In our latest Booked Solid podcast episode, we sat down with Zachary Humphrey, a registered nurse who turned his passion for real estate into a thriving short-term rental business. Zach isn’t just any investor—he’s built his portfolio from the ground up, balancing a demanding W2 job with his growing STR empire, and learning some hard but valuable lessons along the way. From rental arbitrage to ground-up A-frame construction in Kentucky’s Red River Gorge, Zach’s journey is packed with insights—especially when it comes to why direct bookings are the key to long-term success. Summary & Highlights The Airbnb Nightmare That Changed Everything At first, Zach followed the standard STR playbook, listing his properties on Airbnb and VRBO. But a Thanksgiving weekend disaster made him rethink his approach. A guest violated house rules, caused property damage, then falsely reported a gas leak—leading Airbnb to suspend his listing for three days. Not only did he lose thousands in peak-season revenue, but he also had to fight to clear his name. “I don’t have control over this like I think I do. If I had a direct booking site, I could have handled the situation myself without relying on Airbnb.” That’s when Zach realized that depending on OTAs meant giving up control. Since then, he’s prioritized building his own booking channel, collecting guest emails, and taking ownership of his STR business. Direct Bookings = Higher Profits + Better Guests One of Zach’s biggest takeaways? Direct bookings don’t just save hosts money—they attract better guests. As a travel nurse, Zach himself books short-term stays every week. His experience taught him that frequent travelers prefer to book direct, skipping platform fees while still enjoying a trusted experience. “If we’re doing this to make money, then direct booking is the way to go. Guests feel like they’re saving money while, in reality, I’m making more by bypassing platform fees.” This insight shaped Zach’s direct booking strategy: By controlling the guest relationship, Zach ensures more repeat bookings, fewer platform headaches, and higher profit margins. Rebuilding After a $100,000 Loss Zach’s path to success hasn’t been easy. In fact, his biggest learning moment came from a devastating $100K loss on his first A-frame build in Red River Gorge. After trusting the wrong contractor, he found himself entangled in a fraud case with zero recourse to recover his money. Instead of giving up, Zach pivoted. He doubled down on building better partnerships, thoroughly vetting contractors, and diversifying his revenue streams through flips and joint ventures. His story is a raw, real reminder that setbacks are inevitable—but resilience separates successful investors from the rest. Rapid Fire Questions with Zach To wrap up the episode, we put Zach through our signature Rapid Fire Round. Here’s what he had to say: 1. What’s one piece of mindset advice for someone starting something new? “Know who you are first. Your investments shouldn’t define you. Money and real estate are temporary—don’t let them consume your identity.” 2. Any books that have shaped your investment philosophy? “Fake by Robert Kiyosaki. It opened my eyes to how the system is rigged and why you need to take control of your own financial future.” 3. What’s your #1 tip for hosts looking to start or grow their direct bookings? “Don’t overthink it. Start by capturing guest emails with StayFi. Once you have that list, marketing to them is easier than you think.” Listen to the Full Episode Zach’s journey is one of resilience, smart investing, and taking control of your business. Whether you’re an experienced host or just getting started, this episode is full of valuable lessons to help you maximize profits and minimize platform dependency. 🎧 [Listen to the full episode of Booked Solid here] . And if you’re ready to build a direct booking strategy that works, join our CraftedStays community—where top operators share insights, strategies, and tools to help you scale. And if you’re looking for an easier way to build a high-converting direct booking website, check out CraftedStays—the platform built for STR hosts who are serious about owning their bookings. 🔗 [Learn More About CraftedStays Here Follow Zach’s Journey Transcription Zachary: And I also make more profit margin when you book direct. And so that’s what I do. If we’re doing this to make money, then direct booking is the way to go. And it also benefits and incentivizes your future guests or guests you have now, if you know how to approach that correctly to save money too, in their minds, they’re saving money while you as the host are actually making more money by going on a direct booking platform. And when I use Airbnb every week as a travel nurse, I have to go direct booking because I cannot afford all those fees all year long. When you’re really using Airbnb frequently, and guests that are well affiliated with Airbnb, and usually, or short term rental stays, those are usually good guests. They want to book direct, so booking direct also can tend to bring you, I think, a better guest quality, because these people are more savvy. They’re looking for that stay. They’re familiar with short term rentals. Of course, our presentation of that’s got to be a decently good looking website. They’ve got to have confidence when they’re looking at your website. And things like that, things have to flow to give them that confidence that Airbnb gives as a multi billion dollar industry. Hey folks, welcome back to book solid the podcast where top operators share their strategies to help you maximize your bookings, scale your revenue and stay ahead of your short term rentals on today’s show. I have Zachary Humphrey. He’s a W2 nurse in his day job and has done multiple investment strategies. He’s actually going to walk us through a few different learnings that he’s done. I’ve actually really enjoyed the show because we had a chance to talk through what he’s gone through, through his investing journey. He’s done everything from arbitrage. To new ground developments, fix and flips, and all the different things that he’s learned along the way. And I just really love the way that he’s approached it. The mindset, some of the challenges, you’ll be

“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.

