In this episode of Booked Solid, Garrett Brown—BiggerPockets Short-Term Rental Expert and founder of Cameron Ranch Glamping—shares how he turned a single house into a land-hacked luxury retreat business. Using a blend of creative hospitality, structured site analysis, and marketing systems built on influencer content, Garrett achieved a remarkable 76% direct booking rate. He walks us through his strategy, mistakes, wins, and advice for hosts aiming to move beyond Airbnb dependency. Summary and Highlights Meet Garrett Brown Garrett is the BiggerPockets Short-Term Rental Expert and the owner of Cameron Ranch Glamping, a viral Texas-based luxury retreat. He helps investors scale unique, profitable vacation rentals using creative design, data‑driven real estate investing, and proven hospitality strategies. 🎥 He also hosts the BiggerStays YouTube series by BiggerPockets, where he educates STR investors on the power of guest-first independence. 🎧 Episode Highlights & Takeaways 🎯 Topic Insight From Flips to Flagships Garrett shares his transition from fix & flips to building unique stays on strategically chosen land parcels. Land Hacking in Action Using a primary house for financing + utility access, then expanding with domes and mirror homes on the same parcel. 60‑30‑10 Rule Garrett’s formula for selecting unique stay land: 60 min from a metro, 30 from an attraction, 10 from a town. 4 S’s + P The 5 key filters for vetting land: Sight, Sound, Smell, Septic, and Permitting. Content‑First Strategy Before spending on ads, Garrett invested in high-quality video and leveraged influencer stays and UGC. 76% Direct Bookings Through social-driven sales funnels using ManyChat, discount codes, and attribution tracking. Direct Booking Mindset Focus on building a brand, not just a listing. Garrett used platform independence to unlock flexibility, data, and margins. Hospitality Infrastructure Clean design, customer experience, automation, and multilingual VAs power his operations. 📚 Garrett’s Book Picks 🔗 Connect with Garrett 🎧 Listen to Garrett’s full episode here to learn how to scale unique vacation rentals with smart systems, creative thinking, and modern marketing. Then head to CraftedStays.co to start your free trial and take control of your direct bookings with a platform designed for serious hosts. Transcription Garrett: Sometimes you have to just jump in the fire and learn some things while you’re going, but I, you need to make sure you have that basis first, that you can withstand that fire. So I looked at properties for eight months before I found the one that I really liked. I didn’t just find a property like, oh, this is it. Garrett: It needed to be something that when I walked on it, I knew that the things I look for are the site. You need to make sure it has some type of view. It doesn’t need to be on a mountaintop in the middle of. Costa Rica or something, but it’s gotta be nice. Like I personally always look for a water feature. Garrett: You’ll get a higher rate no matter what, but not always mandatory. But anything I’m buying now is gonna have a water feature or it’s such a good deal that I can put in a water feature like a pond or something. Good. Gil: Before we bring on my guest, I wanted to talk just a little bit about something that I’ve been hearing a lot from Host. I keep on hearing the same thing. I know my website isn’t converting, but I can’t afford $8,000 on an agency to rebuild it. Here’s the thing, you’re letting all these marketing strategies, you’re driving traffic and you’re putting it all to work. Gil: But if your site isn’t really built to convert, you’re basically lighting your energy and money on fire. And even if you could afford an agency build, every time you want to test something or make a change, you’re having to pay them again. You can iterate, you can’t test, and you really can improve on things. Gil: You don’t need a custom $10,000 website to get the conversion rates that really matter. You just need the right platform. That’s why I build craft estates. It’s purpose built for short term rentals and designed from the ground up to help you drive more direct bookings. You can finally turn that traffic into bookings. Gil: And you can keep on testing and improving. As you learn, you can make changes all on the platform. You don’t need to learn something new. So if you need some help or you wanna get started, go ahead and go to craft estates.co and start your free trial. Now let’s bring on our guests and dive deep into hospitality and marketing. Gil: Hey folks. Welcome back to the book Solid Show, the podcast where we bring on top operators to discuss marketing, revenue management, and the guest