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

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

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

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

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

Marketing expert Scott Quesnell shares his data-driven frameworks for supercharging your online presence and booking conversions. Let’s discover Scott’s strategies on how to leverage powerful tools like Google Analytics and SEM Rush to uncover insights about your customers, systematically test and optimize your marketing tactics, and build a flywheel of sustainable growth. Whether it’s fine-tuning your website content, refining your Facebook ad creatives, or mastering local SEO, Scott’s actionable strategies will give you a serious competitive edge. If you’re ready to start outsmarting the competition and taking your direct booking game to new heights, you won’t want to miss this conversation. Highlights and Summary In the competitive short-term rental market, being visible online is essential to attract guests. Search Engine Optimization (SEO) is key to improving your property’s online presence, helping your website appear higher in search results and meet what users are looking for. This guide outlines important SEO strategies specifically for short-term rental operators, focusing on a data-driven and customer-focused approach to marketing. Highlights: Summary: This guide provides essential SEO strategies for short-term rental operators to improve their websites and content for search engines. It focuses on three main areas: This approach helps drive growth and engagement in the short-term rental industry. Follow Scott Here Transcription Scott: SEO is marketing where you tailor your website to what people are searching for. So when people are searching for websites like yours, they are using specific terms. And the job of someone who’s doing SEO is to put those specific terms and language And answers to the questions that people are looking for on their website. So you can tell Google, Hey, this is a one stop shop for anybody who is looking for websites like me. And then if Google likes that, they will give it to the people looking for you. And that’s kind of the, the flywheel of SEO is just consistently figuring out what people, what terms people use to find companies like yours, optimizing your website to Rank for those terms. And then just making sure that you’re making that content better, answering all the questions that might come up and have something for every type of searcher that uses those terms. 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 Scott Quesnell. Scott, welcome to the show. Scott: Thanks for having me, Gil. Gil: Yeah. You’re one of the few folks I know in our space specifically that knows. So I’m really happy to have you on the show. I know a lot of folks kind of outside of our industry, but there’s not a lot of folks kind of within the industry that is, uh, well versed in this topic, um, to kind of kick us off, do you mind kind of giving an introduction to our listeners? Silence. Scott: um, talking to other Airbnb owners, like just trying to figure out what the day in the life is like for them, uh, specifically around the financial operations and marketing aspect of things. But then once we started talking about marketing, I Started to realize that they, they were a little confused on the topic, you know, so financials, they didn’t give away that much because they’re just like, who’s this random guy asking, like, to see how much money I make operations. They, they all had it nailed down on their operations, but marketing, I sort of realized that there was, um, a need for knowledge in the space. And so this year in January, I started the STRLF newsletter, and it’s a newsletter, uh, that talks, that gives away marketing tactics, tips that I’ve learned in my marketing career. For short term rental house, hotel, uh, hotel owners and property managers. Um, and ever since I started that, I, it’s been growing really well. I’ve been able to talk to even more short term rental entrepreneurs and really understand where their biggest pain points are in marketing. So that someday soon I’ll be able to, uh, solve that with some sort of service. Gil: Nice. Nice. And you’re getting into hosting yourself as well, too. Is that right? Scott: That’s right. So that that’s kind of what kicked off my my whole Airbnb tour campaign that I did Because I just wanted to learn like, you know What are the permits and like what are all the legal stuff I have to worry about but then my marketing brain automatically went to Asking them questions about that and realize that there’s actually a need in the marketplace and something that I could, I could easily solve. Gil: Yeah. Yeah. Do you feel that our space is much different from a tactical or even strategic level than other industries that you have done marketing for? Scott: Uh, the only difference I would say, I guess