“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

When you think of hostels, the image of a small, budget-friendly, often outdated lodging comes to mind. Nathan and Michael, the co-founders of Howzit Hostels, are flipping that narrative. In our latest podcast episode of Direct Booking Simplified, these two entrepreneurs shared how they leveraged their backgrounds in real estate and luxury short-term rentals to redefine what a hostel can be—and how their direct booking strategy is a game-changer Summary and Highlights Meet the Founders Nathan and Michael are the driving forces behind Howzit Hostels, a brand synonymous with upscale, community-driven hostel experiences in Hawaii. With $10 million in assets, $2.5 million in annual revenue, and awards like “Best Hostel in North America,” their journey is as much about bold decisions as it is about smart strategies. Their story began in the midst of the pandemic when most were pulling back. They took a leap of faith and acquired their first hostel in Maui. By listening to guests, implementing airtight systems, and building a values-aligned team, they’ve turned a once-average property into a high-performing hospitality business. The Secret Sauce: Direct Bookings One of the most valuable insights Nathan and Michael shared was their approach to direct bookings. By increasing their direct bookings by 12%, they’ve not only saved $59,000 annually in OTA commissions but have also increased the valuation of their business by $630,000. As Nathan explained, “Direct bookings are not just about revenue; they directly impact net income, which drives valuation. For a commercial hospitality business like ours, that’s everything.” Direct Booking Tactics That Work Mindset and Tactical Advice Nathan’s mindset advice was simple but profound: “Reframe your relationship with fear and failure.” Michael’s tactical advice? Don’t hesitate to seek help, whether it’s through your network or professionals. Why It Matters For hosts navigating the ever-competitive hospitality market, Nathan and Michael’s story is a reminder that bold decisions, meticulous planning, and leveraging the right strategies can lead to remarkable results. If you want to hear more about how they’ve built their business, tackled challenges, and created a sustainable direct booking strategy, listen to the full episode of Direct Booking Simplified. Join the CommunityWe’re passionate about empowering hosts with tools and strategies to succeed. Join our CraftedStays community to connect with like-minded professionals, learn proven tactics, and discover how our platform can help you build a direct booking powerhouse. Follow Michael and Russell Here ⤵️ Transcription 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 Howzit Hostiles, Nathan, and Michael. Welcome to the show. Nathan: Yeah, it’s great to be on. Thanks for having us, Gil. Gil: this is pretty cool. I’ll admit to both of you that this is our first pairing. We’re like 40, almost 50 episodes deep and we have not yet had a duel on the show. So I’m very interested in how this is going to be and how we can bounce ideas off each other. It’s always been a one on one. I haven’t even done a single show, uh, to be quite honest, but I’m very interested in kind of like having you guys both here and, uh, having you guys talk about just how you guys, Divide and conquer both sides of your business. Gil: Um, but before we get too deep into it, uh, Nathan, Michael, do you mind kind of sharing a little bit about your property management, what you guys have done and kind of how you guys work together? Nathan: Yeah, absolutely. So I’ll kind of kick us off here. Um, so Mike Russell and myself were the, the co founders, uh, of Howzit Hostiles. Um, if you, we each have our own story, obviously that, uh, from a, from an origin story that led to a moment. But, um, I think what people are most interested in with us, there’s, there’s two sides of our story that, that we share. Nathan: That people are drawn to, um, and, and want to hear about. And one side of it is the, kind of the investment in the real estate side where, you know, we, we basically. Took a 400, 000, uh, down payment and investment and, uh, forced about 4 million of equity in under two years. And that has now led to us owning from that 400, 000 down payment, 10 million worth of assets, uh, where we’re driving. Nathan: You know, 2. 5 million worth of revenue, uh, 800, 000 worth of NOI and 500, 000 worth of net income. And so from the investment side, I think that that part of the story is like, wow, you guys really compressed time and utilized your entire life’s work to recognize an opportunity and then jumped on it and, and, and took advantage. Nathan: From the hospitality side. I think that the part that people really go, Whoa, wait a minute, what hostile, what is a hostile? You know, like, aren’t these all dirty dingy things that like, and, um, again, we, we recognized opportunity and when they go, Whoa, they go look at our website, they go look at what we’re doing. Nathan: Um, there’s these two, these two guys. knew nothing about hostels and in the midst of a pandemic when everybody else was, you know, you know, really wait, you know, sitting back going, what’s going to happen to the world. We decided to take massive action and go all in on our vision and uh, purchased an, an existing hostel. Nathan: And in two and a half years, uh, we were awarded as the best hostel in the North America. And so people from the hospitality side are like, wait a minute, you had no experience and you went in and created the best hostel in North America. What the heck? And, um, and so when we look at the hospitality side of what we’ve done, we really attribute that to these three, three major components. Nathan: And

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