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

In this episode, we sit down with Tom Powers, the Market Manager of Guesty. Tom shares insights from Guesty’s founding journey, emphasizing the company’s commitment to innovation and deep industry expertise. We discuss the significant challenges facing the short-term rental sector, including organized opposition and regulatory pressures, while outlining actionable steps for operators to advocate for their businesses. Additionally, we delve into the exciting role of AI in enhancing guest experiences, balancing technological advancements with the personal touch essential to hospitality. Join us, and let’s talk about it. Summary and Highlights Guesty: Built on Industry Expertise Guesty’s journey is a testament to solving real-world problems. Founded by property managers, the company has grown into a leading force in vacation rental management. Tom highlighted several standout aspects of Guesty’s approach: Challenges Facing Short-Term Rentals Tom shed light on significant hurdles in the industry: How Operators Can Respond To combat these challenges, Tom offered actionable steps: The Role of AI in Vacation Rentals We also explored the exciting applications of AI in the industry: Key Takeaways for Newcomers For those entering the vacation rental space, Tom offered invaluable advice: As the short-term rental landscape evolves, success will come to those who balance technological innovation with a genuine commitment to hospitality. We’d love to hear your thoughts: What do you think about the future of AI in vacation rentals? How do you balance technology with a personal touch in your property management approach? Listen to the episode and let’s discuss along… Follow Tom in Linked in, and Guesty on Instagram Transcription Tom: The problem is what the STR opposition has deftly done and that everyone that’s thinking about that’s in this business and thinking about getting in this business that you need to know is they have successfully crafted a narrative that STRs by their nature are bad and negative things. even to emotional levels that it’s like evil, greedy, destroying the community. So when, when people have an emotional buy in to that level, it doesn’t matter if you show up to that town council meeting with some economic report of what it does for the community and how many tax dollars and how many people it employs. It doesn’t matter any of that because it’s bad and evil to begin with. To its core. So there’s nothing good about it. It’s just something we have to deal with, regulate, stop, protect, and all these words. 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 Tom Powers from Guesty. Tom, welcome to the show. Tom: Hey, great to be here, man. Good to see you in the Poconos the other day. Gil: Yeah. Yeah. You’ve been, you’ve been pretty busy. What’s what’s been going on on your side since then? Wow. Tom: the software side of our industry right now. So we are just busy as we can be. I mean, we’ve got new customers coming in every day. Our onboarding pipeline is almost even, I mean, we can always squeeze more in somehow, but like we are really onboarding a ton of people right now. It’s very exciting. It’s an exciting time at our company in particular. It’s an exciting time for this industry. But yeah, man, just been busy. Been road tripping a lot. I’m actually about to plan out the rest of my travel for this year. I probably got seven more events to do this year, , so, Gil: What’s up with the highlight one? So I’m guessing you’re going to be at but what other events are you, are you planning to attend? Tom: Uh, we’re doing one in Portland, Maine is having another small show, kinda like the Poconos. Uh, a lot of the small shows are really good. Um, there’s another one in Vermont. We’re going to do later this year. We’re also doing a road show out your way, uh, the, which I’m going to invite you to, of course, the Palm Springs and San Diego. Um, we should have some, a lot more details on that. That’s going to be in. Early December, I think like December 6th through the 4th. So we got plenty of, uh, there’s a little bit of a ramp there to plan for that, but would love people even listening to the podcast. If you’re in the Palm Springs or San Diego area, this is going to be like a free event. It’s going to be pretty fun. Just like half day type of thing. Um, but yeah, so just busy with that. What else am I doing? God, I don’t even know, man. We’ve got the, the Darm data revenue management conference as well in December. Um, that’s cause it should be exciting. That’s in Sandestin this year, which is actually one of our large enterprise customers too. So pretty cool. Gil: Nice. Nice. Um, kind of introduce, do you mind giving folks a brief introduction on you yourself particular and kind of what you, what you do within guesty? Tom: Yeah, sure. So I’m the market manager for the East coast and, um, I’m a property manager  as well. I, um, I’ve managed, Long term and short term property and done a lot of real estate related things, flipping houses and stuff like that for over 20 years now. And, um, for about 15 years, I was a full time, what I would more call, even a traditional vacation rental manager in a beach market down in Charleston, South Carolina, the Folly Beach Island, and, um, managed full time vacation rental, full staff, private laundromat. You name it, the whole, the whole works for about 15 years. Um, I recently sold that a couple of years ago, kind of cashed out on some personal real estate, took a little break, you know, um, it was a good time to sell obviously in 2021. Gil: Yeah. Tom: for

