Building a 12-Cabin Micro Resort with 30-50% Direct Bookings with Steph Weber

Summary and Highlights

👤 Meet Steph Weber

Steph Weber is a branding and marketing powerhouse who has helped over 100 small businesses scale to six and seven-figure brands. As CEO of The Weber Co., she now focuses exclusively on the vacation rental niche, working with STR hosts, property management companies, boutique hotels, and micro resorts.

Together with three other couples, Steph built Cabins on the Cumberland—a 12-cabin micro resort and event venue along the Cumberland River in Kentucky. She also runs Hosted by the Webers, a co-hosting company she and her husband scaled to six figures in just one year.

With 10 years of experience in brand and marketing strategy, Steph brings fresh energy to the world of short-term rentals, helping investors and guests experience destination properties with rave-worthy experiences. She hosts the Branded & Booked Podcast and lives in Indianapolis with her husband, Collin, and their two boys.

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🏔️ From Construction Site to Micro Resort: The Cabins on the Cumberland Journey

When Steph and her partners started building Cabins on the Cumberland, they were just seven weeks into their short-term rental journey. The timing made no logical sense—she was eight months pregnant with her second child, they had just spent most of their savings on their first STR, and they were pivoting an entire business.

But when opportunity knocked, Steph answered.

The build taught her invaluable lessons about letting a vision grow organically. When their builder questioned whether all 12 cabins needed hot tubs, Steph ran an experiment. The cabin with a hot tub tripled the bookings of the other two. The builder quickly got on board.

By the end of 2025, Cabins on the Cumberland was maintaining 30-50% direct bookings every single month—a testament to the power of intentional branding from day one. Even when the property had nothing but mud, dirt, and porta-potties, Steph was building the brand story that would later drive those conversions.

For operators considering their own micro resort or boutique hotel project, Steph recommends finding a mentor who has made the mistakes and can share them transparently. The underwriting, financing, and sweat equity requirements differ fundamentally from those of standard STR investing.

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📢 2025: The Year Hosts Woke Up to Brand Ownership

The short-term rental industry experienced a collective awakening in 2025. Between Airbnb’s 15.5% host-side fee, changes to cancellation policies, AI-driven review automation, and new experience programs, operators began realizing they had placed too many eggs in one basket.

Steph noticed a significant shift in what her clients were asking for. Instead of social media management, hosts wanted deeper brand strategy work. They wanted to understand who they were beyond their Airbnb listings.

This tracks with what industry experts have been emphasizing at conferences throughout the year. Brand was the recurring theme—not as a nice-to-have, but as the foundation for everything else.

When Steph talks about brand, she means much more than logos and color palettes. Her process includes in-depth target audience analysis, competitive research, and core messaging that gets woven into every guest touchpoint. The visual identity comes after that strategic foundation is solid.

Brand is how trust gets built. Brand is why someone chooses to book with you over a competitor. It creates the emotional connection that makes guests feel confident handing over their credit card to a stranger’s property.

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💡 Why Your Direct Booking Site Means Nothing Without Marketing

Here’s the hard truth Steph wants every host to hear: having a beautiful direct booking website is only the beginning.

Too many operators launch their sites and expect bookings to roll in the same way they do on Airbnb. But that’s not how direct bookings work. You can’t set it and forget it.

If your guests only know you as “another Airbnb property,” your direct booking site won’t matter. You need a marketing strategy that actively drives traffic and converts visitors into paying guests.

The good news? Direct bookings compound over time. The energy you invest today pays dividends for years. Your email list grows. Your social following expands. Your messaging gets sharper. But none of that happens passively.

Steph recommends starting with email marketing as the lowest-hanging fruit. It’s the foundation that makes everything else work. From there, you can layer in social media content, SMS marketing, and even paid advertising.

The key is to be responsible for marketing your brand, whether you do it yourself or hire someone to help.

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🤖 Using AI Without Losing Your Voice

AI tools like ChatGPT have transformed how hosts create content. But Steph has noticed a troubling pattern: too many operators are copying AI-generated text verbatim, resulting in generic messaging that sounds like everyone else.

Phrases like “unforgettable memories” and “your dream vacation awaits” mean nothing when every competitor uses them. This is why Steph advises clients to answer branding questions from their own perspective first, before bringing AI into the process.

She recommends going directly to real humans who fit your guest profile. Ask them about their vacation experiences, their priorities, their best travel memories. That authentic research creates messaging that resonates in ways AI cannot replicate.

Once you have that foundation, AI becomes helpful in refining ideas, generating variations, and speeding up execution. Steph’s team uses ChatGPT to visualize brand experiences for clients—creating images of proposed amenities and guest touchpoints that help operators see possibilities before they invest.

The combination works when you lead with human insight and use AI as an accelerator, not a replacement.

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📊 What’s Coming in 2026: Doubling Down on Brand and Content

For The Weber Co., 2026 continues the momentum of 2025’s brand-focused work. Steph sees even more operators recognizing the importance of parent brands that house multiple properties, personal brands that establish thought leadership, and boutique hotel brands that create destination-worthy experiences.

Email marketing remains central, with SMS marketing emerging as an essential addition to the communication mix.

The biggest shift? Solving the content capture problem. Steph realized that even the best social media strategy falls flat without great content to power it. In 2026, The Weber Co. is actively helping clients capture the photos and videos needed to perform well on Instagram and other platforms.

This matters because 60-70% of millennials now go to Instagram first when planning vacations. Hosts who invest in strong content and consistent posting strategies will see direct bookings as a result.

On the CraftedStays side, the focus is on strengthening the marketing toolkit for operators with larger portfolios. Cart abandonment tracking, improved conversion analytics, and tighter integration across the guest journey are all in development—bringing e-commerce best practices to an industry that’s still catching up.

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⚡ Rapid Fire with Steph Weber

What’s a book you’d recommend to other hosts?

Unreasonable Hospitality by Will Guidara. It resonated deeply with how Steph thinks about crafting surprise-and-delight moments for guests—and how to infuse them with a brand’s core values.

What mindset advice would you give someone starting something new?

Don’t be afraid to share your vision, even when it feels too big or scary. When Steph got into Cabins on the Cumberland, she was seven weeks into her STR journey and asking about partnerships in Facebook groups. People probably thought she was too green. But because she shared the vision, she found her partners, built the resort, and hosted thousands of guests.

When you speak things out loud, you speak them into existence.

What’s one tactical tip for someone trying to grow direct bookings?

Don’t sit on your marketing strategy. Your website is great, but if you’re not actively marketing it, if your guests still know you as “another Airbnb property,” your direct booking site doesn’t matter.

Start with email marketing—it’s the lowest-hanging fruit. But you have to do something. Direct bookings don’t just happen because you launched a site.

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🔗 Connect with Steph Weber

📸 Instagram (The Weber Co.): @theweberco 📸 Instagram (Personal): @stephnweber 💼 LinkedIn: Steph Weber 🌐 Website: theweberco.com 🏕️ Cabins on the Cumberland: cabinsonthecumberland.com

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🎧 Ready to Build Your Direct Booking Brand?