there’s, there’s two differences. So one is, you know, all short term rentals, they’re local. So they’re in a specific location and, you know, More times than not, they attract people from that surrounding area. So that’s one difference, um, that I’ve, that I’ve seen because in my last agency, I worked with a lot of companies that would service the entire U S so their market was specific age groups or like interests versus where they actually live. And then the second one is when you. Advertise for a short term rental. It’s not like if you were selling soap or something to where it’s an impulse buy, there’s a lot of people that will see your ad and not do anything. And then come back days, weeks, months later and book, but it’s hard to attribute that when you start to advertise. And so I think that discourages a lot of short term rental entrepreneurs when they start to advertise because they think, oh, my ads aren’t working. But in reality, The ads are solving the problem

” Making A Difference, One Stay at a Time! “ In this episode of Direct Booking Simplified, we sit down with Debbie Todd, a Hospitable Host and a STR Impact Expert who’s redefining success in the industry. Discover how Debbie transformed her family getaway into a thriving business that gives back to the community. From involving her kids in operations to donating 5% of each booking to charity, Debbie shares her unique approach to creating a purpose-driven vacation home rental. Learn about her transition to self-management, marketing strategies, and the tools she uses for success. Debbie also reveals how her giving-back model has become a powerful branding tool that sets her properties apart from others Summary & Highlights Debbie’s approach to vacation rental management is a powerful blend of business savvy, community focus, and personal development. Here’s a concise overview of her strategies: Meet Debbie Todd: She is a mother of three, a physical therapist, and a Hospitable Host with a passion for giving back. She began her mission to make a difference through her rental properties in 2021 and expanded her efforts to the local community by launching Hocking Hills Gives Back in July campaign. Involving her children, guests, and community, Debbie’s initiative has raised nearly $53,000 and their volunteer hours continue to grow.  She has also partnered with Hospitable Hosts to create the Hospitable Hosts Impact Community, aiming for a greater global impact. Her dedication is unwavering: to make a difference, one stay at a time. Purpose-Driven Business:Debbie’s vacation rental journey began as a family getaway and evolved into a purpose-driven enterprise. Her clear “why” guides business decisions and creates a meaningful foundation for operations. Continuous Learning and Adaptation:Embracing a growth mindset, Debbie consistently learns and adapts to industry changes. This approach allows her to improve operations and stay ahead in the competitive vacation rental market. Family Involvement:By integrating her children into various aspects of the business, Debbie provides them with valuable life lessons and a sense of ownership. This family involvement strengthens both the business and family bonds. Giving Back:Central to Debbie’s business model is a commitment to giving back. By donating 5% of each stay to charities and involving guests in the process, she creates a unique and impactful vacation experience. Unique Branding:Debbie’s focus on social responsibility and community impact sets her rentals apart. This unique branding attracts like-minded guests and creates a strong, positive reputation in the market. Expanding Influence:Through the Hospitable Host impact community, Debbie is spreading her giving-back model to other hosts. This initiative amplifies her impact and inspires industry-wide change. Operational Excellence:Utilizing tools like Hostfully, PriceLabs, and StayFi, Debbie ensures efficient management of her properties. This tech-savvy approach optimizes operations and enhances guest experiences. Strong Guest Communication:Debbie prioritizes consistent, automated communication throughout the guest journey. This approach improves guest satisfaction and helps build lasting relationships with customers. Multi-Faceted Marketing:Leveraging social media, blogging, and newsletters, Debbie engages her audience and shares her journey. This comprehensive marketing strategy builds brand awareness and fosters community. Community Engagement:Initiatives like “Hocking Hills Gives Back” demonstrate Debbie’s commitment to local community involvement. These efforts strengthen ties with local tourism associations and enhance her business’s positive impact. Legacy Building:Debbie views her business as more than just a source of income. It’s a vehicle for imparting life lessons and creating a lasting, positive impact on future generations. Encouraging Action:By sharing her story and strategies, Debbie inspires other vacation rental owners to incorporate giving back into their businesses. This call to action has the potential to transform the industry. Through these strategies, Debbie demonstrates how vacation rental owners can achieve success while aligning their businesses with personal values and benefiting their communities. Learn More From Debbie Here: Transcription Gil: What’s that one piece of mindset advice that you would give to someone that’s starting something completely new?  