AI Native Direct Booking Website Lessons From Building Hostaway’s Pro with Rick van der Plas

Summary and Highlights

👨‍💻 Meet Rick van der Plas

Rick leads product and engineering at Hostaway, one of the largest property management platforms in short term rentals. He joined a little over two years ago, during a period of hypergrowth, to help the company prepare for scale.

He doesn’t come from hospitality. His background is software engineering in SaaS and B2B, and he happily calls himself a nerd who loves figuring things out. That outside view is exactly what makes this episode valuable. Rick holds STR tech to the standard of mature software industries, and he believes our industry has set the bar too low. 📈

🔑 Key Takeaways

• 🧭 Direct booking is a marketing job, not a website project. OTAs earn their fees by bringing you people.
• 🧱 Rick’s three principles for Booking Website Pro: no developer needed, fully integrated with daily operations, and AI native from day one.
• 🔍 The best SEO audit is free. Search for your property the way your ideal guest would.
• ⚖️ AI visibility has two layers: static structure that machines can read, and dynamic relevance that earns citations.
• ⚡ Speed and mobile rendering decide conversion long before your copy gets a chance.
• 🛒 Capturing an email before a guest abandons checkout is one of the most welcomed Pro features.
• 🚀 An okay website today beats a perfect one three months from now.

🧭 Why Hostaway Doubled Down on Direct

Rick puts it simply. Hostaway customers want to hedge their bets. OTAs remain a major revenue source, but operators want more control over how they present themselves. They also want more repeat guests and a stronger position in the niche or region they serve.

At the same time, AI is reshaping how guests search. Rick says that journey is still changing every single day. That’s the same shift we covered with Kin Sio in our episode on how AI search visibility is rewriting the booking funnel.

Hostaway already had a basic booking website. Customer feedback revealed its limits. Many operators ended up putting their own site in front of the booking engine just to control their brand. Booking Website Pro was the answer. If you use Hostaway, you might also enjoy our Hostaway PMS guide.

🧱 Three Principles Behind an AI Native Direct Booking Website

Gil asked how Rick approached such a massive build. Rick named three principles his team will never compromise on.

1. You don’t need to be a developer. 👩‍💻 Operators want control without hiring someone or learning to code.

2. It must live inside your daily operations. 📅 A site that sits apart from your calendar and pricing creates more work, not less.

3. It must be AI native. 🤖 That means no AI bolted on later. For Rick, it means building alongside an embedded AI that handles the broad strokes, so you can iterate on content and positioning much faster. It also means being findable by the AI tools your guests already use.

Rick connects this to Hostaway’s AI CoHost. Because it understands your whole business, your website becomes one more signal it learns from. Gil shares how CraftedStays approached a similar challenge with Aria, which studies a portfolio before it builds anything.

🔍 Search for Yourself the Way Your Guest Would

This is the most practical moment of the episode, and it costs nothing to try.

Rick asks operators to picture their ideal guest. Imagine a surfer looking for a beach property near a local surf shop. 🏄 What would that person type? Which keywords would they use? Now search for your own property the same way. How many searches does it take to find you?

Rick says the honest answer is usually a hard no. Sites miss the right keywords, load slowly, break on certain pages, or lack the semantic formatting that search engines and AI need to read them.

If this exercise stings a little, start with our guide to niching down your SEO with Craig Webb. It pairs well with our ideal guest framework and our post on long tail SEO.

⚖️ Static Structure vs. Dynamic Relevance

Gil and Rick agree that data can overwhelm operators who don’t come from marketing. Agencies read Semrush and Ahrefs reports all day. Most property managers don’t.

Rick splits AI visibility into two parts. The static part is structure. Your markup must be clean so machines can read your site at all. You’d be surprised how many booking sites still fail here. Our breakdown of on site, off site, and technical SEO covers the basics.

The dynamic part is relevance. Rick suggests becoming the local authority on events and experiences near your properties. 📍 That’s how citations grow. Damian Sheridan made the same case in our episode on the bar guide that booked a 16 month stay. For a deeper framework, read our guide to generative engine optimization for vacation rentals.

Rick’s final tip here is simple: make one person accountable. Without an owner, content quietly fades.

🤖 Do You Still Need a Full Time Marketer?

Gil shares what he sees across CraftedStays. The operators with the strongest results either work with an agency or have a dedicated marketing person.

Rick offers a respectful counterpoint. That was more true before AI. Tasks that once filled a full time role can now move much faster with the right tools. The real question, he says, is whether direct booking is a genuine strategic focus for you. If it is, the time investment is now far smaller than it used to be. Michelle Marquis shared a helpful caution in her 30 years of direct booking fundamentals: adopt AI once you know what good output looks like.

🔗 Why Hostaway Built In House

Gil asks the obvious question. Why not use an existing website builder?

Rick’s answer is refreshingly honest. If every partner integrated as deeply as CraftedStays, Hostaway might not have needed to. But customers on WordPress and Wix kept asking how to connect everything, and the pieces never quite fit.

When a booking happens, it should update payments, calendars, and deposit schedules instantly. The guest handoff should feel just as seamless. Gil adds that redirecting guests between domains is where trust breaks. Amber Knight made the same point in our episode on why traffic alone won’t fill your calendar.

⚡ Speed, Mobile, and the Button You Shouldn’t Move

Here’s where the conversation gets fun. Operators sometimes ask Rick why they can’t move a button or change a color. His reply is data. In Hostaway’s A/B testing, one simple layout change like that could cost around 30% of bookings. 📉

Gil connects this to his time around Shopify, where some conversion critical elements are intentionally hard to change. When a platform learns from thousands of sites, every site improves over time.