Steph’s message is clear: brand and marketing aren’t optional anymore. They’re essential for any host serious about long-term success and independence from OTAs.

If you’re ready to take control of your bookings and build a website that actually converts, start your journey at CraftedStays.co. Our platform is purpose-built for short-term rental operators who want fast, mobile-optimized sites that reflect their unique brand.

👉 Listen to the full episode to hear Steph’s complete insights on building micro resorts, navigating Airbnb’s 2025 changes, and creating marketing strategies that drive real direct booking results.

Transcription

Steph: Don’t sit on your marketing strategy like you. It’s great to have the site CraftedStays is great. What you guys have built is great, but if you’re not marketing it, if you’re not telling people about it, if your guests know you as another Airbnb property, your direct booking site does not matter. So you have to have a marketing strategy in place.

Steph: Even if you’re just getting started with email marketing, which is lowest hanging fruit, and that’s where I recommend you do start. You have to do it or it’s, you don’t just have a website and expect it to do again, like what you said earlier, Gil, you know, it’s like we list on Airbnb, we see bookings roll in.

Steph: Okay. Like that’s awesome. That’s rewarding and instant gratification. I understand that direct bookings are not the same. You can’t just have the site and be like. The bookings are gonna roll in. Be responsible for marketing your brand.

Gil: Before we bring on our guest, I wanted to talk just a little bit about something that I’ve been hearing a lot from Host. 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 letting all these marketing strategies, you’re driving traffic and you’re putting it all to work.

Gil: 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 improve on things.

Gil: 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 build 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 and you can keep on testing and improving.

Gil: As you learn, you can make changes all on the platform. You don’t need to learn something new. So if you need some help or you wanna get started, go ahead and go to craft stays.co and start your free trial. Now let’s bring on our guests and dive deep into hospitality and marketing.

 Gil: Hey folks, welcome back to the Books Dollar Show. I wanna be the first to thank you or to invite you to the new year. Today we have a very special show. Um, we are bringing back our first ever podcast guests on the show. Back then, the show was actually called something else. It was called, I think direct booking, simplified, um, kind of has evolved since then.

 Gil: But I’m super excited to introduce Steph Weber. Uh, she is the owner of the Weber Co. Uh, and they are a marketing agency that specifically focuses on the short-term rental agency, really helping folks build strong brands. And we’ll talk a lot about brands on the show today. She’s also the co-owner of Cabins of the Cumberland, uh, which is.

 Gil: A group of cabins, on the Cumberland River. And she’s also the owner of Hosted by the Webers, which is a property management company. So she’s deeply in this space. She has a deep background, in marketing. We actually come from the same industry, e-commerce, today’s episode is really looking back at all different things that happened in 2025.

 Gil: All the learnings that we’ve had along the way. Some, some of the stories that we’ve, we’ve worked with some of our clients on. Really looking forward in 2026 in some of the areas that we’re really doubling down on, both from her perspective and ours as well too, and kind of where we’re seeing folks really spending more of their energy towards really to drive up more direct booking.

 Gil: So I am super excited to bring step onto the show. , I hope you folks enjoy this and I hope you folks have a great year. So without further ado, let’s bring her in.

Gil: Hey Steph, welcome back to the show.

Steph: Gi, I’m so stoked to be here with you today.

Gil: Yeah. For our listeners here that don’t know, Steph was the first ever guest I had on on this show, and I’m so thrilled to have her back. I’m a good friend of hers. She’s pushed me so much throughout the years of how to include our platform and like she’s been a huge supporter along the way. So Steph, welcome back to the show.

Steph: Oh, thanks Gil. I’m so happy to be here and what a great time with like New Year and New Energy. It’s gonna be so good.

Gil: Yeah, everybody still has their, goals set for the year. They haven’t lost steam yet. Uh, so it’s a perfect time to talk about just all the things that we, we look back to and also look forward to. Um, for folks that didn’t catch you on episode number one.

Gil: Do you mind giving a quick introduction to yourself?

Steph: Oh gosh, yes. And also the business has changed. Like I’ve changed so much. What we’re doing has

Gil: I’m gonna compare the differences between how you talked about yourself almost like two years back and now.

Steph: Yeah. Yes. So wild. Yes. So, um, yeah. My name is Steph Weber. I am the CEO of the Weber Co. And we are a creative branding and marketing agency for short-term rentals, boutique hotels, micro resorts, cabin communities, property management company. So all in on this hospitality industry, but. We really pride ourselves on helping people understand that you are building your own brand and you are responsible for that, and it is so powerful to be able to connect guests to and build that emotional tie there, and then also have really great marketing that’s captivating your audience and leading them to those direct bookings so that you truly have.

Steph: Control and ownership over the hospitality business that you’re building. So that’s the Weber Co. We do also have a co-hosting business called Hosted by the Webers. And then we are also done now with I, I’ve said so long, like we’re building a 12 cabin micro resort. And I’m like, we’re done with it. We have it.

Steph: It is alive and well. So it is called Cabins on the Cumberland, and that is a 12 cabin micro resort along the river in Kentucky. And, uh, also event, event, venue, et cetera. So that, that bill just finished at the end of 2025 and 2026 is gonna be wild and we’re here

Gil: Oh, oh my God. I’m gonna pause a little bit because I wanna touch on some of the stuff before we kind of go into. Um, the, the kind of the look back and the look forward of, of, of the year. I’ve always admired your journey and I, I, I think like we’ve talked about this as like this transformational story.

Gil: Bring people along for the ride. And so then when you do launch that you’ve already kind of built a brand not from the beginning, you built or not from start. Like you’re, you’re building it along the way and people can kind of follow along. I’ve always wanted to start a. I don’t know if it’s a micro resort or what type, but like the vision that I, I’ve always had is like here in the Bay Area, there’s not a whole lot of places to escape to, and specifically you can empathize with this specifically for young families.

Gil: I would love to be able to take my family out. We are in San Francisco, drive two, three hours away and have this community where we can spend the entire weekend. We know it’s safe for the kids. We have a lot of fun activities there. Like that has always been a dream of mine. If you’re listening, if you share that vision and you wanna work with me on this, let me know.

Gil: But that’s always been a vision of mine. I don’t know when I’m gonna execute on it, but I would love to know kind of from your perspective, building out CU cabins in the Cumberland. What was like your biggest learnings along the way?

Steph: Wow, so many things Gil. Um, I think, I think number one was that we had to let this vision grow with us, and there was definitely some. Not tension in our partnership, but some of our, like we have, our partners are phenomenal. They’re great. There’s four couples that are in on this deal, but like our builder for example, didn’t really, he was like, I don’t really think that all these cabins need hot tubs.