Debbie: Why are you doing it? That is a huge, and there’s not a right or wrong answer to that, but I think, and it may change your answer may change and evolve over time, which is awesome. But I think it took us a little while for me to figure out why. And once I got a, why I’m like, Oh my goodness. Like it just made decisions easier. It made purchasing easier things that when they don’t go, right. I kind of go back to my why and say, all right, we can do this. But with that comes time. You got to sit and kind of soak in it a little bit of, you know, it’s not like, Oh, it’s my why. And let me move on. It’s something that you really want to like hone in on and think about, ask your, your family about it. Like, why are we doing this? You know, and get their input. I think that would be, yeah, that would be my biggest. 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 Debbie. Welcome to the show, Debbie.  Debbie: Hey there. Thanks for having me.  Gil: Yeah. It’s so good to have you on the show. I’m, I’m really excited. There’s, there’s so much to talk about. I always feel very happy when I have a conversation with you. So I was  Debbie: going to say the same thing about you.  Gil: I don’t know what, I don’t know what it is. You have absolutely one of the most, what’s that contagious energy? I would say in a good way, in a very good way. Um, I, yeah,  Debbie: I try. Yeah.  Gil: Yeah. Yeah. So maybe to kick things off to mind, giving folks a kind of an introduction on who you are. Debbie: Absolutely. Yes. My name is Debbie Todd. Um, I live in Columbus, Ohio with my husband and three kiddos. They’re 16, 15 and 12. So we are busy, busy, but it’s, it’s awesome. Um, we have two vacation rentals in Hocking Hills,

From having no real estate background, to scaling up and managing 22 properties in just two years. In this episode, we dive into the incredible and inspiring journey of Victor Solano, a short-term rental expert who built a thriving business from scratch. Summary & Highlights Victor Solano’s Journey to Success in Short-Term Rental Management Victor shares how he took calculated risks, invested in the right education, and learned to build powerful, trust-based partnerships with property owners. From overcoming financial pressures to leveraging upgrades that boosted revenues by thousands of dollars, he reveals the strategies that took his business to the next level Path to Success: Victor Solano’s journey into the short-term rental industry began in January 2022 with no real estate background. Determined to succeed, he invested in education through The Real System mentorship program, even maxing out a credit card to make it happen. Starting with co-hosting properties allowed him to gain experience without the upfront costs of ownership. Within two years, Victor had grown his portfolio from managing just two properties to 22, proving that with the right mindset and dedication, rapid growth is possible in the short-term rental business. Challenges & Mindset: The first year of Victor’s business was filled with challenges, including financial pressures and self-doubt. However, he leaned on the support of his family, especially his wife, and maintained a positive mindset to overcome these obstacles. Despite the uncertainty, Victor took calculated risks that ultimately helped push the business forward. His perseverance, paired with a strong belief in his abilities, helped him stay focused even when the future felt uncertain. Growth Strategies: Victor’s approach to growing his business revolves around building trust with property owners, whom he views as partners. This collaborative mindset has been key to his success. He also made strategic investments in property upgrades, like adding a jacuzzi and games, which significantly boosted his monthly revenue by $3,000. For his best-performing property, these upgrades helped increase its annual revenue from $80,000 to $125,000. His focus on quality over quantity in property selection and a strong emphasis on guest experience have helped fuel the growth of his business. Additionally, he built a team of experts to handle key areas such as pricing and listing optimization, further enhancing the performance of his portfolio. Direct Booking Strategy: One of Victor’s primary goals is to reduce reliance on online travel agencies (OTAs), and he’s making significant strides in that direction. Currently, around 20% of his bookings are direct, but he’s aiming to increase that to 50%. He plans to invest in a professional direct booking website to help achieve this. Direct bookings not only offer more control over pricing and