What does it take to truly own your guest journey — from the moment they see your property to the moment they return next year? For Joe Rohne, short-term rental operator, investor, and broker, the answer lies in control: control of your brand, your pricing, your data, and your guest relationships. In this episode of Booked Solid, Joe shares how he built a resilient direct booking strategy that leverages automation, email marketing, smart design, and a hyper-targeted ad funnel to grow his business in the Florida Panhandle. Summary and Highlights 👤 Meet the Guest: Joe Rohne Joe is a STR investor, co-host of 12 properties, and founder of the Savvy Emerald Coast real estate team. From owning a preschool to running a landscaping company, Joe’s path into short-term rentals came through relentless learning — including 50+ audiobooks every summer while mowing lawns. Today, he helps investors find and manage high-ROI rentals with a systems-first, guest-first approach. 🧭 What You’ll Learn 📌 Highlights 📚 Book Mentions 🧠 Mindset & Rapid Fire 🔗 Connect with Joe 🎧 Ready to stop chasing listings and start building a brand that lasts? Listen to the full episode and start owning your guest experience at CraftedStays.co. Transcription Joe: We have barcodes in our, in our properties going directly to our direct booking website. Our signs that have our property management company at the street, you know, ’cause we’re in a traditional vacation rental market, has a QR code, the direct booking website for that specific property, not for our management company. Joe: So when people are walking by, they can scan that QR code. And then I’d probably say the most important thing out of all of them is get, is getting repeat guests, getting the person that’s booked, getting their email, getting their phone number, and putting them into our email campaign to. Stay close to them. Joe: 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. Joe: All to work, 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. Joe: 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 and you can keep on testing and improving. Joe: As you learn, you can make changes all on the platform. You don’t need to learn something new. So if you need some help or you wanna get started, go ahead and go to craft stays.co and start your free trial. Now let’s bring on our guests and dive deep into hospitality and marketing. Gil: Hey folks. Welcome back to the 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 Joe Rohne. Joe is actually a real estate broker himself. He’s an investor. He’s gonna walk us through how he’s kind of grown his portfolio to what it is. Gil: Today he’s gonna talk about his marketing tactics. He has a lot of fundamentals that I encourage almost all of our listeners to put into practice today, which is really around targeting your past guest. And he also has some pretty advanced tactics like doing Facebook retargeting campaigns, look at likes and such. Gil: So I’m really thrilled to have him on the show to talk about. What he’s done, how he’s thinking about things. He’s also done things a bit differently than others as well too. So it’s a good perspective on just seeing how folks are doing email marketing, , and even deploying their own direct booking sites for themselves too. Gil: So without further ado, let’s bring him in. Gil: Hey, Joe, welcome to the show. Joe: Hey, how’s it going? Gil: It’s going very well. How have you been? Joe: Can’t complain. We’re getting ready. Uh, you know, for, we’re in peak, peak season and, business is good. I can’t complain. Gil: How’s peak for you? What does that look like for you as, as your management company? Joe: We are, you know, summer, traditional summer markets, you know, uh, so we, we started peak in March and. Uh, it gets a little bit slow in April, may, and then by mid-May, through mid-August, we are gangbusters busy. Gil: Yeah. How’s your team look like now to support you? Joe: Uh, so really it’s my wife and I, um, I have a virtual assistant, and of course I have some great boots on the ground. You know, uh, I, I have, you know, four different cleaning companies, three or four different handymen that I partner with, you know, all the other basics, the HVAC, all that, all that kind of stuff. Joe: Ready to call if I need ’em, but. Uh, definitely don’t have all my eggs in one basket with one cleaning team. Uh, I definitely like to have it go around to multiple. Gil: Yeah, yeah, yeah. I feel like right now, like there’s like two parts of peak for, for us it’s like one is like peak peak in terms of revenue management. So the last. Few months, it’s really around like, okay, how do we fill our

