How Successful Hosts Know Their Ideal Guest with Gil Chan

What if the secret to more bookings isn't just more traffic, but better targeting? In this episode, we're diving into why successful hosts have one thing in common. They know their guests inside and out. Stay tuned to discover how understanding your ideal guest can transform your marketing, increase your conversion rates, and make every booking a seamless fit.

You are listening to the Direct Booking Success Podcast, bringing you all the information you need for your short term rental to stand o aut from the crowd. I'm your host, Jenn Boyles. As an owner and manager myself, I know how hard it can be to navigate the hospitality industry. I'm here to help so you too can have direct booking success.

Hello and welcome to another episode of the Direct Booking Success Podcast. I'm Jenn Boyles, your host. Thank you for including this episode into your day. Today I have Gil Chan with me now. Gil is a short term rental host with several properties in the Great Smoky Mountains in the Branson area. He manages his properties with his wife, and he's also the founder of Crafted Stays, a hospitality tech company. And we'll get to that later on, but first I want to hear more about how he got into hosting. So welcome. Gil. Lovely to see you.

Yeah, it's great to be here, Jenn.

So let's start at the beginning. How did you get started with short term rentals?

Yeah, so I was in tech for a long while and being in Silicon Valley, we were trying to figure out how to offset our W2 income. We were paying a lot in taxes, and I made the mistake of thinking, oh, you can buy real estate and offset your taxes. That's it. That's what we heard. But it isn't true, at least not in America. You have to participate in the business in order to be able to offset or take depreciation on it, and we end up really stumbling upon short term rentals that way. I later found out that a couple of my closest friends were short term rental hosts themselves as well too. So they were actually able to help me really get, like, acquainted with how to get in short term rentals. And there's a lot of different parts to it. You're running and starting a business from the ground up and no one getting into it thinks that it's going to be that big or that you have to learn so many different parts of it. So we have to learn a whole bunch. And ironically, like, it started off as an investment and it turned into a passion. And we're now at a point where everything around us revolves around short term rentals. And it's like my W2 or my business now is all short term rentals. We own a couple properties now. We love being hosts. And I think the investment side is like one very small part of it. But overall, the hospitality industry has been amazing for us.

Wonderful. How did you start with your bookings? Was it Airbnb that kind of got you into your first bookings for short term rentals?

Yeah. Yeah. For like many folks here, Airbnb is a blessing for anyone starting a short term rental business. There's no other industry, or very few other industries where you can buy an asset, put it in service, and start getting revenues from it. There's very little out there like that, and especially that's so successful. You can try Amazon, you can try E Commerce, but none of them are as successful as a short term rental. So, like myself, everybody else getting into it, Airbnb was really helping us grow our revenues for the first year. And probably more importantly, it helped us grow our customer base for the first year. And that's when we figured out that we needed to do something else. We needed to invest into our own bookings. And that's where we kind of stumbled on, on direct bookings.

So what was it that made you go, ah, there's something I should be doing here? More than relying on Airbnb, what was it that made you turn to your own direct bookings?

Yeah, I think at the one year mark, we had all of our systems in place. We've fully refurbished our place. We spent a lot of time and energy refurbishing, redesigning our place, really making it a really nice place. And then we learned how to do guest messaging, knowing how to hire the right cleaners. And once we got all the operational stuff out of the way, we took a step back and we realized that actually a sizable amount of revenues were coming from Airbnb. And at that point, VRBO for us was very minuscule. And we just started getting a lot of anxiety. And we're also in a lot of Facebook groups as well too, where a lot of folks were talking about how they were suspended on Airbnb or they're having trouble ranking on Airbnb. And I started to feel this big, like, power over us, where Airbnb had a lot of control on whether or not we're able to meet our revenue targets, whether or not we're able to meet our mortgage. And that's where we really felt like we had to take the business in our own hands. And we really now treat it as a business and that's where we started really investing into direct bookings.

I love it because we have a very similar, very similar in the sense it was the same with me. I got my operations that were down pat. Airbnb was the thing that got me into it. And then you realize, ah, I need to be doing this on my own. So that's great. That's really great. So let's fast forward a bit. So you're getting started with direct bookings. You created your own website, is that correct?

