“Don’t just sell the cabin—sell the waterfall hike and the glass-cutting workshop nearby.“ That’s Kenny Bedwell’s philosophy on today’s Booked Solid Show. As the CEO of STR Insights and an active short‑term rental investor, Kenny brings a fresh mindset: direct bookings thrive when you market the destination first. Expect this episode to teach you how to build trust with guests through curated local content, harness Facebook’s organic reach, and amplify lead flow with a savvy email system, without being pushy In this Booked Solid feature, we dive into marketing genius, guest loyalty strategies (see How to Use Email Funnels to Drive Repeat Stays), and Kenny’s blend of lead funnels, authentic social media branding, and intentional work-life balance to help you master your short-term rental business. Summary and Highlights 👤 About Kenny Bedwell Kenny Bedwell is the founder and CEO of STR Insights, a consulting and data firm helping investors locate high-performing short-term rentals across the U.S. A former Citibank data analyst, Kenny started investing in STRs in 2017, growing a diverse portfolio through ownership, co-hosting, and arbitrage. Today, he’s known not just for deep market knowledge but for his content-savvy presence on Instagram @kenny_bedwell, @strinsights, and as the host of the Cash Flow Positive Podcast. Whether sharing data-backed insights or a Where’s Waldo STR skit, Kenny leads with authenticity and measurable ROI. 🎯 Direct Booking & Lead Generation Lead flow first. Kenny’s golden rule: “Your property is not the destination.” Sell the area, not just the stay. 🪜 Personal Branding That Sticks ⚖️ Balancing Business & Family 📖 Mindset & Book Recommendation 🎧 Listen to Kenny Bedwell Catch Kenny on the Booked Solid Podcast or listen to his collaboration with Gil Chan on: Explore his Cash Flow Positive Podcast and find him on Instagram @kenny_bedwell. Connect with Kenny: ✨ Ready to Build Your Booking Funnel? Let CraftedStays help you create a direct booking strategy for short term rentals that actually works. 📅 Schedule your crafted session today and start attracting the right guests—with the right messaging—all year long. Transcription Kenny: And I’m feeding them information of what to do. And so I’m telling them, Hey, you’ve gotta check out this glass museum nearby where you can like cut your own glass and make really cool products. There’s like all these things, I’m like pitching other businesses and stuff and events and people are like, wow, this is a lot. Kenny: And then I get them in an email funnel and I’m sending them this information and then I drop in. Oh, hey, by the way, if you need a place to stay, here’s the place to stay. If they’ve never heard of Watkins Glen, why they should come to Watkins Glen. And lo and behold. I get traffic, I get bookings, actual bookings, I get actual money from doing that. Kenny: And that’s the whole point of it. Right? And so you’re, you’re warming people up to why they should come to your area. You’re selling ’em on ’em, and because they trust you, meaning they’re like following it. That’s a form of trust. And they’re reading it and they’re like, wow, this is really cool. And it’s free. Kenny: It’s not like, oh, I need, I need you to pay for it. I just need your email so I can send the information. They’re now more engaged. Gil: Hey folks. Welcome back to the book Solid Show, the podcast where we bring in top operators to discuss marketing, revenue management, and guest experience to drive towards being book solid. On today’s show, I have Kenny Bedwell, the founder and CEO of STR Insights. He’s a host himself and has a wealth of knowledge to share with us. Gil: Today we started to really talk about. How he’s balancing all the different parts of his life. But we started to take a tangent towards really how he’s thinking about direct bookings and how that differs from a, where a lot of folks will focus their attention on specifically in marketing. So I’m really excited to have him on the show and really have him share what he’s learned throughout the years of really marketing himself. without further ado, let’s bring him in. Gil: Hey, Kenny, welcome to the show. Kenny: Yeah, thanks for having me, Gil. Gil: Yeah, it’s, uh, it’s great to finally have you on here. It’s been a, it’s been quite a, not a struggle, but definitely we’ve been, we’ve been trying to manage our calendars together to, to make this happen. Kenny: yeah, yeah, yeah. I just, uh, I think I mentioned earlier I was just moved and set up a bunch of properties and it’s been a crazy past two months, so yeah, it’s good. Good to finally connect and beyond. Kenny: So. Yeah. It’s amazing that, um, even today, like you’re, you’re still buying, buying properties. I think a lot of folks are like, are they holding on the sidelines? And I think also, like a lot of entrepreneurs that get into our space, um, that are not just hosts themselves or property owners, but they’re actually doing something else, serving the market a lot of times, like we kinda get distracted on that stuff. Gil: Like for instance, like I haven’t been able to acquire for the last year because I’ve been focused on my business. But it’s actually very good to hear that you’re still acquiring on your side. Kenny: Yeah. You know, um, it’s a, it’s funny, I had, I just had a conversation with, um, someone on my team and I’m a big believer in working with people who have ownership mindset, you know, and so everyone on my team, I call ’em, like, I don’t call ’em my employees. It’s not how it’s structured, you know, like I have, so I have the business at CR Insights, we do data and consulting, and I was, it was always actually speaking to my engineer and he does a bunch of

