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