Rick also runs a quick test when operators show him their sites at conferences. About one in ten doesn’t render properly on his phone. 📱 On speed, he shares a rule of thumb: every extra second of load time can cost you a big share of conversions. Our PEF mobile framework walks through what to check.

His promise to operators is memorable: “Let me be the nerd.” You focus on positioning. The platform handles the technical work.

🛒 Catching Guests Before They Leave

Among the most welcomed Pro features is cart recovery. When a guest starts booking and then walks away, capturing their email gives you a second chance. 💌

Gil notes that ecommerce has had this for nearly a decade through tools like Klaviyo and Shopify. Our industry is only now catching up. If guest data is your gap, start with our complete guide to collecting guest emails and our repeat bookings email strategy.

Rick also points to what comes next: campaigns, landing pages, and paid social. He stays a little cryptic about Hostaway’s roadmap, but he shares the vision of a Hostaway OS with a dedicated “sell” pillar. You’ll want to hear how he frames it.

🌱 An Industry Still in Its Early Days

Both guests agree on something that should encourage every host. STR tech is still young. Rick points out that the move from separate channel managers to unified PMS platforms had to happen first. Now the next layer of tools can finally arrive. Some operators still deal with double bookings and copy pasted photos, problems that modern platforms solved long ago.

For a look at how quickly tools are shifting, read what we’ve been building for AI search and our note on how quickly AI visibility can change.

⚡ Rapid Fire with Rick

📚 A book that shaped his life: A New Earth by Eckhart Tolle. Rick calls himself a rational, down to earth Dutch guy who isn’t into self help. Yet he has read this book about five times, and each read felt like a completely different book. His conclusion is a good one: the book never changed, he did.

🧠 Mindset advice for starting something new: Don’t listen to everyone. Be selective about whose opinions carry weight, because “there are a lot of coaches and not a lot of players.” Every “you can’t do that” became fuel for him.

🛠️ One thing to do this afternoon: Start. An okay website today beats a perfect one three months from now. Spend a few hours a week improving it. Gil adds that SEO and AI visibility take time to build, so every week you wait is a week behind. Get close to your guests, answer the questions they ask while planning, and turn those answers into content. Our guide to property descriptions that get recommended by AI is a great place to begin.

Rick sums it up with an investing analogy. The best dollar to invest was yesterday. The next best is today. 💡

🤝 Connect with Rick van der Plas

Rick describes himself as “not a very social media person,” but he welcomes connections and feedback.

• 💼 LinkedIn: Rick van der Plas
• 📧 Email: rick@hostaway.com (he reads everything eventually)
• 🌐 Hostaway: hostaway.com

🎧 Listen, Learn, and Build Direct

This recap only scratches the surface. The full episode includes Rick’s candid take on AI “slop,” the story behind the Hostaway promise, and the two builders’ views on where STR tech goes next. 🎙️ Press play and hear it straight from the builders.

If you want to keep learning alongside hosts who treat hospitality as a business, join our community of direct booking operators [add community link]. 🤝

When you’re ready for a site that loads fast, reads cleanly for AI, and syncs with your PMS, visit CraftedStays.co. CraftedStays helps serious hosts create guest first websites that convert. It’s also deeply integrated with Hostaway. Build your brand. Start booking direct. 🚀

Transcription

Rick: If you’re doing direct booking, you need to really also own that part. You need to be able to actually drive content. You need to drive actual people to come to your direct booking engine, and you also need to just be a marketer. And I think this is where AI engine optimization comes in as well, because that is not just a science where you say, “If you do these five things, you’re gonna be the top one in the LLM when somebody asks ChatGPT for a good property to stay.”

And I think this is where we’re trying to help our customers to really continuously analyze their website to say, “Okay, what can you do to rank higher, to really hit the right notes in a way that an LLM wants to get content?”

Gil: Before we bring on our guest, I want to talk just a little bit about something that I’ve been hearing a lot from hosts. I keep on hearing the same thing: “I know my website isn’t converting, but I can’t afford $8,000 on an agency to rebuild it.” Here’s the thing. You’re learning all these marketing strategies, you’re driving traffic, and you’re putting it all to work, but if your site isn’t really built to convert, you’re basically lighting your energy and money on fire.

And even if you could afford an agency build, every time you want to test something or make a change, you’re having to pay them again. You can’t iterate, you can’t test, and you really can’t improve on things. You don’t need a custom $10,000 website to get the conversion rates that really matter. You just need the right platform.

That’s why I built CraftedStays. It’s purpose-built for short-term rentals and designed from the ground up to help you drive more direct bookings. You can finally turn that traffic into bookings, you can keep on testing and improving as you learn, and you can make changes all on the platform. You don’t need to learn something new.

So if you need some help or you want to get started, go to craftedstays.co and start your free trial. Now, let’s bring on our guest and dive deep into hospitality and marketing.

Hey, folks. Welcome back to the Booked Solid Show, the show where we bring top operators to discuss hospitality, operations, and direct bookings.

On today’s show, I have Rick from Hostaway. He’s the Chief Technology Officer at Hostaway. Today, we walk through some of the investments that Hostaway has been making, specifically in the direct booking space, and how he thinks about supporting his customers in building direct booking websites that drive significant direct bookings.

We talk about some of the challenges that sites have with generic solutions and some of the things that he had to solve for. It was really good to deep dive with Rick and share notes on how to build high-performing marketing engines. So without further ado, let’s bring him on.