Steph: Like, why do we need to spend another like 10 K building a deck, adding the hot tubs to each cabin, multiply that by 12, right? Like, that’s a lot of money in hot tubs. All right. And I was like, can I just like, let me just prove it to you. Okay. So we had three cabins that were live and we put a hot tub at one, and that one.

Steph: Tripled the bookings of every other of the other two cabins. And our builder was like, okay, you are correct about this. And so then I was like, all right, additional money. Everybody, like, here we go. Um, but the other thing that we quickly realized as well is that we are in a rural area. We’re in a rural community, which I love and think is great.

Steph: We’re not, I mean, like we’re two and a half hours away from Nashville, Tennessee. We are not that far. It is, it is definitely drivable. Right? Like what you just mentioned, two to three hours away. Um, but because of that, we needed to make a true destination. So having a full game center was not part of our initial plan and our initial build.

Steph: And I think what’s really cool about our partnership is that we all allowed that vision to grow as we’ve started to build this place. And now we’re all over here like, hope this pays off, but you know, it’s gonna be okay. It’s gonna be okay. We had to really like, overcome some, um, challenges just in terms of like. Figuring all of those pieces out, making sure that what we were creating is in alignment with what we wanted to build and is something that like, that target audience demanded and was looking for. And it is. And it was. And so, you know, we’re good and we’re, we’re moving forward and rocking and rolling.

Steph: But building out a micro resort has been no easy feat. That’s for sure.

Gil: For sure. Would you do it again?

Steph: I would totally do it again. I wanna do it again. I’m like, ready? Everyone’s like, Steph, you like got into this in 2023 and we got into this whole world of short-term rentals in 2023. At the time, I was eight months pregnant with our second baby.

Steph: We had a toddler. We had just spent the majority of our savings buying our first short-term rental here in Indianapolis. We were starting a new business. I was pivoting the Weber Co. Like. None of the timing made sense and this opportunity landed in our laps in July of 2023. So people, when I tell this story, people are like, you did a new build, new construction, 12 cabin micro resort, and you were like seven weeks in too short-term rentals.

Steph: And I was like, yeah, I just, this is how I do business. I just go in and if you have the vision and you believe in it. And the opportunity presents itself. Figure it out. You’re gonna find a way to do it. And yeah, so I’m, I’m ready, Gil. I’m like itchy for the next deal. So we’ll see what this year brings.

Gil: Yeah, I mean, on your vision side of things, I, I, I listened to, I was at a conference that Isaac French was at, and he was talking about like, and you probably know his story many, many folds over, like when he built out his, his own micro resort. He shared that vision and it was a vision and it was, it’s like that for all the kind of built he’s done.

Gil: He’s always shared the vision and he found that when you share the vision very, very broadly to folks, you start to attract the right folks in there and you start to solidify that. And that doesn’t mean to say like you have to be setting your set in your ways, but like really sharing that vision and kind of letting it.

Gil: Like percolate, um, that has really helped a lot of folks like break through things is it’s, it’s, it’s oftentimes like, it’s really difficult when you’re doing such a big dream there, but kudos, kudos to you. Kudos to you.

Steph: you. Thanks.

Gil: um, outside of the hot tub thing, like what was, like, what would you say is like your biggest learning?

Gil: Like what would you have done differently this time if you were to, to do your next project?

Steph: I think I would, uh, truly, I think it actually starts at the underwriting. We would’ve done underwriting much differently and the financing side of things much differently, Gil, which is maybe not the answer that anyone was expecting, or maybe it was, but. That I think, you know, again, like when we got into this, we were very new.

Steph: The couples that were in this with are not necessarily new to real estate or new to real estate investing, but they are newer to the world of short term rentals. And so I think we all, you know, we ran our numbers based off of what other cabins in the area we’re doing. It’s very limited data in that area, which was a little tricky.

Steph: And also the bank would not at first finance all the furnishings. So it’s just been a lot of like. Ca Capital investments, sweat equity investments. I mean, this was two years in the making of trying to bring this place to life, right? So now we’re all to the point where we’re like, we’re ready to make some money here and like actually see, you know, the fruits of all of our labor really pay off.

Steph: And I think that’s one thing that for anyone who’s considering doing this, really making sure that you have a great mentor that can guide you through some of this. If you wanna get into boutique hotels or you wanna get into like a micro resort, build out. It is not the same as short-term rentals. Like it’s, it’s, it’s just not the same.

Steph: It is a very different process. And so making sure that you’ve got a good mentor who’s gonna walk you through that, give you the all share transparently all of their mistakes that they’ve made. Um, and like really understanding your goals too, right? All of our partners who came into this deal, we’re like, we’re in this for the long-term equity.

Steph: We don’t necessarily care about the cash flow. Of course we wanna be profitable, but we’re in this for the long-term equity of when we can sell this. So for us, it wasn’t a like, let’s build this and get out. It’s a like, let’s build this, and this is a legacy property for us. So again, really being intentional about defining those investment goals. Realizing too, what that means. Because for us, I think at the beginning of this partnership, we were all like, let’s put in the sweat equity and we’re all fine. And when you’re like almost two years into a project and you’re still putting in sweat equity, you’re like, we are tapped out. We are done with the sweat equity.

Steph: You know, so just being really realistic about what that looks like and, um, knowing that. You’re, you’re gonna have to work together, especially if you’re in a partnership, which thankfully has been really, really great for us. But those are, I would say like some of those biggest learning lessons truly started at the underwriting and the numbers side of things.

Steph: And then also the financing and understanding what continuing to put in capital is gonna look like, and continuing to put in sweat equity was going to look like as well.

Gil: yeah, yeah. And real equity too. Um. When you think about, you mentioned that you would a hundred percent do this again. Do you have a vision of what your next one looks like?

Steph: We are really interested in campground glamp ground still like our whole vibe, Gil is very nature based, so like anything by the water in the mountains where there’s hiking trails, I, I kind of have a vision for this next property that’s maybe. Larger piece of land where we can do tent sites, we can do glamping sites, we can do RV sites.

Steph: And part of that maybe also comes from the fact that we’re gonna do camper life this year. So I’m like, all right, let’s figure this out. Like we’re gonna go be in these campgrounds. Let’s see what there is there and how we can make the experience better. So that’s what I’m kind of interested in next.

Gil: Yeah, you gave me fired up. I definitely wanna like do this project and I think like if it wasn’t for the growth here at Craft as days, like I probably would have taken the plunge. If I still had my W2 i, I would have taken the plunge if. That being said, you were probably right earlier when you said like, there’s no perfect timing.

Gil: Like you just gotta have to do it. And I think what’s gonna happen is like that vision is just gonna get stronger and stronger where you’re like, I cannot do it. So, so yeah. When, when that time comes, when I break, I’m gonna, I’m gonna, I’m gonna text you and ask for some advice.

Steph: I can’t wait. It’s gonna happen this year. Gil. Really

Gil: Yeah. Uh, you’re, you’re putting me on the spot.