“Most people never let a goal become an obsession. They have an idea, it becomes a want, and when the first plan doesn’t work, they abandon it instead of adjusting the plan.” Emanuele Pani, known as “E” in the short-term rental community, is the co-host of the STR Secrets Podcast and a coach specializing in co-hosting and boutique hotels. He shared how shifting his mindset allowed him to build a highly successful direct booking strategy. While many hosts rely on Airbnb and other OTAs, E emphasized that true financial freedom comes from owning your own booking channels. The key? Building long-term relationships and serving others first. His philosophy? Your mindset dictates your success, and achieving financial growth starts with internal transformation. Summary and Highlights Why Most Hosts Struggle with Direct Bookings Many hosts fail to scale their direct booking efforts because they get stuck in cycles of hesitation, fear, and inconsistency. The biggest challenges include: Fixing the Direct Booking Struggle: Mindset, Strategy & Execution 1. The Power of Obsession Hosts who win at direct bookings don’t just try—they commit fully. Our guest emphasizes that obsession is the fuel that drives success. The most successful hosts are relentless in testing, iterating, and learning. They don’t let setbacks define them; they adjust and push forward. Takeaway: Stop treating direct bookings as an optional side project. Make it your primary focus, refine your approach, and stay committed. 2. Build Strong Partnerships One game-changing strategy is partnering with real estate agents and local businesses. Agents have a constant stream of clients needing temporary stays—buyers waiting for a home, sellers in transition, or investors exploring the market. Takeaway: Develop relationships with real estate professionals and position your rentals as their go-to solution for housing needs. 3. Set Higher Standards for Your Business Many hosts settle for whatever bookings come their way, rather than actively shaping their guest pipeline. The key is setting standards: “People get stuck because they set a goal, hit an obstacle, and then change the goal instead of adjusting the plan.” Takeaway: If you want to see different results, you need to change how you think, act, and set expectations for your business. 4. Consistency Wins—Automation & Marketing Matter Direct bookings don’t happen overnight. A clear, repeatable strategy is necessary. Takeaway: Treat direct bookings like a long-term investment. Small, consistent actions compound over time. Ready to Elevate Your Direct Bookings? 🚀 CraftedStays—the all-in-one direct booking platform built for professional hosts. Create a high-converting website, optimize for SEO, and leverage automation to maximize revenue. Follow E Here ⤵️ Transcription E: The biggest epidemic we have as a country is we don’t know how to make decisions, right? We have an idea, the idea becomes a want, the want becomes a goal, but then the moment the goal doesn’t go to plan, instead of going to plan B but still pursuing the same goal, we go back to idea, and we go back to want, and then we go into a new goal. E: And so we never let a goal become an obsession. Every time anybody that has listened to this, and it’s true for me, it’s probably true for you as well, anytime I’ve become obsessed with anything, I have it. Gil: Hey folks on today’s show. I have Emanuele Pani. You might know of him from the STR secrets podcast. I had a chance to be on his show a little while ago and I had a blast talking to him and I’m finding out that he’s actually pretty deep in the mindset game. Um, and he’s attributed a lot of his own personal growth and the growth of a lot of his mentees really around mindset. Gil: So I’m thrilled to bring him onto the show. This is a dense show. It’s a bit different than some of the other episodes that we’ve had on our show, but. I’ve actually quite enjoy it because at least for me, I’ve grew a lot through the years through really tuning in and understanding my mindset. So I thought it was super important for, uh, E to join the show and really talk about how he thinks about things, how he coaches folks through mindset, why he thinks it’s important in the first place. Gil: So without further ado, let’s bring him on. E: Yeah, man. Thank you so much for having me on. It’s been, uh, it’s been a long time coming. And I remember having a blast when you came on our show. And so I’m super excited to, uh, be here with your people now. Gil: Yeah, I’ve been wanting you on my show for a little while now. It’s been hard to get time on your busy calendar. Um, but I’m glad you’re here. Um, one of the main reasons and we’ll, we’ll get into this, but like I, out of like the space, I think there’s, there’s a lot of folks more recently that Is being aware of your mindset and how, how much of a contribution that has towards your growth. Gil: So definitely want to kind of dive into that deeper into the show. And I know you’ve done quite well on the direct booking side. So for you to share some of those as well too, but maybe to kick us off, I’m sure a lot of folks may have heard your voice before, maybe they’re thinking, did they log onto the wrong podcast, but do you mind giving a brief introduction to who you are? E: Yeah, I would love that. So my name is Emanuele Pani. I go by E. I was born and raised in Sardinia, Italy, but I’ve been in the States now for the better part of the last 15, 16 years. And the short term rental community knows me as the co host of the STR secret podcast. And I also have the honor and privilege of being one of the coaches within our community STR secret. E: Uh, we coach people on co hosting and we coach people on boutique

Madeleine Raiford-Holland is the founder of MHM Luxury Properties, a boutique short-term rental company that has scaled to seven figures while maintaining high profitability and time freedom. She also runs a mastermind community at MRH Education, helping hosts start and optimize their rental businesses. Before diving into short-term rentals, she was a COO in the high-security identification industry. Her experience in branding, operations, and hospitality has shaped her unique approach to direct bookings. Summary and Highlights Owning Your Audience is Non-Negotiable One of Madeleine’s strongest beliefs is that short-term rental hosts must control their audience instead of relying on Airbnb or VRBO. She emphasized how capturing guest emails, building a strong brand, and creating direct relationships with guests are essential for long-term success. Madeleine compared this to Instagram, explaining that your followers on social media are essentially rented audiences—you don’t control when or how they see your content. In contrast, an email list is an owned audience