experience to drive towards being booked solid. On today’s show, I have Garrett Brown. You most notably might know him from BiggerPockets. He has the YouTube channel there. Gil: He’s also a short-term rental operator and specializes on unique stays. I. Thoroughly enjoy this entire conversation, kind of walking through one, his kind of his guest or his hosting an investment journey there, but. What I found interesting is kind of like the time and effort that he spent towards really breaking down what unique stays is and really how to approach it if you’re thinking about buying a plot of land and building on it for unique stays. Gil: And then on the flip side, we talk about the marketing side of things and how he was able to get to 76% direct bookings in two, three years. I think he mentioned at the very end he got up to. High double digits in just the first year alone. So he’s gonna break down what his direct booking engine looks like, some of the things that he really emphasizes, and we geek out just a little bit about really the marketing tactics kind of be happening behind the scenes, or the technical parts of the marketing and

“It’s not about how much you make—it’s about how much you keep.” At just 25 years old, Chad Harker is building a high-cash-flow STR portfolio in Edmonton using real estate acquisitions, direct booking strategies, and custom-built AI systems to scale—without burning out. In this episode, Chad shares how he house-hacked his way into the industry, scaled using BRRR-style methods, and now automates his business with tech tools like HostBuddy and custom GPTs. Whether you’re just getting started or scaling fast, Chad’s no-fluff approach to growth, guest retention, and profitability will shift your mindset—and give you real tools to work with. Summary and Highlights 👤 Meet Chad Harker He’s 25. He owns multiple short-term rentals. He’s not flipping arbitrage leases. He’s buying real estate. Renovating it. Renting it. Managing it. Growing a brand. Chad Harker didn’t wait for permission. In the early days of COVID, while most people paused, Chad bought a fixer-upper, moved into a spare bedroom, and listed the master suite on Airbnb. One listing turned into multiple units. One property turned into a management company. Today, he’s building a sustainable STR brand in Edmonton, with cash flow that’s compounding. 💡 What You’ll Learn in This Episode If you’re a host who wants to own more, automate smarter, and stop relying on platforms that don’t care about your growth, this episode is your blueprint. We unpack how Chad got started with zero connections and built his first STR through house hacking, and how he applied the BRRR method—Buy, Rehab, Refi, Repeat—adapted for STRs. That first home eventually became his launchpad for scaling, thanks to HELOCs and consistent reinvestment. Chad also reveals how he gets direct bookings without gimmicks by designing guest-first experiences that leave a lasting impression. (Hint: it’s the same principle behind why guest-first design converts better.) He doesn’t just talk branding. He backs it with systems—like QR codes for guest reviews, UTM tracking to measure traffic, and email funnels to rebook returning guests. 🧠 Mindset from a 25-Year-Old Who Gets It “It’s not about how much money you’re making. It’s about how much you keep.”Chad’s financial discipline runs deep—from manually renovating his first property at 2 a.m. to allocating profits like a CFO using a Profit First approach. And when it comes to tech, Chad’s team isn’t guessing. They use HostBuddy AI to manage guest comms and streamline their ops—freeing up hours each week while improving response quality. For hosts starting from scratch, Chad’s advice is simple: focus on retention, guest loyalty, and starting direct bookings now. Don’t wait for a perfect funnel—start with a solid stay. 🧰 Tools, Tactics & Templates Chad shares how his team uses custom GPTs, AI automations, and simple workflows to: His long-term thinking shows in how he manages LTV—lifetime guest value—and runs his business more like a boutique hotel brand than a side hustle. 📚 Book Mentioned Profit First by Mike Michalowicz — If you want your business to stop running you, start here. Chad uses it to budget taxes, op-ex, and owner draws. 