Dawn LaMattina Asher is the founder and creative director of The Olive Jar, an experiential marketing studio focused on vacation rental design, amenities, and media content creation for visionary hosts. With 20 years of experience in experiential storytelling across entertainment media, hospitality, and brand marketing, Dawn helps hosts transform ordinary stays into unforgettable guest experiences that foster loyalty and connection. “Experiential marketing builds brand loyalty.” That’s the powerful truth Dawn shares in this value-packed conversation. More than good design or amenities, what your guests feel during their stay creates lasting emotional bonds with your brand. We dive deep into what makes a stay memorable and how those emotional experiences convert into direct bookings and repeat guests. 🔍 Key Takeaways for Direct Booking Success 1. Experiences = Loyalty“The stronger the bond, the longer they’re gonna stick with you. That’s brand loyalty.” Emotion is the anchor of memory. Dawn shows how sensory-driven design and subtle storytelling throughout a home can turn guests into lifelong fans. 2. Co-host Marketing PitfallsMany co-hosts or management companies claim they offer marketing, but it often stops at SEO and pricing tools. According to Dawn, “Marketing is so much more than social media.” 3. Brand Clarity Before DesignBefore even placing a bed frame, hosts should define their brand voice and ideal guest. Dawn’s team creates branding guides that set the emotional tone for the entire guest journey. 4. Visuals Are Non-NegotiablePhotography and videography aren’t just visual assets—they’re storytelling tools. Dawn emphasizes, “We’re never layering in amenities without thinking how it’s going to be photographed.” 5. Give Guests a VoiceOne of her favorite tools? A dog guestbook where owners write from their pet’s point of view. “When you give someone a voice, they suddenly have ownership over the experience.” 🧠 Rapid Fire Questions 📚 Book Recommendation: JOYFUL: The Surprising Power of Ordinary Things to Create Extraordinary Happiness by Ingrid Fetell Lee 🧭 Mindset Advice: “Generosity is generative.” 🛠 Tactical Tip for Direct Bookings: Know the story you’re trying to tell. You have seconds to make that first impression on your site. 📲 Follow Dawn Here: Want to stop relying solely on OTAs? This episode is a masterclass in connecting your design and storytelling to build brand equity. If you’re ready to invest in your guest journey, you’re not alone. 👉 Join the CraftedStays community for more episodes, resources, and personalized support on your direct booking strategy. Let your next guest feel something worth remembering. And if you loved this episode, share it or tag us with your top takeaway! 💬 Transcription Dawn: A phrase I haven’t mentioned yet, but is wildly an important part of this. It’s really the core of what we’re doing is that experiential marketing builds brand loyalty. And as you invite and engage your guests into the experience that they want to create, right, they’re building a bond to your brand. Dawn: The stronger the bond, the longer they’re gonna stick with you. That’s brand loyalty. It’s a lifetime. It’s a relationship that is built over a lifetime. I say that emotions are the essential to connectedness and hosts who lean into that, they’re gonna build a loyal following. Gil: Hey folks. Welcome back to the Bo Solid Show, the podcast where we bring on top operators to discuss marketing, revenue management, and guest experiences to drive towards being Bo solid. On today’s show, I have Don LaMattina Asher. She’s the owner of the Olive Jar and STR consulting firm that specializes on crafting lasting guest experiences. Gil: On today’s show, we have a very fun show, really talking about experiential marketing, which is really her focus. We talk about really the entire guest journey and how we can really think intently. About the experiences that your guests want to have and turning that to really crafting that through seating. Gil: we also talk quite a bit about the importance of some of those smaller details. We went into great depth, much more than I would have expected on this show, so I’m really excited to have her on. So without further ado, let’s bring her in. Gil: Hey Dawn, welcome to the show. Dawn: Hi, . Great to be here. Thank you for the invite. Gil: Yeah, I’m so happy to have you on the show. For folks listening in, this is Dawn Laina Asher. I met her at Level Up Your listing and I, we just had a follow up conversation and we just really hit it off. So I’m really happy to have her on and really share really what she’s doing specifically in our industry. Gil: But I would love for you, Dawn, to introduce yourself. Who are you? Dawn: Yeah. So yeah, I am the founder and creative director of the Olive Jar. We are an experiential marketing studio, special specializing in vacation rental design amenities and media content creation. And we say for visionary hosts, because the work that we’re doing, um, is quite nuanced. And so we work with hosts who are really thinking on a, on a different, uh, in a different dimension of hosting. Dawn: And that layer of connectivity with their guests and their traveler, um, that really is, is not, uh, the status quo. So we say visionary host and we really pride ourselves in that. Gil: Yeah, and I think like nowadays, at least the folks that I’m starting to, to be surrounded with are hosts that are actually graduating from just seeing the properties as investment vehicles and they’re trying to build stronger brands and they’re trying to be a lot more independent from the OTAs as part of that. Gil: So I’m guessing that you’re actually starting to see a shift in the industry towards being that visionary host or trying to like get towards that in, in some phase. I’m not sure if you see the same trend on your side. Dawn: Oh yes, for sure. And, and I, I love it. I’m, I’m, I’m all for it. And,

On this episode of the Booked Solid Show, Gil is joined by Kim Herrlein, the Chief Leisure Officer of Purveyors of Leisure. Kim is a short-term rental operator who has mastered the art of large group travel through beautifully designed estate properties in California’s Coachella Valley. She recently expanded her hospitality vision by launching The Fainting Couch, a boutique hotel in Northern California’s wine country. In this episode, Kim shares her journey from real estate investor to STR operator, and now a boutique hotelier, with a focus on curating seamless, luxurious experiences for her guests. Whether it’s hosting multi-family gatherings at her spacious estates or redefining boutique hospitality with a contactless model, Kim’s approach is rooted in understanding her ideal guest avatar and crafting an unforgettable stay. She also dives into her strategies for direct bookings, guest nurturing, and her belief in elevating hospitality through thoughtful design and personalized service. Episode Highlights Rapid Fire Questions: AI, Technology, and the Future of STR Towards the end of the episode, Gil shares his insights on the role of AI in the STR industry. He highlights two main areas where AI is currently making an impact: “For me, AI has shifted from feeling like an agent to feeling like a collaborator.” — Gil Gil also shares his own journey