Gil: Rick, welcome to the show.

Rick: Thanks for having me. Great to be here.

Gil: I’m super excited to have you here. We’ve been working, in our own labs, on two separate things that are very overlapping, so I’m excited to have you here and to do a little bit of geeking out as well on some of the things that you’re doing. But to kick us off, Rick, you’re from Hostaway, and you’ve been working pretty deeply in the lab with the team on a lot of new features. There’s one in particular. I don’t even know if it’s called a feature. It’s pretty much a new product line altogether, or reimagining the product line altogether. I want you to dive deep into that. But before we kick off on that, do you mind introducing yourself?

Rick: Absolutely. Very nice to meet you, Gil. My name is Rick. I’m the Chief Technology Officer of Hostaway, which, as you say, means looking after all the nerdy parts and building, with our product teams, stuff that our customers love. My background is very much in software engineering. I actually don’t come from the STR space. I come much more from a SaaS, B2B background. But really, I would summarize myself more as a nerd. I like nerdy stuff. I like figuring things out and having good conversations with partners like yourselves.

Gil: And how long have you been running the engineering arm of the company?

Rick: I joined a little bit more than two years ago, especially during a phase of hypergrowth. Hostaway just skyrocketed overall in our customer base, the geos that we’re active in, the number of products that we’re launching. And Marcus and Saber, two of the co-founders, I think also realized at some point they just needed a professional nerd to help them deal with all this stuff.

So running a lot of our product teams and engineering teams, figuring out how we get ready for all this scale and deal with all this increased demand, has been my focus for the last two years. I’d like to think it hasn’t been going that badly. It’s a very rewarding job.

Gil: I see you guys come up quite often, so it’s been good seeing the growth there. You folks have raised several rounds of funding, even in the lifespan that you’ve been inside the company, and have been investing in many different things. If you think about the last two and a half years, you’ve invested heavily into AI. You’ve invested pretty heavily into maturing the platform overall. The marketplace has grown quite a bit. What I wanted to dive deeper into is the investment in direct. You folks have invested pretty heavily there, probably more so than a lot of other PMSs in the space. Maybe first off, what is it that you’ve focused on? Let’s start there.

Rick: Let’s start at the basics. I think there’s been a clear demand from our user base and our customer base that they want to hedge their bets a little bit more. OTAs are definitely a large source of revenue for large parts of our customer base. But they also want to sometimes be a little bit more in control. How do they present themselves? How can they drive more recurring bookings through their own channels? How can they position themselves for a specific niche, or regions that they really want to excel in?

I think that’s really been a driver for us to also look at what that looks like from a PMS perspective. How can we support our users by fulfilling those demands and building a product that can help them accomplish those goals? And that’s where, as you said, we’ve been investing a lot in AI. But AI is also changing a lot of the search journey for guests. The way that they find your property has evolved quite a bit, and is still evolving every single day across the STR space. So yeah, we’ve put a lot of effort into this for sure.

Gil: And right now you have almost two products there, with different levels of maturity depending on how much people want to invest in the direct side. Talk to me a little bit about the basic and the pro, and what you’ve been doing.

Rick: We’ve had our basic booking website product for quite some years. As the title suggests, it’s the more basic version of the two. It really helps people that just want to get started and want to get a booking engine live for their properties in the easiest way possible. It’s part of our core offering and has always been a part of Hostaway as a product.

But this is also where we realized, and I realized talking to a lot of customers, that it’s limiting to an extent. You cannot customize it to the level that you want. People often still ended up fronting their own website with our booking engine because they couldn’t change everything or control how they position themselves on the internet. That’s really where the need for our Booking Website Pro product evolved. That is a full what-you-see-is-what-you-get editor, allowing even non-technical people much more influence to build websites that really represent their brand and properties in the right way.

Gil: You mentioned a few things there, definitely Hostaway leveraging AI. I’ve seen some of the more recent announcements of how you’re thinking about AI percolating throughout the entire operations of an STR business, but also the shift in AI search. I definitely want to dive deeper into what led you down that path and what you’re seeing from what we call an AEO perspective.

You also mentioned the what-you-see-is-what-you-get interface. As you were thinking about building out the Pro product, what were some of the principles? Because this is a mammoth thing. We went through something similar. In the very beginning of our lifespan, we basically had form fields that you’d fill out and it would build your website. Over time, there were certain things we needed to change to make sure everyone had the comfort level to build their own website. So as you approached this new product build, how did you think about phasing it, and what were the core principles that were important to you?

Rick: That’s a really good question. There are a couple of things that we designed the product around. First of all, you don’t need to be a developer to build your website. That’s the first and most important principle of Booking Website Pro. We want it to be really accessible to people that want more control but don’t want to become an engineer or have to hire someone to do it for them.

The other principle was that it needs to be integrated into your day-to-day. It cannot be a standalone website that sits in isolation away from your day-to-day operations, your calendars, your pricing. It needs to be automated, it needs to be integrated, and it needs to be seamless. That’s the second principle we were enforcing.

The last principle, and this has been the principle we’ve been applying to the majority of our product launches in the last two years already, is that it needs to be AI native. It’s not something where we want AI bolt-ons after the fact. We really want it to be natively built on AI solutions that help you build faster, but also taking into account the AI world, like you say, with AEO and being able to be found through LLMs as well.

So those have really been the three critical things when we set out on the Booking Website Pro build journey. Those are the things we’re never going to deviate from.