Gil: Okay. That might be a kind of a good transition to what was 2025 like for you. And I’ll, I’ll kind of share kind of my perspective as well, but what was it like for you? What was kind of the beginning of the year? Like, did it pan out the way you expected, both from a business side, but also from like a client facing side?

Gil: Like what are your, what are the transformations your clients are going through?

Steph: Yeah, so I’ll, yeah, I’ll share, I’ll speak to all, all sides of that. So I think. In 2025, we came into the year and number one, I was so excited about really having our offers well-rounded within the Weber co agency and understanding how we serve clients and having great proof of results and what that looked like.

Steph: I think I came into 2025 thinking like we were going to take on so many more clients from a social media perspective where we were like. Managing social media accounts and helping clients like create content and so forth. And actually 2025 was the year of brand and clients really understanding that they do not own an Airbnb.

Steph: They are not Airbnb hosts. But Airbnb is simply a platform where we are able to list the hospitality businesses that we have built. Um, and really having brand autonomy was like highlighted the year of 2025. I think we’re gonna continue to see that into 2026. Um, so that was kind of the big client side in terms of marketing.

Steph: There was a pretty heavy emphasis on email marketing, though I’m still met with some like, oh, you know, Airbnb brings me people and I’m like, Ooh. Right. But then also like, what did Airbnb do in 2025, right? Like, we

Gil: they did a lot.

Steph: because I don’t know about you guys, but when. The 15.5% fee went into effect on fully on the host side, and that impacted not only just our accommodation, our nightly rate, but it also impacted our cleaning fee.

Steph: Also impacted our pet fees, also impacted our resort fees. My brain, from a pricing strategy perspective for a solid three weeks was like, what am I doing here? And trying to make sure that everything. Still made sense and the numbers still numbered, especially ’cause we co-host, right? So that had to make sense for our clients as well, while also taking a look at what’s the rest of our market doing.

Steph: And have we are we like totally out-priced. In the market now because of these different factors that Airbnb has forced us into and didn’t consult with its host, which really provide most of its business. But it’s fine. It’s fine, it’s fine. We provide the product, right? We provide the product. Um, but anyway, here we are.

Steph: So again, I think that when all of that happened in 2025, that was. Kind of a big wake up call that I think a lot of hosts needed, especially those of you that have multiple properties and you’re continuing to scale or you have aspirations of doing a boutique hotel or a micro resort. And now it’s like I’m not just having conversations about property brands.

Steph: I’m having conversations with people about their personal brands, about their boutique hotel brands. It’s so much larger than just an individual property, which I think has been a really interesting thing to see, and also very exciting.

Gil: Yeah. Yeah. I, I, I think like 2025 Airbnb has, I can’t remember one of the most, I can’t remember any, like, real positive change from the host hosting perspective. It’s. Good for them. They are really focused on the overall guest experience of things, but hosts have really gotten a really short end of the stick in 2025, like in the very beginning of the year, did they change their cancellation slash chargeback policy?

Gil: So I think in the beginning of the year, if a guest chooses to cancel or does it actually not choose cancel, but if they don’t pay for their stay, we are now on the hook for that. They, um, they changed. The added experiences in there, allowing folks to enter our home and provide experiences without really consulting with us and really having us to control that.

Gil: Then they did all the, also the 15.5% fee. I think there was one other change. Oh, they really started to roll out, um, AI review automation on their side, and that is a freaking out a lot of hosts where before you can talk to a human being and really give them. Solid foundations on why someone left you a negative review that is unwarranted and now there’s some bot that does it on your behalf.

Gil: Decision is made and you don’t have any control. You have two strike, you have two chances to submit a review dispute. And if it doesn’t go through, even internally, they can’t teach now, like I, I think a lot of those things starts to stack up where folks are now realizing, oh shoot, like I shouldn’t have all my eggs in that basket now.

Gil: I think that, that, that’s been a huge shift. Um, like on our side, it’s good because like a lot of folks are now looking at marketing a bit more and looking at websites a bit more. But I think this is the thing that like has been building over time and it’s, it’s kind of sad that like Airbnb has like resulted in this.

Steph: Yeah, I agree with you. I’ve seen some conversation in this space around like. You’re never gonna outmarket Airbnb, like don’t try to compete with Airbnb. And I’m like, I’m not trying to compete with Airbnb. We are our own brands. We are trying to compete really just with ourselves. And I had a client actually this year say to me, I imagine if I.

Steph: Build my own brand and have my own site. I really start to compete with really with myself or anyone else who’s trying to just like have autonomy over their business and not relying solely on the OTAs. And I was like, you’re a hundred percent correct in that. And in addition to that, I’m also not saying go jump ship and abandon Airbnb.

Steph: We’re certainly not doing that. That’s not happening. Is it still a great listing platform, but call it what it is. It is a listing platform. It is a means for us to be able to get these businesses out there, but. We have to be smart enough and have the systems in place to then own that guest once they’re at our property and we capture them with our brand, not the fact that they, you know, booked another Airbnb property.

Gil: Yeah, and I think like this is one of the very few assets where we get really comfortable of buying an asset, putting in an operation. We put it on some listing site and all of a sudden we get bookings, we get revenue coming in. You can’t do that with a lot of other assets. Like if you did, if you did this in e-commerce, you’re gonna have to build a brand.

Gil: If you do this in anywhere else, you’re gonna have to build a brand. You’re gonna have to build that yourself. And I think a lot of folks have gotten comfortable where they can buy an asset, they can put it in there, or they can put it on Airbnb and they’re like, oh, I’m 60% full, I’m 70% full, or whatever it may be.

Gil: And they’re not having to worry about building a brand. But any other type of business there, if you’re running a restaurant in the very beginning, it’s going to be slow. You’re going to have to attract people, even if you’re on Yelp, even if you’re doing other things, like you’re gonna have to attract people.

Gil: Same thing with e-commerce. I think like we take it for granted that we have Airbnb and, and Airbnb has done a great service to the industry. They’ve helped us fight for regulations in a lot of places. It helps a lot of folks kind of get into it. But I think we are at a point where folks got a little too comfortable with it.

Gil: Um, and now they’re, now folks are kind of waking up and figuring out like, oh, wait, wait. Maybe I should be focusing on my brand and my own, my own portfolio.

Steph: Yeah. Yeah, absolutely. And I think that trend will continue. I, I love that you brought up the e-comm side of this skill or just like any other business, you’re right. Like it’s going to take time and that’s how I’ve actually, that’s how I felt a little bit with cabin. On the Cumberland that in 2025 we were maintaining 30 to 50% direct bookings every single month, which was absolutely fantastic.

Steph: And the reason for that is because we’ve been so intentional about our brand and our marketing from day one when we had like mud and dirt and porta-potties in our, on our land from like construction, right? Like that’s the reality of where we were. But because we were focused on that and focused on our brand and the guest.

