“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

“If you’re expecting direct bookings to work overnight, you’ll be disappointed. But if you treat it like building a real business, you’ll see long-term success.” Parker, a powerhouse in the short-term rental space. Not only does she self-manage 12 properties across Tennessee and Florida, generating over a million dollars in annual revenue, but she’s also a seasoned mortgage expert. As the founder of Wealth Builders Mortgage Group, she specializes in helping short-term rental investors navigate financing options to scale their portfolios. This conversation dives deep into Parker’s unique approach to hosting, financing strategies, and her growing focus on direct bookings. Summary and Highlights Introducing Parker Borofsky Parker Borofsky is a powerhouse, multi-year national award-winning Mortgage Loan Originator and the visionary Founder of Wealth Builders Mortgage Group, powered by Movement Mortgage. A trailblazer in the short-term rental financing arena due to her investor-friendly approach, Parker combines passion, expertise, and an unrelenting drive to help real estate investors succeed. Over the past five years, she has financed an impressive $1.1 billion in loan volume, making her a trusted partner for clients looking to build and expand lucrative investment portfolios. 1. Why You Shouldn’t DIY Your Debt-to-Income Ratio (DTI) Parker emphasizes that many investors miscalculate their debt-to-income ratio, often limiting their own borrowing power. Loan programs have different ways of calculating income, and working with a knowledgeable loan originator can open up more financing opportunities. For hosts looking to expand, understanding how lenders evaluate rental income, self-employment income, and bonus pay can mean the difference between qualifying for another property or getting stuck. 2. The State of Short-Term Rental Markets Parker sees two markets where investors keep coming back—The Smoky Mountains and Kentucky’s Bourbon Trail. While some claim the Smokies are oversaturated, she argues that demand is still strong. “Some hosts are struggling, but the market isn’t oversaturated. The bar has just been raised. You have to market smarter and differentiate your property.” The takeaway? Short-term rentals remain a solid investment if you’re willing to put in the effort. 3. Direct Booking Strategies That Work Parker’s approach to direct bookings is refreshingly simple yet effective: If you want to build a sustainable direct booking strategy, start with small steps like Parker did—get a booking site up, engage with guests, and introduce a follow-up system. What’s Next for Parker Beyond growing her own portfolio, Parker is taking her expertise on the road. She’s speaking at major industry conferences, including Level Up Your Listing and her own event, Take the Lead, which focuses on empowering women in short-term rentals. Final Thoughts: Direct Bookings Take Time, But They’re Worth It One of the biggest mistakes hosts make is giving up on direct bookings too soon. It takes time to build an audience and gain momentum, but consistency pays off. Looking to improve your direct booking game? Join CraftedStays to get expert-built direct booking websites that actually convert. Follow Parker here ⤵️ Transcription Parker: I like to tell people don’t DIY your DTI and the reason for that is so many clients I feel like sell themselves short. They go on, they try to google, there’s somebody out there that’s got a debt to income ratio calculator which it just makes me cringe because there’s so many different ways to calculate debt to income ratio and the The problem is that these different loan products and loan programs allow us to count income differently. Parker: So, you know, self employment income, it’s not gross, it’s net, but we can add back depreciation. Uh, rental income. Some loan originators think you have to have one or two full years of short term rental income to use it, whereas I know that the Fannie Mae guidelines. So if you purchased a rental in July of last year, we can take that calculation and divide it up. Parker: by the number of months it was in service, not a full 12 months. And so if I’m doing your debt to income ratio and somebody else is doing your debt to income ratio, they’re using a full year, counting it against you, I’m doing seven months, your debt to income ratio is going to be lower with me. Gil: Hey folks on today’s show. I have parker. She was actually my loan agent when I end up buying my brands and property I’ve been wanting to have her on the show for a long while now We met uh in person also again at str nation and she’s has a wealth of knowledge specifically in really helping folks get their loans. So today we’re going to deep dive into kind of one, her experience to watch trends. She’s seen how she thinks about closing loans. It’s actually a pretty deep discussion. So we get into that. And it’s really interesting to how to hear how she approaches loans a bit differently than others. Gil: And then we get to dive a little bit deeper into her direct booking tactics. she actually deploys a lot of more traditional marketing that has helped her raise in, uh, direct booking. So I’m really excited to have her on the show. I hope you guys enjoy it as well too. Gil: Parker, welcome to the show. Parker: Thank you, Gil. Excited to be here. Gil: Yeah, I’m excited to have you. I personally know you. I’ve worked with you. I was a client of yours. I’m delighted to be, to have you on our show. Parker: Thank you. And you were a great client, by the way. Gil: I’m sure you say that about everybody. Parker: No. Gil: Uh, for folks that don’t know, Parker actually helped me close on my last short term rental in the Branson market. Uh, so she’s the one that helped me, uh, help me close that one. And that was when interest rates were really going up at that point. Um, I think we closed close to almost 8%, not quite, but almost there. Gil: We paid a pretty penny on points too. Parker: Oh yeah.