Gil: Talk to me about AI native, because a lot of our listeners may not come from a technical background. To you, what does AI native mean, and how does that percolate into the website builder side of the world, but also some of the other features you’re thinking about?

Rick: Sure. When you say what-you-see-is-what-you-get editor, we’ve had these things since the ’90s almost. I can remember myself building what-you-see-is-what-you-get editors in the early 2000s that were seemingly easy, but you ended up still spending quite a lot of time to make it look exactly the way you want.

AI native for me, in this case, means a much more interactive way to work with an embedded LLM in our Booking Website Pro product, to build out those websites at a much more rapid pace than you would historically. Of course, you can always be precise and in control in the editor, but getting the broad strokes and iterating on content, images, and details on how you position your properties, with an AI sitting next to you to help you, is what I mean by AI native on the building front.

On the platform front in general, I’m not sure if you’ve seen this, but we announced our AI CoHost functionality just a couple of months ago. The adoption has been really, really good. There’s been very high activation, and there’s a huge number of requests from people who want to extend that capability. That’s what we’re working towards with Booking Website Pro as well. Booking Website Pro is another thing feeding into your day-to-day operations, which means our AI CoHost takes it into account as another signal for future opportunities to optimize your pricing strategy or your distribution strategy. So our AI CoHost is also helping you get the most out of your Booking Website Pro as well.

Gil: That’s interesting. It’s really tying the different products together and asking, okay, how can we take what could seemingly be independent product features and combine them to help the overall objective of that property manager?

Rick: Yeah, exactly. And the most important thing for me with AI CoHost specifically is that it’s context aware. It knows your business, it knows your properties, it knows all the ways you normally run your business, and it can learn from that and start giving you recommendations on how to improve. Booking Website Pro, as a channel in a way, is part of that. We have some cool things that we’re going to be announcing in the next couple of months about this as well.

Gil: Nice. It reminds me a little bit of our own journey at CraftedStays. We had to build Aria, and we knew that building out a website wasn’t necessarily just about making sure we had pretty pictures and that it looked really good. There’s a heavy component of understanding the portfolio before you put pen to paper. If you went to an agency to build out a website, the good ones at least would try to understand your portfolio, your market, your specific niche, and make sure they build a website that really tailors toward that niche, rather than taking a template and swapping your portfolio in for the placeholders.

I think this is really important in AI search specifically. I’d love to hear your perspective on this, but what we’ve been seeing is that the type of content, the way you write on your page, has a huge influence on whether or not you actually appear in AI search. I’m interested in hearing, Rick, whether you’ve done any studies or seen any data that points to why leaning on what makes your properties unique is a contributor to building really high-performing websites.

Rick: It’s a really good question, and a very multifaceted one. What is sometimes a slightly naive take, and I’m not sure if you see similar responses when you’re talking to CraftedStays customers who are just starting to figure out what they want to do for direct booking engines, is that just creating a direct booking engine is the recipe for success. Just create your website, make it beautiful, spend an evening fine-tuning it, and then lean back and wait for all the bookings to come in. That’s sometimes the perception of direct booking websites, and it couldn’t be farther from the truth.

The reason OTAs are able to charge large fees is because they bring you actual people. They do a lot of marketing. They get people into your funnel and get guests to book your property. But if you’re doing direct booking, you need to really own that part too. You need to be able to actually drive content. You need to drive actual people to your direct booking engine, and you also need to just be a marketer.

I think this is where AI engine optimization comes in as well, because that is not just a science where you say if you do these five things, you’re going to be the top one in the LLM when somebody asks ChatGPT for a good property to stay. This is where we’re trying to help our customers continuously analyze their website: okay, what can you do to rank higher, to really hit the right notes in the way an LLM wants to get content, and that therefore grades you on a certain scale to position you higher when somebody asks ChatGPT, for example, or Gemini on Google.

Gil: So what are some of the data points you find helpful to analyze there? What are some of the things you want to present to your property managers so they can optimize their websites?

Rick: I’m always asking our customers, “Can you imagine your ideal guest?” Act like your ideal guest. That can be a person that loves to surf, and you have a beautiful property at the beach with a nice beach shop nearby. Okay, what would that person actually do? They would probably start using beach or surfing keywords. They would probably use that shop next door as a starting point. Then actually try to find yourself. How many clicks, how many searches, how many keywords does it take you to find yourself? And if you actually find that website, do you feel it’s representative of the experience you’re trying to give your guests?

More often than not, the answer is a hard no. They can’t even find it. It doesn’t hit the right keywords. They struggle to find themselves in the first place. Or, if they’re on other products, what I’ve seen is things like speed issues, pages getting broken, or no semantic formatting applied. So even if all the content was there, the Googles or ChatGPTs of the world couldn’t find it.

Again, you don’t always have to overcomplicate it. This is a perception with booking engines as well. It feels like a very big, scary topic, but it isn’t that difficult. You just have to put yourself in the position of a guest trying to find you.

Gil: We’re going through several iterations of Aria. We’re trying to figure out how to present this type of data and how to help our users with it. We’re now thinking about bringing in external sources so they know which things they should be looking at. If you work with an agency, for instance, they’ll very much be using tools like Semrush, Yoast, and Ahrefs, scanning the web to see where you fall in search. Do you come up? Are you on the first page? The second page? In the AEO space, how many times are you cited? Do you have citations? We’re trying to bring those types of things back in so people know, “Oh, I made this change recently. Is it making an impact? Where am I?”