because you can reach them directly anytime. She emphasized that successful direct booking hosts must actively collect and nurture guest emails to build long-term loyalty and reduce dependence on OTAs. “If you’re relying on OTAs, you’re just renting an audience. The real power comes when you own the relationship with your guests.” Affiliate Marketing: Turning Guests into Buyers Direct bookings aren’t just about avoiding OTA fees—they also open up new revenue opportunities. Madeleine has integrated affiliate marketing into her rental business, generating over six figures in affiliate revenue last year alone. Her properties now feature QR codes that link guests directly to products they’ve enjoyed during their stay, creating a passive revenue stream. By making her rentals shoppable, guests can purchase everything from linens to appliances, all while driving additional income for the host. Direct Booking Starts with the Right Systems A huge takeaway from our conversation was the importance of implementing a Property Management System (PMS) from day one. Madeleine is a strong advocate of Hostfully, which she credits for streamlining her operations and keeping her business scalable. By automating guest communication, syncing calendars across platforms, and integrating dynamic pricing tools, hosts can run a professional and efficient short-term rental business while focusing on growth. Rapid-Fire Questions with Madeleine Towards the end of the episode, Gil asked Madeleine three insightful questions: These simple but powerful insights highlight how small adjustments can lead to long-term success in direct bookings. ⭐️ Madeleine’s Elevate Your STR Workshop If you’re looking to increase profitability in your short-term rental business, Madeleine is hosting a live workshop and training from March 3rd to 6th at 11:00 AM -12:00 PM EST via Zoom. The event will cover: The event is ticketed, with general admission including access to replays until the Sunday after, and VIP tickets granting 60 days of access to the recordings. Be ready to take your properties from surviving to thriving in your highly competitive market in just 4 days! Register Here: madeleineraifordholland.com/elevate  Listen to the Full EpisodeMadeleine shared even more strategies, from navigating local regulations to maximizing profitability. Don’t miss out this 51st episode special of Direct Booking Simplified, now rebranded to Booked Solid 🎧 Listen to the full episode here Follow Madeleine Here ⤵️ Transcription Madeleine: The difference between your followers on Instagram versus if you’re running a business and have an email list, your Instagram audience is a rented audience because Mark Zuckerberg and company controls who sees your post when they see it. All of that. You’re reliant on an algorithm. You have no control over. Madeleine: Rented audience. Your email list is an audience that you can type an email out and send to you at any time and it’s going to show up in their inbox because they have opted in. That is an audience you own, you control. Airbnb, Vrbo, your rented audience. It is their job to bring you a guest for the first time and then it is your job, once they stay with you, to keep them coming back. Madeleine: Booking directly for the next 10 stays because you’ve captured their email. They understand how to get in touch with you and you’ve directed them to their direct booking site and created a sticky customer. That’s how you own your audience in short term rentals. And it’s so important to leverage all the tools that you have in your playbook to get people to book directly. Gil: Hey folks, welcome back. We actually just rebranded the show. The show is now called book solid. I’m super excited about it And the reason why is actually through the life cycle of actually publishing the show. There’s actually a lot of depth in Not just direct bookings, but really how do you market yourself more effectively across all the marketing channels? So I’m delighted to kind of rebrand the show We actually have a special guest with us this time Madeline Raiford, I’m excited to have her on the show. I just met her recently She is a big proponent of book direct. She actually has a a one week course that she’s going to be running through next week, which I’m excited for her to kind of share with us. But she has an amazing story. She has a lot of dedication into really the book direct movement, but she also has some unique ways that she’s approaching it as well too. not just the typical marketing side of things, which I really love because I find that a lot of folks get into this industry from many different verticals and they also bring in. Um, and so she, outside of her W2 job, she had a side hustle where she was building out her own personal brand. and when she really got into short term rentals, she brought along that experience. So I’ll have her share that in there. So I’m actually really delighted to have her on the show. So without further ado, let’s kind of bring her in. Gil: Hey, Madeline, welcome to the show. Madeleine: Thanks so much for having me, Gil. It’s a pleasure to be here. Gil: Yeah. I’m glad we’re able to track you.

Mike is the co-founder of The Hideaways and Build Your Hideaway, where he specializes in helping hosts maximize revenue through unique short-term rental builds. With a background in digital marketing, Mike has scaled from 0 to 19 properties in just three years, mastering the art of market research, design differentiation, and direct bookings along the way. In this episode of Direct Bookings Simplified, Mike shares his strategies for building a strong short-term rental business that isn’t solely reliant on OTAs like Airbnb. If you’re looking for practical insights on how to strengthen your direct booking pipeline, this one’s for you. Summary and Highlights Building a Direct Booking Strategy That Works 1. Control Your Business, Not Just Your Listings Many hosts rely entirely on platforms like Airbnb. But what happens if your listing is suddenly delisted? Mike emphasizes that while OTAs are a great tool, they shouldn’t be the foundation of your business. Instead, building a direct booking strategy gives you long-term control over your revenue streams. 