in building an AI assistant that aligns with his personal goals and business operations. His vision? To leverage AI for intentional living and smarter business practices. Looking for an exceptional stay that goes beyond the ordinary? Discover the luxury and thoughtful service at Purveyors of Leisure and The Fainting Couch. From estate properties designed for large groups to exclusive boutique experiences, Kim and her team elevate every stay with personalized hospitality and seamless service. Visit Purveyors of Leisure | Visit The Fainting Couch Connect with Kim here: Transcription Gil: Hey folks. Welcome back to the Booked Solid Show, the podcast where we’re bringing top operators to discuss marketing, revenue management, and guest experiences to drive towards being booked solid. On today’s show, I have Kim. She is an STR operator with properties in Coachella Valley, or the Palm Springs region. She has really large estates, which sleep anywhere from 16 plus to 20-something guests, and she’s really dialed in and figured out how and what her guests are looking for, specifically the person that’s booking. Some of the conversations that we go through are really around the service of really how do you think about that guest, what they’re going through, and the service that you want to provide. We go into a pretty deep conversation, specifically about this and specifically about her avatar as a reference point. Some of the things that we’ll kind of get into is really knowing that a guest that is coordinating between 16 different people, how do you actually craft the services for that? So she has, for instance, onsite staffing to make sure that the guest that is booking is really hosting for the rest of the family and has everything that they need. She also talks really about what it is, the feeling that that person has, how she really messages that person both before and after the stay, really understanding that guest avatar. So she is a person that really has dived deep into really understanding the ideal guest avatar at a different level.At the very end, we also talk a little bit about AI and how it’s being used in both our industry and AI in general. So this is a really fun show. I’m really happy, happy to have her on here. So without further ado, let’s bring her in. Gil: Kim, welcome to the show. Kim: Thanks, Gil, for having me. Gil: Yeah. I’m so excited to see you at the summit in a little bit. I don’t know when this show is gonna air, so this may air before or after that. But I’m excited to just meet a lot of the hospitable hosts over there. Kim: I know! It’ll be nice to finally connect in person with a number of people. Gil: Yeah. Yeah. I’m excited for that. It’s amazing. It’s amazing how much of the industry that you just meet remote. And I don’t know if this would’ve happened if the pandemic didn’t happen, but like, I felt like the pandemic has really opened up everybody’s ease to meet someone and get personable with someone even though they don’t get to see them. Kim: Absolutely. And it’s amazing. There are a lot of horrific things that came out of the pandemic, but there’s also a lot of great relationships that were built along the way too. Gil: Yes. The way I got involved with Hospitable Hosts was completely through Julie George from Clubhouse Days with Jody. It’s amazing what it’s grown to, and having been an author in the first volume and now seeing where it’s gone, it’s exciting. Kim: Yeah, I think that’s probably a good segue into just kind of giving folks an introduction on who you are. So Kim, do you mind giving folks a glimpse of who you are? Kim: Sure. I started Purveyors of Leisure about 10 years ago. We just celebrated our 10-year anniversary, and I wound up in this industry accidentally. I think that some of you may resonate with that. I said yes to a friend, a dear friend of mine who was a real estate investor. I also was a real estate investor and had my, you know, what handed to me in ’08 and was a little bit nervous about investing again.But I was certainly a hell yes when it came to looking at properties and designing them. And so it started off with literally my good friend asking me to look at some properties with him. And it was in the Coachella Valley, and the first property that he purchased was across the street from Coachella Music Festival.And soon we learned what an incredible opportunity and incredible margins we were dealing with in this, in this particular valley, Palm Springs. As some of you

In this episode of the Booked Solid Show, we sit down with Jay Ulrich, CEO and Co-Founder of HostBuddy AI, the platform that’s shaking up the short-term rental industry. Jay is a property manager turned tech innovator, known for transforming his 50-unit portfolio in San Diego into a blueprint for smarter, more resilient hosting. With a deep understanding of the challenges hosts face from OTA over-reliance to endless guest messaging, Jay built HostBuddy AI to give hosts real control over their business. His approach blends laser-focused niche strategy with cutting-edge AI to boost direct bookings, streamline operations, and enhance guest experiences. Whether you’re a solo host or scaling a full-blown STR empire, Jay’s insights will change how you think about tech, hospitality, and growth. This episode is your backstage pass to the future of property management one where hosts call the shots. Summary and Highlights Jay Ulrich, CEO and Co-Founder of HostBuddy AI and COO of Select Stays, is on a mission to shake up the short-term rental (STR) industry. After launching his own property management company in 2021 and scaling it to 50+ rentals across San Diego, CA, Jay saw firsthand the cracks in the system—especially the dangers of relying too heavily on platforms like Airbnb. That experience inspired him to co-create HostBuddy AI, the market-leading messaging platform built to streamline guest support, slash operational costs, and empower hosts with smarter, tech-driven solutions. Today, Jay is redefining what success looks like for property managers by helping them take control of their bookings, their brand, and their bottom line. 🛠️ Game-Changing Lessons from Jay 🔥 Turning the Tables on Airbnb 🎯 The Magic of Micro-Niching 🌐 Tech + Hospitality: The Perfect Blend 🚦 The Roadmap: From STR to Boutique Hotels 🛎️ Lessons from the Trenches 🚀 3 Power Moves to Steal from Jay Jay Ulrich’s vision is crystal clear: empower hosts with tools that don’t just work they win. Whether you’re a solo host or scaling a property management empire, Jay’s blueprint is all about control, consistency, and growth on your own terms. 