Are you thinking about it the same way, or differently? I think the challenge is not overwhelming people with too much data they don’t know how to read. An agency can read that stuff because they’ve been trained to. But a lot of property managers don’t come from a marketing background. So it’s a really fine balance.

Rick: It’s exactly that. It’s a fine balance. There’s what I call the static part of optimization: making sure your website is structured in the right way. Use something like Aria and CraftedStays to make sure the markup is correct so AIs can actually read your website in the first place, because you would be surprised how many booking websites still have issues with that.

Then the second part is much more the dynamic part, and that’s more about relevance. How do you not just try to hit every static keyword on your website, but remain relevant and get content going on your website that makes it interesting for LLMs to cite you, like you say? For example, one of the things we often try to figure out with our customers is: hey, are there local events? Are there specific things local to your neighborhood or region that people look for, where you can become a source or an authority on things that are very relevant to your type of properties? That’s also how you get those citations up.

And as you mature a little bit more… The first version is just doing it. Just start somewhere. Then, as you get a bit more mature, you start using tools like AEO scanners, citation trackers, or things like Semrush that keep track of how your website is actually performing.

The other thing I would say is make someone accountable for it, because it often ends up being just one more thing to take care of that doesn’t really happen. Then all the work you’ve put in just fades out over time if you don’t keep it up to date and keep that relevancy going up.

Gil: I think that’s a really good point. The property managers we’ve seen have the most success on our platform are ones that either work with an agency and farm that out, or have a marketing person. That person can be local or abroad, but they’re someone dedicated on the team who thinks about everything marketing: social media, email campaigns, the website, and how it all comes together. The challenge is when an operator is a jack of all trades, still building things up and juggling many different things. They may see successes here and there and build toward that, but it takes a little bit longer because they’re not putting in as much dedicated energy as someone whose nine-to-five is obsessing over the entire funnel and how the pieces fit together.

Rick: I think that is true, but I think it was more true in a pre-AI era than it is today. All those tasks you just described used to be full-time jobs. I’m not saying they’re not today, but a property manager can get a lot further with AI tools now, in a much shorter time frame than before. So I don’t think the default always needs to be hiring a full-time marketer. You can do that, and you’ll still get the expertise. They’ll probably know what to look for in fewer iterations than you. But the question you have to ask yourself as a property manager is: is direct booking an actual strategic focus for you or not? If it is, and you really want to be serious about driving more direct bookings, then you have to invest the time. And that time is a lot less than you needed before AI could help you there.

Gil: You mentioned something earlier about integrations and what you’ve seen prior to building Pro, and what the industry has been using quite a bit. We talked a little bit before the show about the prevalence of WordPress sites. I think WordPress is probably the better of the bunch, but you have people on Squarespace and Wix that feel very disconnected. What led you to make sure the site is really integrated?

Rick: Coming back to the design principles I mentioned before, we deliberately didn’t want to create the disjointed experience that a lot of our customers were already having by using WordPress, Wix, or Squarespace. We really wanted to make sure everything sits in one place. If Hostaway is your system of record, you really only want your content managed in one place. You don’t want to change it in three, four, five different places.

So when somebody books, it should tie directly to your payments. It should immediately update your calendar. It should automate things like payment schedules the way you’ve configured them, with specific deposits. That’s a really critical part of making this a much more valuable product for our users.

And then there’s the handoff to guests. As a PMS, we look at the full cycle. You guys are very much focused on getting people in to book, but we also tie that back to our guest portal. Once the guest has booked and is about to arrive at the property, maybe you need to collect some information, or you want an opportunity to do an upsell. The entire journey should be just as native as when they originally booked on your booking engine.

Gil: Why did you feel you needed to create this in-house? There are outside website builder platforms you could have leveraged that are quite established. GoDaddy, for instance, isn’t a website creator at heart. They’re a domain host, but they have website capabilities, and they didn’t build that in-house. They were able to take something off the shelf. Why did you decide to lay the bricks one at a time rather than leverage something that’s already out there?

Rick: It’s a really good question, and I would almost say that if everybody worked like CraftedStays, we probably wouldn’t have needed to. What I mean by that is the deep integration you’ve built with Hostaway is very seamless. It’s already hitting a lot of the notes I was mentioning before. But the reality is that that’s not the case when you’re using WordPress or a Wix website. We ended up getting a lot of questions from customers like, “How do I connect these things, and how do I make them work more natively?” They were trying to put a square peg in a round hole, and it never quite aligned.

That’s where we took a step back from a product perspective and asked how we can help our customers get a serious direct booking channel going without it becoming a distraction, where it’s just a real value add. That made us decide, okay, let’s build something that we think makes sense end to end.

Gil: Yeah.

Rick: And it’s quite difficult to own end to end if you don’t own the product.

Gil: Or, like for us, we work pretty intimately with our PMS partners. We’re really well integrated with Hostaway, probably more so than most of your other marketplace partners. We do checkouts. We pull and sync all the property information, bookings, rates, and availability, without using widgets. But it was a lot of work. I’m not going to lie. It was a ton of work. Not to say you don’t have good APIs, but if you think about all the different connections, every piece of the journey, how to make everything seamless, how to make sure it loads really fast, it was a mammoth amount of work.

So I’m not surprised you went down the path of not taking a generic website builder and trying to build on it. You’re right. You want to make sure that when you onboard a new property, you can easily add it to the page, and that any changes to that property reflect back on the website. Or that when you do the handoff from the property page to checkout, it feels native and you’re not redirecting someone from one domain to another. That’s where you start to lose people. You start to lose trust. You see the nav acting differently. That’s not the experience you want.

