Rodman Schley is a seasoned real estate investor and short-term rental expert with an impressive career spanning decades. Starting with fix-and-flip properties to pay for college, Rodman’s journey evolved into a passion for short-term vacation rentals. With over $20 billion in valuations as a certified appraiser, he’s mastered the art of analyzing markets and making strategic investments. Today, his portfolio focuses on high-performing properties in Costa Rica, where he blends his love for travel with his investment expertise. Rodman’s philosophy is simple: align with your purpose, strive for excellence, and create exceptional guest experiences. Summary and Highlights In our recent episode of Direct Booking Simplified, Rodman shared invaluable insights into his journey, strategies, and mindset for mastering direct bookings. Here are the key takeaways: 1. Purpose Over Profit Rodman emphasized the importance of aligning with your purpose. “Make sure you love what you do,” he said. By combining his passions for travel and investing, Rodman found success in the short-term rental space. His advice? Be an outlier. Don’t settle for mediocrity—strive to be exceptional. 2. Why Direct Bookings Matter With a 50% direct booking rate, Rodman’s properties stand out for their exceptional guest experiences. He highlighted how direct bookings not only reduce fees but also reflect the strength of your operations. According to Rodman, each guest’s stay is a testament to your management, systems, and property’s appeal. Quote: “Think of that guest in your property right now as your most valuable opportunity to grow your direct booking rate.” 3. Building Relationships for Repeat Bookings Rodman’s approach to guest relationships is unparalleled. With an attentive onsite manager and a concierge service, his team ensures every guest feels like family. From arranging surf lessons to hosting community-style retreats, Rodman’s properties deliver more than a stay—they create lasting memories. 4. Effective Email Marketing Rodman’s email marketing strategy is simple but powerful. Monthly newsletters keep guests engaged with updates and offers, while post-stay thank-you emails nurture relationships. By focusing on value and maintaining consistent communication, his properties remain top of mind for past guests. Pro Tip: Include updates about the community and special offers in your emails to encourage repeat bookings without overwhelming your audience. 5. Conservative Planning, Exceptional Execution Rodman stressed the importance of realistic financial planning. By underestimating revenues and overestimating expenses, he mitigates risk and ensures his properties consistently perform. This conservative approach allows him to focus on outperforming his projections. Follow Rodman Here ⤵️ Transcription Rodman: I was led with profit and purpose was always second. And those don’t work out. Make sure you love what you do. If you’re coming to the short term vacation space, make sure you love it. For me, I love to invest and I love to travel. That was a perfect thing for me. So I, that’s why I love the short term vacation rental space. But the other thing I tell people is, you know, there’s so many people, if you think about life as being this big bell curve, right? So many people are in this easy space right in the middle of the bell curve. And I always say, you know, if you’re going to do something, be exceptional at it, be an outlier in it. So if you’re aligned with your purpose and you put in the work, be an outlier, be, be exceptional, be an expert at what you do. Gilbert: Hey folks, welcome back to direct booking. Simplify. We break down the strategies and tactics to win and direct bookings on today’s show. I have Robin Schley. Robin, did I say that correctly? Rodman: You said it, right. Gilbert: Awesome. Well, it’s great to have you on the show. Gilbert: Um, it’s great to, I met you a couple of weeks back and I’m, I’m thrilled to have you on the show and kind of talk about how you’ve grown in real estate, what you’re doing now, um, and share with us, uh, some tips on how to really amp up that direct bookings basically, because when I learned what your direct booking rate is, I definitely wanted you to, to share that with the group here. Gilbert: Awesome. Rodman: Yeah. Yeah. I’m excited to be here. Excited to talk. We had a great conversation when you were on my podcast and, uh, you know, it’s always just nice to be able to share this knowledge and this, this information that you collect with people and pass it on down to those folks who maybe want to figure out how to be an outlier in the space, how to be great, how to be an expert. Gilbert: Yeah. Yeah. And I always find that like through the podcast, like the best way to do that is really to get a mixture or like almost like a melting pot of different perspectives because I find that like, there’s not one, you know, that’s like going into real estate investing, starting your own business, doing anything. Gilbert: There’s not run one way to do it. Right. Um, and it’s often. Yeah. Many, many different ways of doing it. Right. And it may have different outcomes. They may have different timelines, but people approach it different ways. But the best thing to really do is really educate on what people are doing and finding out what, what works for you. Rodman: Yeah. How do you optimize, how do you get better at what you’re doing and how do you learn from others and optimize what they’re doing? And, you know, it’s a really small community of people who are doing what we’re doing. And so when we get a chance to lift other people up, teach, educate, learn from them, you gotta, you gotta jump on that. Gilbert: Yeah, absolutely. Well, before we get too far into it, do you mind giving a quick introduction on who you are, what you’re doing now, kind of how you got here? Rodman: Yeah, of course. No, of course. Like you said, I’m Robin Schley. I, uh, I’m a real estate

In our latest podcast episode, we had the pleasure of hosting Breanna Williams, founder and principal designer of Mumford Designs. Breanna specializes in short-term rentals (STR) and mid-term rentals (MTR), blending interior design, market research, and marketing strategy to create unforgettable guest experiences. With over 15 years of design expertise and a particular passion for hybrid rental properties, Breanna shared invaluable insights into leveraging thoughtful design to boost direct bookings. Summary and Highlights From Retail Showroom to STR Design Specialist Breanna’s journey began in high school, where her love for design was sparked by her parents’ homebuilding projects. After completing her degree in interior design, she worked at Lazy Boy Furniture Galleries, where she oversaw design projects for homes across diverse settings. In 2020, she founded Mumford Designs, focusing on STR and MTR properties. This transition allowed her to merge her design expertise with marketing strategies tailored to maximize occupancy and revenue. The Power of Knowing Your Guest Avatar One of the key takeaways from the episode is the importance of understanding your “guest avatar” before setting up your rental property. As Breanna explained: “If you’re trying to appeal to everyone, you’re not giving anyone a true custom experience. Knowing your guest avatar fully directs every decision, from design to marketing.” Breanna recommends starting