In our latest episode of Direct Booking Simplified, we discover a fascinating journey through the evolving landscape of short-term rentals with Rafa Loza. As we dive into Rafa’s wealth of experience and industry insights, you’ll uncover the latest trends and strategies that are shaping the rental market. Summary and Highlights Podcast Experience: Sharing Knowledge and Building Connections Both Gil and Rafa embarked on their podcasting journeys with a clear mission: to share their expertise and help others thrive in the short-term rental sector. Their approach focuses on delivering genuine value rather than getting caught up in the metrics. This commitment to quality is reflected in their careful selection of guests, ensuring that each episode provides actionable insights and practical advice. Rafa’s Business Journey: From Rental Arbitrage to Boutique Hotels Rafa’s entrepreneurial journey began in 2017 with rental arbitrage in Southern California. Scaling to 60 units before the onset of COVID-19, he faced significant challenges that led to a pivotal shift in strategy. During the pandemic, Rafa pivoted to mid-term rentals, leveraging email marketing to connect with previous guests. Today, his portfolio spans properties across the U.S., including boutique hotels and resorts. Challenges and Growth Rafa’s journey hasn’t been without its hurdles. From partnership breakups to the impact of COVID-19, he learned the importance of building robust systems, automating processes, and managing teams effectively. Hiring Virtual Assistants (VAs) became a cornerstone of his strategy, allowing him to create Standard Operating Procedures (SOPs) and focus on strategic growth rather than day-to-day operations. Business Evolution Both Gil and Rafa underscore the significance of transitioning from maintenance mode to growth mode. By implementing effective systems and delegating tasks to VAs, they’ve been able to shift their focus from operational details to scaling their businesses and exploring new opportunities. Time Management and Mindset: Valuing Freedom Over Profits One of the key takeaways from the conversation was Rafa’s approach to time management and mindset. He emphasizes valuing time over money, working only about three hours a week on his business to prioritize freedom and lifestyle. This perspective allows him to maintain a balance between professional success and personal fulfillment. Team Building and Delegation: Empowering Your Team A major focus of the discussion was on team building and delegation. Rafa shared his strategy of hiring and training VAs, valuing them as integral team members rather than disposable assets. By allowing his VAs to use their expertise and learn from their mistakes, he fosters a growth mindset and encourages personal development. Direct Booking Strategies and Creative Business Tactics Rafa and Gil delved into various strategies for boosting direct bookings and exploring new business opportunities. Key tactics discussed include: Rafa also shared innovative approaches like leveraging business bookings to identify new property acquisition opportunities and expanding marketing efforts through social media and local Facebook groups. Future Plans and Networking: Looking Ahead Rafa’s future plans involve acquiring more businesses to boost cash flow and continuing to adapt and grow his ventures. He emphasized the importance of networking, which has been instrumental in uncovering new opportunities and building valuable relationships in the industry. Leadership and Management Philosophy Rafa’s leadership style has evolved from top-down management to a more collaborative approach. By focusing on clear communication and empowering his team, he creates an environment where team members can thrive and contribute their best. Follow Rafa Loza 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 Rafa. Hey Rafa.  Rafa: What’s up, man? How are you?  Gil: I’m good. I’m good. How are you?  Rafa Great. Thanks for having me on the show. I appreciate it. Gil: Yeah. I met you at STR nation Was that right? You were on stage.  Rafa:Yeah.  Gil: How’d you enjoy it?  Rafa: A lot of fun, man. I love speaking on stage and sharing with people what I know. It’s one of the, one of my favorite things to do.  Gil: Yeah. Yeah. And you have, um, you have a podcast yourself. Is that right?  Rafa: I do. It’s called the big break show. Um, right now it’s season two. Rafa: Yeah. We’re about 78 episodes in or something like that.  Gil: How was that? Like building up the, to those episodes, like whatever, um,  Rafa: you know, well, I’ve learned a ton number one. So, I mean, having a podcast is one of the best things I’ve ever done, to be honest with you. I did it for fun because I wanted to kind of get my name out and teach people like how to get started with short term rentals, just based on my experience. Rafa: Um, I got, I got featured on bigger pockets, so it kind of changed my life that way and I figured, Hey, if I can help other people by doing my own podcast. Um, you know, that would, that’s something that I would really like want to do. So one day I decided to do it, um, at the time and I had my, my old co host. Rafa: So I have a new co host now, my old co host, Jesse Vasquez. He’s the one that does all the midterm rental stuff. Um, he, uh, we were co host together. We did about 76 episodes together. And I mean, the amount of people that we’ve interviewed, I mean, just all that you get to ask them, like, intimate questions that you really wouldn’t ask anybody else just by having them on the show and you get to promote the brand and so you’re kind of doing something for them and they kind of do something for you by giving you info and feedback and knowledge that you can share with the public. Rafa: That’s the best part about it. And then just the relationships I’ve built throughout it, just having people that I now can call or text because podcast, we resonated, we chatted and I would

