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