with a property audit that combines: Bonus Article: Unveiling the Art of Guest Communication: “WHO-WHERE-HOW” Designing for Hybrid STR/MTR Properties Hybrid properties that cater to both STR and MTR audiences require a unique design approach. Breanna’s framework involves creating a Venn diagram of overlapping guest needs. For example: In a recent project in Newport Beach, Breanna designed a property targeted at families displaced due to home repairs. The home featured practical amenities such as twin beds for kids, a dedicated homework area, and a pet-friendly setup—a stark contrast to the impersonal nature of hotel stays. The Role of Photography in Marketing Photography can make or break a listing, and Breanna emphasized the importance of aligning your visuals with your target audience: “Every photo should tell a story about who your property is designed for. If you’re targeting families, show the pack-and-play, board games, or a cozy firepit perfect for roasting s’mores.” To achieve this: Breanna’s Top Tactical Tip for Direct Bookings When asked for her top piece of tactical advice, Breanna didn’t hesitate: “Know your guest avatar fully before purchasing items or setting up your property. It saves you money and ensures every design decision attracts your ideal guest.” A Mindset Shift for Hosts Starting something new can feel overwhelming. Breanna shared a mantra that keeps her motivated: “Not ‘I have to do this,’ but ‘I get to do this.’ Embrace the opportunity to learn and grow through every challenge.” Join the CraftedStays Community This episode was packed with actionable insights, but there’s even more to discover. Listen to the full episode to dive deeper into Breanna’s frameworks and strategies for STR success. Looking to take your direct booking game to the next level? CraftedStays offers tools to help you build a website tailored to your brand and guest avatar. With features like customizable templates and integrated booking flows, we simplify the process so you can focus on hosting. Join our community of like-minded hosts to exchange ideas, learn from experts like Breanna, and optimize your short-term rental business. Ready to elevate your STR strategy? Book a demo or explore CraftedStays today! Follow Breanna Here ⤵️ Transcription Gil: Hey folks, welcome back to direct booking simplified. We break down the strategies and tactics to win in direct bookings on today’s show, I have Brianna Williams, Brianna, welcome to the show.  Breanna: Hi, thank you for having me.  Gil: Yeah, I love doing this because we actually had our podcast recording a couple, actually about probably a week back now, and I’m actually thrilled to have you on this show. Gil: To talk, to have you as the guest on here. Um, so welcome, welcome here. Um, before we get too deep into it, do you mind kind of giving folks an introduction on who you are?  Breanna: Sure. So my name is Brianna Williams. I am the founder and principal designer for Mumford designs. So we specialize in short term rentals and midterm rentals. Breanna: Um, and we handle interior design, a little bit of marketing strategy, a lot of market research. And essentially we just take all of the data in that market research phase and point it straight, straight towards the design, um, and kind of gear all of that towards how we’re going to market their property. Gil: Nice. How did you get started in, in, in this business?  Breanna: Oh, it’s been a long journey. I’ve been designing for almost 15 years. So in high school, it kind of clicked for me that interior design is something that I wanted to do. When I was growing up, I would go to model homes with my parents all the time. And my dad built a lot of our childhood home with his own hands. Breanna: My mom would always do the decorating and so on and so forth. So it’s kind of just something that I knew that I wanted to do for so long. So right out of high school, I went to school for interior design, and then I got out of school and I’m like, wait. How do I get a job in interior design? So I ended up falling into retail and I worked as a designer for a retail showroom for, um, almost 10 years. Breanna: And in 2020, I left there and I started my own business and it kind of just happened by happenstance that I fell into working specifically with investors on everything from fix and flips, you know, consulting on paint colors and tile selection, you Into short term rentals and eventually midterm rentals, which is kind of midterm rentals and hybrids are like my niche, my, that’s my favorite thing to do. Gil: Interesting.

In our latest episode of Direct Booking Simplified, we had the privilege of hosting Stacy St. John, a powerhouse in the short-term rental (STR) industry. She is a Cincinnati-based STR investor and host with properties located 10 hours away in Myrtle Beach, South Carolina. She is the founder of the STR Sisterhood, a vibrant community exclusively for women in the industry, with over 62,000 members. Stacy also hosts the STR Sisterhood Podcast and runs coaching programs designed to empower women in STRs. From building thriving communities to mastering direct bookings, Stacy shared invaluable insights that both seasoned hosts and newcomers can learn from. Here are some highlights from our conversation that will inspire you to take actionable steps toward increasing your direct bookings. Summary and Highlights Meet Stacy St. John Stacy St. John’s journey into property management is a story of resilience and learning. “From the start, I built a team around me,” Stacy shared. “It was an absolute necessity given the demands of my corporate job.” Fast forward to today, Stacy operates a full-fledged property management company with a team dedicated to excellence and guest satisfaction. Key Takeaways on Direct Booking Strategies Stacy emphasized the importance of blending strategy and personalization when driving direct bookings. Here are some of the strategies she uses to stand out: 1. Leverage Local Directories “Being part of the Chamber of Commerce and other local directories is one of the simplest yet most effective ways to increase visibility,” Stacy explained. These listings not only help attract local guests but also improve your website’s SEO by generating high-authority backlinks. 2. Optimize for Repeat Guests Stacy ensures every guest knows how to book directly with her in the future. From branded materials in her properties to personalized follow-ups, she creates a seamless path for repeat bookings. “If they’re great guests, we always invite them back with a discount offer,” she added. 3. Email Marketing Done Right Email marketing is a cornerstone of Stacy’s direct booking strategy. She’s focused on creating segmented campaigns tailored to specific guest profiles. For instance, golfers receive updates about upcoming golf events in Myrtle Beach, while families get tips on family-friendly activities. “It’s all about delivering value that’s relevant to their experience with us,” she emphasized. 4. Invest in SEO-Driven Content To drive organic traffic, Stacy’s team regularly publishes blog posts optimized for SEO. “We’re focusing on topics that resonate with our audience, like seasonal events and travel tips, and repurposing this content into our email campaigns,” she explained. 