Quite honestly, I see that quite a bit on a lot of WordPress websites. You don’t have that continuity. I think that’s one of the challenges people face. They see WordPress being used ubiquitously across the board, but it’s quite a challenging platform because it was never built for ecommerce. It wasn’t built for that type of connection.

Rick: No. And this is another key thing we focus on: conversion optimization. We try to make sure that whatever lead arrives on your website has the highest chance of converting into an actual booking. That’s very difficult to do without any control, or when you outsource things. So that’s one of the other reasons we said, “Let’s make sure we’re able to control this, but still give hosts the flexibility they clearly want,” because that’s the feedback we got from our basic booking engine product. We’re trying to find the best of both worlds.

We want to give our customers as much flexibility as they want to represent themselves a certain way on the internet. But at the same time, there are specific parts of Booking Website Pro where we control the journey. That’s not because we don’t trust you or don’t want you to change it. It’s because we can optimize based on the tens of thousands of data points and websites we have running. We can keep optimizing which journey gets the highest conversion rate.

This is also the conversation I sometimes have with people who are just starting out with booking engines. They ask me, “Why is this button here? I want it on the left,” or “Why can’t I change the color of this specific thing?” And then I show them our data: “Look, we’ve tested this. We’ve A/B tested this across thousands and thousands of sessions. Moving the button from left to right is going to cost you about 30% in bookings. Do you still want that?” And they say, “Okay, no, probably not.”

But exactly as you say, a lot of people don’t see that hidden work. They start out building something on WordPress or Wix or whatever, and they end up doing exactly what you just described. They have to jump through a lot of hurdles to make it work and feel seamless to the guest.

Gil: That’s one of the biggest things I’ve learned and come to really appreciate. When you build on a platform, you’re able to make changes, test with a segment of your customers, try things out, and see how they positively or negatively impact conversion. When you see a positive change, you can flip the switch and enable it for all customers. It’s almost as if the website gets better and better over time. That’s really challenging on a static website builder that’s disconnected from your operations and from everybody else’s websites, because you don’t get to learn from that.

I learned a lot working with Shopify, seeing their internal operations and their team, how they think about page load times at checkout, the things they obsess over, what they load and don’t load, and what they test. A lot of work goes into those things, and it shows in the quality. That’s why Shopify is known for having some of the highest converting ecommerce websites out of the box. They’ve done a lot of iterative testing. They try different things, to the point where they won’t let you move that button from left to right. They just won’t. Yes, you can go back and manipulate the Liquid files and do some of that, but you have to very intentionally want to make those changes. They discourage it, for very good reasons, because they’ve learned what works and what doesn’t, and they want everybody on their platform to always get the best. I feel like both of our platforms, from a product perspective, have attacked it the same way.

Rick: Yeah. And this is what I talk to customers about when they come talk to me at conferences or events, or when they visit our user conference and aren’t using our booking engine. If we’re talking about this, I always ask them, “Hey, can I see it?” And about 10% of the time, it already doesn’t render the right way on my phone, because they built it for desktop only. They didn’t think about that, even though the majority of searches nowadays come from mobile phones.

The other thing you mentioned is really, really key, and that’s speed. It might not feel that slow if it takes three or four seconds to load, but that’s an insane drop-off. Don’t quote me on the numbers, but I think every second your website takes to load beyond one second, your conversion rate drops by about 30%. So every second you’re waiting, boom, it’s down 30%. Boom, it’s down another 30%. You’re making it very, very difficult for yourself to be successful with direct booking if you’re not relying on an engine that can deliver the speed people expect nowadays.

Gil: And you probably do the same thing: lazy loading, loading images progressively, those types of things. If you’re thinking about ecommerce and conversion funnels, you’re driving someone who may or may not have the intent. You may have gotten them to your website because they found you on social media. They’re interested, but their interest, like you mentioned, only lasts so long. If you caught their attention and don’t take advantage of it, and leave them with a bad experience because you thought loading another script would make things better, that’s a problem. You have to be very mindful of those types of things.

Rick: And coming back to our design principles for Booking Website Pro: I don’t want property managers to have to know what lazy loading means. I don’t want them to know what minifying images means. I want them to just focus on positioning themselves on the internet the right way, and I’ll take care of all the nerdy stuff. Let me be the nerd, and let my team be the nerds. We’ll take care of all the minifying and speeding up. You focus on how you want it to look, and we optimize it endlessly to get you the highest conversion rate.

Gil: Rick, you’ve rolled out Pro for a little while now. I forget how many months it’s been live. I think at least four or five months, if I remember correctly. I could be totally wrong. And you actually announced it back in November of last year, because I was at your user conference, Hostchella, last year. So you’ve been working on this for a while. What reactions have people had, and what successes have they seen?

Rick: That’s a really good question. People love that we now have the ability for much more personalization. We’re able to capture people’s email addresses and prevent the abandoned cart problem. Somebody starts booking, and in the middle of their booking they leave, or at least want to leave. Having the ability to grab an email or contact details from that person to recover that cart in the future has seen a lot of uptake from our users.

I’ve seen some really creative, beautiful designs. Some people have really poured their time and energy into it, and it’s clearly paying off with much higher conversion rates than their previous booking engine. Overall, the feeling of being constrained has been removed for a lot of our users. This is something many people have been asking for for years, and now they’re actually getting it and able to play with it. We also don’t charge for it if you want to play with it, so you can experiment with different variations until you go live. That’s been another well-received thing.