📲 Connect with Jay Ulrich: 📞 Phone: (240) 357-6127 📧 Email: jay@hostbuddy.ai 🔗 Instagram (Personal): @jaytullrich 🔗 LinkedIn: Jay Ulrich 🔗 Instagram (HostBuddy): @hostbuddy_ai Transcript: Jay: Make sure that you don’t send retargeting messages directly through Airbnb so that Airbnb sees it, because we did that a few times at the very beginning, and they will immediately remove your listing. So that puts you in a kind of a bad position. You gotta be kind of sneaky about it, but if you wanna look for direct bookings, find a way to collect that. Guest information. There’s a lot of cool tools out there. Guidebooks, the phi. Great, great tool. People can collect their information for direct bookings. Find a way to retarget these guests, ask them for their information, and that way they can feel like they’re, you know, part of something, part of your business, and that they know you personally and then they’re happy to consider you and they come back to, to the city that you’re hosting in. Gil: Hey folks. Welcome back to the book Solid Show, the podcast where we bring in top operators in the STR space to share their experiences in marketing, guest experiences and operations to get books solid. On today’s show, I have JO Rich, he’s the founder and CEO of host Buddy ai. I met him last year at the STR Nation Conference. At that point, he was just starting off his company. He was just growing it. And what they’re really trying to do is really help host automate their guest messaging so that they can spend more time on other things and have a very consistent guest experience. I have seen and have used their product. It’s a very phenomenal product. In this show. We get to pick apart why he started the company in the first place, where the problems that he wanted to solve, how he has built host buddy, and why it’s different than some of the other Chi Chat agents and kind of where he sees AI going, where he’s taking the company. And some of the things around direct bookings as well too. Jay is actually going to be a customer of ours pretty soon. He’s gonna be building his direct booking stack on top of craft his days, and he’s looking to collaborate together on how direct bookings and his chat agents are able to kind of work together. So tune in on the show. I think there’s a lot to, to kind of dive into and learn about really AI in general by someone that’s specifically building AI for the industry. So I’m excited to have him on. Gil: Hey Jay, welcome to the show. Jay: Thanks, Gil. Appreciate you having me. Gil: Yeah. I’ve seen you a bunch of times at many different conferences. I know you just came back from, uh, from your leg abroad. Um, so definitely welcome to the show. Um, for folks that don’t know who you are, do you mind giving, uh, folks an introduction on who Jay is? Jay: Yes, so I am a property manager first. It’s usually how I introduce myself because. It’s probably the most important part of everything that I’m involved in. It’s, it really fuels my, um, you know, my vision for creating the software that I’m involved in and also the business. Um, so kind of taking it back to where I got introduced to short term rentals as in 2021, um, I began managing. Jay: Short term rentals in San Diego, California with my business partner, Sam. Um, I started as a civil engineer right outta college and just tried to find a way to kind of get outta that. I really wanted to own my own business and take it a different direction. Um, and short term rentals was that path for me. Jay: So in about nine months, I was able

In this episode of Booked Solid, Amy Corbett reveals how she’s transforming quirky spaces like vintage train cars and grain bins, into sought-after escapes. Discover how her brand, All Belong Co., is redefining what it means to be a host by creating inclusive, unforgettable experiences that go beyond the ordinary. From harnessing niche communities to building direct bookings that aren’t dependent on Airbnb, Amy’s journey is all about breaking the mold and making guests feel truly at home. If you’re ready to take your STR game to the next level with bold, one-of-a-kind stays, this episode is for you! Summary and Highlights 🎤 Meet Amy — Founder of All Belong Amy is the founder of All Belong, a distinctive accommodation brand inspired by her personal experiences and her family’s journey. She has transformed her life and business by focusing on creating a space where everyone feels like they truly belong, despite being different. From her daughter’s battle with alopecia to offering one-of-a-kind stays like a 1950s train caboose and a grain bin lodge, Amy is not just about providing a place to stay—she’s about creating a community. Her vision goes beyond booking platforms like Airbnb, aiming for direct bookings and personal connections. 🧠 What You Can Learn From Amy Building a Brand from a Personal Story 🏠 Tapping into Niche Markets 🚂✈️ Leveraging Local Networks for Direct Bookings 🌍 Manifesting Success and Consistency 💭 Networking for Growth 🤝 Her Book Recommendation 📚Amy recommends “The Gap and The Gain” by Dan Sullivan. This book teaches the powerful concept of measuring progress not by where you fall short (the “gap”) but by how far you’ve come (the “gain”). For Amy, this book has inspired a daily habit of reflecting on three wins every day, keeping her mindset positive and focused on growth. 🌐 Connect with Amy Corbett 🌐 Follow All Belong Co Transcript Amy: This is something I think all of us as hosts, if we’re not doing it, we should be doing it. So, you know, a lot of things are, sometimes it’s just throwing spaghetti on the wall and just try things. And one of the things that right now I’m trying is that leveraging the skills of other people to help us get more visibility and get our brand more out there. Amy: So I would say going after direct bookings can take a number of different paths and. I’m reaching out. I’m not thinking I have all of the answers to get them, but I wanna be, be wise and see if the other people that are out there to, to help me with this, if they can help me. Gil: Hey folks, welcome back to Book Solid. The podcast where we interview top operators in short-term rental industry to share their secrets on how their book solid. On today’s show, I have Amy Corbett. I met Amy at Level Up Your Listing, and she has an amazing story. I had so much fun interviewing her. I think you guys will really enjoy this episode as we kind of walk through how she has progressed in her short term rental journey, some of the projects that she is digging into, and how she approaches direct bookings and SDR marketing in general. Gil: I think. You guys will get a lot of value out of this. Her story is just amazing. The properties that she’s building out are unlike what I typically hear. So it’s amazing just how she thinks through some of these projects and some of the more unconventional ways on how she even found some of these. Gil: So I think you guys will really enjoy this. So let’s bring her in. Gil: Hey Amy, welcome to the show. Amy: Thanks so much, Gil. It’s great to be with you. Gil: Yeah. I met you last week at the Level Up your listing, uh, summit or conference, and I immediately knew that I wanted to have you on the show to talk about many different things. We’ll, I won’t spoil it right now, but you have some pretty unique properties that I want you to. To talk to me about what’s, what’s going on in there. Gil: Um, so it was a huge pleasure to meet you last week. Was it last week? Maybe two weeks now. Uh, a few weeks back. Amy: Yes, Gil: it’s great to record with you now. Um, maybe to kind of kick us off, do you mind introducing yourself to, to our listeners? Amy: sure. Yep. So my name’s Amy Corbett. Um, my business name is Lanco. We have 45 properties in our collective. Um, only four of those are my personal ones. So we’re managing for a lot of homeowners and around 25 of those are in the Lynchburg, Virginia area. Um, we just picked up 13. Two hours down the road in Hot Springs, Virginia. Amy: And then we’ve got a few that are like sprinkled throughout the country. So, you know, one outside of Memphis, one in Ohio on a lake, and just kind of some, um, standalone places. Gil: That’s amazing. And how, how long have you been hosting now? Amy: We officially started as a business, um, January 1st, 2019. Gil: Wow. Okay. Okay. So you, you got in right before the, the big pandemic waves then. Amy: we did. Yes. And you know, that was so scary because we all thought everything was gonna, you know, collapse for us. It ended up being Gil: opposite. Amy: Yeah, exactly. Gil: Yeah. That, that’s funny. Where, yeah. I think a lot of folks, um, I think a lot of folks got in like 2020 right? When things started to pick up. But I do remember very early on the folks that were investing prior to that, um, they weren’t sure whether or not they could even rent out their place because Airbnb was pulling listings off or bookings down. Gil: Um. Because they didn’t know whether