5. Guest Verification Tools “When you’re handling direct bookings, tools like Superhog are game-changers,” Stacy said. These platforms help ensure guests are verified, protecting your business from chargebacks and disputes. Mindset Matters Beyond strategies, Stacy shared powerful mindset advice for hosts navigating the complexities of STRs. “The person holding you back from your next level is often yourself,” she noted. By investing in personal growth and confidence, you can unlock your full potential as a host and business owner. Take Your Direct Bookings to the Next Level Ready to implement these strategies? Don’t miss the full episode of Direct Booking Simplified for deeper insights and actionable advice from Stacy St. John. Looking to grow your direct booking business? Join the STR Sisterhood community or check out Stacy’s coaching programs to learn from one of the best in the industry. Visit Stacy’s website to connect and explore her resources. CraftedStays: Your Partner in Direct Booking Success At CraftedStays, we’re here to empower hosts like you to build professional, SEO-optimized direct booking websites without the hassle. From intuitive templates to advanced features that make managing bookings seamless, we’re committed to helping you thrive. Learn more about our platform and how it can support your direct booking journey. Book a demo today! Follow Stacey Here ⤵️ Transcription Stacey: I think the one piece of tactical advice I would say is utilize a third party tool that can help you verify your guests. As we know, if Airbnb takes a booking and someone pays Airbnb, Airbnb pays us out. If someone disputes a charge on their credit card to Airbnb, Airbnb is not clawing back the money from us. Stacey: They are eating that, right? When we have a direct booking situation, if someone disputes a charge on their credit card, it is coming out of our bank account. Right. So having a third party verification tool, I use super hog in my own business. That has been tremendously helpful, but I think whether you use super hog or someone else, make sure that you’ve got the right resources to be able to. Stacey: Dispute a charge back, but then also hopefully avoid them altogether. 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 Stacy, Stacy, welcome to the show.  Stacey: Thank you so much. Thanks for having me. I’m excited to be here.  Gil: I’m so excited to have you on here. I’ve heard your name from so many people. Gil: So many people referred me to you to have, have you on my show. So I’m really glad to finally have you here.  Stacey: Awesome. That’s great.  Gil: And  Stacey: thanks to all the people who referred me.  Gil: Yeah. And it was good to be on your show just, uh, just a few weeks back too. That was really fun to kind of walk your, your audience through kind of what we’re doing and. Gil: Kind of how we approach things. I appreciate you, uh, lending me your audience to, to spread our word.  Stacey: I think you’re doing amazing stuff. So it’s, it’s my pleasure.  Gil: I appreciate that. Well, I, your, your name is pretty well known in the industry. Um, but for those that haven’t come across the name, Stacy St. John, Who, who are you? Stacey: How much time do we have here? No. So I, uh, well, I, my name is Stacey St. John. I live in Cincinnati, Ohio. Um, most of

In this episode of Direct Bookings Simplified, Alex opens up about his journey from facing early challenges in real estate to building a thriving STR business, complete with seven properties, a coaching program, and innovative direct booking strategies. Discover how he uses guest videos, monthly inspections, and smart email marketing to create standout guest experiences and win loyal repeat bookings—all while balancing life as a father of four. This is an episode packed with refreshing short-term rental perspectives, and heartfelt lessons you’d be interested to learn from Summary and Highlights Here are the top takeaways that every host can learn from. 1. Competition in STRs is Fierce—How to Stand Out Alex highlighted how the landscape for short-term rentals has shifted dramatically. Guests today expect more than just a clean space—they want unique experiences and thoughtful design. He emphasized the importance of market research, working with designers, and creating memorable, Instagram-worthy spaces. Key Tip: “It’s not about what looks nice to you—it’s about what stands out in the market.” 2. Building Systems for Quality and Guest Experience Alex shared his approach to operational excellence, including monthly property inspections. Unlike cleaners, who are focused on turnover tasks, inspectors evaluate the overall property condition and ensure readiness for guests. He also creates short instructional videos for common guest issues, like operating appliances or resetting a Wi-Fi router, embedding these into his digital guidebook. Why It Matters: Small steps like this help reduce last-minute guest inquiries and elevate the overall guest experience. 3. The Power of Keeping Guest Relationships Alive One of Alex’s early mistakes was failing to maintain contact with past guests. He’s since corrected this by implementing email marketing campaigns and tagging VIP guests for personalized follow-ups. Practical Advice: 4. Embracing Direct Bookings Alex’s focus on direct bookings includes using platforms like OwnerRez to automate processes, creating his own direct booking site, and leveraging OTAs strategically. He cleverly integrates his branding into listings to encourage savvy guests to book directly. Alex’s Favorite Tip: Add your property’s name to listings (e.g., “Stay at Hillside Bungalow”) to make it easy for guests to find you outside the OTA. 5. Giving Back to Your Team and Community From offering temporary housing to cleaners during natural disasters to paying for tasks just to keep his team employed during slow seasons, Alex shared how he fosters loyalty and supports his staff. Takeaway: “This is a people business. A simple gesture can build long-lasting relationships with your team.” Mindset and Advice Mindset Tip: “You will make mistakes in this business, but persistence pays off. It’s not about avoiding failure but learning from it and growing.” One Action to Take Today: Start collecting emails from your guests—every single one. Build a communication system that keeps you top-of-mind and encourages repeat bookings. Follow Alex here ⬇️ Transcription Gil: Hey folks, welcome back to direct booking simplified. We break down the strategies and tactics to win direct bookings on today’s show. I have Alex W Alex, welcome to the show.  Alex: Hey Gil, thanks for having me on. Gil: Yeah, it’s uh, it’s good to have you on. It’s been, it’s been a long while since we caught up. I don’t know how many months it’s been, but it’s been, it’s been a little while.  Alex: Yeah, it’s been a while. Uh, just been busy with life, so.  Gil: Yeah, what’s, what’s, what’s going on nowadays with you?  Alex: Um, yeah, so just running the business. Uh, we have our coaching business that we have. We have our short term rentals. Uh, we own seven, we have a fund where we have our hotel, uh, started co hosting. So, um, we have a few units there. Um, hurricane season came through and kind of threw a wrench in our plans, but that’s business. So yeah.  