figure out like how do we leverage the APIs, how do we make sure that we're doing things sufficiently, how do we make sure that we're getting the right type of outputs there? Um, and we're constantly learning and tweaking and kind of going back. So, like tomorrow morning I have a call with the Google team and we're gonna talk about some of the things that we're trying to do and how can how they can help us with it. But it's a relationship that we had to kind of build over the three years that we've been building the company. Yeah, it's really cool.

Annie Holcombe

It's definitely one worth bragging about. I think everybody wants to have like a front seat, a front seat with Google.

Alex Husner

Before we get back to today's episode, I want to share something that we believe matters for the future of this industry. Every property manager wants more direct bookings. You invest in your website, your brand, your guest experience, because owning that relationship matters. But travelers still need a trusted place to discover vacation rentals before they decide where to book. That's why Savvy exists. It's a direct booking marketplace built exclusively for professionally managed vacation rentals, and it's not just another OTA. When a traveler books through Savvy, you remain at the center of the relationship, so there's no platform standing between you and your guest. You communicate directly with the traveler, receive payment, set your terms and conditions, and nurture the ongoing relationship. Here's what really got our attention. Since launching in early 2025, Savvy's monthly booking growth has averaged nearly 40%. Travelers are finding this option and fast. We love what the team at Savvy is building for property managers and the direct booking movement. If you're looking for a distribution partner that's actually built for you, not around you, check out savvy at savvy.comslash Alexandra. Annie.

Annie Holcombe

So I have like one not serious question and then one serious question. So we were actually just uh talking to Jamie Lane um from Air DNA and we were talking about like a the future of everything. And I said that I feel like you know, maybe my my big prediction is that the one of these LLMs is going to become an OTA. And so we were joking about Google. And I was like, you know, Google has been trying to do Google vacation rentals for as long as I've been on the technology side of the space. So maybe this is finally like their golden ticket to make that happen. So, like, curious to think, hear what you think about that aspect of it. But just going back to Ari, I'd love to hear more about that because I know like I've just seen you talking about it and just there's so many things moving on the AI side of the of the world that it just feels like it's a I don't know, it's like drinking from a fire hose, just trying to get all the information to make sure that you're tapping into the right tool. But I feel like what you've done with it is you've given it a a persona, but you've given it something that people can tangibly understand what's happening with it.

From Google search to conversational travel discovery

Gil Chan

Yeah. So I'll I'll speak to kind of like the Google side first. Like I do think that, like, quite honestly, I think Google, Google Vacation Rentals was somewhat of a flop. A lot of us in the industry thought that Google Vacation Rentals, when it came out and when it was coming out, like, oh, this is gonna be amazing because like where do people start their searches? They're starting them on Google. And what do you look for? Like they have just a mass amount of data, and they also have the consumers that are going to them to be able to do this. But for whatever reason, I think a lot of it has to do with like the overall experience there. It wasn't really a good experience, both on the property management side and also on the guest side of things. It just didn't pan out. But we're now moving into this world of conversational search where we're now having conversations about how we want to go about our trip, these chat engines, whether or not that's Gemini, ChatGPT, Claude, they they all have so much information about us. And you also have all this infrastructure that Google has been building for so long, GVR, and now they're releasing UCP, which allows you to transact inside chat. Like those are like kind of the perfect recipe pieces to come together. It's still early to say kind of like where it lands, and hopefully Google does a better job than what they did with G VR. But I'm I'm so looking forward to kind of what they're investing into. And I'm a little bit sad a little uh about them kind of siding on the hotel side. Like if you look at what they've done, they are starting off on the hotel side of things. And I do think that like probably nine to 12 or nine to 18 months later, we're probably gonna see that on the short-term rental side. But keep an eye out on all the things that Google is doing on the hotel side because that's gonna give you a good indication of whether or not it's gonna land when it comes to us.

Alex Husner

Yeah. No, so Aria.

