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