2. Finding the Right Market Matters Mike scaled quickly by testing different markets, from Spokane to Blue Ridge to Red River Gorge, before discovering where he could generate the highest returns. For hosts looking to expand, Mike suggests analyzing: 3. The Power of Unique Stays Mike’s success comes from designing properties that stand out, whether through amenities, location, or design elements that create an emotional response. He advises: 4. Building a Direct Booking Engine Mike uses a combination of marketing tools to drive direct bookings, including: He emphasizes starting simple: “Even if you only have one property, start collecting emails now. Use Google Sheets if you have to, but build your list and nurture it.” 5. Leveraging Social Media for Direct Bookings Mike’s properties gain traction because of strategic content marketing: “We don’t use our own photos for marketing. We hire professionals or trade stays with influencers who know how to capture the magic of our places.” Final Thoughts: Take Control of Your STR Business If you’re looking to reduce your dependency on Airbnb and scale a sustainable short-term rental business, focus on: ✅ Market research & selecting high-potential locations ✅ Making your properties truly unique ✅ Consistently collecting & leveraging guest data ✅ Using professional content & influencer marketing to boost visibility 🚀 Interested in an optimized direct booking site? CraftedStays helps hosts build high-converting websites that drive direct bookings.  Book a demo today! Follow Mike Here ⤵️ Transcription Mike: If you’re going to build a business, you need to either control the whole thing, or you need to diversify the income sources that you have. So for the people that are only on Airbnb or only on booking. com or whatever they’re on, right, that’s a very dangerous place to be because you have a mortgage, you have utility bills, you have loans, you have all this stuff. Mike: And if Airbnb turns around tomorrow and says, Hey, nevermind, I’m not going to let you stay here. You broke our policies or whatever. And I’ve heard that happen to so many people where all of a sudden it’s like, it was just D listed. It’s like, what are you going to do? So I’m hyper focused on building my business, right? Mike: And Airbnb is a part of that booking. com Verbo. They are a part of that. The core of what I have is my marketing and my direct booking. Right. And that’s what I want because I can control that. So what I’ve done since day one is tried to build all of the database that I can apply customers. Gil: Hey folks, welcome back to a direct booking simplified where we break down the strategies and tactics to win in direct bookings on today’s show. I have Mike Sebastian, Mike, welcome to the show. Mike: Thank you. It’s good to be here. Gil: Yeah. Mike is, uh, the co founder of the hideaways. Um, you might hear from it as hideaways as the, the state that you can do, but also he has build your hideaways, which is actually more on the host consulting side of things. Gil: Um, Mike, do you mind giving folks a kind of an introduction to yourself and. Maybe it’s just first starting off with like how you got, and it got started with the hideaways to begin with. Mike: Yeah, absolutely. So I think my journey was kind of similar to a lot of people’s just stumbling into real estate side and then Airbnbs and then figuring out the boring houses weren’t really doing it for me. So getting more unique, more fun and then finding the results in that. But my, my background is marketing. Mike: Um, I ran a digital marketing agency for about 10 years and as I was in that, I realized that I was getting a little burnt out and there wasn’t a whole lot of tangible asset to the marketing agency. It was just the software systems and employees. And I wanted something that had a little more, you know, girth to it, I guess. Mike: And I started looking around at my, the friends that I thought were successful, the people that I would consider mentors and all of them were in real estate. So I dove into real estate. I started loving it immediately. I got a long term rental. Then I got a short term rental. And then I started researching how to grow, how to scale, how to get investment, all that kind of stuff. Mike: And really digging into the numbers and I, you know, went from, what was it? 2022 to 2025. So three years, I went from zero to 19 properties that we managed today. Um, pretty spread out across the United States for the initial ones, but now we’re honing in on a market in Red River Gorge, Kentucky, and we are getting more and more unique with every build that we do. Gil: Yeah. Was Red River Gorge the one that you first start off with, or is

Heather Bayer is a pioneer in the short-term rental industry, with over two decades of experience. She founded and ran a successful property management company overseeing 200+ properties before selling it in 2022. Now a full-time coach, consultant, and educator, Heather shares her deep knowledge of vacation rental best practices through her platform, Vacation Rental Formula. With a strong focus on trust, responsibility, and hospitality, she helps hosts and property managers refine their operations, improve guest experiences, and drive more direct bookings. Summary and Highlights 1. Trust is the Foundation of Direct Bookings One of the biggest challenges for direct bookings is convincing guests to trust your site over an OTA like Airbnb. Heather emphasizes the importance of strong trust signals, such as transparent policies, clear communication, and visible safety measures. “If someone lands on your website and doesn’t immediately trust you, they’ll head right back to Airbnb.” Practical Steps: 2. Direct Booking Success Starts with a Strong Website Your website is the first impression guests get of your brand, and it needs to feel as professional and reliable as any major booking platform. Heather suggests doing a thorough website audit as if you were a first-time guest. Does it clearly state where your properties are located? Are cancellation policies easy to find? Does it showcase why guests should book directly? Action Item: Take an hour to review your website, ensuring that it is visually appealing, easy to navigate, and packed with trust-building elements. 3. Why Safety & Sustainability Should Be Marketed, Not Just Managed Many hosts focus on safety and sustainability for risk mitigation, but Heather argues these are powerful marketing tools. Today’s travelers actively look for eco-friendly stays and secure properties. Steps to Leverage This: 4. The Power of Guest Experience in Repeat Direct Bookings Heather emphasizes that direct bookings are built on relationships. Guests who trust you and have a seamless experience are more likely to book directly in the future. Proven Guest Retention Strategies: “Your guests aren’t just booking a stay—they’re looking for an experience. If you provide an unforgettable one, they’ll come back and book directly.” Heather’s insights highlight that direct bookings aren’t just about technology or automation—they’re about building trust, ensuring responsibility, and delivering outstanding hospitality. If you focus on these elements, you’ll naturally grow your direct booking rate over time. Checkout Heather on heatherbayer.com Transcription Heather: Trust is the absolute primary. element that has to be