Gil Chan

Yeah. So Aria, I'll I'll speak to the persona first. So so Aria is actually named after my daughter's middle name. Um so uh, yeah, I I was trying to figure out something that's approachable, something fun. I wanted to give a name that people can can kind of refer to. And Aria kind of has two parts of it today. I guess like maybe going back to it, like why we even started doing ARIA in the first place. We were building these really beautiful sites that perform really well. But a lot of property managers were not optimizing their site for SEO. Like the headlines, they were, they just weren't great. They weren't creating the right type of pages, they didn't know what to create in there. Um, and again, these are probably for small, some some of our smaller property managers. Um, usually when we have like big marketing teams or we're working with an agency, they know what to do. But for everybody else that didn't have their own team or didn't come from a marketing background, they didn't really know what to do and know how to do it. So we created ARIA to kind of help address that problem or try to attack that problem. And it kind of breaks into two parts. We kind of think about it as like one, ARIA, we have our what we call the sight line report. It reads your entire portfolio, it reads all of your amenities, your descriptions, what markets are they in. It tries to understand like what does your portfolio look like, where are they located, and then it reads all your reviews. It reads and tries to figure out what's the overall sentiment, what are people saying about it, what they love about it, who are they visiting, why are they visiting? And then it goes out and does third-party research. It it tries to look online and figures out what are people searching for specifically in your market? And then it gives you kind of a preliminary result of what it found. And then it gets your reaction on like, how do you want to position yourself? What does your brand look like? Uh, what do you see as your differentiator? Where do you see yourself going? And it uses all four of those pieces of information and tries to figure out like what does your positioning strategy look like? How should you position yourself? And if you're working with an agency, very likely your agency probably is doing something that is far more sophisticated on that. Um, but it gives you a base to start off with if you don't already have that strategy part in place. And we think of that as almost like the brain of things because what we didn't want to do is like create a website that was disconnected from your portfolio, from the business side you're operating. And then we started creating ARIA, the website editor. So now you can take all that information and you can say, ARIA, help me build a landing page for our large family gatherings. And it knows where your properties are, what the value prop is, what people are searching for, what key terms to put into the headlines, and it will build out your page for you. Uh, you can have it create an about us page if you don't already have one created, but it starts to be able to build those pieces piece by piece for you. And we're learning a ton. We've only released it for about two months now. Um and we're seeing how people use it, we're seeing what other tools that they want to use it with, and we're we're thinking already, we're actually planning our next like two versions of ARIA because we just we we've done a lot of like AI research on like what makes your website citable by these chat engines, and we're trying to now bake that into the next rev of ARIA.

Alex Husner

I love that. And actually, uh, when we were just talking to Jamie Lane earlier too, I've got another thing to mention from that conversation that's applicable here. We were talking about, you know, like what the focus needs to be for companies if they're trying to show up in the LLMs and how Annie and I have done searches where she gets the local property management company direct website and I for the same destination and I get the Airbnb or Verbo or Expedia links for the same properties and why that happens. And, you know, generally speaking, I think there's a lot of foundational parts of SEO that are still applicable for the LLMs. But I mean, one of them is the reviews, and and the reviews, and from how I've looked at it, is more that's like reviews of the company. But are you saying that the reviews on the individual properties could end up helping the property manager's direct website, not that listing, surface in the results too? Or is it just looking at the Google or Trustpilot or like, you know, any of like the generic review sites that are business

Reviews, structured data, and helping AI understand your business

Alex Husner

like that?

Gil Chan

So when when we pull reviews and we have them kind of associated to the property manager, we pull them on a property-by-property basis. And what we're trying to do is we're trying to help all these AI engines kind of build that entity graph there. So a little bit of kind of like backstory there is that when the kind of the difference between LLMs and traditional SEO is that LLMs try to understand like what is your entity and in in this case or vacation rentals, and and they're trying to figure out what properties are in there, what the reviews are, what local knowledge it is. So it's trying to basically shape like what is this organization about and what's their domain expertise in and how reputable it is. So it's trying to understand like this overall profile of things. So the better that we can structure this data for it to be able to pull all that information, that's kind of why structured data is so important in the world of LLMs, the better that they are able to kind of reference and cite you. If you don't have much information, if it's not easily readable, it's hard for anyone to be able to recommend you.

Alex Husner

Yeah. As far as the reviews of the brand, though, like how important is it to still have an effort spent on getting company-wide reviews versus really just focusing on the properties?