Steph: Experience that has been huge and instrumental for us. But now we’re adding in this weddings component and I’m like, this is a whole new side of things that where I’m like, we’re going to trade shows early this year. We’re like really doing some different things that we. Don’t necessarily have like a listing platform where we can just go be like, we’re a wedding venue as well.

Steph: Like, come host your wedding here. So we have to be strategic in our marketing plan, and I think that’s the shift that we’re gonna see for hosts this year as well. Again, especially those hosts, you know, if you’re in this because you’re like, well. Those, these people are not listening to your podcast scale.

Steph: They’re here because they’re like, how can we have autonomy and control over the business we’re building? But if you have really taken a look at what Airbnb has done and you’ve scaled and you’re continuing to scale and grow in this space, like building brand and having a marketing strategy, it’s a non-negotiable.

Steph: It is not optional. It is absolutely essential to, to your longevity. Right. Which I would imagine most of us are in this game four.

Gil: Yeah. Yeah. Going back to kind of like the, the brand side of things, like what was kind of the, like you mentioned. In the very beginning of the year, your thought of and your goals were really to focus on helping folks really amplify their social media, but it turns out that they’re really looking more introspective about like, oh, what’s our overall brand?

Gil: Why do you think that shift happened? Why do you think that? Is it kind of a push on your side where you’re, where you’re talking to hosting, you’re now realizing they don’t have a brand, or are they doing self introspection and realizing that themselves? Like where, where’s that coming from?

Steph: I think it’s a combination. I think it’s definitely not only just hearing me talk about brand, but about hearing some of the industry e experts talk about brand as well. I mean, that is a, I I was not able to attend, um, a, a handful of conferences this year, but I had a friend say, I. Steph, I went to this conference and the number of times that I heard brand, brand, brand over and over again, I was like, right, because it’s important and people are talking about that.

Steph: And again, whether it’s like you’re building it based on your property or your co-hosting business or property management company, or it’s your personal brand and you’re showing what you’re doing in your real estate journey. People have realized that that is crucial and brand is these like foundational work that you need to do in order for your marketing efforts to be what they need to be to reach the right target audience.

Steph: And when we talk about brand, it is so much deeper. If you didn’t listen to my first episode with Gil, it is so much deeper than the fonts and the logos and the colors, right? Like we are doing in-depth target audience analysis. In-depth competitive analysis. We’re going through all of the core messaging that gets woven into every potential touchpoint a guest could possibly have with you, even on the OTAs.

Steph: So we’re infusing all of that and then bringing those visuals to life as well, again, so that you have like that visual recognition for the brand too. But what I think my audience and what I think so many people realized in 2025. Was that brand is where trust is built and brand is the reason people say, yes, brand is how you’re perceived.

Steph: It’s the emotional connection that people have to you. It is the reason that people are choosing to say, yeah, I do trust you enough to deliver upon the promise and the experience that you’ve shown me that I’m going to have, and I’m gonna say yes to that booking decision, right? This is why when I, when I hear people say, oh yeah.

Steph: We booked an Airbnb, or Oh, I bought another Airbnb. I’m like, kudos to Airbnb. They’ve done a really good job at building their brand. They have. They really have like great for them. I don’t wanna ride the coattails of that, and I don’t want you to ride the coattails of that either, but they have done a good job of it.

Gil: Yeah. It, it definitely has turned into a verb in the last few years. It’s almost like the taxi industry and, and I’m taking an Uber like that, that happened almost a decade back there. It’s, it’s happening definitely within the short term rental industry where folks are saying like, yeah, I just bought another Airbnb.

Gil: I’m like, no, you didn’t. You bought another short term rental. You bought another investment. Like, I, I, I see those being now conflated and I think folks are now realizing that like. Oh, I’m catching myself on, on that, and they’re realizing that, but it, it, it, I think there’s a lot of folks still kind of stuck in that world where they think that they operate in Airbnb, even if they’re on multi-channel, they still think that they’re, they operate in Airbnb.

Gil: So it’s, it’s, it’s kind of funny.

Steph: it’s very interesting.

Gil: Yeah. And I, I, I think, like, I’m seeing the same thing on, on our side too, on, on the, on the branding perspective and why. Some hosts really succeed in direct bookings, where some just kind of flounder in that 15% range there. Um, I think when I look back, I, I, I do a lot of audits on our sites to make sure that the booking engine works correctly, the reviews are being pulled.

Gil: I do very constant audits to make sure that our pmms connections and overall. The folks are actually putting energy into their websites. And I find still like the folks that are floundering are the folks that are kind of like in that said and forget it type of way. They’re like trying to get their website up and running quickly as possible.

Gil: And they just put it out there and they, they expect bookings to come in. But it doesn’t work like that. Um, and I’m glad you kind of brought up the brand, the brand perspective because yes, you have to have that marketing engine to bring folks in there, but you also have to make sure that. The content, the way that it feels when you land on the site feels natural to someone that is specifically visiting you.

Gil: You’re not gonna hit everybody, but the folks that you do hit and that you’re meant for, it should hit home for them. And I think a lot of folks are now realizing, oh, I can’t just have generic copy there. And we try to make it where. Folks don’t have to learn a whole bunch. They don’t have to like figure out what are all the different parts that they need to have on their website, their social media logos or FAQs, all those different things.

Gil: And we try to put placeholders there Too. Often enough folks just leave the placeholders there and I’m like, no, don’t do that. Like, we try to make it easy, but like don’t, don’t think of it as like, oh, I’m not gonna put in the energy whatsoever.

Steph: Yeah, yeah, yeah, a hundred percent. I think I, I mean, we see the same thing in just like talking about AI for a moment. Chat. GPT Man has tried to do so many brand strategies for people in 2025. I was like, wow, like the copy on your website, I can tell you went into chat. GPT gave it a little bit of a prompt and then took verbatim whatever it said.

Steph: And this is why we hear people say like. Unforgettable memories and make like your lasting dream vacation come true here. And it’s just like. What are you even saying? Because it’s the same fluffy language that gets used so often in this industry. So I actually tell my clients, like I have a program called STR Marketing Bootcamp.

Steph: And so I have clients go through a series of questions and I’m like, answer these questions on your own. Don’t go to cha GPT to answer them. Answer them of whatever comes from you first and or your target audience and think like your target audience, then if you wanna go into chat GPT, you can, but here’s a list of words to tell chat GPT not to use when it is building, helping you build out the brand or the copy or whatever.

Steph: But yeah, you cannot just, it’s not copy and paste. And in order to understand that, you have to really know the target audience too, right? Because the language that you’re using in your brand. Should resonate with your target audience so much so that it’s like verbiage, verbiage that they’re saying, it’s words that they would be using to describe their experience or their stay with you, what they’d be telling their friends.

Steph: That’s what it should feel like. Yeah. And, and making sure that it’s aligned there, not just, you know, from ai.

Gil: Do you, do you still encourage, or do you still kind of weave AI in the later parts of that branding journey, or do you kind of try to keep it. Where folks have to think really through the entire experience themselves. Like how do you, how do you kind of like where you, where are you on that spectrum of, of, of using AI within specifically brand marketing.