Yeah, we. So I did a lot of homework. I'm one to really dive deep and really get to know what the different options are and try to figure out my way around it. And I'm very hands on. And I didn't have $6,000 or $10,000 to spend on a direct booking site. And all these agencies were building their sites off of WordPress. I was like, okay, if they're building it off WordPress, maybe I should too. It took me four weeks to build our site, which is way longer than we expected. I thought that it would be very easy. Since I was in tech, I knew how to put products together. I thought it was going to be much easier and I can do it faster. I was so wrong. The learning curve was high there and the end result was it was a really good looking site. It wasn't as integrated into the PMS that we were using as much as we wanted to, but from an overall aesthetic standpoint, it really, really looked really good. And then ended up sharing it with my Mastermind peers and they really liked it and they were like, gil, can you create our site? And I was like, no way, I'm not doing that ever again. That was way too difficult and it was not fun at all. It just wasn't a great experience. But overall, that's kind of how we got started into direct bookings in the first place. And that's kind of like the impetus of why we even started the company.

Yeah, yeah, because. But we're told WordPress is the best. You know, Wix, Squarespace, these other platforms. A free website with a PMS is great to get started with, but the ultimate goal is a WordPress site. So what I love about what you're doing with crafted Stays and we'll get more into it later on, is the fact that you're challenging that you're challenging that belief of WordPress being so amazing. Can you give us a little bit of background of what you did and who you worked for that sort of helped you with your wanting to get direct bookings for your own business and treat it as a business, but also with your job and who you're working with, how did that come together?

Yeah, so I've been a product director for the last 15 years. I worked at many, many different major tech companies in the Silicon Valley area. And my most recent W2 gig was in E commerce. And specifically I was working partnering with Shopify. So we were working on a lot of backend projects with Shopify. And when I was building my site and I had it, my mastermind peers asked me to create their sites. I said no. And then I realized that my day job, I was working with one of the biggest e-commerce platforms out there and I just saw what Shopify was able to do for so many different entrepreneurs out there. If you had a physical product that you wanted to sell, no matter what it was, you can actually go on, set up a Shopify account, and by the end of the day you can be selling and having a really beautiful functioning website. You can take payments, you can have your inventory all in there. And I just like, there's nothing like that in the short term rental industry. You have the PMS websites, which are often very limited, or you can hire an agency and spend thousands of dollars to build it. But there's nothing really that was built around direct bookings or built around really helping hosts be really successful in direct booking. So I basically coded the first version myself. I'm not an engineer, but I learned really, really quickly. And I coded the first version, I shopped it around with a lot of my peers and people were blown away by what I was able to create. And I was like, well, maybe we're onto something. So I left my W2 job and I went full in on it. I ended up hiring engineers to take on the engineering side of it because engineering is not really necessarily my background. It's a product. And I really focused my energy on really understanding what the market needed, what other tools our customers are using, how do I make it easier there? And basically we're on the mission to create Shopify for short term rentals.

Oh, I think it's great because I know I told you this, but in a previous life I actually had a Shopify shop and I loved the platform and I loved how intuitive and easy it was. So I think it's really cool what you're creating. So let's talk about websites and how we can get people to actually book. Airbnb makes it really, really easy for the guests. So we want to do the same. But how did you first realize that understanding your guest was the key to increasing bookings?

Yeah, I think we ended up stumbling upon this and ended up being reinforced as we start the company. But the more that we knew about our guests, the better that we actually did. On the OTAs, we were designing our places much more efficiently for our ideal guest avatar. We were able to write a copy, we were able to take the right imagery and our photography into it, and that extended back into our direct bookings. So, like, even for our own customers, before they get into direct bookings and starting to build out their website, we tried to coach them on, really, who are you trying to target there? Who are you trying to target? What are you trying to do? What's the message? What's the service that you're trying to provide? And really making sure that you understand who your ideal guest avatar is even before you start cobbling together your website, it really starts there. And even when you're designing the place, that's utterly important.

So, in your experience, what are some of the common mistakes that hosts make when they don't know who their ideal guest is? And trying to just get bookings from anyone and everyone?