In this episode of Booked Solid, Jamey shares his approach to building a thriving STR business through strategy, consistency, and intentionality. From choosing one big idea at industry events and turning it into tangible results, to leveraging guest psychology, dynamic pricing tools like PriceLabs, and review engagement, Jamey outlines what it takes to rise above the competition. If you want to stand out in a crowded market and make your marketing actually work, this episode is full of takeaways you can put into action. Summary and Highlights 🎤 Meet Jamey King — Senior Marketing Executive at eviivo Jamey King is a Senior Marketing Executive at eviivo, where he brings deep expertise from years in the vacation rental and short-term accommodation industry. With a background that includes leadership roles at Sony Electronics, VRMA, PointCentral, and Safely, Jamey has shaped strategies in business development, partnerships, and marketing across the board. Now based in Indiana, he leads efforts to grow eviivo’s brand awareness and bridge its presence across European and U.S. markets. 🧠 What You Can Learn From Jamey 🌐 Connect with Jamey King 📧 Email: jamey.king@eviivo.com📱 Phone: 317-629-6100🌐 Website: www.eviivo.com Follow eviivo on Socials🌟 Facebook🐦 Twitter📸 Instagram🔗 LinkedIn📺 YouTube Transcript Gil: Hey folks, welcome back to book solid, the podcast where we bring on top operators onto the show to break down the elements to keep you book solid. On today’s show, I have Jamey King from Avivo. In this show, we break down how he thinks about PMS is and how they serve their hosts, their customers. We also talk about some of the things that Avivo specifically is doing to really help operators maximize their returns specifically in . It’s not what you expect. I was expecting to hear more things around AI and they’ve already been doing a few things, but they’re thinking about things more from the traditional product management point of view of really some of the needs for some of these smaller operators there. And lastly, we talk a little bit about the guest journey and really what does it mean to understand what the guest journey looks like and the impacts that it has on your marketing and some of the things you should be thinking about as you’re trying to go into direct. All right, so without further ado, let’s bring them in. Gil: Hey Jamey, welcome to the show. Jamey King: Hey, thanks for having me. Gil: Yeah, it’s good to, good to, good to meet you. well, kind of to kick things off. Do you mind kind of giving folks that introduction on who you are? Jamey King: Sure, happy too.  And number one, thank you for having me. Jamey King for everybody listening or watching. I’ve been in the industry for almost  years, hard to believe. I started out with Sony Electronics. And basically my story is I was in charge of all the Marriott’s and all the branded hotels and selling clock radio. So at one point I used to tell my friends whenever you go to a hotel and you see a Sony clock radio that probably came from a relationship I had at that property. So that was fun to get me into hospitality. then I transitioned and went over to the VRMA, which is the Vacation Rental Managers Association. They were looking for a business development manager. And luckily for me, they chose me. And really I started planting my roots, my seed into this industry. And really growing and I love it because you what it was is that you had the ability to learn about you know, what about relationships right every single person that is in this industry is in it because there’s relationships relationships with their peers that are also property managers or the relationships with their guests right and keeping that that guest journey in place and looking to how do I continue to evolve over time and you know the exciting part about hospitality is you’re consistently seeing the advent of technology. And in my period of time in this industry, we’ve seen a lot of changes, but changes for the good when it comes to automation and really streamlining the day-to-day operations. I am now, fast forward  or years, I’m the Senior Marketing Manager for Avivo. We’re a London-based company. My territory is a very small North America. So that doesn’t take up much time looking at Canada and of course, North United States. And I’m excited because Avivo is really a wonderful company that has a unique story that a of people don’t know. A lot of people don’t realize that Avivo has been around since . We actually, you know, we offer the ability to manage reservations. We can do online distribution, seamlessly connect to all the OTAs. We can help you with your guest communications. We can do channel management, integrate your payment systems. And of course, we provide revenue management tools. So what does that mean to you, Gail, and to the listeners? Well, that’s about , different accommodations with over , bookings per month on the Avivo Suite platform. Gil: That’s impressive. That’s impressive. It sounds like I was wondering where the Sony connection actually went back into short term or vacation rentals. And I didn’t pick it up until you just said it where you are at Sony under the consumer electronics division getting into hotels. And that’s kind of your entry point into this whole can of worms that you committed your last  years into. Jamey King: Yeah, it’s amazing. I started out as a national trainer for Sony and then I got into sales and I had a mentor, what a great mentor, who said, you know, there’s an opportunity for you here with this little kind of redheaded stepchild division of Sony that nobody really manages, but you’re young, you’re flexible. Why don’t you come over here? And I said, well, you what does this mean? know, Jimmy, what does this mean? And he’s like, well, it’s