customer relationships but also contribute to building his brand and reducing the business’s dependency on third-party platforms. Advice for Newcomers: Victor advises newcomers to the short-term rental industry to prioritize education and networking. He believes that ongoing learning and connecting with others in the field are essential for success. Additionally, taking calculated risks and investing in self-confidence are key components of building a strong foundation. Victor emphasizes that passion for the process and maintaining a positive mindset are vital in overcoming the inevitable challenges of growing a business. Future Plans: Looking ahead, Victor plans to explore opportunities in subleasing and property purchasing as he continues to scale his business. He’s focused on acquiring properties that are not just high in quantity, but are profit-generating, to ensure long-term growth. Another area of focus is further enhancing his direct booking strategy and continuing to build his brand, as these efforts are essential to achieving his broader business goals. Key Takeaways: Victor’s success can be attributed to a combination of education, calculated risks, and a strong support system. His focus on quality property management, trust-building with owners, and strategic investments in upgrades has fueled his growth. Above all, his story highlights the importance of adaptability, perseverance, and a growth mindset in achieving success in the competitive short-term rental market. Follow Victor on Instagram 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 Victor Solano. Victor, welcome to the show. Victor: so much for having me. Appreciate it. Gil: Yeah, it’s, it’s really good to have you on, uh, and kind of have you talk about your hosting journey and dig a little bit deeper into, uh, direct bookings, um, to kind of kick us off folks. Uh, do you mind giving folks a introduction on who you are? Victor: Yeah, of course. So my name is Victor Solano. I’m a local here in Southern California by the Los Angeles area. And we have a STR management business that has rentals, mostly in the Southern California area, also in a couple of other states. So we 100 percent focus on management of Airbnbs, church room rentals in this area. Uh, we have created a, significant portfolio in the past 2 years and have generated almost over a 1, 000, 000 in revenue for our partners. So, uh. It’s been a, it’s been a long and a hard journey that we have to kind of really work hard to get to this point. But, um, yeah, it’s we started about April of 2022 and then slowly started, uh. Networking and getting more partners up to over 22 properties that we have now that we’re managing and, you know, we offer full management service services to our partners. So excited to be on. Gil: Yeah. Talk to me about kind of the journey there. You mentioned like there was a long kind of hard road there. What was like some of the most challenging parts? I guess like what was it? I was the most challenging part of growing your coasting service. Victor: Just because there’s so much competition in the beginning, you know, I, I kind of started with no funding available to, moving to a purchase or like a sub strategy. So,

In this episode, we discuss the dynamics of social media marketing with our special guest, Ben Wolff. Discover how he and his team’s approach transforms the vacation rental industry by harnessing the power of influencers. Ben shares his strategies for identifying the right influencers, creating compelling content, and building authentic connections that resonate with travelers.nJoin us as we explore how a tailored approach to influencer partnerships can elevate your marketing game and unlock new revenue streams for your unique properties. Summary & Highlights In the fast-changing world of vacation rentals, it’s important to stand out in a crowded market. We recently spoke with Ben Wolf, who has a fresh approach to using social media influencers and content creators to help unique, upscale vacation properties attract guests. Here are some key takeaways from our conversation that can benefit property owners and marketers. The Power of Influencer Partnerships One of the standout strategies Ben and his team employ is identifying the right influencers—not just those with the largest followings. By focusing on local micro-influencers who have engaged audiences, they create more authentic connections with potential guests. This targeted approach allows them to achieve remarkable returns, with top-tier influencer collaborations yielding 7-10x ROI on direct bookings, even with investment levels ranging from $1,500 to $3,500 per collaboration. Quality Over Quantity Ben emphasized the importance of influencer authenticity. The most valuable influencers are those who maintain a discerning selection process, promoting only properties they genuinely believe in. This builds trust and drives more meaningful engagement with their audiences, leading to higher booking rates. Building a Robust