Gil Chan

I think both of them both of them are important because they're they're scouring the entire web and it's fluctuating quite honestly. Um, different LM providers look at these sources very differently. So, for instance, like we you might have read that ChatGPT and Reddit kind of cut ties recently, where ChatGPT historically has looked at Reddit posts as one of the most cited sources. So people that were investing into having good reputation on Reddit did really, really well a month back. And now, like we're now seeing in kind of like the middle of August, things start to shift where all that reputation goes to waste. So it might be different. Like if you look on, and that might be why Alex and Annie, like you might be getting different sources because if you're one using Chat GPT, one's using Perplexy or Claude, like you might get very different results. But also, these chat engines know a lot about you. It knows your preferences, it knows your memory, all those things. So it knows what's important to you versus the other person out there. So we're starting to get to this world where you one, you're getting more personalized results, but two, from a property management point of view, you're able to reach customers that quite honestly it might have been hard to reach prior to this, which is very interesting. It's a very fun puzzle to kind of like tune and test and try to figure out like how do we help more and more property managers appear in those searches?

Annie Holcombe

A lot of hosts specifically, and the one the groups I work with, like smaller hosts, they were again all in on Reddit. Like absolutely six months ago, that was like Reddit, Reddit, Reddit, Reddit, you gotta be there. And I got in there and I was like, oh my gosh, this is like being in like a middle of a high school lunchroom. It was just so noisy. Um, but the they're they're all in on like Instagram or TikTok. And so they're not necessarily paying attention, you know. I I always find it like just mind-numbing that you ask someone for their website and they'll send you their link to Airbnb or their link to the RBO and they're like, there's my website, and it's like, oh my God, that's not a website. Like, and and then and then they'll follow it up with, oh yeah, I'm buying keywords to send to that listing. And you're like, okay, what first of all, who told you that was a good idea? But going back to the social side of it, if someone is all in on social, and you know, maybe they do have a booking site and but they haven't really built that content out, like, is there a way to harness what's in their social to the LLMs? And are the LLMs all searching social equally? Like, I that's what just confuses me. It just feels like there's no like uh rules of engagement for all of

What CraftedStays learned from 24,000 AI search queries

Annie Holcombe

this.

Gil Chan

Yeah. And quite honestly, it's it's it's very, very confusing. And like uh unless you live into this day in, day out, and you obsess over these types of things, like it's it's rather hard. And I think that more challenging part is like it's one thing to understand what's the current state, but how things are moving and what and where it's going, it's even it makes it so much more hard, like harder because it's so volatile there. And I think that that's one of the challenges that a lot of property managers have today. I think one of the fundamental things that we found, if you kind of were to like boil down to like things that I should be wasting my energy towards, like the thing that I should be obsessing towards now that are unlikely to change, is more also on like the traditional SEO side of things, the content side of things, the things that you own. That is one of the things that we found through all of our research. I think we did a research where we did 24,000 queries across four different chat engines to try to figure out which properties managers got cited. And then we went onto their page and figured out what do they have, what content do they have on their page, and how do we help our property managers kind of recreate that for themselves. And so we found that there's a lot of misinformation out there, even information that I thought were true were end up not being true. But the one thing that held up was the property managers that had really rich content that was specifically towards their niche did the best. It's not saying that you want to build an infinite amount of pages. You don't need a hundred different landing pages. On average, the top performers had about 34 landing pages, either on the types of stays or things to do around the area, things that people will search for when they're planning their trip specifically for their niche.

Annie Holcombe

That makes sense. And I think I was gonna say my husband has built websites. I'm like Alex's husband, same way, like build websites. And that was always something that he would tell people on is like always have pages for the various types of like, you know, stay that somebody's gonna experience so that, and I think not knowing that any of this was coming 15, you know, 10, 15 years ago when he was building things like that, but it was just really important to just kind of cover all your bases. And so I think that that makes good sense.