Steph: Yeah, such a good question Gil. I am on the spectrum of like somewhere in the middle, and this is how I am in so much, in so much of my life. But I think it’s really important for you to understand and identify who is the target audience, who is the avatar, what is their story? Go have some real conversations with people who you fit, who you feel fit that profile, because they probably exist in your world, like they’re probably on Facebook or they exist in your world, or you have daily conversations with those people.

Steph: Go ask them a handful of questions about their vacation experiences, about your property, about what they want, about what they’re looking for, about their best vacation memories, like go have some real conversations, take that data and information, and then if you want to bring it into chat, GBT to help you piece together brand core messaging.

Steph: Fine. And again, like there are some things that just like don’t use, don’t make things overly wordy. Branding that’s overly complicated and overly wordy typically doesn’t work. Unless that’s like a part of your brand, then maybe it does. But for most people that’s not the case. Sometimes branding is about, how can you say.

Steph: What you mean and strike an emotional connection in the simplest way possible. And that’s really like the root and goal of, of what branding does. Like how are we making someone feel quickly, um, so that they have that connection to us. So we use it that way. And then what, we’ll, what we’ll do once we have a client’s kind of brand core messaging built out is we’ll take that and we’ll go into chat GBT and we’ll say, okay, here’s this client’s brand messaging.

Steph: Here’s all the target audience information. Now we wanna build out the brand experience. So what are some really intentional ways that we can build out a true branded experience at their property? This goes so much beyond just like the fact that they have Asana or just the fact that they have a hot tub.

Steph: And what’s really cool about what chat GPT has helped us be able to do. In 2025 is it will give you images of those things. So we have a client who has a boutique hotel located in South Lake Tahoe and it’s called the Iceberg Hotel, or I’m sorry, the Iceberg Tahoe. And we did all of their branding this year and it was phenomenal.

Steph: But they were like, yeah, we have these different amenities or these different ideas. And so we were like. We’re gonna take this and put it in Chad, GBT and be like, here’s the brand experience we wanna create. Build us a photo of this that we can share with the client. And what was so cool about that is that it helped the client be able to see, oh, here’s how we bring this to life.

Steph: Here’s how we take a sauna and turn it into a, a wellness circuit for our clients. It’s like a guided experience for them. So that’s how you’re bringing brand to life. And so yeah, it’s been, it’s been a combination of both.

Gil: Yeah, it sounds like you’ve kind of gone through this enough where you. Understand some of the fundamentals, the strategy there. At this point, AI is not going, and, and I find this a lot, AI is not really good at the overall strategy of things. It’s often very, very terrible. It’s good at a lot of like small, little tactical things if you know how to insert it in all the right places there.

Gil: And I’ve fallen into this many times myself, where I’ll go on this huge AI binge, I’m like, I can do this, and I’ll run really fast. And I, I find like, wait a minute, like I’m completely off course. I’m in a place where I’m working on things I shouldn’t not necessarily be working on, and it was all because of the guidance of, of ai and I’m, I’m always having to check myself, like trying to figure out what that right balance of like, oh, how do I use this tool most effectively?

Gil: And I, I find that over and over again. It’s oftentimes like. Taking a paper notepad or whatever it is that you wanna write on. Um, and really thinking through the strategy yourself and then try to validate that strategy with ai. But if you lean in and even open up a new chat and you start thinking through an idea specifically with ai, they’re often gonna times lead you to a place that is not really, your vision, is not where you want to go.

Gil: It’s maybe. Really not very good strategy overall thing, but it’s really good at some of those like tactical things of like, oh, I have this idea. Help me think of other things to think about. Like kinda like what you’re mentioning of like, oh, you’re feeding the target audience there and you want to be intentional about the entire guest experience.

Gil: You can probably come up with five, 10 different things, but having AI to really help augment that and really think through every single touch point, it’s really, really good at that type of stuff. So I can see how that really works out.

Steph: Yeah. Yeah, it’s very helpful. And I also like, I will just go and talk to chat GBT, and I feel like this has helped me as well. Instead of it being a, uh, and I know there are many different AI tools, chat, GBT is the one I choose to use the most. But anyway, I’ll go and just talk. So it’s my voice and it sounds like me and it’s my language.

Steph: And then I get better responses typically when I do that, which is also really helpful. But it’s a good brainstorming tool. Don’t use it as your end all, be all strategy. That’s what I would say.

Gil: I like the idea that you, you mentioned of like. Having AI paint you a picture of what the vision could look like, because it’s one thing to be able to describe it and then show it to a client like, oh, actually this is what I had in mind. Um, I don’t know if you ever used nano banana yet.

Steph: Uh,

Gil: I would try that one.

Gil: Uh, anytime I’m generating images, I don’t do, I don’t use chat GPD anymore because I felt like all the images look. Really funky. Like they look very glossed, glossy, and it’s really obvious to tell. But, um, I, I use nano banana whenever I need to make changes or need to generate image. I just find that it’s, it’s a lot more realistic on things.

Gil: Um, and I think for your purposes it might not, might not make a difference altogether, but if you’re having to edit anything like the sky or something like nano banana is really good at that. Like if you’re taking a picture and you wanna like capture what the sky looks like on, on a really pretty night when it’s probably quite gloomy, nano banana actually does a phenomenal job at that.

Gil: It’s not to say you should not fake amenities, you should not fake moments that don’t necessarily exist. But if you are at a place where like you’re trying to create content but you just weren’t there at the right time, um, or there’s a car in the driveway that you really like, oh, you forgot to move.

Gil: Like, those are the types of moments like nano banana, like really excels at.

Steph: I love that. That’s fantastic. Great. I love it.

Gil: So now, kind of like in 2026, like what are the big things that you want to. Really double down on.

Steph: Brand strategy for sure. This will still be that year of really understanding well-rounded brand strategy, and we’re specifically, again, focusing on. Uh, we honestly have a lot of hosts that are like, listen, we have this one individual property. We know that this is going to be so much bigger. We wanna continue to grow it, and so help us build this sort of parent brand where all of our properties will live underneath and have a presence underneath that.

Steph: We’re also really focusing on the micro resorts and the boutique hotel side of things. So this will continue to be the year of brand understanding, messaging, and understanding how brand is woven into the entirety of the guest journey and experience, not just like. When they’re at your property and you slapped a logo on something, right?

Steph: So it’ll still be that. Um, still heavily focusing on email marketing and making sure we’re infusing SMS marketing this year too will be a, a crucial component of the overall marketing picture and then also social media. But what I was telling you, Gale, before we hopped on here, I realized that in this last year, one of the problems that we were not necessarily solving for our clients is, uh, content capturing.

Steph: So it was like, yes, we’re putting together this great social media strategy for you. Yes, we will handle putting reels together and posting on your socials, and we’ll execute the strategy and you will see direct bookings as a result. But we weren’t solving the, who’s going to get this content problem. And so now this year we are solving that problem and we are getting content for our clients.