In the future, I think if you’re serious about direct booking, and coming back to the marketer part, you really need to run campaigns. You need to understand how to do Instagram advertising. How do you build landing pages? How do you use Facebook ads to your advantage? That’s still where I see a lot of opportunity. I know you didn’t ask for that, but my mind always goes to the next thing. How do we get to the next phase?

Gil: You’re one step ahead of me, because that was actually going to be my next question. Now that you’ve done this, what’s next for you folks? You just seeded it: it’s not just about the website and making it convert as high as possible. There are a lot of pieces that go into what we call the direct booking engine. You have social media, you might have ads, you have email marketing. Is that the direction you’re heading, providing people with a full suite? Or are you thinking about it differently, not providing the full suite but using integration partners? How are you thinking about the next wave of unlocking the potential here?

Rick: You’re putting me in a tough spot now, because you’re asking me for all the things we’re going to be building and thinking about.

Gil: That you’re comfortable disclosing, I’ll say that.

Rick: It’s clear that Booking Website Pro wasn’t something we built in isolation. It’s very clear that this is a stepping stone for us to add more and more functionality to help people get more direct bookings. There’s a lot of cool stuff in the pipeline that’s going to support that. I’m going to stay slightly cryptic. We have our user conference in Tampa this year in November. I’m not sure if there are still tickets, but if there are listeners who want to come and it’s sold out, send me an email at rick@hostaway.com. That’s when we generally announce what we’re going to focus on and the new products in the pipeline, which we did last year as well, like you said, for this product.

Gil: It was a huge announcement. There was a lot of buzz. I remember being there and seeing the unveiling, some of the things you’re thinking about, and screenshots of what it would be like. That was really exciting.

Rick: We always try to do this. That’s also why I don’t want to say “this is all the stuff we’re going to do,” because I could say whatever. One of the principles I work with alongside our product and engineering teams is that we don’t sell vaporware. Especially in the AI era, where a lot of AI slop is being produced, we don’t announce things until we can say, “This is really what’s going to work. This is the way it’s going to work. This is what it looks like. This is what you can expect from us.” This sounds very corny, like “the Hostaway promise.” I don’t want to call it that, but we don’t pitch things that we’re not really intending to build the way we’re sharing it with our customers or future customers.

Gil: But what I gather is that it’s not really stopping at the website side of things. The vision is really helping folks understand what their marketing engine looks like, and how Hostaway helps that user throughout the entire journey, not just, “Okay, now you have a pretty website.” That’s the sense I get.

Rick: Exactly. And I think—

Gil: You don’t have to acknowledge or deny that.

Rick: I’m going to plead the fifth. But referring back to my presentation at the time, which was very humbling to be honest, because it was great to see all the positive reception, you may remember that I talked about Hostaway OS. It’s an operating system to run your property management business from A to Z. One of the pillars in the OS is “sell.” We want to help you sell as much as possible. What you’re alluding to is quite in line with us deliberately investing in that pillar of tools to help you sell more, and more effectively. There’s definitely more in the pipeline on that front.

Gil: I’m excited. The PMS space is a very dynamic space, and I’ve seen so many PMSs take different angles on how they want to serve their customers and think about their product roadmap and philosophies. In contrast, I get to speak to folks on the hotel side, and hotel PMSs are much slower moving than on the STR side. Sorry to any of our hotel listeners, but I see phenomenal speed in terms of really helping mature the entire short-term rental industry. In many ways, people feel like we’ve matured as an industry, but I think we’re still very much in our infancy. There’s so much—

Rick: Sorry to jump in, but this is what I said at the beginning. I don’t come from the STR industry. I come from a SaaS, B2B background. And I think that maturity is a really important thing, because we have the bar as an industry still way too low. There’s still so much to gain to be on par with other SaaS verticals. We are nowhere near our full potential as an industry yet.

Gil: I say this all the time on this show. I come from ecommerce, and some of the stuff we even talked about here, minus the AI native stuff, like the WYSIWYG editors, all existed in the ecommerce space 15 years ago. Cart abandonment existed eight or nine years ago with Klaviyo and Shopify. So if you were a small operator in ecommerce, you had a pretty heavy toolbox to drive more sales. I feel like we’re now just scratching the surface and catching up. I don’t want to say tactics, but the tool set just hasn’t been there historically.

Rick: And I think there were also other problems to solve historically. The whole evolution from channel manager to PMS had to happen first, and I think that moved the needle quite substantially. It’s no longer that you find a channel manager separately, then connect it with a PMS, then make another choice about your booking engine. It’s a natural progression of the industry that had to happen first, and now we’re starting to hit the next level of unification, where things can be much more seamless than they were ten years ago in the STR industry.

Gil: That’s actually an interesting point. “Channel manager” isn’t a term anyone uses much in the industry anymore. It’s almost an archaic relic of what PMSs are today. There aren’t many property managers solely reliant on a channel manager for distribution, because there are other pieces like messaging and having a single source of truth on bookings. There’s a whole lot more you can automate once you start using a PMS. That’s actually a good reminder that we’ve evolved quite a bit.

Rick: Exactly. And this is still mind-boggling to me, to be honest, because I still hear from some customers coming from competing solutions. I’m not going to call them out, but let’s call them legacy solutions. They’re still talking about double bookings and copy-pasting images, and I’m like, this is a solved problem. It sounds like you’re really holding yourself back by not using a modern PMS, let alone an AI native PMS. I think there are still a lot of people living that reality today, Gil, and we’re probably in a bubble where we don’t even think about those people anymore.