Vee Venski’s insights provide a practical roadmap for building a successful short-term rental business. By starting small, building a strong team, focusing on quality, leveraging technology, driving direct bookings, and seeking mentorship, you can enhance your operational efficiency and deliver an exceptional guest experience. For further details and a deeper dive into Vee’s strategies, don’t miss our full podcast episode Summary and Highlights Navigating the short-term rental market requires a blend of strategic planning and practical execution. In our recent podcast, Vee Venski shared his expertise and experiences, offering actionable advice for both newcomers and seasoned hosts in the short-term rental industry. Below, we delve into the core strategies Vee discussed, providing a comprehensive guide to help you enhance your short-term rental business. 1. Start Small to Gain Essential Experience Vee’s journey began modestly with a single spare bedroom listed on Airbnb. This approach allowed him to learn the fundamental aspects of short-term rental management without the complexities of larger properties. Starting small offers several advantages: Actionable Tip: Consider beginning with a single listing or a smaller property to master the basics before expanding your portfolio. 2. Build a Strong Team and Embrace Automation As Vee’s business grew, he emphasized the importance of building a reliable team and incorporating automation into operations. This approach can significantly enhance efficiency and scalability: Actionable Tip: Invest in automation tools and hire skilled professionals to handle key functions like guest services, property management, and marketing. 3. Prioritize Quality Over Quantity Vee shifted his focus from acquiring a high volume of properties to improving the quality of each listing. This shift had a notable impact on profitability and guest satisfaction: Actionable Tip: Evaluate your current properties and consider upgrading or focusing on fewer, higher-end listings to maximize revenue and guest satisfaction. 4. Leverage Technology and Data In the competitive landscape of short-term rentals, technology and data are vital tools for staying ahead: Actionable Tip: Integrate technology solutions that offer dynamic pricing, performance tracking, and streamlined communication to enhance operational efficiency. 5. Drive Direct Bookings Vee highlighted the importance of driving direct bookings through various strategies, which can reduce reliance on third-party platforms and enhance profitability: Actionable Tip: Invest in your website, optimize it for search engines, and develop marketing strategies to boost direct bookings and reduce dependency on booking platforms. 6. Seek Out a Mentor Reflecting on his own experiences, Vee stressed the value of mentorship in avoiding common pitfalls and accelerating growth: Actionable Tip: Seek out a mentor who has experience in the short-term rental market to gain guidance and accelerate your learning curve. Follow Vee Venski here Transcription Vee: What’s been interesting. One thing I came to realize, which was kind of fascinating for me is probably it’s not surprise to most of the people out there, but the person with the most data who can analyze this date in the most efficient timely manner will win. And as you add more properties. Or as you grow your average revenue, like a monthly revenue, you get access to better tools that you can make a better and a more well informed decisions. Vee: So when we had two properties, we’ve had none of this software that we use it because right now we spend around 700 pounds just on a software loan every single month, which is roughly around a thousand dollars. And for a person who just starting out, they just simply can’t afford it or it will not be viable to them. Vee: However, because of this, we will have a competitive edge over their listing. Vee: Hit me! Hit me! 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 Vee. Hey Vee, welcome to the show. Vee: Hi Gil. Hi everyone. Gil: Yeah. Welcome back. Welcome back. You, uh, you took a little vacation there recently, um, to visit family. Vee: Yeah. Yeah. It was lovely. Went to Turkey and need some sun in my life because in the UK we don’t get a lot of sun sadly. Gil: When’s, uh, when’s the last time you took a vacation prior to that? Vee: Oh, I mean last time I was in a warm sea where it’s not like three or five degrees, it was five years ago. Gil: Okay. Okay. Okay. How, how’s your business set up right now? Were you able to completely disconnect or were you the. The digital nomad and running all your short term rentals from remotely. I was just set up now Vee: I’m actually quite lucky. I do have a director now who oversees all the operations. So I was able to completely turn off my head for 23 days. Don’t think for a second about the work. Everything was working as it should. Of course, we’ve made a few mistakes, but nothing crazy that I could not fix upon my return. Vee: But I’m just so happy I do have a good theme that actually helps me to run our properties. Gil: that’s, that’s amazing for you, 23 days is a decent amount of time for you to, to, to walk away and have like minor, minor things that you have to address when you come back. That’s, I would say that’s a huge win. Vee: I mean, it was just a little things. It was just some cleaning issues because we also offer cleaning services to our landlords here in the Northeast. We clean over 40 properties. And because when I left, uh, our business partner gave us another 20 properties. Without the proper introduction. So as you can imagine, it was a bit of a rocky start, but as I said, our team pulled this off Gil: Awesome. Awesome. So kudos, kudos to your team. Um, what was, uh, Well, how did you get to the place where you build out your team? Actually, maybe rewind back just a little bit. Can