Alex Husner

Yeah. I mean, it's it's the it goes back to the fundamentals, some of those things, you know. I mean, building out in the Myrtle Beach area, Myrtle Beach is a broad name for actually 60 miles that you have North Myrtle Beach, you have Myrtle Beach, you have Garden City, Surfside, Lichfield, Polly's Island, and they're each their own beach community. And it's like if you have properties that are across the entire area, you need pages for each of those different actual towns or communities. And then within those communities, there could also be smaller pockets of beach areas, which it's like it just gets super confusing anybody listening to it. But if you live here and you do business here, you know there's a difference between each area and each different community and the the condo resorts, you know, or the different plantations or whatever groups of accommodations it is and in these various destinations. Like there are reasons that people are seeking that out specifically. And you can't expect that one page that just has all your properties on it is going to rank for that. I mean, you have to build content around it. But I think the other part of the content side is the way that I always have looked at it is okay, we're going to build these pages, but then now we have so much more that we can actually do with them from a marketing perspective. That if we're sending out an email and we know that this is to people that have stayed in Crescent Shores or if they've stayed in Litchfield, now we've got content that speaks to those accommodations specifically that they don't have to go search from. But then also, you know, some of the higher level content of like the best things to do in those areas, the newest attractions for this year, or the best restaurants, or you know, any any of those listical type pieces of content do really well. And I think they're for sure still favored in the LLMs. So it's like, don't go away from doing some of those fundamental marketing activities because it's going to help you not only with the LLMs, but I'll help you just have content to be utilizing when you're thinking about your social posts for the week or your email blasts. Like there, there's still a lot of value in having those. And I think as it relates to you, Gil, one thing that I've seen as an issue is companies will buy a website and they're kind of told that they can easily spin up those types of pages on their own once the site is turned over to them and come to find out that's not necessarily the case. And sometimes that's because it's a PMS thing, sometimes it's a website thing. But ultimately, if you have an idea in your head that you want to do a page that's about like the best girlfriend getaways and you want to be able to pull easily content about the restaurants, the places to stay, you know, the best bars, whatever it is, you want to be able to do that without spending a week figuring out how you actually do it. So within your system, how does that look? Like if if you want to build these one-off pages, is that something that can be done pretty easily, or is it also kind of more of a you got to commit to a big project kind of thing?

Using AI to create and optimize direct booking landing pages

Gil Chan

No, it's actually rat rather, rather easy. And we're we're probably gonna make it even easier at the end of this year. So Aria already kind of knows your portfolio and knows kind of which target market you are, and then you feed it information. Like if that is a persona, if girlfriend stays are kind of like your your niche there, you can actually define that in in our platform when we ask you questions on who your ideal guest profile is. And when you want to create different pages, you can actually talk with Aria and you can let them know like, I'm trying to create a page for this, I'm trying to track these types of people. What type of information should I put in there? And it can also create the collections for you. It can create the like the right sets of properties that are in those areas and can kind of like then help you build out that page without having to like surgically kind of like back in the day, drag and drop like your hero image, your your um your value prop, basically building a piece by piece. You're now having kind of AI kind of help you with this. It's not to say like you don't want to go back in there and actually make those manual edits yourself to make it sound really authentic to your brand and fix anything and replace those images that we might generate for you, because we do generate placeholder images for you by kind of default there. Um so we do integrate into Gemini Nano Banana, for instance. Um, but that's more kind of like to help you understand like how the page should look, how it should be structured, and really give you a North Star to go from. And then you can make any changes. And then down the road, we're already kind of testing this out with a few of our customers. I don't know how many of our listeners here are like avid, like claude users, and they're using a thing called MCP that allows you to connect your claud into other systems. Um, so we built an MCP that allows Claude to actually go into your website and make changes for you straight from within your cloud. So if your cloud already knows an immense amount of information about your business, you can then tell it to create your website for you or the whatever landing pages, and it's then able to talk to ARIA and make those changes for you. And then you can kind of go back and kind of refine things. Um, but we're constantly thinking about like where things are headed, how do marketers want to kind of manage their entire website? And it's not just about pretty pages, it's like it's really making sure that it's hitting the targets that you guys are looking for. And we're constantly thinking about how to make that easier and easier.

Annie Holcombe

Talk to me about um PMS integrations, because I think that that's always something that stumps people kind of back to earlier, like, you know, stuff's in the PMS and stuff's on the website, but like how is it all interacting with the, you know, the the checkout and and all these things? And I think I I talk to a lot of people that they just assume, well, probably they were told by their PMS salesperson that everything is seamless from once it's in your PMS, it can go to everybody without a problem and you don't have to do anything. And that's like I don't know of the that being the case anywhere. But how how do your integrations work with the PMSs? And you know, I think to your earlier point about having to do updates and not having to update like just across multiple connections. How do you factor on that? Because I feel like the the PMSs are all trying to, it's like an arms race with the AI to who can do the most, the best, the quickest. How are you keeping up with that in in terms of what how you operate for one of your customers?