Gil: Yeah. Talk, talk to me a little bit about actually maybe before we do that, do you mind like kind of, kind of giving me, giving folks an introduction to kind of who you are and kind of how you got started in, in, in rentals in the first place? Alex: Yeah. So, uh, I wish my story was a little bit better than everyone else’s. I think everyone has like a Cinderella story, but I think that wasn’t my case at all. Uh, Alex Sabio, married father of four, live here in Southern California, started investing in real estate probably like 20 years ago with longterm rentals and made almost every single mistake in the book. In fact, my first ever investment property, I think was a scam and got scammed out of 16 grand. A guy went to jail. It was like a Ponzi scheme pretty much But luckily I just kept going with investing in real estate and just slowly over time Kind of fell into short term rentals during the pandemic, uh 2020 it’s been over four years now, uh, and really grew to love the short term rental industry because Uh, number one just the cash flow the tax benefits appreciation. I made some good choices there And really enjoyed the whole experience. So, you know, um Hosting guests. So on and so forth.  Gil: Yeah. So you’ve seen, you’ve been, you’ve been hosting in kind of like two areas of, of short term rentals now, like in the heart of the pandemic and afterwards now, like what, what do you see as being like the big differences as like what you observed? Alex: Competition. The competition’s definitely a lot more stiff. Uh, back in the day, and I say back in the day, I feel like an old dude, and that was four years ago, where anyone was making money, right? You could buy any home, but now everyone’s putting pickleball courts in, like having those crazy coffee makers in, and spending so much money on design. And that’s probably where we should be, right? Where we’re providing guests an amazing experience other than a hotel. And people going into, like, these mini resorts. Uh, and having this personalized

In a special episode of Direct Booking Simplified, we sit down with Abby from Hospitable to explore how simplifying the guest experience can transform your short-term rental business. From guest vetting and payment innovations to building a niche that resonates with your ideal audience, Abby dives into innovative strategies and highlights powerful examples of how simplicity can drive success in the world of direct bookings. Stay tuned for a game-changing conversation that will inspire you to take your hosting strategy to the next level! ⚠️ Special Offer from Abby: Listeners of the Direct Bookings Simplified podcast get 25% off the first 3 months https://hospitable.com/craftedstays/ Summary and Highlights In our latest episode of Direct Booking Simplified, I had the pleasure of speaking with Abby Grous, product manager at Hospitable, one of the top PMS of today. From simplifying guest booking experiences to tackling the complexities of direct bookings, Abby shared actionable insights that every host—whether managing a single property or a large portfolio—can learn from. Here are the key takeaways from our conversation: Simplifying Direct Bookings for Everyone Hospitable’s mission is to “gift time back” to its customers by creating tools that are simple to use and quick to implement. Abby emphasized the importance of designing features that work seamlessly for the majority of users, rather than catering to niche requests. This philosophy is reflected in Hospitable’s 14-day free trial, during which users can fully set up and start taking bookings in as little as a day. What this means for you: Whether you’re new to direct bookings or a seasoned host, Hospitable make the process straightforward and accessible for both the host and customers Understanding the Full Guest Journey Direct bookings are more than just creating a website. Abby broke down the guest journey and how Hospitable supports it at every stage: What this means for you: Direct bookings don’t have to feel overwhelming when the right systems automate these processes. Carving Out Your Niche Abby and Gil discussed the importance of understanding your guest avatar. By focusing on a specific audience—like young families in my own business—you can tailor everything from property amenities to marketing copy, creating an unforgettable experience for guests. Pro Tip: Highlight features that matter most to your ideal guest. For example, families might appreciate photos of high chairs or baby gates in your listing. Tools for Hosts of All Sizes While Hospitable is often seen as a platform for small hosts, Abby dispelled the myth that it isn’t suited for larger property managers. Recent updates, like owner statements and rental agreements, now make Hospitable a strong contender for scaling operations. What this means for you: Whether you manage three properties or thirty, Hospitable can grow with your business. The Power of Partnerships We also discussed our partnership between Hospitable and CraftedStays, which simplifies onboarding and makes direct bookings more seamless. Abby shared the story of a joint customer who increased their direct bookings to over 30% of total reservations, with a 75% conversion rate boost after adopting our tools. Key Mindset Advice from Abby Abby’s advice for hosts and product developers alike: “Get as close to your customers as possible.” Understanding their needs and challenges will help you craft better experiences, whether it’s for your guests or your business tools. Take Action Today If you’re ready to simplify your operations and take control of your direct bookings, start by leveraging tools that are designed for ease and success. Hospitable and CraftedStays ensure you spend less time managing operations and more time delighting your guests. 🚨 As a special thank-you to our listeners, Hospitable is offering 25% off your first three months. Click here to learn more and start your journey toward more streamlined hosting. Follow Abby Here ⬇️ Transcription Abby: I think hospitable takes a really unique approach to product development. And this is one of the things that drew me to hospitable and it’s looking for new opportunities. And that is that hospitable’s mission is to gift time back to our customers. And in doing so, we know that we need to simplify things. So we are in a relentless pursuit of simplifying our product. And when we deliver a feature, it needs to be as easy to, as possible to start using that feature. And this is like a, a kind of a unique change for me coming from the B2B world, especially the enterprise B2B world, where you might have. One particular customer who needs the product to work in a specific way. And you design a feature for that customer, or you have a million feature flags to make it super customizable because everyone has different preferences on how the product should work. And that’s just not hospitable approach at all. There’s a true mission to make the product work for the majority and to alienate the, what we might call like the. The loud minority at some time. So that’s something that’s really interesting. And you can see it even in like our, in the settings and configuration of hospitable, it’s, it should be easy to get set up and using it. You can do it within your 14 day trial. It doesn’t take a month to start using hospitable and see value from it. Gil: Hey folks. Welcome back to direct booking. Simplify. We break down the strategies and tactics to win in direct bookings on today’s show. I have Abby from hospitable Abby. Welcome to the show. Abby: Hey, Gil. Thanks for having me. Gil: Yeah, it’s good to good to see you again. We saw each other last week. I don’t know when, when this is going to specifically air, but last week we were at Burma together. So I got a chance to meet you for the first time, even though we’ve had Slack conversations and work together elsewhere. So it was really good to see you in person. Abby: Yeah, same. It’s such a treat to get to see people in person in this remote first world. So it’s great to see you. Gil: Um, you