Recently, I had the pleasure of being interviewed by Avery Carl on The Short Term Show. This interview was even more special because Avery and her team were kind enough to agree to a crossover episode for Booked Solid to spotlight direct booking strategies and tools that help STR hosts take control of their business. We discussed a topic near and dear to my heart: building sustainable, long-term success through direct bookings. While we covered a lot, I want to share a few takeaways that I think will especially resonate with hosts. Building a Direct Booking Site in 15 Minutes. Here’s How…. Summary and Highlights Why Direct Bookings Matter (And Why They’re Hard to Start) One of the things Avery and I both agreed on: direct bookings aren’t just about saving on fees — although that’s certainly a benefit. It’s about regaining control. “When you build a direct booking site, an email list, and a social presence — you’re building something that compounds over time.” But let’s be honest — the barrier to entry can feel high. I tried building my first direct booking site on WordPress, and it took me four weeks. It looked good, but it wasn’t integrated with my PMS, and it wasn’t scalable. That’s when I knew there had to be a better way. Tips for Getting Started with Direct Bookings Whether you’re just exploring the idea or knee-deep in building your own site, here are a few lessons I shared during the episode: 1. Start before you’re “ready.”You don’t need to be tech-savvy. Use what your PMS gives you, collect guest emails, and build from there. Every early action compounds later. 2. Focus on mobile performance.We found that nearly half of our traffic comes from mobile devices — but most bookings still happen on desktop. That means mobile is where first impressions are made. If your site loads slowly or doesn’t feel “native” on a phone, you’re leaking trust. 3. Use your past guests to power future stays.I shared our 12-month nurture sequence we built inside Klaviyo. It took a couple of days to set up, but now it’s automated — sending tips, travel content, and a special offer around month 9, just in time for rebooking. 4. You don’t need to go it alone.During the episode, we talked about the power of community. Whether it’s two or three friends or a mastermind group, having people you can bounce ideas off of can be game-changing. What About Google Vacation Rentals? Avery brought up a great point: one of the biggest reasons to have a direct booking site today is to get listed on Google Vacation Rentals. While it’s still early days and the traction is light, we both agree: if Google leans in the way they did with Google Flights and Hotels, it could seriously disrupt the OTA space. Just know this: Google won’t send traffic to Airbnb. They require a true direct booking site. Rapid Fire Questions At the end of the episode, Avery hit me with three rapid-fire questions we ask every guest: What advice would you give 20-year-old Gil?Take more risks. It’s way harder when you have a family and a mortgage. Starting this company has taught me more in the last year than I ever expected — and I wish I had made a leap like this sooner. What advice would you give a new STR investor in 2025?Find your tribe. Don’t go it alone. Even a small circle of smart, generous hosts can help you navigate decisions faster and more confidently. Favorite book that’s impacted your mindset?Definitely Start With Why. Knowing your purpose makes decisions easier. For me, this business was born out of my own pain as a host. That keeps me centered every day. Conclusion If there’s one thing I hope listeners take away from this conversation, it’s this: direct bookings aren’t just a nice-to-have. They’re the future. But it’s not about perfection. It’s about momentum. Start small, start scrappy — just start. If you haven’t listened to the full episode yet, I’d love for you to check it out. It’s a special one — a true collaboration between The Short Term Show and Booked Solid. 🎧 Listen to the episode here Building a Direct Booking Site in 15 Minutes. Here’s How…. If you’re looking for tools to make the leap into direct bookings faster, easier, and way more optimized — that’s exactly why we built CraftedStays. We’re a platform built by hosts, for hosts. With PMS integrations, beautiful templates, and mobile-first performance — you can go from setup to a live site in 15 minutes. Seriously. 🗓️ Let’s talk about your property! Book a call with me today, ⁠here⁠ Transcription Gil: It’s not like you’re gonna be able to build out your website and you’re able to drive traffic to it and get bookings immediately. It takes time for you to build that engine there. The, the earlier that you start, the easier it gets to, to that point where you actually can drive significant amount bookings. And I think the realistic goal is like in two to three years, you should be able to get 40, 50, 60, 65, 80% direct bookings. So the earlier you can start in that journey, the easier that you’re able to be much more independent. Hey folks. Welcome back to Booked Solid, the podcast where we interview top operators in the short-term rental industry to share their secrets on how they’re booked solid. On today’s show, it’s gonna be a little bit different. I’m actually going to be collaborating with Avery Carl from the Short-Term Rental Shop. Uh, I’m excited to share this episode with her because she had a chance to interview me on why I ended up starting CraftedStays in the first place. How we’re thinking about things differently, uh, in terms of direct bookings and really how to leverage the best tools possible. Um, so I had a lot of fun recording this with her. It’s actually very interesting and nice to be on the other side

When it comes to growing a short-term rental business, many operators rely on online travel agencies (OTAs) or job boards. But Owen Johnson, took a different route through Direct Bookings. In this episode of Booked Solid, Gil dives into Owen’s unconventional approach to direct bookings, where the focus is on building systems and loyalty that don’t depend on third-party platforms. Owen shares his journey of growing a thriving remote team, mastering pricing automation, and crafting a seamless guest experience that keeps customers coming back for more. Summary and Highlights 🧑‍💼 Meet Owen — Founder, CEO, and STR Operator Owen runs a short-term rental business that he built from the ground up. What started as one property has grown into a remote-managed portfolio, thanks to a strong team, solid systems, and a clear focus on what works. He’s not just a host—he’s built a company that helps others succeed with STRs. His approach combines smart tech, consistent marketing, and hands-on team management—even while working from a boat off the coast of British Columbia. 