brought into any direct booking strategy, because without trust you’re not going to get anybody who’s been out on Airbnb who spend billions to get guests to trust them to come to you with your website, small, medium, large website, but trust you enough to part with their money with you. Because you’re not showing those trust signals that Airbnb are. So that’s at the core of what we train and teach. And then we go into responsibility, which means your responsibility to safety, to, uh, regulatory compliance, to sustainability, to having the right insurance, all these things come together to actually create that trustworthy business. Gilbert: Hey folks, welcome back to Direct Booking Simplified, where we break down the strategies and tactics on how to win in direct bookings. On today’s show, I have Heather Bader. Heather, welcome to the show. Heather: Thank you so much. Thank you for having me on. This is, this is always, I always love being on the other side of the mic. Gilbert: Yeah, yeah. It’s fun to do this both sides. I actually, I think if I had a preference, it’s more fun to be a guest on the show than a host on the show. I don’t know why. It just, I don’t know. Maybe it’s because it’s change of pace and you get to relax and be the one to consume all the questions rather than thinking ahead about the next set of questions. Gilbert: I think it is a lot of fun being the guest. Heather: Well, as As I’ve been podcasting for nearly 14 years now. Every Wednesday for 14 years. It, it just is a great contrast to, to be asked the questions and not asking them. So, yeah, far away. Gilbert: maybe, maybe slight tangent there. Well, any word of advice for myself or anyone that’s getting into podcasts, thinking about it, how did you 14 years of quite a run in terms of pace there. And a lot of folks, I think even like the first six months, they start to give up. Like, what’s, what’s your secret to, to lasting quite, quite that time. Heather: Um, well, it is consistency. The only way to, to grow an audience is to be consistent. And if you’re continuously consistent, um, and this is why I’ve never done, I’ve never done, you know, Series 1, Series 2 or Season 1, Season 2. You know, I just. just publish every week and, and it becomes habit. It is, and you batch record. Heather: So, and, and the other thing is, is, is that if you really love the business and have passion for the business, you just love talking to people. So that just converts into a 45 minute recording. What, you know, what, what more can it Gilbert: hear you. I 100 percent hear you on that one. I, I’ve met so many people through this show and I’m sure it’ll resonate with you, but like, it’s a great way to tap into the greatest minds in the industry and ask the stupidest questions that you can think of. And you just feel very vulnerable about asking those types of questions because it helps a lot of folks. Heather: I, I’ve met, I think I’ve met just about everybody that has, you know, been at the core of this industry for so many, for decades. And, and it’s a huge honour to be in that position. And, and yes, get to ask whatever you want. And, yeah, get some, get some crazy answers sometimes. I, I, I will share, share one. Uh,

On this episode of Direct Booking Simplified, we sat down with Jodie, the Founder of Hospitable Hosts – a multi author book. She is also a property manager originally from Australia who built a thriving short-term rental business in the UK—all while managing it remotely from the other side of the world. Jodie shared her journey, the challenges of scaling a direct booking business, and why hospitality should always come first. Summary and Highlights Jodie started her short-term rental business in a small country town in the UK. After moving there with her family, she converted a separate cottage on their property into a short-term rental. What started as an experiment turned into a full-fledged business that survived regulatory changes, COVID-19, and the influx of competition in the market. Despite the growth of the industry and increasing competition, Jodie’s focus on guest experience and direct bookings has helped her stand out. Scaling a Direct Booking Business While Managing Remotely Jodie shared insights on how she successfully transitioned to managing her UK-based business from Australia. One of the biggest keys to her success? Building a reliable team and systemizing operations. Why Hospitality is More Important Than Ever As more investors flood the short-term rental market, Jodie sees a major divide between those who treat it as a real hospitality business and those who chase quick profits. As Jodie said: “A lot of people got into this business thinking they could make quick money, but they underestimated the work involved. The ones who truly enjoy hospitality and have built solid systems are the ones thriving right now” Her advice to hosts looking to stand out? Make hospitality a core part of your business strategy. The Birth of Hospitable Hosts: A Community Focused on Raising the Standard Jodie is also the founder of Hospitable Hosts, a collective of professional short-term rental operators dedicated to elevating hospitality standards. What started as a book project—bringing together 40 hosts to share their stories—has grown into a movement. Hospitable Hosts aims to educate hosts on the power of putting guests first. They believe that Hospitality isn’t just about a bottle of wine at check-in; it’s about genuine care and service. A New Initiative: The Hospitable Hosts Summit Jodie announced an upcoming Hospitable Hosts Summit, happening in April 2025 in Denver, Colorado. Unlike traditional conferences, this summit will be hands-on, focusing on real strategies hosts can implement immediately to enhance their hospitality game and increase direct bookings. Jodie’s #1 Direct Booking Tip One simple strategy that has helped Jodie increase repeat guests? A tangible takeaway. “I leave a branded postcard in every property that thanks guests for staying and offers them 15% off their next visit if they book direct. Having something physical they can take home really makes a difference.” Follow Jodie Here ⤵️ Transcription Jodie: There’s a lot of people out there stating you can make X amount of money when you have an Airbnb or a property business, but it’s, it’s hard work and not everybody can keep up with that. And the hospitality side of things. So dealing with people, dealing with the guests, dealing with the public, you know, um, that’s, that can be tricky. Gil: Hey folks, welcome back to Direct Booking Simplified, where we break down the strategies and tactics of direct bookings. On today’s show, I have Jodie. Jodie, welcome to the show. Jodie: Hi Gil, thanks for having me on. Gil: Yeah, I am so happy to have you here. You are