“When guests walk in and discover a gourmet snack or high-end facial mask, it’s more than an amenity—it’s delight.” That’s the unforgettable touch Rachel Vigil brings to vacation rentals through UpClose Marketing—a platform connecting hosts with premium brands for product placements that wow guests and reinforce their brand identity. In this episode of the Booked Solid Show, Gil sits down with Rachel to unpack how these carefully curated in-property experiences—from zero-alcohol Heineken to luxury sleep gummies and open-box mattresses—do more than elevate the guest experience. They drive reviews, reinforce your property’s positioning, and—when paired with a solid direct booking strategy—help small hosts operate like full-fledged brands. Whether you manage two properties or twenty, this conversation is packed with insights on how to create that “I need to book this again” moment the minute guests walk through the door. Summary and Highlights Meet Rachel Vigil Rachel Vigil is the CEO of UpClose Marketing, a platform helping short-term and mid-term rental hosts upgrade their guest experience through strategic brand partnerships—without costing them a dime. If you manage over 10 properties, Rachel’s team will even onboard you personally. 👩‍💼 Rachel’s Expertise with Up Close Marketing: Transforming Guest Stays Through Strategic Product Placement Rachel Vigil, founder and CEO of Up Close Marketing, brings her own experience as a short-term rental host into an innovative model that connects vacation rental hosts with premium brands. Her key contributions: 💡 Rachel’s Direct Booking Journey: From Manual Hosting to Building a Professional Brand In the second half of the episode, Rachel flips the script. Curious about launching her own direct booking strategy, she asks Gil: Key Takeaways & Highlights 🔗 Connect with Rachel Vigil & Up Close Marketing Rachel Vigil is the CEO of Up Close Marketing, a platform helping short-term and mid-term rental hosts upgrade their guest experience through strategic brand partnerships, without costing them a dime. If you manage over 10 properties, Rachel’s team will even onboard you personally. 📧 Email: rachel@upclosemktg.com📞 Phone: 858-220-6275🌐 Sign up: upclosemktg.com/signup📱 Instagram: @upclosemarketing📘 Facebook: @upclosemarketing💼 LinkedIn: @upclosemarketing She also shares upcoming campaigns and referral perks in her Wednesday newsletter—and is open to collaborations with coaching programs, Facebook groups, and host communities. 😊 Final Thoughts & Next Steps Rachel’s journey is one of empowerment—using guest-first details to enhance stays and now preparing to launch a branded, scalable direct booking strategy. ✅ Listen to the full episode to hear both sides of the guest-host partnership and learn how direct bookings can start with as little as two properties.👉 Visit craftedstays.co and start your free trial today! Transcription Rachel: So we partner with brands who want to have a unique experience with their consumer, and guests are consumers. Vacation rentals are an amazing place to place a product. So I think just like in the movies, there’s product getting placed. Well, this time we’re moving it into the vacation space, and it’s a fun experience for a guest to walk in and be surprised and delighted by some amenity they would never expect. Rachel: It could be some cleaning supplies or a very high-end shampoo, face mask, cosmetics, snack products, all the way to mattresses. We’ve done massage guns, we’ve done workout equipment. So there’s a whole variety of different brands that just wanna have that experience and trial with potential consumers. So the product is free to the host and to the guest because it’s a marketing play. Rachel: The brands honestly are. They’re paying for their marketing budget up close for the access to our network and to oversee the whole process. Gil: Before we bring on our guests, I want 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. Gil: All to work, 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’t 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 and you can keep on testing and improving. Gil: As you learn, you can make changes all on the platform. You don’t need to learn something new. So if you need some help or you wanna get started, go ahead and go to craft stays.co and start your free trial. Now let’s bring on our guests and dive deep into hospitality and marketing. Gil: Hey folks. Welcome back to the Books Solid Show, the podcast we bring on top operators to discuss marketing, revenue management, and guest experience to drive towards being books solid. On today’s show, I have Rachel Vigil. She is the founder and CEO of up close marketing. They do something quite unique that I haven’t found in this space. Gil: I measure at Level Up your listing. But what they do is they allow hosts to be able to. Explore new brands and have those brands give them free products that they can put into their properties for their guest experience. When I met Rachel at Level Up and she told me about the idea, it was something quite unique. Gil: And what I really love about it is really around the guest experience that you’re able to provide. that’s pretty unique. the second half of the show is actually pretty interesting where she had a bunch of questions. She’s trying to get into direct bookings herself, so actually turning the script