🔑 What You Can Learn From Owen 1. Tech Stack & Tools That Work 2. Hiring & Managing Virtual Assistants 3. Direct Booking Done Right 4. Early Investment in Marketing 5. Running the Business with the Right Mindset 6. Book That Shaped His Thinking 🌐 Connect with Owen Johnson 📧 Email: ⁠team@nwpads.com⁠ 📞 Phone: (425) 516-7928 📸 IG: ⁠@northwestpads⁠ 🌐 Website: ⁠www.nwpads.com Transcript Owen: To build businesses, you know, don’t be afraid to fail. ’cause I’ve done a lot of failure too. I’ve failed more than I’ve succeeded to get where I’m at today. So you have to stick your neck out there. You have to build grit with it at the same time and get a thicker skin in the process. So my idea would be, you know, be dedicated. Don’t let somebody else build it for you. Build it yourself. Own your decisions. You know, there’s a lot there. I mean, there’s not one piece of mindset, but other than the fact is those are your dollars and you don’t, you’re not rich by giving it all away. You have to protect your money. You have to protect your people ownership mentality. There you go. That’s the one piece of mindset I. You’re not an employee. This is your business Ownership mentality is a state of mind, and when you’re brand new in business, you better have it. Otherwise your business will fail. If you treat your business like you’re an employee, you’re gonna be an employee for somebody else. Good. Gil: Hey folks. Welcome back to Book Solid. The podcast where we bring in top operators to share their strategies, to help you maximize your booking, scale, your revenue, and stay ahead of short-term rentals. On today’s show, I have Owen Johnson. He’s actually a new client of ours that we brought on, uh, to craft his stays. I wanted ahead to, to come to the show because he has grown his social following and he has just a, just a. Interesting story on how he’s approached things, the learnings that he’s done along the way, uh, how he grew his account to 46,000 followers, and how he’s leveraging that now that he’s. Broaden in that following. And we’ll also talk about some of the things that he’s doing along the side around the technology. Uh, now that we’re implementing a site, we get to approach things like advertising, uh, retargeting ads, conversion funnels. So we’ll talk a a bit into really how he’s thinking about his tech stack, uh, and how we’re leveraging the new platform together. So I’m really excited to bring him onto the show and I hope you guys enjoy it. Gil: Hey Owen, welcome to the show. Owen: Hey Gil, how’s it going? Thanks for having me on. Appreciate the, the get together here today. Gil: yeah. I’m excited to have you on. Uh, we met a couple weeks back, uh, because we were doing a, an onboarding call and I was just looking at your portfolio and I immediately knew that you are a customer that I wanted to work with, and I also wanted you to be, uh, be on the show and kinda share your knowledge on, on what you’ve done as well too. So I’m excited to have you here. Owen: Yeah, yeah. Great, man. No, I was really impressed with, uh, your, um, your portfolio, how you guys do your websites and stuff and the way you reach back and showcase the build and stuff like that. So I’ve, uh, gone through quite a few different builds on websites since I started my journey. And, um, I could see that the talent was there and, and that, you know, you understood the deliverables that everybody’s really looking for. And a lot of times we don’t see that. So, Super excited to work with you. Gil: I appreciate that. I think one of it has to do with just, I think two things. Like one, us being hos ourselves and, and knowing what you’re trying to do with the websites. It really helps understanding like what you’re trying to communicate. And I, the second part is like, I still onboard almost all of our clients, so I get to talk to hosts all the time. I, I get to see the best of the best and in terms of the websites and what people were trying to build and what you’re trying to get to. So I was super excited to kinda help showcase your properties, because when I saw your, I actually, I think it was your Instagram feed. I just saw some really beautiful properties and the way that you are able to communicate that story there through your social profile, that was really impressive. So definitely I wanna have you talk about that and I think like, because of that, I, I wanted to make sure that I showed you what we can do

When most people think about real estate agents, they picture the transaction — the showing, the contract, the close. But for Tyler Coon, it’s just the beginning. On this episode of Booked Solid, Gil sits down with Tyler, founder of Savvy Realty, a nationwide real estate team laser-focused on helping investors buy (and succeed with) short-term rentals. What sets Tyler apart isn’t just his knowledge of STR markets or his deep portfolio of investor clients — it’s how he turns a real estate purchase into a launchpad for long-term profitability. This conversation goes beyond the sale — into operations, trust-building, design strategy, and the critical role of direct bookings from day one. Summary and Highlights 👤 Meet Tyler Coon Tyler Coon is the founder and CEO of Savvy Realty, a nationwide team of short-term rental agents known as Savvy STR Agents. Based in Asheville, NC, Tyler has specialized in short-term rental investment real estate since 2019. What started as a solo passion quickly scaled into a full-service operation helping investors acquire high-performing STRs across the country. Now with a presence in over 20 markets nationwide, Tyler continues to expand Savvy’s footprint — aligning clients with smart, profitable opportunities and supporting them long after the sale. 🧠 Key Takeaways from This Episode 1. Treat the Purchase as the Starting Line, Not the Finish Tyler doesn’t just help clients “buy a house.” He helps them understand if they’re ready to operate an STR successfully. That means: 2. The Best STR Agents Know the Whole Game With access to real-time revenue data, local vendor networks, and design professionals, Tyler ensures his clients aren’t flying blind. 3. Direct Bookings Should Start From the First Stay Whether it’s capturing emails with StayFi or hiring influencers to drive traffic to a direct booking site, Tyler believes in planting the seeds for independence early. “Guests are making core memories at your property. Why wouldn’t you want them to come back — directly?” 🔁 Direct Bookings in a Changing OTA Landscape Tyler doesn’t mince words about what’s coming: “If you’re not building a direct booking strategy now, you’re going to be behind. Airbnb’s algorithm will be pay-to-play before long.” Tyler’s long-term vision? Market-level direct booking sites — collaborative platforms that bring the top listings in each region together, owned and promoted by the operators. (Spoiler alert: we may be partnering on that very thing in Asheville soon.) ⚡ Rapid Fire with Tyler What’s one mindset shift you’d share with someone new? “You’re going to screw it up. Forgive yourself early and often. Make the repair, then move forward.” What’s one book that changed your life? Rocket Fuel – “It helped me understand that I’m a visionary. I need integrators around me to execute.” What’s one tactical move to grow direct bookings? “Collect every guest’s email — StayFi, emails at checkout, whatever it takes. Then send a video after their stay with a discount code and your direct booking site.” 🎯 Final Thoughts: It’s More Than Real Estate Tyler’s approach is a masterclass in long-term thinking. It’s not about the closing table. It’s about helping investors build something that works — not just today, but years down the road. If you’re ready to get serious about your STR portfolio, this episode is a must-listen. 