“You never want to compete on price. You want to compete on experience.” — Brianna Amigo In the world of short-term rentals, one thing is clear: good design isn’t just pretty—it’s profitable. On this episode of Booked Solid, Gil sat down with Brianna Amigo, founder of Brianna Michelle Interiors, to uncover how design directly impacts bookings, guest experience, and your bottom line. From her marketing roots to transforming over 300 properties nationwide, Brianna is leading a movement where curated spaces and outdoor amenities aren’t luxuries—they’re expectations. Summary and Highlights 👤 Meet Brianna Amigo Brianna is the founder and lead designer at Brianna Michelle Interiors, a Southern California-based firm specializing in short-term rental design. What started as a side hustle in 2019 quickly scaled after she identified a market gap: no one was designing with the guest and the investor in mind. With a background in corporate marketing, she fused aesthetic vision with ROI-focused strategy to help investors boost bookings through scroll-stopping, experience-rich properties. 🌟 Highlights from the Episode 🏡 Outdoor Spaces Drive Bookings “Outdoor experiences really are sometimes the number one driver on why someone will book the property or not.” Whether it’s pools, firepits, or pickleball courts, outdoor amenities can be the tipping point. Brianna emphasizes leveraging good weather and maximizing external space to stand out in competitive markets. 📈 Design Backed by Data Before selecting a throw pillow or tile, Brianna conducts comp analysis: who are your competitors, what amenities are most common, and where are the gaps? Her approach merges creativity with cold hard numbers to ensure every design decision delivers ROI. 🌟 Refresh vs. Full Gut Renovation Not every property needs a full remodel. Brianna advises against over-renovating, especially when holding costs and delays outweigh the return. Small cosmetic updates like new countertops or tiles can make a world of difference. 🪡 Underrated Investment: Experience Many hosts splurge on amenities but skimp on essentials like kitchen stock, linens, or water pressure. Brianna argues these “invisible details” have a lasting impact on reviews and repeat bookings. 📅 Branding is the Next Frontier Building on her marketing background, Brianna is now expanding services to include brand identity, websites, and social presence for hosts. Her goal: ensure that online brand experience matches the elevated in-person stay. 🔹 Rapid-Fire Wisdom 📚 Book Recommendation “The Let Them Theory” by Mel Robbins — A mindset book that helped Brianna silence imposter syndrome and stay focused on her entrepreneurial journey. 👤 Connect with Brianna Amigo If you’re ready to transform your rental into a scroll-stopper that guests can’t resist, this episode is your blueprint. Listen now and start designing for ROI. 🚀 Ready to take control of your short-term rental success? Start your direct booking journey at CraftedStays.co. Transcription Brianna: Outdoor spaces. Outdoor experiences really are sometimes like the number one driver on why someone will book. The property or not, especially in markets where there is potentially really beautiful weather and you’re in Florida, there’s pool, a pool at the property, those stays, you wanna make sure you really maximize the potential that you have on the outside because it is a huge driving force. Brianna: And when you see the amenities, the checkbox now that everyone has probably in their back pocket, a lot of them now are outdoor amenities because the, on the inside you can only do a few things. You can make sure you have. A game room, for instance, or a theater or a workout space or, or something that inside would be, you could implement. Brianna: But on the outside, the kind of possibilities are a little bit more endless. Gil: Hey folks. Welcome back to the book Solid Show, the podcast where we bring in top operators to discuss marketing, revenue management, and the guest experience to drive towards being booked solid. On today’s show, I have Brianna Amigo. She’s the founder of Brianna Michelle Interiors. It’s a great pleasure to have her on the show. Gil: I think we’re starting to see this big rise where people are really investing into their stay. In this conversation, she actually talks about how she’s thinking about not just. Designing the interiors of her space, but really all the guest experiences and the different touch points. And we actually go into some of the services that she’s extending her services to, that starts to dig into digital marketing as well too. Gil: So I’m really happy to have her on the show and really tap into kind of how she’s thinking about really the guest experience and what guests are expecting from here on out. So without further ado, let’s bring her in. Gil: Hi, Brianna, welcome to the show. Brianna: Thank you. Thanks for having me. Gil: It’s great to, it’s great to finally have you on. I know that we’ve been talking for a little while now, so it’s Gil: really good to one chat again with you, and two, have you record on the show with us. Um, so excited to have you here. Um, Brianna, maybe to kick us off, do you mind giving folks an introduction on who you are? Brianna: absolutely. I’m Brianna Amigo. I am the owner and founder of Brianna Michelle Interiors. And we are a short term rental, um, specific design business that is really focused about driving increased ROI with scroll stopping design. Um, that provides a really great five star guest experience. Gil: That’s awesome. It’s amazing how the industry has changed, even like the last five years and maybe even more, even Gil: more recently, but. I think like this whole industry of STR design a couple years back or maybe a half a decade back, it wasn’t that important, but it almost feels like now it’s become almost status quo that you don’t launch without really thinking about that. Gil: I don’t know if you saw the same, and that’s kind of why you got into this. Brianna: Yeah, exactly. So we, um,