one of my favorite people that I met in, I think 2024. Um, Jodie: We did meet in 2024. Yeah, Gil: it feels like a long time ago. Um, Jodie: does. Yes. We’ve had lots of conversations. Gil: yeah. Um, do you mind giving folks a quick introduction on who you are? Jodie: Sure, sure. So, um, hi everyone. My name is Jodie. Um, I’m a host just like you, uh, listening in. Um, I have a property management company in the UK, but you can probably tell from my voice that I’m Australian. So, um, I have a pretty unique standing where I I’m a very remote host. I host from the other side of the world because I’ve not long relocated back to Australia, but I kept my business operating in the UK, which has all sorts of, uh, shall we say challenges, but it’s working. So far, so good. Gil: Yeah. Jodie: So I, Gil: how many units in the UK do you have? Jodie: uh, so I have 15 properties that I look after. Um, I have different styles of doing that. I look after, I manage two people’s properties and the rest are mine that I have on rent to rent or rent to arbitrage as you call it there. Gil: Wow. So you, when you started that, were you living in the UK before moving to Australia or how did you kind of land on this? Jodie: Yeah, I was. So I’ve lived out of Australia for a long period of time, 12 years, actually, and we were living in Europe, and then we decided I’ve got three children. Um, we were homeschooling as we were traveling, and, uh, it was time for the older two to kind of knuckle down and get some qualifications in their schooling. So we settled on the UK and we found ourselves in a beautiful little country town called Tetbury, which is actually where the the king lives. He has a house there. Um, so it’s one of those unique places. Um, you know, when you think of like stone cottages and green rolling hills. That you see on the television and in movies, that’s the type of environment that it is. And we got a home with some land and it had a separate cottage on it and just near the house. And we thought, what are we going to do with this? And we can store bikes or we could just keep it for when

Ever wondered how to break free from OTAs and take control of your bookings? Sarah Pell did just that. She went from teaching elementary school to managing a thriving short-term rental portfolio using a mix of ownership, arbitrage, and co-hosting. In this episode of Direct Bookings Simplified, Sarah reveals the exact strategies she used to scale her business, build a strong direct booking system, and maximize profitability—without overcomplicated tech. Summary and Highlights Building a Portfolio with Three STR Strategies “Arbitrage really opened up my world. Just within a year and a half, I had acquired four. Compared to saving for a single purchase, it was a game-changer.” Sarah’s path to STR success wasn’t conventional. After getting into real estate through house hacking, she realized that long-term rentals weren’t providing the cash flow she wanted. Instead, she turned to vacation rentals. She initially purchased a condo in Orange Beach but quickly recognized that saving for down payments would take too long. That’s when she discovered rental arbitrage, allowing her to scale faster. Within a year and a half, Sarah went from one STR to four through arbitrage, while also co-hosting for other owners. Balancing ownership, arbitrage, and co-hosting has given her a well-rounded perspective on managing STRs and optimizing guest experiences. Direct Booking Strategies That Work Sarah emphasizes that while starting on platforms like Airbnb and Vrbo is essential, building direct bookings is what truly allows STR owners to scale. Here are some of the strategies that have worked for her: 1. Leveraging Facebook Groups for Direct Bookings One of Sarah’s biggest game-changers was tapping into Facebook groups to promote her listings. Instead of relying solely on Airbnb, she joined vacation rental and travel-related groups in her market. “I found that Facebook groups were like a secret sauce. I would join groups for vacation stays in my area and respond to travelers looking for dates with a direct booking link. That was a huge boost early on.”  2. Using Repeat Guests to Drive More Direct Bookings Sarah actively encourages repeat guests to book directly. She offers a 15% discount to returning guests who book through her direct website and includes promotional business cards and magnets inside her properties. “We text every guest after their stay with a promo code they can share with friends and family. It’s a simple way to encourage direct bookings.”  3. Capturing Guest Emails for Long-Term Success Sarah initially collected guest emails manually but later streamlined the process using her property management software. Her team now sends email campaigns and promotional offers to past guests through MailChimp. “Even before I had MailChimp, I was manually emailing past guests with BCC. You don’t need a fancy system to start—just start collecting emails.”  4. Setting Up a Strong Direct Booking Website While Sarah started with a simple site, she’s now investing in making it more streamlined and guest-friendly. She plans to integrate better search functionality and branding to make it easier for guests to find and book her properties. Automation vs. Personalization in Direct Bookings One key takeaway from Sarah’s journey is that automation is helpful, but personal connection matters. While she uses automated text and email follow-ups, she still handles guest communications manually to ensure a personal touch. “I still handle my guest messaging personally because I want to interact with them. It helps me understand their concerns and improve my guest experience.” Scaling Direct Bookings with the Right Tools Sarah’s experience shows that you don’t need a complex system to succeed with direct bookings—you just need the right mindset and simple, effective strategies. Whether you’re just getting started or looking to scale, her approach proves that taking small steps, like leveraging Facebook groups and collecting emails, can make a big impact. If you want to hear Sarah’s full journey and her step-by-step direct booking tactics, listen to the full episode of Direct Bookings Simplified [link to podcast episode]. Join the Community Want to connect with like-minded STR owners focused on direct bookings? Join our community, where we discuss strategies, share insights, and support each other in building sustainable short-term rental businesses. [Link to community] Looking to optimize your direct booking site? At CraftedStays, we help STR owners create high-converting, mobile-optimized direct booking websites. If you’re ready to take control of your bookings and maximize revenue, check out CraftedStays today. Follow Sarah Here ⤵️ Transcription Sarah: Part