👉 Listen to the full episode here 🔧 Built to Book? We’ve Got You Covered If you’re building a direct booking strategy, check out how CraftedStays can help: 🌐 Connect with Tyler Coon Transcription Tyler: Collecting email addresses, right? Something like stay fi to make sure that you’re truly collecting email addresses from everybody you possibly can in that group. Because at the end of the day, those folks are gonna know someone else. So the more email addresses you’re collecting, the more you can market to these people and try different tactics, right? Don’t just send some bland newsletters, something like that. You know, Bill Faeth preaches this a lot about his new bookings. He sends them a video. Send everybody after they check out, send them a video, email all CC’d together and say, Hey, we loved having you guys. Thank you for leaving the place so clean. We’d love to have you back. I’m gonna send you a little discount code for if you guys want to come back next time. Here’s my direct booking site. Nothing’s stopping you from sending that email nowadays, and I guarantee. 0.001% of reservations are getting something like that. If anyone. Gil: Hey folks. Welcome back to Book Solid, the podcast where top operators share the strategies to maximize bookings, scale your rentals, and get ahead of the short term rental game. On today’s show, I have Tyler Kon. Tyler Kon is the founder of Savvy Real Estate. He has many agencies throughout the Nation to help folks get into short term rentals. I’m bringing him onto the show mainly because. I found his tactics, his way of approaching acquisitions of rentals. Very different than a lot of other brokerages, and I wanted him to share kind of how he thought about. Getting people into short-term rentals, how he thinks about that relationship between an agent or the brokerage and the client themselves. And really how does he think about long-term success to really make sure that they’re, they have what they need to be successful. Um, we dive into a lot of meaty topics. I’m really happy to have him on the show and really just have him share some of the vision, some of the values that him and his team has. Gil: Hey Tyler, welcome to the show. Tyler: Thanks Gil. Good to be here, man. Gil: Yeah. On the show today we have Tyler Kon from Savvy. Um, Tyler, before we get get started, do you mind giving a quick introduction on who you are? Tyler: Yeah, absolutely. Uh, my name is Tyler Coon. I’m the founder and CEO of Savvy, STR agents, a nationwide, uh, real estate team that specializes in helping investors buy and sell short-term rentals. Gil: Yeah. You’ve been, you’ve been in this industry for a little while

In this week’s episode of Booked Solid Show, formerly Direct Booking Simplified, we sat down with Paul Anderson—also known as The Social Media Hotelier. Paul is a marketing strategist specializing in leveraging Instagram to drive direct bookings for short-term accommodation businesses. As a retired guest house owner, international bestselling author, and expert in consumer psychology, Paul transforms complex marketing concepts into actionable strategies tailored for hosts. Known for his practical insights and engaging delivery (and yes—his now-iconic orange beanie), Paul helps hosts cut through the noise and turn lookers into bookers with ease. Paul’s journey—and his proven framework—offers a timely reminder: social media isn’t about going viral. It’s about showing up, consistently, for the guest you actually want to host. Summary and Highlights We covered a lot in this conversation, but here are the takeaways that really stood out: 🎯 Post Less. Measure More. Paul doesn’t believe in endless posting. In fact, it almost broke him. Instead, he came back with structure. Three posts a week. Same time, every time. And most importantly: a system for tracking performance, so he could double down on what worked and ditch what didn’t. “I was halfway through a 30-day content challenge, and I found myself tossing and turning at 2 AM trying to come up with something to post. I realized the content was rubbish—and it was hurting my mental health.” 📊 Track What Actually Matters Paul is not impressed by follower counts or vanity metrics. What does he look for? He teaches his students to measure profile conversion rates—how many visitors hit ‘Follow’—and link clicks, because that’s where bookings begin. Not likes. Not reach. Just action. “Link clicks as a proportion of profile visits is the holy grail. There is no target. What we want is everyone who visits our profile to hit the link in bio and come off the platform… and ask three things: Do they have vacancies? Can I afford them? Where’s the book now button?” Paul’s 3 Quick Wins for Better Instagram Performance Before wrapping up, Paul shared three specific, actionable tactics that every host can implement today to improve their Instagram strategy: 1. Optimize your Instagram name fieldThe name field (that bold line right under your profile photo) is keyword gold. It’s one of the first things Instagram’s algorithm scans when users search. Instead of repeating your handle, use keywords your guests are likely searching—like “Smoky Mountain Cabin” or “Pet Friendly Rental Lake Tahoe.” It’s simple SEO that most people miss. 2. Always post in 4:5 portrait formatTall images (1080×1350) take up more screen space, helping your content stand out in the feed. Square or horizontal content gives away real estate to other posts—and can reduce visibility. For reels and feed posts alike, fill the screen. 3. Don’t stress about trends. Focus on fundamentals.Forget the trending audios and the perfect posting time. Instead, get clear on who your ideal guest is, what they care about, and how you can communicate that consistently. Nail the basics. Everything else is just noise. “If you haven’t got the fundamentals down, you’re literally doing the proverbial in the wind and hoping something sticks. It’s a complete waste of time.” These aren’t hacks—they’re habits. And they compound when practiced consistently. Want to Go Deeper with Paul? Paul’s coaching program, Instabooked, is packed with practical tools for hosts who want to stop posting aimlessly and start building momentum. It’s not a content template library or a done-for-you service. It’s a system you can own—built from trial, error, and a whole lot of spreadsheets. And Paul is offering 30% off Instabooked exclusively for our listeners and subscribers.🎁 Use code CRAFTED at checkout:👉 thesocialmediahotelier.com/instabooked Rapid Fire with Paul Anderson As always, we wrapped up the episode with a few quick questions: 📚 One book everyone should read?Decline and Fall by Evelyn Waugh (for laughs), and Building a StoryBrand by Donald Miller (for clarity). ⚡️ One piece of tactical advice to take action on today? Connect with Paul Want to reach out or follow along with Paul’s latest content? Final Thoughts This episode wasn’t about hacks or algorithms. It was about getting back to the fundamentals—knowing your guest, telling your story well, and building trust at every touchpoint. And if you’re looking to build a website that reflects those same principles—clear messaging, fast performance, mobile-optimized for bookings—our team at CraftedStays is here to help. We believe great hosting deserves a great online presence.🧡 craftedstays.com Transcript Paul: And so the journey from the piece of content to the profile and onto the website need that, that slide as such needs to be as smooth as possible. Link clicks is a proportion of profile visits, is the holy grail. There is no target for that. What we want is everyone who visits our profile to hit the link in bio and come off the platform, see our beautiful website, and essentially within the hope that they would have only three questions. Paul: Does this host have vacancies? When I want to travel, can I afford them? And where is the book now button? Gil: Hey folks. Welcome back to direct booking simplified, where we break down the strategies and tactics to win in direct bookings on today’s show. I have Paul Anderson, Paul, welcome to the show. Gil: Yeah, Paul: spoke last time. Very, very excited to share direct booking tips with your Gil: yeah. I’m, I’m glad to see the, the orange beanie again, uh, the very on brand. Paul: Yeah, it’s also very, very cold here, so it is keeping my head warm at the moment. The United Kingdom is kind of frosty and snowy and floody at the minute, so yeah. Gil: Do you, uh, do you wear the beanie in the summers as well too? Paul: Ordinarily, no. So, the beanie was bought, um, when My firstborn was very, very young and we lost him very briefly in a crowd. And I’m sure as most parents would remember, if you lose a child, even for five seconds, it feels like an hour. Totally freaked out. Um, and so I thought, well, what