“One man’s trash is another’s treasure. We all have our things we obsess over. If we were all doing the same things, we’d have major problems.” When Jonathan Wicks launched Well & Good Professional Services, he wasn’t just starting another cleaning company — he was reimagining how professionalism and consistency in vacation rental servicing can elevate the entire guest experience. In this episode of the Booked Solid Show, Jonathan shares his journey from being a Chicago-based host with a lake house to leading a national STR servicing company built on hospitality-grade standards. Summary and Highlights 🎧 Episode Highlights 🧹 The 3 Pillars of a “Certified Home” Jonathan breaks down the core services of Well & Good: This trifecta doesn’t just standardize the guest experience — it builds trust, especially for direct bookings. 📈 From Idea to Impact: The Origin Story Jonathan’s first client came from a direct message — before the business even existed. That host later became Well & Good’s first partner. He discusses: 🤝 The Power of Obsession “Be obsessed or be average” isn’t just a book title — it’s a mindset Jonathan and host Gil share. Whether it’s logistics, inventory control, or consistent gifting, Jonathan is all in. His secret to scaling? Deep obsession with quality + the right who, not how. 🛠️ Inventory, Systems & Scaling Smart With 20+ active servicing hubs, Jonathan reveals how: 💌 Curation Meets Consistency Jonathan’s take on personalization: ⚡ Rapid-Fire Wisdom 📚 Book Recommendation The Three Signs of a Miserable Job by Patrick Lencioni — a must-read for anyone building or managing a team. 🔗 Connect with Jonathan Wicks Website: wellandgoodpro.comInstagram: @wellandgoodproLinkedIn: Well & Good Pro This episode is packed with real-world strategies for hosts ready to level up their operations and build real trust with guests. Want to attract more repeat and direct bookings? Learn from someone who’s making that possible — at scale. 🎧 Listen now and take the next step in your direct booking journey at CraftedStays.co! Transcription Jonathan: Think this is a great one to consider for host managers. If you have a property, I believe that property should have its own Instagram account. Make an Instagram account for your property. It does take maintaining. You gotta make sure you’re posting, you gotta make sure you’re involved in order to have it be active, but then start to engage and you engage with anything local, right? Jonathan: Wherever your local is, follow all of those. And of course, you’re gonna have your direct booking link right there in the link tree right there. As soon as they click in. And that home now starts to have a personality and you get to curate that personality. You get to connect with vendors. We have so many of our partners who have homes that they then follow well in Good Pro on Instagram, and we’re able to tag each other. Jonathan: We’re able to talk about all of that. They get a lot of exposure. We have customers who take 52 bookings a year on Instagram, and it all flows through Instagram because our houses have become viral and all that, and you don’t need it. Ultra curated home. To do that, you just need to have consistency, and I encourage people do that and then involve yourself locally with your vendors as well as with your local community. Gil: Hey folks. Welcome back to the Books Solid Show, the podcast we’re bringing top operators to discuss marketing, revenue management, and the guest experience to drive towards being booked solid. On today’s show, I have Jonathan Wicks from Welling Good Professional Services. Jonathan is the founder and CEO. Gil: he started a cleaning service company. That is a bit different than what others expect out of a cleaning service, especially in our SDR space here, he takes on more of a hospitality from a hotel experience, so really delivering that hotel cleanliness into the SDR space. And he has certain principles and certain services that he abides by. Gil: To make sure that everything has strong expectations through and how that really drives to more repeat bookings, more direct bookings, and really a better rating and experience overall there. So I’m ecstatic to bring Jonathan onto the show. So without further ado, let’s bring him in. I. Gil: Hey Jonathan, welcome to the show. Jonathan: Hello, Gil. Thank you for having me. Gil: Yeah, yeah. I’m, uh, happy to do the whole conference road show with Gil: you, uh, seeing what the last one, and I’ll probably see you in a couple weeks as well too. Jonathan: Yeah, it is, it is. Uh, FOMO is real in the conference world. You know, there’s so many options to go to and, uh, you know, which one to choose is important. But, uh, yeah, we’re lucky enough to cross some paths here, both at the level of your listing and then some future ones that are coming up in, uh, in conferences here this spring. Gil: Yeah. What’s, uh, what’s been your favorite ones of the, of the entire year? Jonathan: It is fresh, but the level up your listing was fantastic. I think that was their best one that they’ve done. Uh, Tatiana and Natalie have continued to evolve that conference, and I think that this iteration was their best one. It was their third, which I think you sometimes find those great rhythms at that point. Jonathan: And, uh, yes, a level up your listing was a highlight. And I’ll tell you, I’ve been going to some of the advocacy groups. Uh, we had a, we had an advocacy meetup with the, the Idaho Vacation Rental Association. So it was folks from all across the state of Idaho that were gathering together. Those advocacy meetups end up being much more mission forward, and so where we’re all on that same team, we’re moving towards, hey, we’re advocating for our industry. Jonathan: Finding those meetups, they’re more localized, but

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