I think it's common that people will basically market to anyone. On Airbnb, it's very easy to list out all the amenities that you have, all the rooms that you have, and just kind of list them out there and let the picture, like, really nice photography kind of lean into it. But when you get into direct bookings, it takes a lot more to convert someone. It takes a lot more marketing activities. And I find that if you really understand who your ideal guest avatar is, you can really resonate with them. But on the inverse side of it, if you're being too generic on your marketing, you're being too generic on the copy on your website, you're being too generic on the emails that you send out on a monthly basis. It's really not going to resonate with folks and you're not going to get people to book with you.

Yeah, yeah, no, I see that. There's still going to be pushback from. Someone's listening to this, going, okay, I'll try and figure out who my ideal guess is. But how can they start doing this if they have no idea if this is the first time they've heard that phrase, ideal guest, and trying to define who they are, how can they start?

Yeah, one of the tactics that I use is I will look at my reviews. We also look at all of our, like, our Messages and everything. But if someone's starting off and they don't know who their ideal guest avatar is, the best place to look is the feedback that your guests are giving you. Every single time they stay with you. They'll talk about the amenities that they like. They'll talk about what, who they brought on, what type of trip it is. So what we've done in the past is we actually will do a data dump. We'll actually pull all those reviews into a tool and it's like a word bubble where the biggest word will appear the largest. And we found that a lot of the biggest words for us were always family. For our pool cabin, it's the pool amenity there. So we know what amenities are looking at who they're staying with. And we're using that to help us get a big macro view of it. And then we start diving deeper into the reviews to figure out like, okay, why are they staying with us? Why did they choose us over other stays? And that allowed us to mold our copy over time to really understand how we resonate with our guests much.

More impactfully and how does this impact your marketing? So if you've got your ideal guest in your mind and you hold all your reviews, you're seeing what is coming up there, you've got different words and different amenities that keep coming up and you're like, okay, this is the person who's booking. How can you translate that into your marketing?

Yeah. So for us, we now realize that we are tailored towards young families. And that's kind of. And it didn't necessarily happen by accident. It's because we've designed our own properties to be useful for ourselves as well too. And we realized that our guests are also ones that have young families. So now when we do emails, we don't just talk about all the great things to do in the area, we talk about things to do in the area that are specific for this guest avatar. In there, we talk about things that. The places, the restaurants that we would like to go to, the attractions that we like to go to. So even though we have this 12 month marketing email that goes out over time, it's very tailored towards our specific avatar there. So we don't try to appeal to everybody. We don't try to talk about all the great things that are generically available in the Smoky Mountains, for instance, we try to make it really pinpointed towards that. And on top of that, it also help us hone what channels we should be marketing on. So social media, for instance, we are only really present on Instagram, we're not on LinkedIn. We're not marketing in other areas because we're not tailored towards businesses, we're not tailored towards other types of stays. So we try to really understand who's staying at us, who's staying at our places, where are they looking, what are they looking for? Oftentimes we realize that the person booking is often the mom. And so we put ourselves in that shoe and say, okay, if it's a mom looking for a stay in the Smokies, for instance, what are they looking for? They're often driving long distances to our place. And so we try to make sure that they have everything that they need when they come to our place. We provide them high chairs, pack and plays, baby gates, all that stuff, because we know that we would need those things if we were driving to the area as well too. And then we tried also then put that into our listing descriptions and our photos and everything. So it kind of threads through every part of marketing that we do.

I guess it's understanding them so well that when they're reading your listing or looking on your website or looking at a social post, they go, oh, this person gets me. This is going to make it really easy for me and my family to travel there. And that's what you want. You want them to feel like you've thought it all out for them, isn't it?

Yes, yes. And for us, we think about value props and so there's two main value props that we think about for all of our properties. One, we want to make it stress free for specifically the mother in the stay. And then two, we want to make it fun. So each one of our properties has one unique amenity that we put in there that makes it fun. So for our bigger Gatlinburg cabin, we have a mini golf course, a putt putt basically on our front lawn. So we took, we utilized all of our big lawn space and we put a putt there and we put a fire pit in the middle so that the parents can stay and enjoy a fire pit in the middle while their family's around. And we also have a one bedroom cabin not too far away, but we have a pool in there. And we made a movie theater in the pool room so that the parents can stay in the pool room and really enjoy a movie while their kids are wrinkling in the pool. And then our brand's in place. We actually have a triple bunk slot, triple bunk with a rock climbing wall on one side and a tube slide on the other. So we try to really amenities it and really think about what will excite my kids if they ever go to any of our cabins. So, we take our kids to our cabins. They love it. They love each one in their own unique ways. But we really try to put ourselves into who's actually what we call the buyer persona, who's actually booking the place and then using that to really carry us through for design amenities, copy photography. So one thing we do is we actually aid our photographer and tell them that we're actually targeting this type of stay. Can you make sure you take a picture of the pack and play unpacked next to the bed? Can you make sure you take a picture of the high chair and place it next to the dining table and put out the kids bowls and plates there so that when a mom, a young mom sees it, they know, okay, this family gets it. This is for me. Yeah.