📲 Connect with Chad 🎧 Listen to the full episode now to hear the exact playbook Chad uses to build guest-first, tech-enabled, high-cash-flow stays in his 20s. Then visit CraftedStays.co to build your own direct booking brand—no custom dev agency required. Transcription Chad: It’s not necessarily about like how much money you’re making, it’s about how much you keep. And you could have the guy, uh, working, you know, at McDonald’s making minimum wage. However, they’re saving more of the money they’re making than the attorney that’s working at a prestigious firm and they’re spending all of their money on like all the luxury things, the cars, the home. Chad: I feel like if you’re able to set up a system where you’re taking a certain percentage of your income, then you’re gonna be in a really good position to like. As you increase your income, like you’re also able to maybe increase some of the rewards you give yourself, but you’re also able to increase your savings and how you’re gonna use and invest that money based on whatever your goals might be. Gil: Before we bring on my guest, I wanted to talk just a little bit about something that I’ve been hearing a lot from Host. I keep on hearing the same thing. I know my website isn’t converting, but I can’t afford $8,000 on an agency to rebuild it. Here’s the thing, you’re letting all these marketing strategies, you’re driving traffic and you’re putting it all to work. Gil: But if your site isn’t really built to convert. You’re basically lighting your energy and money on fire, and even if you could afford an agency build, every time you want to test something or make a change, you’re having to pay them again. You can’t iterate, you can’t test, and you really can improve on things. Gil: You don’t need a custom $10,000 website to get the conversion rates that really matter. You just need the right platform. That’s why I build Crafted Stays. It’s purpose built for short term rentals and designed from the ground up to help you drive more direct bookings. You can finally turn that traffic into bookings and you can keep on testing and improving as you learn, and you can make changes all on the platform. Gil: You don’t need to learn something new. So if you need some help or you wanna get started, go ahead and go to Crafted stays.co and start your free trial. Now let’s bring on our guests and dive deep into hospitality and marketing. Gil: Hey folks. Welcome back to the book, 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 Chad Harker. He’s one of the youngest guest that I was able to bring onto the show, but he has grown his portfolio in an amazing way, especially for his age.

“When you’re doing something hard, it’s supposed to feel hard… but know that you’re on the right path.” Skyler knows firsthand: building a direct‑booking short‑term rental business from the ground up is not easy, but it can be extraordinary. In this week’s episode of the Booked Solid Show, Skyler shares how he and his wife, Maddie, went from furnishing arbitrage properties in San Diego to launching investor-backed, luxury wellness retreats in Upstate New York—complete with custom saunas, cold plunges, and bridal‑ready properties. You’ll learn their scrappy strategies, brand‑building secrets, and how they’re leaning into a book club community to fuel expansion—without losing balance. Summary and Highlights Skyler and Maddi Vaughn’s Journey Skyler Vaughn and Madi Johnson are the founders of The Short Term Rental Book Club and For the Love of Upstate, a boutique real estate brand that renovates historic homes into high-end short-term rentals across Upstate New York. Their specialty lies in blending timeless architecture with modern comforts—turning late 1800s houses into memorable wellness retreats. Episode Highlights & Key Takeaways ➤ From Rental Arbitrage to Real Estate EquitySkyler and Maddie started with rental arbitrage in San Diego, scaling from 2 to 4 units before using profits to buy their first vacation home in Big Bear—where a savvy exit funded their move to Upstate NY. ➤ Wellness Retreats as Destination PropertiesTheir portfolio emphasizes immersive, wellness‑focused stays with on‑site saunas, cold plunges, hot tubs, and outdoor showers—transforming properties into unforgettable experiences. ➤ Strategic Branding & ConsistencyEvery toilet, wallpaper, and postcard is consistent across properties. From website to in‑property signage and photography, they bolster their direct‑booking funnel. ➤ Tech‑Enabled Guest ConversionIntegration with HostAway, Google Maps, email funnels, and partnerships (like Fede’s property management) is powering both direct bookings and event rentals. ➤ Investor Structures & Sweat EquityHolding individual property LLCs and funneling renovations through a master company gives them flexibility for investor partnerships and future client‑based design work. ➤ Community Through STR Book ClubThe monthly $30 subscription includes books, Zoom discussions, breakout sessions, and real networking—fostering property partnerships and ongoing growth. ➤ Mindset & IdentitySkyler’s mental health