Steph: That is what need, what the content needs to be for it to perform well on social media platforms specifically.

Gil: I, I, I, it’s, that’s a really good point. Like I’ve, I’ve onboarded a couple clients and they have a really strong vision. They have a really nice property, but the, the content doesn’t really kind of fall into place and we’ve, I’ve had to have discussions where, if I’m gonna be creating a custom site for you, you’re investing time and energy.

Gil: We’re, we’re, we’re investing time and energy on building a custom site for you. I wanna make sure that it shines. And I’ve had to go back and say, make sure that you allocate budget within this website redesign to make sure that you can upgrade your, your, your videos and your your photos. Um, because if you don’t, it doesn’t matter how many pixels like that, I, I can make pretty all around it.

Gil: Like, it’s not gonna make a difference if the content that you have in there does not, doesn’t inspire people to book with you.

Steph: Yep. Yep. Yeah, no, that’s so true and especially when we’re thinking about, you know, the way in which. I heard a statistic this past year at Boutique Telecon. It was a conference where I spoke, and I also got to be a participating audience member, but the statistic that was shared was like 60 to 70% of millennials are going to Instagram first to plan their next vacation, and I’m like, hello.

Steph: Opportunity, opportunity, opportunity. Because in this industry, what I find to be so interesting about the world of short-term rentals and, and this hospitality space in general, and you’ll get this from the e-com side, but this industry is like two to three years behind when it comes to marketing compared to most other industries that I’ve worked in.

Steph: And because of that, if you get started with social media this year and you have a really strong strategy and you have got great content and you’re leveraging influencers and maybe you’re leveraging paid ads. You’re going to blow it out of the water and you will see direct bookings as a result of those efforts.

Steph: But it’s not a, like, let’s just wait and, you know, wait till peak season situation. It’s like, no, start, just like stop making excuses and get it done.

Gil: Yeah, that’s a good point for, for us on this year. So we’ve learned a lot over this past year or so and we’ve, I think towards the end of last year we started working with hosts with much larger portfolios. In the very beginning, it was a lot of folks that have maybe a dozen doors. Um, and that was kind of our bread and butter and where a lot of our kind of.

Gil: Given templates. We had a handful at the be very beginning of the year. I think we had only started with maybe three or four at the beginning of last year. But over time we started realizing that folks wanted to represent their brand in different ways. They wanted different styling, they wanted to, to really have a different kind of feeling when you went on there.

Gil: So we ended up investing really, really heavily on our template library there. Um, and we’re still adding a few more, but what I realized is that like now we’re starting to ramp up towards. Really serving higher portfolios. So we have a handful, a large handful of clients that now have 60 to a hundred and 130 properties there.

Gil: And they’re now having folks like either marketing consultants like yourself, or they have full blown marketing teams and they’re like, I wanna do this, I wanna do this. So last year we saw this and we’re like, okay, we had to roll out our blogs. We ended up. Redoing a whole like blog hosting platform on it.

Gil: Built in house. Like we didn’t take anything off the shelf. And now I think this year. We’re spending a lot of energy on figuring out what are the right tool sets that we need to build into our platform. We have ambitions of being the platform for direct bookings, and that’s across different categories and we’re trying to figure out like where can we make the most impact?

Gil: And we were talking about this the other day, or just earlier before the call, like one thing I wanna do is like bring in all the elements that we learned from e-commerce. I want to bring in card abandonment directly into the platform. And I thought in the very beginning that it was gonna be a lot easier, but.

Gil: For folks that have hosted checkout, like for instance some of the PMSs, you are required to use their checkout pages to transact on things or to, to end up paying for the stay. And when we do that, we lose the ability to know, okay, we, we got someone through social media, we can track them there. We maybe even know like, which influencer actually like drove that traffic in there.

Gil: They went on the website, they searched for these properties. Then we punt them over to a PMS checkout when we now lose ability to know like whether or not that person converted or not. Because if they did not convert, I wouldn’t target them and I wanna target them with a very specific messaging. And right now we, we didn’t, we didn’t have the ability to do so.

Gil: And after like talking to so many different CTOs and product managers from those PMs, we now figured out a way to really make sure that we can have like full tracking on conversion across the entire suite of pmms. So like we’re going to be going back and really. Strengthening our platform and making sure that we can do that.

Gil: Because ultimately, like what I would love is for us, when you are working with a client and you’re working with them on their email campaigns, like one of those email campaigns should be card abandonment. Like yes, you wanna make sure that you’re nurturing folks, but there’s post, like when we think about like post-purchase experiences, we think about like the leaky funnels and how to bring people back.

Gil: I wanna really make sure that like craft estates is really there to help folks throughout the entire journey.

Steph: Yeah, it’s an definitely important. I feel like your background in e-Comm Gil is so helpful for this industry because you can see so many gaps that you learned in e-comm and now bring them into the vacation rental industry.

Gil: You say it’s two, three years behind? I think we’re much further behind than that, to be honest. Like Shopify existed 15 years before we started craft two estates.

Steph: Yeah, might, I might be being a little bit generous.

Gil: You are, you are. Awesome. Steph, it was so good to bring you back onto the show and really talk through kind of what you’ve seen in 2025 and really what you’re doing in 2026, and it sounds like it’s actually not a whole lot changed in terms of 2025 into 2026. It’s really doubling down all and all the learnings in 2025 around really centering around brand and helping more.

Gil: Owners, operators, property management companies really, really figure out like what their, what their brand is, what their messaging is, how are they gonna attack the market, and really how to create really inspirational content that makes people wanna book with them. And it sounds like you’re doubling down on that.

Gil: You’re also doubling down and figuring out how do you help brands really figure out how do they get the right type of content so that you can be, you’re not just on your website, but all over the place. You can contin continually to really. Dish out content that really resonates with folks.

Steph: Yeah, absolutely. It’s that and it’s also helping our clients be able to execute. Like it’s, we have, we learned so much in 2025 in terms of what. We needed to offer and how we needed to package things. And now it’s also going, okay, yes, you have this like beautiful brand guide and you have all of your brand assets.

Steph: Now how can we help you bring that to life even further? Right? How can we take it a step further? So adding in different pieces of brand collateral that our clients can go and have printed. We’re actually, you’re gonna appreciate this. I’ll have to share with you what we’re doing, Gil. We are creating, um, basically swag stores for each of our clients that they can come and buy merchandise that has their branding on it.

Steph: That is specific to their property. And so we’re creating that for them. They can come and order, and it’s kind of a like at cost situation where they’re just like buying it. We’re not handling any of the like printing or the inventory or any of that. We’re just the vehicle that you can purchase these things.

Steph: So it’s like done for you and you don’t have to worry about it. But we, uh, we’re, we’re building that out for clients. So definitely like just continuing to build out. And add more value to make host lives easier. Really like your life, easier if you’re hiring us for branding and marketing. We want it to be this all-encompassing, inclusive experience and that’s what we’re creating.