Gil: I agree with you. Being in San Francisco, I definitely feel like I’m in a bubble sometimes.

Rick: San Francisco is definitely a bubble. You’re definitely in a bubble, Gil.

Gil: Awesome. Rick, we usually end the show with three questions. First question: what’s a book that has inspired your life or career?

Rick: Ooh, inspired my life or career. It’s going to be very different. It has nothing to do with nerdy stuff, and nothing to do with Hostaway. I think A New Earth by Eckhart Tolle. I’m honestly not really into life coach or philosophy type books. I’m really, really not. I’m quite a rational, down-to-earth Dutch guy. But I found that book interesting because I’ve read it several times in my life, maybe five times, and every time I read it, I read a completely different book.

The letters haven’t changed. The book stayed the same. So the common denominator is probably me, because I was the one reading the book five times, and I probably changed. It formed my views on things like ego, what the purpose in your life really is, what you’re trying to accomplish. It also answered some things for me, like, okay, that’s probably why I respond a certain way in certain situations. So it’s not a fun, nerdy answer, but it’s a book I find fascinating, because every time I read it, I read a completely different book.

Gil: That’s a deep answer. A very, very deep answer. I appreciate that.

Rick: A very honest Dutch guy, Gil.

Gil: Rick, second question. What’s one piece of mindset advice you would give to someone starting something completely new?

Rick: Don’t listen to anyone. I’ve been on both sides. I’ve been building companies since I was very young. I’ve launched startups. Some were pretty okay. Some failed miserably. It is very, very easy to get a lot of very wrong advice. There are going to be a billion people saying, “You have to do it like this,” and a lot of people saying, “You cannot do that.” Every time somebody told me in my career, “You can’t do that,” it lit a fire in me to prove them wrong, and I used that fire to build companies and get things off the ground.

You can take the average of all the answers you get around you, but be selective about whose opinions you put weight on. Because there are a lot of coaches and not a lot of players.

Gil: I like that. Rick, last question. What’s one tactical takeaway our listeners can put into practice, perhaps this afternoon, to either get started with direct bookings or amplify their direct bookings?

Rick: Really good question. The simple answer for me: if you’re really serious about getting some sort of direct booking channel going, it doesn’t need to be perfect. Starting with an okay-ish website today is already a lot better than no website three months from now because you’re trying to create the perfect art, image, logo, whatever. You probably learned a lot of this in your ecommerce days, Gil. Start somewhere, iterate, and test what works. Spending a couple of hours a week, or even a month, just making things better is already a thousand times better than putting it off because it feels like a huge, major project you have to get to at some point, sitting on your very long to-do list.

Gil: I think that’s even more important nowadays with the focus on organic. For anyone doing SEO optimization, or optimizing for the new AI search, AEO and GEO, those take time to get out there. If you wait until you have all the right pieces and you’ve done all the research, you’re going to be left behind. You’ll be starting from a later date, and things are changing so fast.

I would encourage our listeners, like you mentioned, Rick, to get really intimate with who your guests are. Why are they visiting your place? Why are they choosing you over someone else? Try to answer the questions they ask as they plan their stay. If you create content on just that alone, you’re far ahead of a lot of other folks. When someone searches on ChatGPT, Perplexity, or Google for those answers, and you’ve been intimate enough to answer those questions, you now have a front door leading them to your website.

But if you wait until you have the perfect website, you understand all the keywords, you understand how AEO works and all the mechanics, and only then get started, that’s way too late, especially now when everything is changing so darn fast. You may be optimizing for one thing and then something shifts. That’s not to say you shouldn’t optimize and keep iterating, but you need to get started. Start with something simple and really get intimate with your niche.

Rick: It’s similar to investing. The best dollar you could have invested was yesterday. The next best is today. I think the same goes for direct booking.

Gil: Absolutely. Rick, it’s been a huge pleasure having you on the show, and I can’t wait to see you in person at VRMA and geek out some more. It’s been great understanding why you approached this problem in the first place. You could have taken something off the shelf, but Hostaway decided to invest heavily in direct bookings because of what’s driving demand now: property managers wanting more control over distribution, and building their own brand and business, much more than just listing a property on the OTAs. And what led you to create some pretty mature systems to help property managers do that. I really appreciate you diving deep and helping us understand why you’re attacking it the way you are.

Rick: Thanks for having me, Gil. I really like working with you guys. CraftedStays is a great partner in our marketplace. I’m looking forward to seeing you at VRMA and seeing if we can learn something from CraftedStays as well.

Gil: It’s a very intimate space. There’s only a handful of us, and in many ways everybody knows a lot about each other. We’re all learning how to serve the market, but it’s not that big of a space.

Rick: It’s a pretty small world. It’s a pretty small bubble, and it’s changing heavily, especially with AI search. It’s still changing every day. I think a lot of companies are still figuring out how to deal with this.

Gil: Awesome, Rick. If folks want to keep in touch with you, where can they learn more about you? How can they follow you?

Rick: I’m honestly not a very social media person, but you’re very welcome to connect with me on LinkedIn. It’s a very Dutch name that you can probably see in the description: Rick van der Plas. That’s probably the best place to follow me. If you’re one of our customers and have any questions, or want to become a customer, I always love to hear feedback from CraftedStays customers and prospects, existing or future. My inbox is very simple: rick@hostaway.com. I’m not the fastest responder, but sooner or later I will always read everything.

Gil: Awesome. Thank you again, Rick, and until next time. See ya.

Rick: Thanks.