In the latest episode of Direct Bookings Simplified, we had the pleasure of speaking with Dr. Tosin Obata, a former university professor turned successful short-term rental entrepreneur. Tosin shared his remarkable journey from academia to managing a thriving property portfolio of 30 units—and all the invaluable lessons he’s learned along the way. From turning a one-bedroom apartment into a launching pad for his business to building lasting relationships with corporate clients, Tosin’s story reveals the unconventional strategies and fearless mindset shifts that helped him carve a unique path in the short-term rental industry. If you’ve ever wondered how to balance risk, ambition, and practicality, this episode is for you. Summary and Highlights Facing Fear: The Key to Starting Something New Tosin’s journey began with a simple resolution: to start a business in 2019. With no clear idea of what kind of business it would be, he took the first step by registering his company, Sigma Place Limited. His advice? “Some of the things we are afraid of are not as bad as we think. If you just start, you’ll find that the first step is possible, and then the next, and the next.” This mindset shift became a cornerstone of Tosin’s success. He compared it to walking on broken glass—a fear he literally conquered during a training session. “What I learned was that the things I was most afraid of were not as big as I thought. Starting a business was no different.” Scaling a Portfolio: From 1 to 30 Properties Tosin’s property journey began with a single one-bedroom apartment in Bristol, UK. He described how he set it up using Facebook Marketplace to source affordable furniture and managed everything himself—from cleaning to guest communication. That first property became a training ground, teaching him the processes he would later replicate to scale his portfolio. Key takeaway: “The first property gave me the confidence to realize it was possible to do another and another. That confidence is everything.” As his portfolio grew, Tosin strategically outsourced tasks, hired a team, and built systems to free up his time. Today, he operates a business that runs independently—even when he’s away for weeks at a time. Mastering Direct Bookings: Tosin’s Three-Part Strategy Direct bookings are at the heart of Tosin’s business. After facing a challenging winter with low occupancy, he and his team shifted their focus to achieving a 75% direct booking rate. Here’s how they’re getting there: Evolving the Business: Quality Over Quantity Tosin’s current focus is on fine-tuning his portfolio by phasing out underperforming properties and reinvesting in high-performing ones. He’s also leveraging cash flow to purchase properties outright, ensuring greater control and profitability. Mindset and Lessons Learned When asked about his biggest piece of advice, Tosin emphasized the importance of starting, even if the path ahead is unclear. “You don’t need to figure out all the steps before you start. The resources and ideas for the next step will come as you take action.” Take Action Today If you’re inspired by Tosin’s story, consider how you can apply his tactics to your own business: For more actionable insights, check out the full episode of Direct Bookings Simplified. CTA: Ready to elevate your direct booking strategy? Book a demo with CraftedStays to discover how our platform can simplify and optimize your booking process. Follow Tosin here Transcription Tosin: The message from there is that some of the things we are afraid of are not as bad as we think. Some of the things we think is a big deal, it’s not a big deal. If you just start, a lot of people say, Oh, I don’t have money. You don’t have to have money. I didn’t have money when I started. So the goal is to face it head on, because if you don’t face it, it will just be there. You think it’s big. It’s actually not as big as you think. So that’s the first mindset. That helped him to overcome that inertia. Uh, and as you overcome that, you see, Oh, the first step is possible. And then you get, Oh, let me do the second step. And then that’s possible before you know it, you are doing 10, 20, 30 steps. 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 Tosin Tosin. Welcome to the show. Tosin: Thank you very much for, for having me on this show.  Gil: Yeah.  Yeah. It’s good to, good to meet you. I met you through Vee, one of our previous guests on the show. He, he definitely recommended it. Have you jump on and kind of share your story? So maybe let’s start off there. Um, can you give folks a quick introduction on who you are, what, what you do, what your portfolio is like? Tosin: Right. Thank you very much. So my name is Tosin Obata. I, I’m a Nigerian, so I have lived in the UK now for about, uh, 15 years. So initially I came, I went to the UK to study for my master’s degree, and then I had a, I did a PhD, uh, for my, uh, after my master’s degree. And then I started to work in the university as a researcher and then as a lecturer. But over this time I, I’ve been interested in property so. My goal was to find a way to invest in property, uh, in a, in a cheaper way, because I know that property is very expensive. So the plan was then to find a way to try and get into property without spending too much money. So I found a way, uh, by leasing properties from landlords and then setting them up nicely and putting them online and, uh, charging for, uh, per night. And so that, and that’s how I built from one property in 2019. So right now we are about 30 properties. So and they range from one

The latest episode of Direct Bookings Simplified dives into a critical yet often misunderstood topic: Search Engine Optimization (SEO), or better yet defined as “Serving Excellent Opportunities” according to our special guest. SEO can unlock new opportunities by driving direct bookings and reducing reliance on OTAs, making it invaluable for short-term rental hosts. This week’s special guest of Direct Booking Simplified, Craig Webb, an SEO expert with a hospitality background, shared practical advice to make SEO accessible for everyone. Why SEO Matters for Short-Term Rentals? What is SEO? Why Invest in SEO? Let’s break it down Summary and Highlights Why SEO Matters for Short-Term Rentals 3 Key Components of SEO Craig explained SEO in three clear sections: Actionable Steps to Start SEO Step 1: Create a Keyword Plan Step 2: Register on Google Search Console Step 3: Start Blogging Common SEO Pitfalls to Avoid How SEO Pays Off Long-Term Craig compared SEO to planting an apple tree:“Unlike ads, which only drive traffic while you’re paying, SEO is a long-term investment. The sooner you start, the sooner you’ll reap the rewards.” Craig’s Advice for Choosing an SEO Agency If you’re ready to hire an SEO agency: Key Mindset for Success Craig’s powerful reminder:“You are where your attention is.”Focus on becoming the person you aspire to be, rather than waiting for the perfect moment. Take action now, and the results will follow. What Should You Do Next? SEO doesn’t have to be overwhelming. Start small: Ready to dive deeper and learn more? Join our conversation and listen to the podcast – exclusive on Direct Booking Simplified Podcast! 