Your places sound amazing. They sound really cool. And I love it because we talk about unique stays. It doesn't have to necessarily be a unique structure. It can be something unique at the property.

Yeah, I mean it's really on who are you tailoring your toys? Even unique stays for young couples will look for something very, very different than us. It's, it's going back to who are you serving and how do you serve them? The best way possible.

Yeah. And I have something else that I wanted to ask you and another thing, the same that we're talking about WordPress being what we're told is as the best and the ultimate. We're always talking about driving traffic to your website, like getting people onto your website. But is that enough? Like if we're trying to get more bookings, should we just be driving more and more traffic to the website?

It's. You have to think of it like it's a funnel, like, so every marketing there's a funnel with it. And driving traffic is probably one of the most important things that you do because you can't just build out a website and expect it to convert. But inversely, you also need to make sure that your website performs. So making sure that you have a copy that really resonates with folks is really, really important. Making sure that it's performant, making sure that the navigation is really easy. And for us, we spend a lot of time on this. So we actually have several templates in our library that our users can choose from. And each template's different based on their Portfolio size and what they're trying to convey. But when we're building out these templates, we actually go through a pretty rigorous process of really making sure that it meets our standards. So we have this framework called the PDF framework where we go through when we're designing these. So the P stands for performance. Is it load really well? Is it fast? And then second is experience. Is the booking experience a very pleasant one? So we think about how people visit these on a mobile device versus a desktop? How are they navigating through the search capabilities? And then it leads into the third, which is the functionality, the F, which is really about making sure that functionally the site performs really well. So we synchronize with the property management softwares, for instance, so we make sure that the listings are always fresh, we always pull all the right content, the right pictures, the availability, and make sure that when someone's searching for something, they're finding the stay as easy as possible. So we kind of thread that through all of the templates that we have.

And I guess what you're saying is, yes, we gotta drive traffic to our site, but if we know our ideal guest so well and our content there is targeted, then the right people will come and the right people will book. Is it really that simple?

Yeah, yeah, There's. There's other things to it. One of the things to realize is that most folks don't book on the first visit to your website. Most folks will take up to eight times before they decide to book with you. So running retargeting ads, being able to collect emails and retarget them, it's a very effective way to make sure that they don't forget you and they end up going on Airbnb or VRBO for the booking. So you want to make sure that you understand what the whole funnel looks like and that you're really making sure that you're, one, driving traffic, two, making sure that your website converts, and three, that you have funnels built in to drive people back in should they bounce.

Right, right. All right, so let's talk about crafted stays. So you started this because you wanted to build, can I say the Shopify for short term rentals. Is that fair?

Sure. Yeah.

So why didn't you choose WordPress? What platform are you on? And pros and cons.

Yeah. So we built everything from the ground up. So we're not taking any white label solution, we're not taking someone else's product and rebadging it. We're not built on WordPress. And the reason being is that we wanted control over how the product was built. We know that a lot of hosts that we serve are not super tech savvy. They're not in technology themselves. Like, for me, it took me four weeks to build out my WordPress site. I don't want to put even any of our customers through that same pain. So we knew that we wanted to make sure that the customer experience was forefront and also that we can make tweaks to these websites that will drive up conversion there. And the difference between building a site off of WordPress and building it on a platform is that on WordPress, you're building one site at a time. So if you're hiring an agency and they're building it off WordPress, they're installing a WordPress instance, they're installing a template, and then customizing that template each time over. And that's kind of why they need to charge you an upfront fee for you to set up the website, because it takes a lot of manual effort on their side to be able to spin up your website, even if they're using the same template over and over again. But for us, we've actually built it from the ground up, where we have a dashboard that you get to log into, sync, or connect your different PMS. We'll pull in all the property information, and then you get to choose from different templates and customize it yourself. So it's almost like a Squarespace or WIX, but it's tightly integrated back into your pms. So all your properties are always synced, your availability is always there, and then down the road. It also allows us to make tweaks along the way. So, for instance, we were working with Hospitable and one of our customers said, can I actually have the actual price listed if someone's searching for specific dates? And I was like, okay, let's see if Hospitable does allow for this. And we were able to actually work with Hospitable to fetch live rates for someone if they're searching for dates. And we implemented that and we rolled it out for every single one of our customers. We didn't have to go into each one of those WordPress instances, update their plugins, and actually, like, roll it out individually. We're able to do a sweeping change very easily. For me, it's pretty common because in tech, that's kind of how platforms are built. But I feel like in our industry, we're not using the right tools or there's better tools out there that folks aren't leveraging. So I'm hoping to bring some of those technologies into the short term rental space.