of my direct booking as well is Facebook groups. So I do have a business Facebook page and you wouldn’t even need to do a page. I’ve done it even just personally. And I will have a little message with my direct booking link. And so what I do is join these groups. So like, um, you know, vacation stays of orange beach, and I will go in there and I will look for people that are searching for dates to come and I will just copy and paste my little message about my condo and. I have found that was like a, in the beginning to a huge boost in like my direct bookings is I found that a lot of people would find me on Facebook and then reach out on my direct booking website. And so I would say that, uh, I feel like Facebook groups are kind of like a secret sauce. I mean, cause you can find co hosts, you know, arbitrage, properties, direct booking clients. Like it kind of, it’s all, all there. Gil: Hey folks, welcome back to direct booking simplified, where we break down the strategies and tactics to win in direct bookings. On today’s show, I have Sarah Pell. Sarah, welcome to the show. Sarah: Thank you, Gail, for having me. I’m excited to be here. Gil: Yeah. As we get into it, do you mind giving folks a quick introduction on who you are? Folks may have seen you on Instagram or other places, but yeah. Introduce yourself. Sarah: Yeah, of course. So, I’m originally from Pierce, South Dakota. That’s where I was born and

 “Trust comes from having a secure site and a seamless booking process. If your site instills confidence, guests will book without hesitation.” – Jennifer Spencer In the latest episode of Direct Booking Simplified, we sat down with Jennifer Spencer, a seasoned host with over a decade of experience in the vacation rental industry. Jennifer owns two stunning properties: one nestled in the Canadian Rockies and another in the sunny paradise of Maui. Her journey from renting a family ski getaway to running a thriving vacation rental business offers a wealth of insights for both seasoned hosts and newcomers alike. Summary & Highlights A Journey from Ski Enthusiast to Business Success Jennifer’s story began ten years ago when she purchased her first vacation rental property in the Canadian Rockies. Initially intended as a home base for her family’s ski trips, Jennifer soon realized its potential as a vacation rental. “Back then,” she shared, “Airbnb wasn’t even in my market. The primary player was VRBO, and there were no guest fees.” Her entrepreneurial spirit led her to transform the property into a six-figure revenue business. Fast forward to 2021, Jennifer expanded her portfolio by purchasing a property in Maui. This move showcased her ability to diversify not just geographically but also seasonally, offering her guests a choice between the ski slopes and the sea. The Turning Point: Building a Direct Booking Website In 2017, Expedia’s acquisition of VRBO was a pivotal moment for Jennifer. Recognizing the growing control OTAs were gaining over her business, she decided to establish her own direct booking website. “I didn’t want to be 100% reliant on a large multinational company,” she explained. “Having my own site gave me the ability to capture repeat bookings, reduce guest fees, and build direct relationships with my guests.” This decision not only provided Jennifer with more control but also helped her retain a larger share of her revenue. Key Strategies for Direct Booking Success Jennifer shared several actionable strategies during the episode that have been instrumental in her direct booking success: The Importance of Taking Action Jennifer’s advice for hosts looking to grow their direct booking strategies is simple: “Take action.” Whether it’s setting up a property management system, building a direct booking website, or sending your first marketing email, she believes progress comes from doing. “You’ll learn and grow from the process,” she encouraged. Join the Conversation This episode is packed with more insights, including Jennifer’s mindset on overcoming perfectionism and how she cross-markets her properties. Be sure to listen to the full episode for a deep dive into her strategies. Want to connect with like-minded hosts and learn more direct booking strategies? Join our Direct Booking Simplified community and continue the conversation. And if you’re ready to take control of your bookings, CraftedStays can help you build a secure, guest-friendly website that reflects your unique brand. Book a demo today and see how we can help you grow your direct bookings. Follow Jennifer Here ⤵️ Transcription Jennifer: Trust comes from having a secure site from having a tool in place that is seamless for them to book. And when you start to put kind of roadblocks or friction or things that make them question, they may not proceed with the booking, right? So I think a testament to your site is if people book and you have had no conversation with, like, I get that. Jennifer: You know, someone just books off my site, my, my direct booking site. And I’m like, awesome. I don’t know necessarily. I mean, I could find out where they came from, Google analytics and things like that, but like when I initially get that, I’m like, awesome. That means my site looked trustworthy enough that they would just go ahead and make that booking without reaching out to me, without asking me any questions. Jennifer: Right. And that’s what you want, right? You want the credibility and the authority and trustworthiness that people get from booking on an Airbnb or on Airbnb or VRBO. That’s why they’re working there, right? So if you can instill that confidence in your own site, then that’s when you’ll have a lot of success with direct bookings. Gil: Hey folks. Welcome back to direct booking simplified. We break down the strategies and tactics to win and direct bookings on today’s show. I have Jennifer Spencer, Jennifer. Welcome to the show. Jennifer: Thank you. So great to be here. Thanks for having me. Gil: Yeah. Where are you calling in from right Jennifer: Uh, I am in Calgary, Canada. Um, it’s a little bit chilly here right now. Um, so yeah, I’m, I’m located in, in, uh, Canada. Gil: Yeah. And you’re also, you have properties also in the States, not the, not the major islands, Jennifer: Yeah, Gil: but the minor islands. Jennifer: yes, well, I have exactly. Yes, that’s true. So, yeah, I own 2 vacation rental properties. 1 is in the Canadian Rockies here close to my house. It’s still 4 hour drive and the other 1 we have in Maui, we just bought in 2021 so and I have owned my Canadian property for 10 years and actually just celebrated 10 years. Jennifer: So, like, 10 years, about 3 days ago, we got the keys to that property and it’s, uh. Totally changed my life. Gil: Wow, what was the story behind getting that first Canadian Rockies property there? Jennifer: Yeah. So, I mean, I’ve always been into real estate and I bought my first place when I was like, 24. It’s always been my thing. Um, but the reason we actually bought this particular property is that we are a ski family and all three of my kids were ski racing and we were coming back and forth from the mountains a lot. Jennifer: And so we decided, okay, let’s, you know, get a, Home base in the mountains and so we bought this property and really with not the intention of having it