insight: stress and anxiety often signal progress. His mindset tip—embrace the difficulty and stay grounded—aligns directly with how they built a thriving business. Rapid‑Fire Round Questions 📚 Connect with Skyler here Finally, 🎧 listen to the full episode to discover how material details—from wallpaper to saunas—build a seamless guest experience, and why they believe “Focus on your product. Direct bookings follow.” Then explore CraftedStays.co for more expert strategies. Transcription Skyler: When you’re doing something hard, it’s supposed to feel hard, you know, and it’s gonna give you that stress and it’s gonna give you that anxiety. But at the end of the day, you really have to kind of take a step back and I, I have to do this daily and I have techniques that I have learned to make sure that I’m not going crazy daily. Skyler: But in terms of just like, you know, it’s gonna be okay, at the end of the day, it is just work. At the end of the day, it is just money and investing in things and you know, making sure you’re doing right by other people. But this doesn’t define who I am as a person, and so. Allowing yourself to like understand your stress and understand your anxiety, and kind of just be able to live with it, but know that you’re on the right path is a good thing, even though it may not feel like it in the moment that you’re feeling those feelings. Good. Gil: Hey folks. Welcome back to the book Solid Show, the podcast where we bring on top operators to discuss marketing, revenue management, and the guest experiences to drive towards being booked solid. Gil: On today’s show, I have Skyler from For the Love of Upstate. He’s a short term rental investor from originally California. He’s doing a whole bunch of things in the space. He has a phenomenal story of kind of how he started investing in California, in the Northern Cal Southern California market and how he’s now investing in upstate New York. Gil: He’s also the founder or one of the founders of the STR Book Club. We get to talk a lot about really how he has grown throughout his career, all the different phases in his vesting career, how he approaches really designing out his space, the building a brand, and really how he attracts people to come back to his days. Gil: We talk a bit about how he is approaching direct bookings, how he approaches partnerships, and then we cap it off with really something pretty unique where he talks about one of the other. Ventures that he has, which is the STR book club. So definitely this is a show that’s worth listening to, and I just love his story. So without further ado, let’s bring him in. Gil: Hey Skyler, welcome to the show. Skyler: Thank you so much, Gil. I appreciate it. Gil: Yeah, it’s, uh, it’s great to have you on. Uh, I knew when we first met at, uh, level Up that I wanted to have you and or Maddie on the Gil: show, so definitely I’m excited to have you here. I, Skyler: Awesome. Yeah, thank you so much. I know Level Up is always such a good time. One of our favorite conferences. Shout out to Natalie Palmer and Tatiana as well. They do a great job there. Gil: they do. It’s a Gil: very different type of conference, like our Gil: listeners here, if you’ve never been to a Level Up before, it’s not Gil: like any other STR conference, um, that you get to experience out there. Skyler: Absolutely. I think everyone is like the most welcoming you’re ever gonna find at a conference setting. At that conference. Yeah. Gil: Yeah. Did you, um, did you go to the previous years as well? Skyler: So we only did the one

🛠️ “Design isn’t just about what it looks like—it’s about what it earns.” Our guest is Ishita Lalan, founder of Ishita Interiors and architectural designer behind over 150 short-term rental transformations across the country. From $500,000 gut-renovations to quick-turn landscape upgrades, Ishita approaches every STR with the mindset of an investor and the precision of an architect. This episode is for the host who’s ready to stop “furnishing a unit” and start building a direct booking brand. Whether you’re managing your first property or optimizing your tenth, Ishita breaks down the key frameworks behind design decisions that pay off—financially and emotionally—for your guests and your business. You’ll leave this episode thinking differently about your layouts, your finishes, and even your photos—because design, when done right, isn’t decoration. It’s strategy. Let’s get into it! Summary and Highlights 👤 Meet Ishita Lalan Founder of Ishita Interiors, Ishita is an architect and STR design powerhouse. With over 150 projects completed, including landscape work and structural transformations, her mission is to blend visual appeal with high functionality and long-term value. Her work has earned national recognition, including a Shorty’s Best Interior Design Award finalist spot. 