🎙️🎤 Follow Craig Here Transcript Craig: You are where your attention is. And my attention was always on the problems. And I just moved my attention to where I wanted to be. And I wanted to be a business owner running a digital marketing agency. So that’s where I kept my attention. And I didn’t say, Oh, when I leave my job or when I do this, I can be that. I had to be it now. You can’t say, I’ll do that when you have to live and be the person you want to be for it to happen and live within that mindset, within that framework, rather than it being a one, two, three process that you follow, you’ve actually got to start becoming that person and live in that space to be able to achieve it. Cause otherwise it won’t come. It won’t ever arrive. It will always be in the distance. Gil: Hey folks, welcome back to Direct Booking Simplify, where we break down the strategies and tactics to win in direct bookings. On today’s show, I have Craig Webb. Craig, welcome to the show. Craig: Thank you for having me. Wonderful to be here. Really pleased to be invited. Gil: Yeah. It was hard to find someone like you. I’ve been hunting for someone like you for a long time. I’m glad Jody from Hospitable Hosts referred me to you, but I’ve been wanting to bring more folks that were experts in the technical side of, um, of marketing specifically around SEO, because there’s not a lot of marketing experts in this domain, specifically in, in hospitality in our little world. Um, so I’m really glad and happy to have you on the show to kind of share kind of your knowledge on all things SEO. Craig: Thank you. Yeah, I hope I can pass some of that knowledge today to some of your listeners. Gil: Yeah. And from what, what I gathered You are what I consider an expert. You have a course, you have services as well, too. We’ll get a little bit into, into that. So, but all in all, I think you come with a wealth of knowledge. Um, so I, I, I bet that our listeners will get a lot of value out of today’s, today’s conversation. Craig: hope so. I hope so. Gil: Yeah. Maybe to kick us off, Craig, do you mind introducing yourself kind of how you got into this in the first place? Craig: Yeah. So I, I’m in the UK, probably tell by my accent. I’m in Oxfordshire. Um, I was a hotel manager for the last 20 years and before that in hotels, hospitality for, for 32 years. In fact, um, I’ve done every job in hospitality, washing up to running restaurants, weddings, events, catering, uh, accommodation. accommodation hotels. So that’s really where my, my skills lie, but sort of food and beverage led, um, high end hotels is where I ended my career. And I ran hotels where it is for a company who managed hotels on other, on behalf of other people. And one of the hotels I was running was in administration. So it was actually, owned by the bank. The bank pulled it from the owner, gave it to us as a management company to run and said, there you go, there’s the keys. Um, if you do a really good job, we need to sell the business and you’ll lose your job. So that was, that was a good start. So if I did a good job, I’d lose my job. But cause came with that is that because it was an administration, we couldn’t spend any money. So that created this pain point where I felt like I had two hands tied behind my back and I had to be creative of how I could try to get a business. You know, I didn’t have a sales and marketing team. I didn’t have a sales manager. There was just little me and a, and a laptop. So I just tried to find ways of giving myself a bigger digital footprint by listing on different sites, trip advisor and things like that. Now we’re talking 2000. 2009 I think it was. So there wasn’t Instagram or anything like that around Facebook just about, um, you know, so it wasn’t like it was now. There wasn’t the digital

Are you a short-term rental host looking to grow your business and build stronger guest relationships? In this episode, Jeff Chisum, mortgage expert and successful STR operator, shares his invaluable insights on everything from securing financing for your vacation properties to creating a memorable guest experience that keeps people coming back year after year. Jeff’s real-world strategies on targeted marketing, leveraging your guest database, and maintaining consistency will help you tackle common challenges and unlock new growth opportunities in your rental business. This episode surely goes well with a cup of coffee ☕️. Another episode of Direct Booking Simplified, just for you! 🎙️💜 Summary and Highlights 1. Financing Your Short-Term Rental Property Understanding Financing OptionsA big misconception in the STR world is that you need to put 20% down when buying a vacation home or rental property. Jeff explains that’s not always true, especially if you’re buying a second home or investment property. There are special financing options that can help you buy with as little as 10% down. Tip for New Hosts:Before buying your property, talk to a mortgage expert who understands STR-specific loans. This can help you find better financing options and save money. 2. Mindset Matters: Overcoming Challenges Facing Challenges with a Positive MindsetOne of the most important things Jeff emphasizes is having the right mindset. In the STR business, you’ll face obstacles—whether it’s managing your property, dealing with guest issues, or handling market changes. Jeff believes these challenges should be seen as opportunities to grow, not as roadblocks. Tip for Hosts:When you hit a bump in the road, instead of getting discouraged, think about how you can solve the problem. This mindset will help you move forward and get stronger as a host. 3. Building Relationships with Guests Keep Guests Coming BackJeff shared how important it is to build strong relationships with your guests. When he bought a golf course cabin, the previous owners had loyal guests who returned year after year. By honoring these relationships, Jeff kept those guests coming back. Tip for Hosts:Even if you’re new, you can start by getting to know your guests. Small gestures, like remembering their preferences or offering special deals for repeat visits, can build loyalty and keep people coming back. 4. Using Social Media to Get More Guests Targeted Marketing on Social MediaJeff talks about how he uses Facebook and Instagram ads to target the right guests for his properties. Social media allows you to reach specific audiences—whether it’s golfers, families, or pet owners. By running targeted ads, you can attract guests who are most likely to book your property. Tip for Hosts:Start experimenting with social media ads to attract guests. You can run small, targeted ads without spending a lot of money. It’s all about reaching the right people with the right message. 5. Building an Email List for Direct Bookings The Power of Email MarketingOne of Jeff’s top tips is to collect guest emails and build a database. This gives you a way to connect with past guestsand encourage repeat bookings. Jeff also recommends creating lookalike audiences in Facebook ads, which helps you find new guests who are similar to your best customers. Tip for Hosts:Start building your email list from day one. Use it to send booking reminders, special offers, and updates about your property. And don’t forget to upload those emails to Facebook to target similar guests. 