Gil Chan

Yeah, so we don't have a huge library of PMS integrations, and that's very much intentional. Um, there's no way that we can maintain the kind of like the level of quality that we want to hit with a library of 20 different PMSs. So right now we support five PMSs, we're adding a few more. So we support guesty, hostaway, hostfully owner res, and hospitable. And we're adding streamline, hopefully track. Um, and then we're also getting pulled into kind of the hotel space with Muse and CloudBeds as well, too. So we're expanding our PMS integrations, but we go really, really deep. Where in the very beginning days, and kind of when we were starting off, we were using a lot of widgets. So we were using kind of the widgets that the PMS would typically kind of provide you to be able to fetch rates and all that. But we found that the widgets didn't perform that well. It didn't look the same. It looked very bifurcated from the rest of your website. It didn't carry the same fonts. You can't track and know, like, oh, did someone search for these particular dates? You can't actually optimize the funnel. So we ended up getting rid of that. We did a very deep integration where all that's on our side. So if someone's doing a quote, we have an API integration on that, we maintain that all ourselves. And we have logging. So if something fails, we know about it and we'll fix it. So if one customer is having an issue where one of the PMS is changes, kind of their API response, then we'll make that, we'll fix it and then we'll make that change for everybody. So we're trying to make it as seamless as possible so that your integration is very, very reliable. Very much the same way as like a PMS would integrate with an OTA. You want to make sure that's super reliable because that is ultimately a channel source there. Whenever you do a PMS integration, we pull property details, amenities, the rates, availabilities, photos, even the captions that you might have on your PMS, because we use those for alt text for accessibility reasons, yeah, reviews as well too. So we try to pull as much information as possible from the PMS. And then we also have our own kind of data on top of that that may not be on the PMS. Um, so maybe you might want to have specific house rules or FAQs, for instance. PMSs don't have property-specific FAQs in a structure format. And with AEO now, that makes it much more important. Um, so we now have the ability to add FAQs on a property-by-property basis, for instance. So we take a lot of information from the PMS, but we also augment it with our own as well, too.

Alex Husner

Yeah, it makes sense. 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 vacational 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. 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. You guys have been, I don't know if it's launched already, but you were telling us about it when we talked a couple months ago, doing the natural language language search too. So if somebody comes on and says that they're looking for a condo in this destination for X amount of people and they have to have this amenity, they can just, just like they're talking to Chat GPT, they can do that on your site. Has that been ruled out for any of your clients yet?

Gil Chan

Yeah, so we've been running like small little spreadsheets. Test on that. So we actually filed a patent for this back in November of 25 there. And then we run several tests and we'll kind of go back and go work with the Gemini team to see kind of how we can refine it. Because what we don't want to do is degrade the experience. We want to make sure that it performs better than the traditional searches. And we found that in some cases it's not giving the best answers as much as possible. So we're constantly going back and tuning it. And we've been rolling out several times kind of throughout the year with different clients and see how do we make sure that it's overall generally available for everybody. But yeah, if that's if that's something that anyone like listening here that's interested in, we're definitely open to kind of doing a pilot there and seeing kind of how it performs and how it helps with conversion because ultimately that's what it's meant to do. The way that we kind of approached it was rather than having your traditional search where you have a drop-down, your dates, and then the number of guests that may be staying with you, you could use natural language. So you can say, I want to go to the mountains with our two young kids and their grandparents. We need something that's ADA accessible and we want to be within 15 minutes from the national park. And it'll go through the entire portfolio and figure out which properties kind of match that criteria the most. And then we'll then prioritize which properties meet that criteria the best. And then rather than showing the kind of the normal descriptions that we would normally have on Airbnb, that's 500 characters, we will uh surface a change tagline based on what their search intent is. If they mention that some they need something that's ADA accessible and within 15 minutes of the national park, we should be putting that in the description when we're serving them back up those results in there. So that's that's the one kind of big thing that we did different than than other folks that may be kind of approaching kind of natural language search, um, and then carrying that through into the property page of not just showing all the different attractions nearby, but how do we surface and prioritize attractions that that specific person may want to go? So if you're traveling with kids, perhaps we should be recommending the petting zoo nearby. Or if you're traveling with young as a couple, maybe the Ryan Wander. It changes quite a bit on what we want surfacing. Um, so we're playing with different things. Uh, and I'm excited to kind of roll that out kind of more generally, um, and just learning about like how people search, what they're searching for. What we don't want to do is someone searches for something and it doesn't get with them what they want. So we have a pretty high bar that we want to make sure that we meet.