Yeah, I love that. I can see that from a host point of view when you make a major update or a major upgrade to the platform, that I can benefit from it as well as everyone else. And you're not having to go into each individual website and make that change over and over and over again. So it's a win win, isn't it, for both sides, yours and the short term rental property manager.

Yeah. And we do a lot of tests on our side, so we will choose and partner up with specific hosts that are looking to try different things out. And a lot of our feedback comes from our users. I still do all of our customers onboard. I love talking to our customers. I love understanding what they're doing and how I can help them. And we will test things out and if it functions well and it works well, we will then roll it out to all of our customers. That's where most of our features will come from, is from feedback.

Yeah. It just seems like a streamlined way of doing it rather than having all these individual websites.

Yeah. And I'm so thrilled that we have such a vocal community of hosts that are really trying to drive more and more direct bookings coming to me with great suggestions on how we can improve it. And even if you're not one of those, you'll start to see your site getting better and better every single week. Like today we just released it where we found that if we pinned the Book now button on the top of the page, if you're scrolling up, that actually will increase conversion. They're not having to find that Book now button. It's right there. So we made that sweeping change and that rolled out this morning. So I. It's just fantastic.

Yeah. No, well, thank you so much for coming on today. It's really an exciting product that you're creating and I love how you've married together your life as a host and what you need and your life in the tech world and putting the two of them together. Now, for anyone listening and they're curious about it, where can they go when you've got a special offer, don't you?

Yeah, yeah. So specifically for your listeners, I created a custom code. So we'll. I'll share it with you on that link. But it's $35 off of our price for the first year. So normally it's $89 for two properties and then $8 for each additional one with Your specific link, you'll be getting $35 off. So I'm excited to help more and more hosts really get into direct bookings.

Yeah, brilliant. And I'll put that link in the show notes. Gil, thank you so much for coming on today. I've learned a lot. I think this is really great and I love how you're making things easy.

Yeah, yeah.

You know, we don't need harder things in our lives.

I think my main mission is really to lower the barrier to entry so that folks can get started in direct bookings as early as possible. I don't want folks to kind of go through the same experience that I did where I only had one property when I first started out, and I had this anxiety that I wanted to get in direct bookings, but it was unachievable for me. So if I can help hosts get in as early as possible, start building that direct booking engine there, because it does take time. It'll take two or three years for you to really drive up that direct booking to that 40, 50, 60, 70, 80% rate. But the earlier that you start, the earlier that you start messaging, collecting emails, the earlier that you're able to really take independence.

Thank you, Gil. Thank you so much for coming on today.

Thank you. Bye.

A huge thank you to Gil for coming on the podcast. Don't forget to check out the show notes@directbookingsuccess.com podcast. If you enjoyed this episode, please let me know by leaving a rating and review on your podcast app or on YouTube. I'd love to hear from you. Now, do you want to turn your ordinary stays into an unforgettable experience? On the next podcast episode, you'll discover simple yet powerful ways to wow your guests from the moment they arrive. We're going to be diving into first impressions, trust building, and budget friendly personal touches that can create lasting loyalty and rave reviews. This episode is perfect for anyone ready to elevate their guest experience without breaking the bank. Until then, go out and take action for your own direct booking success.

Hey, thanks for listening to the Direct Booking Success podcast. For more information about this episode and others, head to the website directbookingsuccess.com podcast. See you next time.