In our latest Booked Solid podcast episode, we sat down with Zachary Humphrey, a registered nurse who turned his passion for real estate into a thriving short-term rental business. Zach isn’t just any investor—he’s built his portfolio from the ground up, balancing a demanding W2 job with his growing STR empire, and learning some hard but valuable lessons along the way. From rental arbitrage to ground-up A-frame construction in Kentucky’s Red River Gorge, Zach’s journey is packed with insights—especially when it comes to why direct bookings are the key to long-term success. Summary & Highlights The Airbnb Nightmare That Changed Everything At first, Zach followed the standard STR playbook, listing his properties on Airbnb and VRBO. But a Thanksgiving weekend disaster made him rethink his approach. A guest violated house rules, caused property damage, then falsely reported a gas leak—leading Airbnb to suspend his listing for three days. Not only did he lose thousands in peak-season revenue, but he also had to fight to clear his name. “I don’t have control over this like I think I do. If I had a direct booking site, I could have handled the situation myself without relying on Airbnb.” That’s when Zach realized that depending on OTAs meant giving up control. Since then, he’s prioritized building his own booking channel, collecting guest emails, and taking ownership of his STR business. Direct Bookings = Higher Profits + Better Guests One of Zach’s biggest takeaways? Direct bookings don’t just save hosts money—they attract better guests. As a travel nurse, Zach himself books short-term stays every week. His experience taught him that frequent travelers prefer to book direct, skipping platform fees while still enjoying a trusted experience. “If we’re doing this to make money, then direct booking is the way to go. Guests feel like they’re saving money while, in reality, I’m making more by bypassing platform fees.” This insight shaped Zach’s direct booking strategy: By controlling the guest relationship, Zach ensures more repeat bookings, fewer platform headaches, and higher profit margins. Rebuilding After a $100,000 Loss Zach’s path to success hasn’t been easy. In fact, his biggest learning moment came from a devastating $100K loss on his first A-frame build in Red River Gorge. After trusting the wrong contractor, he found himself entangled in a fraud case with zero recourse to recover his money. Instead of giving up, Zach pivoted. He doubled down on building better partnerships, thoroughly vetting contractors, and diversifying his revenue streams through flips and joint ventures. His story is a raw, real reminder that setbacks are inevitable—but resilience separates successful investors from the rest. Rapid Fire Questions with Zach To wrap up the episode, we put Zach through our signature Rapid Fire Round. Here’s what he had to say: 1. What’s one piece of mindset advice for someone starting something new? “Know who you are first. Your investments shouldn’t define you. Money and real estate are temporary—don’t let them consume your identity.” 2. Any books that have shaped your investment philosophy? “Fake by Robert Kiyosaki. It opened my eyes to how the system is rigged and why you need to take control of your own financial future.” 3. What’s your #1 tip for hosts looking to start or grow their direct bookings? “Don’t overthink it. Start by capturing guest emails with StayFi. Once you have that list, marketing to them is easier than you think.” Listen to the Full Episode Zach’s journey is one of resilience, smart investing, and taking control of your business. Whether you’re an experienced host or just getting started, this episode is full of valuable lessons to help you maximize profits and minimize platform dependency. 🎧 [Listen to the full episode of Booked Solid here] . And if you’re ready to build a direct booking strategy that works, join our CraftedStays community—where top operators share insights, strategies, and tools to help you scale. And if you’re looking for an easier way to build a high-converting direct booking website, check out CraftedStays—the platform built for STR hosts who are serious about owning their bookings. 🔗 [Learn More About CraftedStays Here Follow Zach’s Journey Transcription Zachary: And I also make more profit margin when you book direct. And so that’s what I do. If we’re doing this to make money, then direct booking is the way to go. And it also benefits and incentivizes your future guests or guests you have now, if you know how to approach that correctly to save money too, in their minds, they’re saving money while you as the host are actually making more money by going on a direct booking platform. And when I use Airbnb every week as a travel nurse, I have to go direct booking because I cannot afford all those fees all year long. When you’re really using Airbnb frequently, and guests that are well affiliated with Airbnb, and usually, or short term rental stays, those are usually good guests. They want to book direct, so booking direct also can tend to bring you, I think, a better guest quality, because these people are more savvy. They’re looking for that stay. They’re familiar with short term rentals. Of course, our presentation of that’s got to be a decently good looking website. They’ve got to have confidence when they’re looking at your website. And things like that, things have to flow to give them that confidence that Airbnb gives as a multi billion dollar industry. Hey folks, welcome back to book solid the podcast where top operators share their strategies to help you maximize your bookings, scale your revenue and stay ahead of your short term rentals on today’s show. I have Zachary Humphrey. He’s a W2 nurse in his day job and has done multiple investment strategies. He’s actually going to walk us through a few different learnings that he’s done. I’ve actually really enjoyed the show because we had a chance to talk through what he’s gone through, through his investing journey. He’s done everything from arbitrage. To new ground developments, fix and flips, and all the different things that he’s learned along the way. And I just really love the way that he’s approached it. The mindset, some of the challenges, you’ll be