Alex Husner

Yes.

Gil Chan

Yeah.

Alex Husner

Yeah, that's that's the hard part. And I think like, you know, it'll be interesting to see when searches like that become more prevalent on websites, like what that actually does for conversion rate, especially within our industry. I mean, you know, 1% is kind of like a goal, you know, sadly, but it's like, you know, you don't see a whole lot of sites that are that convert over 1% if they've got a lot of traffic coming in that they're doing the things that we're talking about as far as building content that's not the commercial directly, you know, point A to point B to book a vacation rental, but it's content that's making people aware of the brand. But because of that, your your conversion rate will go down because you're going to reach a lot more people that they're looking for something else. But to be able to measure this from when somebody types that in on the home page to when they land on search results, now they open up a unit page and then they move to the booking page. And since everything's across the board as far as your platform staying on that same domain, it'll be interesting to track that and see if that really becomes as much of a thing as people, you know, are saying that it could. And you know, I think about myself personally, like I use chat and Claude to ask questions that I'm more for sure just talking in like natural language. But to this point, when I'm going to book a vacation, and I do know the dates, like I'm I'm still used to just putting in the fields that I need to put in. But then it's like I'm doing that, but then I'm also got I have one of the LLMs open on another monitor. So I'm like, well, if it was like for Italy, the Indian I went to last year, if I have more questions, I found some hotels on the one OTA, but now I'm like, well, what's the best one for and describing, you know, who I am, who we are, why we're going there. And you know, I think it's the the sweet spot is a hybrid between the two. And I and I'm sure the OTAs are gonna be following suit in this. But I mean, like, what's kind of your predictions of like where where they will go? Like, do you think that they're also gonna follow this path of it being more natural language search?

Gil Chan

Yeah, I do think that like they are gonna try, like try to. I think OTAs have a has has a disadvantage because they're they're reaching a very wide market, they're trying to create content across a very entire, like big market. And so one of the searches that we found is in our AI research is that the OTAs perform phenomenally well. If you were to go in chat and say, I'm looking for a place that has X, Y, or Z, where there's at least three different amenity constraints there. This is where OTAs win. When you start having less than two, that's where the individual independent operators win. So, like in terms of like word of advice for anyone that's creating any type of content there, I would focus much more my attention towards area stay or guest type stays that are constricted only by two minute to two different amenity types there. So, like if you if one of the things is like hot tubs, like like don't try to make it hot tubs with a pool, with a golf course. Like that's the OTA is gonna win that type of search, like left and right. But if you're talking about your, like, for instance, your your previous example of your girlfriend stays, like those are ones that independent operators will will kill it in. Um, and it will continue to because Airbnb just doesn't have the content machine to be able to produce those things of quality and of uniqueness. Uh, when LLMs does a search, it looks at uniqueness as one of those things that it wants the site one over the other. If one has better content, more tailored for that type of stay or that type of search, they're more likely to surface that one. So that's like one of the kind of like the fundamental things. Like, yes, I do think that OTAs are gonna try to be more aggressive in kind of that AI search and natural language stuff, but we independent operators have a huge advantage over it.

Annie Holcombe

Yeah. So I was I was gonna ask that. So, you know, an operator who's got their website and they think like, oh, yeah, everything's working great, I'm happy with it. Like, what do you think are maybe three or four fundamental things that they need to take a look at and focus on for you? Probably, I don't know, I say the short run because I feel like it's gonna six months from now, it'll be obsolete. But what do you think they should focus on

How to audit your visibility across AI search platforms

Annie Holcombe

right now?

Gil Chan

I would do an audit. Go look at yourself, go go do a search. And not, I'm not talking about like a branded search. Don't do a branded search. Do one without your name being cited. Open a new window. If you need to create a different cloud or ChatGPT account to play around with that doesn't have your memory in there or or just have an incognito type, do a search on what your guests will be searching for. If they're going to your place or your area, what are they searching for? Do you even come up anywhere at all? And I would start there. Are you coming up for the terms that you want to come up with? And if you are, your job is to hold that position. It's not to create an endless amount of new content there, but stay abreast of like what's happening in the industry. Don't try, don't try to keep on building more and more content. Um, just really try to figure out like how do you make sure that you strengthen that. Um, I see like one example, for instance, is like there's this concept of backlinks. And that was really, really important in the SEO days of oh, this is how Google knows that you are a reputable business, and this is what Google will cite. It's different in LLMs. Actually, we found that the top property managers that got cited had less backlinks than those that did. And that was so surprised. Um, and so if you did, you could go out there and buy, you can buy backlinks, and that would hurt you more than help you. So I don't know.