Steph: So we, our goal is to become the number one go-to branding and marketing agency in this space. So that’s, that’s my mission. I.

Gil: Yeah, and I think that because you have your own property management company, plus you have cabins on the Cumberland, that forces you to kind of walk through the things that. A host would go through, like you, I think you have a swag store for cabins on the Cumberland as well too. And you’re like thinking like, how do I enable this for our clients?

Gil: Um, so it’s, it’s amazing to have an operator that’s in the short-term rental industry, living, breathing, doing all that, and then now figuring like, how do I actually scale this and help others kind of on that same journey there.

Steph: Yeah, a hundred percent. Yeah. And Gil, you’re awesome. You’re crushing it. And I’m so excited for everyone who’s going to get on the CraftedStays platform this year and have a wildly different direct booking experience than maybe they do right now.

Gil: Yeah. Yeah. We usually end the show with three questions. I may have asked you these before, but it might be good a, a refresher. What’s a good book that you really enjoy reading, you enjoy sharing with others? What’s a, what’s one, what’s one that you would wanna share with us?

Steph: I would say unreasonable hospitality. It’s so funny that you’re asking this question because I. In 2025 had this goal to like read a book every month and do all these things and life just didn’t go that way. And I didn’t make it a priority to be honest. So I’m trying to change that for 2026. But Unreasonable Hospitality is one of those books that I think really deeply resonated with me and how we want to craft these experiences for our guests and how we go the extra mile and how we create these like surprise and delight moments.

Steph: And then for us on the branding side of things, it’s like how do we infuse that as part of our core values as part of the overall, like what is that defined brand experience? So unreasonable hospitality.

Gil: Awesome. I I have that one on my shelf. I haven’t gone through the whole book yet. And that, that’s actually one thing that I, I’m fought at. I can easily pick up a book and read a few chapters in, and then I get shiny object syndrome and I’ll look at the next book. And I don’t know if you’re in the SDR book club.

Gil: I am on the SDR r book club, so I get a book delivered to my doorstep every single month. And so I. Every, like every month I get another thing that I wanna pick up and read. So I haven’t finished Unreasonable Hospitality, so it’s a good push for me.

Steph: Yeah, it’s great. It’s a good one.

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

Steph: Don’t be afraid to share your vision, even if it feels big, and even if it feels scary, because you may find someone in your circle that wants to support you, wants to help, has a piece of advice, can connect you to somebody who can help you along the way. Just keep sharing. I mean, when we got into cabins on the Cumberland Gull, we were, again, we were seven weeks into this journey of short-term rentals.

Steph: And I started asking in Facebook groups about what it looks like to form partnerships. And people were probably like, wow, you are so new and you’re so green. And I’m like, I don’t care. Yeah. I am new and I am green and I’m here to learn and I’m gonna figure it out. And now we have a micro resort that’s done and I’m like, great.

Steph: Next deal. And we’re gonna. Continue to grow and scale that. And I have, I have learned a lot. I’ve, I’ve learned a lot, but because I shared the vision, we found all of our partners and this place is coming to life and we’ve hosted thousands of guests already and that’s really cool.

Gil: Yeah, it’s often very scary to to have. A big idea and then share with others and not knowing like whether or not you can actually do that, because it feels silly. Like, oh, I have this dream and I’m never gonna fulfill it. But like, if you don’t ever share it, it’s never, it’s never gonna happen. And I, I’ve had folks on the show that share.

Gil: People that they’re looking for things that they’re trying to do. And it’s interesting, they get like, I’ll get someone to DM me and they’ll like, can you make a connection? And it’s actually quite rewarding to be part of kind of that journey there. I actually might make that one of our, like, one of one of our questions that, that, that, that would be a neat one of like, what is the vision that you would want to wanna, that you have, that you wanna share with others?

Gil: That might be a good one.

Steph: do it. I love it. It is good. Yeah, it can, it definitely can feel a little bit scary, but it’s also. Like you gotta take that bold step and voice it out loud when you speak. Sometimes when you speak things out loud, you speak them into existence.

Gil: You’re manifesting. Yeah, that’s right. Awesome. Last question. You’re a very good person to ask one, add this one. What’s one tactical advice that you would give to someone that’s either trying to get started in direct bookings or trying to amplify the direct bookings?

Steph: Don’t sit on your marketing strategy like you. It’s great to have the site crafted. Stays is great. What you guys have built is great, but if you’re not marketing it, if you’re not telling people about it. If your guests know you as another Airbnb property, your direct booking site does not matter. So you have to have a marketing strategy in place.

Steph: Even if you’re just getting started with email marketing, which is lowest hanging fruit, and that’s where I recommend you do start. You have to, you have to do it or it’s, you don’t just have a website and expect it to do again, like what you said earlier, Gil, you know, it’s like we list on Airbnb, we see bookings roll in.

Steph: Okay. Like that’s awesome. That’s rewarding and instant gratification. I understand that. Direct bookings are not the same. You can’t just have the site and be like, the bookings are gonna roll in. Be responsible for marketing your brand.

Gil: Yeah. Yeah. And. Think more often now, like when I’m having onboarding discussions with folks, I almost now like I don’t stop if like, oh, now your website’s up and running. Like I now like steer them towards our podcast. I steer them towards our blog. I steer them towards you. Like, I wanna make sure that folks don’t feel like, oh, I now have my website.

Gil: I’m good, I’m done. I’m gonna walk away and now I’m gonna start to get bookings because I’ve seen too far often, and like that folks just feel like this is gonna be a sin and forget. It’s gonna be just like how they launch on Airbnb. They’re gonna put it up there and they’re gonna start getting bookings and that’s not the case.

Gil: The great thing is that direct bookings compounds over time. The, the energy that you put into it will pay dividends down the road. You may not see it in the first few months, but. Your follower account’s gonna go is gonna steadily grow. The way that you hone in on your messaging is gonna get better. Your Instagram followers may, may grow as well.

Gil: Like those things start to grow over time and start compounding on each other. But like it’s direct bookings is not one of those things that is said and forget. There are a lot of things that you could set and you can kind of walk away creating your nurture campaign. You set it once. You don’t have to worry about it for a little while until you wanna update it, but it still takes effort for you to do those things.

Steph: It does. It sure does. Yep. So either do it or hire someone to do it for you.

Gil: yeah, yeah. Hire someone good. Hire someone. Good. Don’t, don’t just take anyone off the street.

Steph: True, true.

Gil: Awesome. Steph. It was a huge pleasure having you on the show, helping us kick off 2026. It’s going to be a fabulous year. I’m looking so forward to it. Huge thanks, and I can’t wait to talk to you again.

Steph: Thanks, Gil. I’m so stoked for what this year brings.

Gil: Awesome. Talk to you later. Bye.

Steph: Bye.