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

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

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.