6. Consistency is Key to Success Stay Consistent in Your EffortsOne thing Jeff learned from his own experience is that consistency is crucial. Whether you’re marketing, responding to guest inquiries, or keeping your property in great shape, consistency leads to steady growth. It’s not about doing everything perfectly, but about doing the right things regularly. Tip for Hosts:Pick a few important tasks (like marketing or guest communication) and do them consistently. Even small, regular actions add up over time and help you grow your business. 7. Podcasting as a Tool for Networking and Learning Sharing Knowledge Through PodcastingWhile Jeff is primarily a mortgage expert and STR host, he also runs a podcast. He shares that podcasting or guesting in podcasts is a great way to learn from others and connect with experts in the industry. Plus, it helps you build a personal brand and stay visible to potential guests or collaborators. Tip for Hosts:If you enjoy sharing your experiences, consider appearing in podcast. It can help you build relationships, share useful tips, and even attract new guests. Key Takeaways for Hosts: By applying these key takeaways , you can set yourself up for long-term success in the STR industry. Whether you’re just starting or you’re already managing multiple properties, Jeff’s advice will help you stay on the path to growth. Follow Jeff Here ⬇️ Transcription Jeff: And then there was the other issue of we really felt like Airbnb, Vrbo, the OTAs were killing the industry to an extent because of the fees and their rules and their regulations and the way they treated hosts, the way they treated guests, and we really wanted to take control and take some power back from the OTAs and The way to do that was direct bookings to help people save money to increase our profitability. Also go out and market those sites to those people that were interested in those activities. And then the golf course cabin had a 10 year history as a Airbnb. And that’s really the main reason why we bought that. So we bought that property after the lake house about. Six or seven months after we closed on the lake house. And that was the big attraction is it had that 10 year history. So when we purchased the property, we got a check written to us for those bookings, those bookings transferred, the database transferred. We had all the emails. And so we really started pushing those people to our direct booking site. Gil: Hey folks, welcome back to direct booking simplified. We break down the strategies and tactics to win in direct bookings. And on today’s show, I have Jeff. Jeff, welcome to the show. Jeff: Hey, thanks for having me

In our latest podcast episode, we sit down with Isaac French, founder of the iconic Live Oak Lake, to discuss how he built a unique hospitality experience that caught the attention of guests and influencers alike. From design tips to marketing strategies, Isaac shares actionable advice for anyone looking to turn their property into a must-book destination. Summary & Highlights We break down the key lessons from Isaac’s journey and share simple, actionable advice that anyone new to the hospitality industry can use to succeed. 1. Start with a Unique Experience Isaac’s first piece of advice is simple but powerful: the key to standing out is creating a truly unique experience.When Isaac started building Live Oak Lake, he didn’t just want to create another vacation rental. He wanted to create a place that guests would remember forever—a place that felt special and different from anything they’d ever experienced. For Isaac, the focus was on designing a memorable experience. He made sure every detail—from the decor to the activities available—was carefully thought out to make the property stand out. The takeaway? If you’re starting in hospitality, think about how you can make your property unique. What can you offer that other places can’t? Whether it’s the design, the location, or special activities, make sure your guests feel like they’re getting something special. 2. Don’t Be Afraid to Experiment Isaac didn’t have formal marketing training, but he made up for it by being willing to try new things. Instead of following the same old marketing strategies, he took a bold, experimental approach. This included using tools and strategies that were common in other industries, like pop-up forms on websites to collect emails, and remarketing ads to stay in front of potential guests. Isaac says that his curiosity and willingness to experiment helped him discover what worked for his business. He learned from other industries, like e-commerce, and adapted those strategies to the hospitality world. If you’re new to marketing your property, don’t be afraid to try different things. Use your website, social media, and email marketing in creative ways. Test what works for you, and learn from your results. 3. Tell a Story and Build a Community One of the things that helped Isaac’s property grow was his ability to share his story on social media. People love following the process of building something new, and Isaac shared everything—his design choices, challenges, and wins—along the way. This built a loyal following even before the property was open for bookings. Isaac also used storytelling to connect with potential guests. He shared the unique aspects of his property and the vision behind it, making people feel like they were part of something special. If you’re starting a new hospitality business, think about how you can tell your story. Share the process of building your property, talk about why it’s different, and connect with people on social media. People love to follow along and support businesses they believe in. 4. Passion and Dedication Will Drive Your Success Isaac believes that one of the biggest keys to his success was his passion. He was genuinely excited about creating something special and making sure everything was perfect. He says that when you’re passionate about your business, it attracts people—whether that’s guests, investors, or collaborators. Isaac shared two key quotes that drive his mindset: Passion is contagious. If you’re excited and dedicated to your property, it will show in everything you do—and that will help you attract guests and grow your business. 5. Don’t Be Afraid to Change Course if Needed Sometimes, the best way to improve your business is to be willing to make changes. Isaac stressed that it’s important to regularly assess your property and business. If something isn’t working, don’t be afraid to pivot or even start over. Sometimes, the best opportunities come from reimagining your property or business model. Isaac mentioned that he could have chosen to scale his business quickly, but he took his time, refining the experience before moving forward. He encourages entrepreneurs to evaluate their businesses honestly and be open to making changes if needed. If you’re just starting, it’s okay if things aren’t perfect from the beginning. Be willing to make adjustments as you learn what works best for your guests. 