“I didn’t know there was a thing called direct bookings. I just knew I needed to do what I had to do—build my own brand and go after my own bookings.”   In our latest episode of Direct Bookings Simplified, we sat down with Jenn Boyles, a trailblazer in the world of direct bookings and marketing strategies for short-term rentals. Jenn has a wealth of experience as a host, marketer, and coach, and her journey from hosting an apartment in France to launching her marketing platform, BookDirectPro, is nothing short of inspiring. Jenn’s insights into building a successful direct booking strategy are invaluable. Here’s a snapshot of what we discussed—be sure to listen to the full episode for more tips on Simplifying your Direct Bookings Summary & Highlights Meet Jenn BoylesJenn Boyles is the founder and CEO of Direct Booking Success – the podcast | the summit | the program. Her mission is to help vacation/short-term rental property managers, owners and hosts increase their revenue and control with the power of direct bookings. She started as a property manager and owner herself, managing her own award-winning properties from 2013 to 2024. Finding herself with a property in an over-saturated area was what initially led her down the path of building her own direct booking business. She is the host of the weekly Direct Booking Success Podcast which is produced with a mix of educational solo episodes and interviews with Hospitality and Accommodation professionals along with fellow property managers and owners.  Jenn is also the founder of the annual Direct Booking Success Summit. This event is a FREE marketing and hospitality educational online summit for vacation/short-term rental property managers and owners who want to increase their revenue and control in their own business with direct bookings. Her latest venture is founding Book Direct Pro, the all-in-one marketing platform built for vacation rental pros by a vacation rental pro. With Book Direct Pro, Jenn aims to simplify and streamline the entire marketing process, giving hosts more control over their bookings and profits. It’s designed to cut out the middleman, empower property managers, and make direct bookings a breeze. 1. The Power of Storytelling in Marketing Jenn’s success in the UK stemmed from building a strong brand before launching her property. By documenting the construction and branding of her unique canal boat in Liverpool, she created a buzz and established trust with potential guests. “People followed the journey and joined a waitlist, so when we launched, they were ready to book.” Tip for Hosts: Share the story behind your property—whether it’s a renovation project, local attractions, or memorable guest experiences. Use social media, email newsletters, and even simple videos to bring your journey to life. 2. Start with One Property (and One Strategy) Contrary to popular belief, direct bookings aren’t just for large portfolios. Jenn emphasized how smaller hosts can leverage their personal touch and storytelling to compete with big players. “You don’t need 50 properties to make this worthwhile. Even with one or two, you can create a personal connection that larger operators can’t match.”  Actionable Idea: If you’re a remote host, batch-create content during visits. Showcase your property’s personality, local attractions, and unique amenities. 3. Focus on Guest Data Collection Jenn highlighted the importance of owning your guest relationships through email marketing. Platforms like Airbnb won’t share guest data, so hosts need to find ways to capture it independently. “Once you have their email, you can connect directly, nurture relationships, and bring them back for future stays.”  Practical Advice: Use tools like Wi-Fi sign-ups, digital registration forms, or automated guest surveys to collect guest emails. 4. Leverage Automation and Tools For busy hosts balancing multiple responsibilities, Jenn stressed the value of automation. Her platform, BookDirectPro, simplifies marketing by combining email marketing, social media scheduling, landing pages, and more into one tool. “Marketing doesn’t have to take over your life. Set up systems, automate what you can, and focus on what matters.” Pro Tip: Use automation to schedule social media posts and email campaigns. Dedicate time monthly to batch-create content, then let technology do the heavy lifting. 5. Build Trust Through Personalization Jenn shared how personalization drives direct booking conversions. Adding an “About Us” section, featuring reviews, and showcasing local attractions on your website can make all the difference. “People want to know who’s behind the brand. Share your story—it builds trust and encourages bookings.”  Quick Win: Update your website with a personalized bio and real photos of your team or family to foster trust with potential guests. Start Building Your Direct Booking Strategy TodayJenn’s journey is a testament to the power of storytelling, relationship-building, and leveraging the right tools to grow your direct bookings. Whether you’re just starting or looking to scale, her advice is clear: take one step at a time and focus on strategies that align with your goals and resources. If you’re ready to take control of your bookings, don’t miss the chance to try Jenn’s all-in-one marketing platform, BookDirectPro. Use code DIRECTSUCCESS for 50% off your first month, and schedule a free onboarding call to get started. Follow Jenn Here ⤵️ Transcription Gil: Welcome back to direct booking. Simplify where you break down the strategies and tactics to win in direct bookings on today’s show, I have Jenn Boyles, Jenn, welcome to the show. Jenn: Aw, thanks Gil. Thanks for having me. Gil: Yeah, it’s, it’s such a familiar voice. I’ve listened to your podcast on my car drives a lot. Um, so it’s really good to have you on, on this show as well. Jenn: Aw, thanks so much. I hope I haven’t caused any accidents. Gil: No, no, it’s a, it’s a, it’s a very calming conversation. So if anything, it helped me focus. Yeah, there’s not many shows in the direct booking space, um, that talks about direct booking. So I think there’s like the R2 shows and maybe a two or three others. And that’s pretty much it about direct bookings. Um, there’s a lot of more general, um, short term rental ones, but not