Annie Holcombe

So, do people need to remove backlinks then now?

Gil Chan

You could you should remove toxic ones for sure.

Annie Holcombe

I'm not saying that's an interesting thing. Like you said, they focused on that because I know that was something that Pat, my husband always talked about was like backlinks are what gets you that traction. So, like now, how do you know they're toxic?

Gil Chan

Like what well you said audit, but I mean Yeah, that there are tools like SEMrush, Yoast, Href, like uh any big marketing team will have this. And if you have an SEO team or an agency that you're working with, they'll have these types of tools. We're going to we're going to be able to be baking these things into ARIA so that we have a more of a clear list of what you should be paying attention to. And it's going to be ever evolving. Like we're still in its very infancy days there. But all to say is like, I don't want people to figure out like, go out and go download this Claude scale and try these different things out and try to do do more and more and more. If you're actually in a good position, continue to do that and monitor it over time. And pay attention if things start to drop, then figure out what's happened, what changed in the industry and do a little bit of homework on that. But I wouldn't stress out too much if you're already doing quite well. If you're not doing it, then try to figure out what are your competitors doing, what types of pages are being presented. You'll find that the ones I get cited, they probably have like area guides or these guest type pages. They typically have 13 different sections on those types of landing pages. So they're very, very deep pages. They go very deep. And so you can then start to figure out, okay, do I need to create one of these for my specific persona type that I'm trying to attract in there? And start to learn specifically like what will help there. But this is always changing. It's I think that's one thing I'm concerned about for our industry is that there's just so much to learn. And it's so hard to keep track of all these changes.

Alex Husner

It is. And at the same time, though, the cool thing is like if you're trying to figure out why your company doesn't show up for some something in the LLMs, once it gives you the results of what you do get back, you can ask it why didn't XYZ management company make the list? And it'll tell you. I mean, it'll say sometimes it'll point to a better business bureau review or something that, like, if it was a review site that you don't really pay attention to a whole lot, that there's only one review, but it's a negative one. And, you know, that can be the one thing that's dragging you down. But that's that's kind of the nice thing is like the rules are they're being written and we don't really have complete access to them, but we do have access to ask as many questions as possible to try and figure things out. That with SEO, that wasn't really the case. I mean, like it's this is transparency, but in a new era, I would say, as far as what we're able to see as marketers. And it's it's kind of cool. And it's changing, it's changing every day. And that's like the point on Reddit is huge. I have a um technology company that I was working with that that was a big part of our strategy. And then it was like all of a sudden, that's not the strategy anymore. You know, the rug is literally pulled out from underneath you, but it's uh it's tough.

Gil Chan

Yeah, and I would just say try to learn and just be hungry about learning about these types of things. Like you'll find that if you're trying to optimize for perplexity and Gemini, they they typically do more web searches. So if you made a change recently, you're more likely to see that change actually result in traffic. But if you're optimizing for Claude, for instance, you're probably not gonna see a change for six months because Claude changes it it cites a lot from its trick training models. And the training models are often six months plus behind there. So you could be investing in the right thing and not know it for a little while there, uh, where other LLMs will give you more immediate feedback. Um so I would just advise kind of the listeners here just to get just arm yourself with knowledge and just follow the right sources and just just be hungry to learn these things because I bet two years from now it's gonna be a very different space. And I think the folks that figure it out are going to win because unlike traditional search, there's no page two. There's there's no there's there's nowhere else.

Alex Husner

Um

Alex Husner

I did see today though on Chat GPT, I did see it pop up. It said um advertise with chat GPT, pushing me to like buy ads. So I was like, hold and it like it went away quickly because I was doing something fast, but um, but that it's gotta be coming. I mean, there's no way the chat gt is.

Annie Holcombe

Yeah, there's a pilot, there's a pilot. I know some people that are in a pilot for it.

Alex Husner

And that'll be the really interesting thing to see because it's like if the LLMs are supposed to be delivering the most relevant content based on you and your searches, then how do they balance that with paid? You know, I mean, I I don't know how you how you do that. I mean, like that's if it's it's the OTA coming. That's what I that's what I'm saying. Right. The OTs will pay.