In-House Team To support their content-driven marketing strategy, Ben has developed a dedicated in-house team of 8-9 professionals, including videographers, editors, copywriters, and social media managers. This cohesive unit ensures that their messaging is consistent, engaging, and tailored to showcase the unique aspects of their vacation rentals. Unlocking Direct Bookings By implementing these influencer strategies, Ben’s team has successfully driven about 80% of their bookings directly, offering competitive pricing to OTAs like Airbnb. Interestingly, guests acquired through social media tend to be less price-sensitive, often opting for higher-value stays. This not only boosts profitability but also allows them to capture fees typically allocated to third-party platforms. Content Creation Strategies Standout Features Engaging Narratives The Importance of Shareability Leveraging Email Marketing Navigating Advertising Challenges Technology Solutions for Direct Bookings Mindset and Continuous Learning Follow Ben here Follow Onera here Follow Oasi here Transcription Gil: Hey folks. Welcome back to direct booking simplified, where we break down the strategies and tactics on how to win in direct bookings. On today’s show, I have Ben Wolff. Ben, welcome to the show. Ben: Thanks Gil. Gil: Yeah. Do you mind giving folks a kind of a brief introduction on who Ben is? Ben: Sure. Yeah. I’m, I’m the co founder and creator of Onera, which is an upscale tree house hotel or tree house vacation rental community. Um, we have one location in Fredericksburg, uh, which is Texas wine country. And then we’re opening our second in Wimberley, which is, uh, also Texas Hill country with some incredible views. Ben: Our new location has 28 units. Our first one had 11 and we’re expanding that actually to 35. So that’s opening up. Next year in May of 25. Um, and separately, I have a, another company called Awasi, which is a services company for unique stays, landscape hotels, um, very unique vacation rentals, and our whole shtick is helping people to drive a massive amount of bookings direct at very high rates. Gil: Nice. Nice. Talk to me a little bit. What is a landscape hotel? What is that? Ben: Yeah, it’s, it’s a hotel that is, is seamlessly integrated and blended into the natural environment. So typically we’re trying to find properties that have amazing views or topography or landscape, um, that, that really, you know, draw a guest in, and then we’re creating these one of a kind stays architecture and design that, you accentuates what’s already there with the natural landscape. Gil: Nice. Nice. Do you, when you’re looking for these, are you looking at for any particular areas, any market specifically, or it’s more about like really finding the plots of land that that do well for these things? Like, how do you search for it? Ben: two hours ideally and three hours at most from a major market or major markets ideally, right? So, um, Onero Fredericksburg and Onero Wimberly are both in the Texas Triangle. Um, we are within that radius from Dallas, Houston, Austin, and San Antonio. Ben: So we get a lot of drive to traffic from those markets. Um, and, you know, but there’s tons of these markets across the country, right? Um, anywhere that’s, that’s kind of outside of a, a major metro that has people with disposable income and, and a sizable population is, is a good fit. And then you just need a piece of property that, Is so beautiful that when somebody goes there, they feel like autonomically compelled to whip out their phone and take a video or take a photo. Ben: Um, just cause it’s, it’s that stunning and what we call shareable, right? If it compels you to do that, then it’s a shareable. Location or vis Vista or, um, uh, property. Gil: Yeah. How did you get into the UniqueStays Landscape Hotel? Like, how did you transition from kind of like that being the smaller operator into what you’re doing today? What was that journey like? Ben: Yeah. So I, I was actually, I think a mid sized operator, probably in the STR space. We had about 200 properties under management. We were in like 10 markets across the U S um, and that was all pre COVID, but most of our inventory, most of what we managed was city, you know, urban STRs. Um, and that. Really got shook up pretty hard, especially early COVID. Ben: So that’s what really pushed me in the direction