🔑 Key Takeaways 📚 Book & Inspiration Highlights While no specific book was mentioned, Ishita’s design strategy is heavily influenced by boutique hospitality principles and architectural rigor—offering a lesson in aligning aesthetics with income-generating performance. 🔁 Connect with Ishita 🎧 Ready to transform your STR business with smarter design?Listen to the full episode now and explore more ways to grow your guest-first brand at CraftedStays.co. Transcription Ishita: I think it’s like two, three things going together. It’s just not one mindset shift, but a, when you’re starting something new. What worked for us was having a W2 income until you don’t replace your W2 income. Don’t leave it. Just don’t go all in something else. Yeah. So you know, probably that a side hustle would have you work more hours, like after your W2. Ishita: You’ll have to put in extra hours. Your weekends would get away from you to build something that you are passionate about, that investment in time and everything that you should be ready for it once you’ve replaced. At that time, you can take that leap of faith and be like, okay, fine. Now I’m all in. But I just feel like that mindset shift of just putting yourself all in, like in terms of time, resources, everything, it has to be a hundred, not even a hundred percent. Ishita: It has to be 200%. You have to sacrifice your social life. You won’t be able to go party, you won’t be able to go on travels, and you should be okay with that. Gil: Hey folks. Welcome back to the book Solid Show, the podcast where we’re bringing in top operators to discuss marketing, revenue management, and the guest experience to drive towards being booked solid. On today’s show, I have Ishita Lalan. She’s from Ishita Interiors. She’s a very humble person. Gil: I love, love, love talking to her, but she’s also a big powerhouse in terms of designs and really thinking through. How to think about not just the amenity that you have, but how do you think of a project as completely being value add? We got into really what does that mean for her and her, the design processes that she has in place, all the different levers from a investment standpoint that she starts to pull. Gil: We talk about forced appreciation, we talk about cashflow and really tax benefits. It’s was an amazing conversation. And we also talk about some of how she has approached. Working with influencers and how much of an impact that has had on her direct bookings as well too. So without further ado, let’s bring her in. Gil: Hey, Ishita, welcome to the show. Ishita: Thank you for having me. Yo. I’m super excited.  Gil: Yeah. You’ve been pretty hot recently. I’ve been seeing you almost. All over the place. I don’t know what, and maybe it, maybe if I had my blinders on and you were always like, pretty big, but like, talk to me a little bit about, like, if I, maybe just first off, like, who are you? And kind of Yeah. Tell me, talk to me a little bit about yourself. Ishita: Well, I hope in a good way. You’ve been hearing about me everywhere, so, Gil: been good. It’s been good. Ishita: okay. That makes me happy. Ishita: I am Ishita, I am a short term rental designer and, um. You know, I’ve started my own design studio in 2021, have been in this industry for four years now, have done more than 300 projects, uh, in our portfolio. Uh, so that’s how the journey began. But, uh, it actually started as us being investor. Ishita: So my husband and I, we started our own investment journey in short term rental design, uh, in 2020. And, you know, it. We were completely, when at the, in the beginning we were completely bootstrapped, like we were the ones, you know, getting these pro properties and doing the painting and flooring and, uh, everything that had, uh, um, the work related was completely us from staging to cleaning. Ishita: Um, we didn’t have a big team. We didn’t have big budgets, uh, but our goal was to convert and, you know, create an experience for our guests. Um, and. You know, we believed in our vision and worked relentlessly. Uh, and that literally gave birth to my design studio, my, my background in architecture, uh, that surely helped and, uh, got traction. Ishita: And here we are, you know, four years down the line and working on almost 50 to 60 projects a year. Gil: Wow. And what’s your portfolio look like with between you and and your husband? Ishita: Uh, so we have 10 short term rentals of our own. Uh, we, we have in various states.

“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