“If you rely only on OTAs, you’ve lost control—direct bookings give you the freedom and stability to weather anything.” — Federico Zimerman From a spare bedroom in Buenos Aires to managing 75+ properties and opening a boutique inn in the Catskills, Federico Zimerman’s journey is anything but ordinary. On this episode of Booked Solid, Gil welcomes Federico to unpack how an airline trainer turned STR operator is now helping hosts future-proof their businesses through intentional branding, operational systems, and direct booking strategy. Summary and Highlights 🧰 About Federico Zimerman Federico, also known as @strguide on Instagram, brings a global lens to the short-term rental industry. After 10 years traveling as a corporate trainer for a major U.S. airline, he transitioned into STR property management—first remotely from Argentina, and later building a multi-state management firm after moving to the U.S. He now manages properties across 16 states, holds equity in a boutique hotel, and is opening a bar in New York. His mission? Empower owners to run resilient, guest-first businesses. 🔍 What You’ll Learn in This Episode 📚 Federico’s Book Recommendations 🪡 Mindset Takeaway “Be persistent and patient. You won’t see results on Day 1, but if you trust the process and keep showing up, the seeds will grow.” 💬 Connect with Federico Transcription Federico: Even though I relied on this OTAs to grow my business and they were amazing and they were simple to use, I understand that to have a healthy long-term business sustainable all time, I had to have control of my bookings on my traffic and my properties. And if something happens, because we had a property being the listed and fairly, in my opinion, I was able to get it back up after like three months of challenging the LTA. Federico: In the meantime, we got a few direct bookings on other platforms I hadn’t used before, like booking.com. And that was good because you know, you get the list of the, one of the big platforms, it’s like is a death sentence for a lot of people. It’s like you lost your investment. Yeah. Like everything’s gone. Federico: And by building this, we were able to, oh look, we’re getting Google vacation rental bookings. Again, direct bookings. 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 Craft Estates is 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 stays.co and start your free trial. Now let’s bring on our guests and dive deep into hospitality and marketing. Gil: Federico, welcome to the show. Federico: Thanks, man. I’m excited to be here. I know we’ve been trying to schedule this for a while and finally we made it happen. Gil: Yeah. Yes. It’s been, it’s been a long while, I think on both parts.  Federico: Oh yeah. Mostly of mine. So Gil: for what it’s worth, the last one was My fault. Um, so we do, I think both of us, actually, a lot of folks in the industry actually live pretty busy lives, so I’m not surprised, uh, that some of these times we, we get things, uh, rescheduled. Federico: things get crazy, uh, in this industry Federico: du moment.  Gil: Yeah. Never tell him for sure, for sure. Um, we met at Level Up, I think you were probably the tallest guy I saw at Level  Gil: for that specifically that conference, um, being a male there and being the tallest male there, you definitely stuck out like a, like a nail there. Federico: I know, I know, but I’m used to this being Federico: all my life like that. But I know it’s weird and it’s pretty funny as well. I know people look at me like this, Federico: uh, like I’m not used to looking at people in the eyes when I’m standing up or less like looking up. So it’s, it’s pretty funny when I see someone’s my height or taller. Federico: I’m six six. I think. Uh, Federico: listen, I’m from ARG today. I use mirrors. I’m still like, I’m trying to remember fits and inches and all that, but I think I’m six six. Gil: yeah. Uh, that’s still pretty tall. Um, I was, uh, I saw Justin last, last week and I just realized that you actually had a picture with Justin. You  Federico: Oh, yeah. Yeah.  Gil: next, like you’re basically the same height and I feel so small next to Justin. Every time I’m next to him. Federico: Yeah. Where, where do you see him? Gil: was he at VR Nation? Gil: Yes, he was at VR Nation and he was also at the STR Hospitality Summit as well too. Federico: nice. Yeah. Justin, I did a certification with, uh, we, we got along pretty well because I did the, the,

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