For this week’s special episode of Direct Booking Simplified, we collaborate a joint podcast with STR Investing, The Podcast Gil sits down with Taylor Jones, a seasoned STR investor and data analyst, as they equally share their experiences and strategies on how to stand out in a competitive market in the world of short-term rentals. Together, we discover how understanding your ideal guest can transform your property approach and why a data-driven mindset is more crucial than ever. From creative marketing techniques to creating unique amenities, this episode is packed with practical realizations and humble lessons learned along the way, accompanied with actionable insights that will help you stay ahead of the curve and maximize your returns. Don’t miss this master class in data-driven STR success – consider this discussion as an investment for your property’s future. Summary and Highlights This conversation between Gil and Taylor (Mr. Jones), an experienced STR investor and data analyst, covers a wide range of topics in the STR industry. They discuss the evolution of the market, strategies for success, and the importance of data-driven decision-making. The podcast highlights the shift from simply acquiring properties to strategically developing and marketing STRs to stand out in an increasingly competitive landscape. Key Highlights: Overall, the conversation paints a picture of an evolving industry where success increasingly depends on strategic thinking, data analysis, and a deep understanding of target markets and guests. It highlights the shift from a period of easy growth to one where differentiation and efficient operations are key to thriving in the competitive STR landscape. Follow Mr. Jones on Instagram, and listen to more episodes of STR Investing, The Podcast Transcription Taylor: I understand exactly who your ideal booking client is upfront because acquisition is going to lead everything downstream. If you acquire the wrong property in the wrong market at the wrong price, if you set it up wrong, design it well, it doesn’t matter if you’re the president of, you know, the four seasons resort, you can’t out operate a bad starting block. So really understand exactly who your target demographic is upfront. And then you’ll be able to collect significant wins above your competition every step of the way downstream from buying the right property, setting it up correctly, designing it correctly, and then lastly marketing it correctly. And if you mess up up front, it becomes significantly harder to kind of catch up downstream. So to me, I know I live at the front of the funnel in data and acquisitions, but It’s truly, I think, one of the most impactful starting points and SKUs of this asset class. 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 Taylor on actually our unique collaboration podcast. He has a podcast of his own. Welcome Taylor.  Taylor: Thank you, Gil. Appreciate it. So Gil, tell me a little bit more about, you know, your background, how you got into the space and what you do. Gil: Yeah, so I’m a short term rental operator myself. My wife and I, we have a couple cabins here, actually not here, but in the Smoky Mountains and in Branson, Missouri. We’re located on the West Coast in San Francisco. Um, I come from a technology background. So I’ve been a product director for the last 15 years for some pretty big brands, um, pretty big tech companies. Um, and now more recently, I went into entrepreneurship. So we ended, I ended up leaving my W two in tech and starting my own, my own startup basically. So the company name is practice days. We basically make it super easy for anyone to get into direct bookings. We connect into all the different PMSs. We pull in all the property information and we allow you to build a really beautiful, really high converting direct booking site in less than a day. It’s amazing.  Taylor: Cannot emphasize this enough. Gil showed me live how easy it was to build and you’ve heard the horror stories. Oh, I gotta get build this on WordPress and it takes forever. It is truly same day, uh, you know, dumb it down to a fifth grader can handle it. It’s absolutely incredible what they’ve built from a simplicity standpoint. And if you’ve been on the edge or thinking it’s overwhelming, um, this is a great option to seriously consider.  Gil: Yeah, yeah. And hopefully I think we have you doing doing your onboarding pretty soon. So I’m excited about that. Um, I actually asked you not to onboard last week because we’re doing our rollout. Um, and that went really well. Actually, um, we did our big rollout. Last Friday. It’s it’s really actually our third generation of our platform. I made the first version, the really crappy version. I’m not an engineer, but I ended up coding the first version just to demo it out and see if, like, if this is worthwhile to get into. Um, and it did his purpose. And then I end up hiring engineers to bring, um, to actually create our like first production version. And we’ve been rolling on that. That’s for the, like the first eight months out of the year. And we started working with like really big hosts that had 40 to 80 properties. And that first version was just too rigid. It didn’t allow you to drag and drop things. It just didn’t work as well. So I was like, Taylor, hold on, don’t sign up yet. Starting Friday, we’re going to launch our new version. And oh my God, it’s so amazing. We’re at the Poconos conference on Friday. And, um, we were having this VIP dinner and I actually had Bill Faith was there, Justin Ford from Breezeway was there, a lot of like big names, Guesty was there as well too. And we were doing all of our intros