6. The Future of Hospitality Is About Experiences Isaac believes that the future of hospitality is all about offering unique, memorable experiences. People are moving away from traditional luxury hotels and looking for places that offer something different—whether that’s a beautiful design, a cool location, or fun activities. Isaac believes this trend is just beginning, and there’s huge potential for businesses that can offer unique stays. If you’re just starting out, think about how you can create an experience that stands out. Focus on the experience your guests will have, not just the place they’re staying. This could mean designing a unique space, offering personalized services, or creating an unforgettable atmosphere. Key Takeaways for Beginners in Hospitality Isaac’s story proves that when you combine passion, creativity, and a focus on unique experiences, you can turn your ideas into something truly special. Want to learn more from Isaac? Transcript Isaac: The way you do one thing is the way you do everything. And so you really have to care, and you have to pursue excellence, and that’s part of like going back to that initial vision of like every single detail, every single aspect of this, even the parts people aren’t going to see matter. And if you have that attitude, that will put you in very good stead to create something that truly is word of mouth worthy and one of a kind. Isaac: And then, Number two, there’s this great quote by this gentleman named John Wesley, who was like an English preacher 300 years ago, but I just love this quote. He said, light yourself on fire with passion and people will come from miles around to watch you burn. So I feel like you have to be energetic. You have to have like, believe in whatever you’re going to do. Isaac: And then you will become a magnet. When you have that dream that turns into a conviction,

In this episode of Direct Booking Simplified, we discuss Niche Marketing Strategies for Short-Term Rental Hosts with marketing expert Nihal Salah. Together, we brainstorm how to elevate your property by targeting specific guest segments, from dog lovers, digital nomads, unique guest needs, and personalized experiences. Key Takeaways In a recent podcast episode, we spoke with Nihal Salah, a seasoned marketer with experience across various industries including short-term vacation rentals. The discussion focused on the power of niche marketing for STR hosts. Key Takeaways: The top advice from Nihal was to consistently talk to your guests – through reviews, data, and direct conversations – to deeply understand their needs and adapt your property and marketing accordingly. Embracing discomfort and a “get to” vs “have to” mindset were also highlighted as key mindset shifts. Overall, the episode provided a compelling case for short-term rental hosts to identify and cater to a specific niche, rather than trying to be everything to everyone. Careful segmentation and personalization can lead to outsized results. Connect with Nihal here: Transcript Nihal: I think good marketing is simple. The principles are the same. The principles are almost timeless. So I know everyone’s talking a lot about AI and stuff with marketing content. And, but when you start looking at the principles of solid marketing, They are the same across industries. It’s about understanding who your best audience is to serve, how you articulate what you offer your value proposition, how we articulate what you do in the most clear and succinct way to that audience and what channels you use to reach them. You do all, you do those three things and you know your audience really well and you build a strong brand around all of that. That’s marketing. It’s not complicated. Gil: Hey folks, welcome back to direct booking simplified on today’s show. I have Nihal. Nihal, welcome to the show. Nihal: Thank you for having me. Gil: Yeah. Do you mind giving folks a quick introduction on yourself first, before we get started? Nihal: Sure. Um, well, let’s start at the very beginning. Um, I’m half Egyptian, half English. Um, I live between Spain and, uh, Wales in the UK. Um, and I am a marketer by trade. I have been doing marketing for, um, For about 17 years now, across a number of different sectors, and I’ve worked with organizations all the way from Fortune 500 to tiny early stage startups, so, and everything in between and across the A number of sectors, um, from education technology, learning technology, blockchain, um, cybersecurity, did auction tech once, which was incredibly boring. And I recently fell into the wonderful world of short term vacation rentals, which I absolutely love. And at the moment I work with a payment processing company called Yapstone, um, who specialize in payment processing for short term vacation rent. Gil: And yep. So it has different variations depending on kind of where you live. Right. So we might not be familiar with the app stone parent company. What’s the two subsidiaries. Nihal: We’ve got vacation rent payment in the U S. And we have holiday rent payment in the UK and Europe so that yeah different products because finance is so regulated lots of compliance and stuff so you need to make sure that you’re adhering to all of the rules and regulations in each of the markets. Gil: Yeah. What was your, um, your first experience in, in short term rentals? Like how did you Nihal: Um, like everyone I speak to in this industry by accident, I’ve not spoken to anyone who intended to come into short term rentals. And so when I, I was speaking to said something to me that made me laugh, he’s like, no one grows up thing saying, Oh, when I grew up, I want to be a property manager. I’m like, that’s a good point. But, um, I have a friend who I’ve worked with before who started working with, Um, And he reached out to me and said, I need some help with product and content marketing, would you be interested in, in joining me? And I said, you know what? I know nothing about short term rentals from, um, from the business side. I know a lot from the guest side, because I probably stay at about 15. Short term rentals a year because I travel a lot. Um, so yes, let’s do it. And here we are. Gil: Yeah. Yeah. And from what I hear, and this is probably across many different industries and like verticals, but the marketing that you put into. Short term rentals is not all that different than possibly other industries. There’s a lot of the same foundational pieces. Would you agree with that? Nihal: I completely agree with that. I think good marketing is simple. The principles are the same. The principles are almost timeless. Um, so I know everyone’s talking a lot about AI and stuff with, with marketing content and, but when you start looking at the principles of solid marketing, They are the same across industries. It’s about understanding, you know, who, who your best audience is to serve, you know, how, how you articulate what you offer your value proposition, how we articulate what you do in the most. Clear and succinct way to that audience and what channels you use to reach them. You do all, you do those three things and you know your audience really well and you, and you build a strong brand around all of that. That’s marketing. It’s not, it’s not complicated. It’s simple. It’s difficult. Um, So yeah, Gil: Yeah. Yeah. And you have, um, you have a specific passion or a passion topic that you’d like to talk about specifically within short term rentals around niche marketing. Can you tell folks a little bit more about what is niche marketing to begin with? Silence. Nihal: you will, you, I guarantee you, and if you