Gil Chan

They will definitely pay.

Alex Husner

Yeah, it's gonna be fascinating, Gil, but we're excited to have you in our orbit now, a little bit more closer than we had in the past. And and you're you were spot on when you said a couple years ago the biggest problem or one of the biggest problems is direct bookings. That has not changed, it's still an issue, but we're excited to just kind of dive in more of this year with you and see what you guys are building and track it along the way and and you know, just hopefully keep everybody that is interested in this as part of these conversations because no one has time to be researching all of this every day like you do. I mean, that's your job, but property managers don't have time to do that. So we're we're relying on you to bring back all the information that we need to know. No pressure.

Gil Chan

So I write a lot on LinkedIn. Um, and I read a lot. I I read a lot as well, too. I appreciate it. Um, and I try to synthesize that down. So we run a quarterly kind of AI search overview because things are changing and maybe I might have to run it more often. And so if you go on to craftistays.co and go to the resources tab, there's two different links on there. One is a kind of like a research link, it's which is like more raw data. And then the other one is a landing page that has six, at least right now, six different articles on things that we found. The things that we talked about about backlinks, uh, what smaller operators that have less competition in smaller, less less competitive areas should be optimizing for. Um, the types of content that you should be having on your page. Do LMTXTs and JSLM LD and all those technical stuff that all those acronyms that you see thrown around, are they all important there? So we're trying to like distill it down because honestly, like I need to distill it down for myself because I'm like I'm consuming so much and I'm trying to like figure out like what are the fundamentals that I need to advise our customers on because ultimately I want our customers to be successful. Um, so if like you're trying to get like a snapshot in time of like what's happening out there and what I should be optimizing for, that's probably the best resource that I can provide to anyone that's listening.

Alex Husner

Okay, that's great to know. And we will see you at VRMA this fall for sure.

Gil Chan

Yes. Yep.

Alex Husner

Okay. Did you have any sessions or anything?

Gil Chan

I do. I actually have a session with my peer in the group, uh Mark Simpson. Uh we have a a panel together uh with John as well. I'll have also a booth as well.

Alex Husner

Oh, good. Yeah, that'll be a good one. That's good crowd right there.

unknown

Anyway.

Annie Holcombe

Well, Alex and I will be there. Alex and I will be there for the podcast, so we'll be sure to stop by and or have you come by to our booth and and see us there. There'll be a podcast booth set up. So definitely get some more talking for you. Yeah. Well, Gil, thank you so much for coming. I I know we're gonna have you back, and I feel like when we get you back the next time, we're gonna talk through all this stuff again and it's all gonna change. So just just we're gonna need a running update. Prepared for the roller coaster.

Gil Chan

And hopefully next time I'm I'm prepared to kind of give some some strong guidance on on where what we're finding out. Um, there's just so much volatility right now that we're like, I feel like we're all breathing or drinking from a fire hose right now. Um, but there are some really, really fundamental things that I think folks should start to paying attention to and some of the things that they should not be paying attention to already. But hopefully next time we talk, we'll have much greater clarity and um some guidance there too.

Alex Husner

Yeah, that's awesome, Gil. We're excited to continue the conversation. If anybody wants to get uh more information about you and the websites, maybe how your team can help them, then go to craftedstays.co. And if anybody wants to get in touch with Annie and I, as always, you can go to alexandanniepodcast.com. And until next time, thanks everybody.

Gil Chan Profile Photo

Founder, CraftedStays

Gil Chan is the founder of CraftedStays, a direct booking platform for short-term rental operators focused on conversion and discovery through AEO and GEO.

He spent 15 years as a product manager at six Silicon Valley startups, including about six years in e-commerce. He worked with brands like Gap, Sephora, Nordstrom, and The Home Depot, and on e-commerce platforms including Shopify, BigCommerce, Squarespace, and Wix. He saw the gap between the two industries. E-commerce had sophisticated platforms that let brands launch high-converting stores in days, plus tools to find and target customers. Hospitality was still running on bespoke WordPress sites. He started CraftedStays to bring the same infrastructure to the vacation rental industry.

Gil is also a property manager with rentals in Tennessee and Missouri. He is a coauthor of Hospitable Hosts: Couples Edition, was named a 2026 Truvisionary by Truvi, and hosts the Booked Solid Show podcast.