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

In this episode we are joined by Leo Walton from Superhog, as we dive into the dynamic world of short-term rentals and uncover how it’s evolving. We discuss how hosts are transforming stays from basic lodging to personalized, unforgettable experiences, and how this shift mirrors a growing demand for tailored travel adventures where guests seek more than just a bed—rather immersion. Also, we explore the anticipated rise in direct bookings over the next 5-10 years, and how hosts can leverage this trend through compelling brand and story for their properties. Highlights and Key Takeaways Building Trust in the Industry One of the standout topics was the role of trust-building in short-term rentals. SuperHog, a leader in de-risking bookings, emphasizes the importance of fostering trust between guests and hosts. In today’s market, creating a professional and secure booking process is crucial for direct bookings. This trust not only enhances the guest experience but also boosts the reputation of the host and the platform. The Evolution of Short-Term Rentals The short-term rental industry has evolved significantly from its origins of basic accommodations. Today, hosts are curating highly personalized and memorable experiences, going beyond mere lodging to offer unique, customized stays. This shift reflects a broader trend towards more bespoke travel experiences, where guests seek more than just a place to sleep—they want an immersive experience. The Rise of Direct Bookings Looking ahead, direct bookings are predicted to surge in popularity over the next 5-10 years. To capitalize on this trend, hosts must focus on building a strong brand and narrative around their properties and destinations. Direct bookings offer a chance to create a more personal connection with guests and differentiate oneself in a crowded market. Marketing and Social Media Strategies Marketing strategies are evolving, with a growing emphasis on showcasing the entire experience rather than just property features. Social media is a powerful tool for attracting guests and crafting a compelling narrative around stays. By highlighting local attractions and unique experiences, hosts can better engage potential guests and create a buzz around their properties. Google’s Role in Vacation Rentals Our podcast also touched on the current limitations of Google Vacation Rentals and its potential future impact. While Google has made strides in the vacation rental space, there is still room for improvement in terms of integration with property management systems and optimization tools. Addressing these gaps could significantly enhance the visibility and efficiency of vacation rental listings. Personalization and Curation Personalization continues to be a key trend, with hosts increasingly curating unique experiences and activities for their guests. Technology, including AI, plays a growing role in this personalization, helping hosts offer tailored recommendations and enhance the overall guest experience. Challenges and Opportunities Hosts face the challenge of balancing scalability with a personal touch in guest communications. Understanding the target market and local attractions is essential for creating meaningful connections and ensuring a memorable stay. Despite these challenges, there are numerous opportunities to enhance guest experiences and drive more direct bookings. Industry Trends The travel industry is witnessing a shift from repeat visits to the same locations towards more diverse and aspirational travel experiences. Social media influences travel choices and destination popularity, making it crucial for hosts to stay ahead of these trends and adapt their strategies accordingly. The Importance of Thoughtful Hospitality Finally, even as the industry scales, the importance of thoughtful, personal hospitality cannot be overstated. Creating welcoming, memorable experiences for guests, with subtle touches that show attention to detail, is essential for standing out in the competitive short-term rental market. Follow Leo and Superhog’s Social Media Accounts Here Transcription Leo: Every property manager knows they need to have a risk management strategy. And by that, I mean, as I’m not just saying, you know, buy our product far from it, I’m saying you understand as a property manager and a host, what market you’re in, what the risks are. Are you in a party market? Are you in a market where you might have people refusing to leave? Leo: You know, drugs, all that sort of stuff, you understand your market implicitly. So you create a risk management strategy. And if you didn’t create a risk management strategy, you’d get your homes damaged all of the time. So we’re just helping facilitate and be part of people’s risk management strategy. So that is a very evolving thing. 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 Leo from super hog. Leo. Welcome to the show. Leo: Thanks. It’s so nice to be here. Gil: Yeah. It’s great to have you. We’ve been chatting for a long while now back since I think we met at a wealth con. Leo: It’s been a while, hasn’t it? Yeah, I, I must say it’s, um, I guess we’re both in the, in the sort of, uh, cave, aren’t we busy building our businesses? And so we, we touch base and chat every month. And it’s always great to hear how things are going on, on your side of things. So yeah, I’m, uh, excited to come and do this and speak to your audience. Leo: Absolutely. So, Gil: Yeah. Yeah. Well, before we get too deep into it, do you mind giving folks a introduction on who you are? Leo: while, uh, while Gil was meeting me, um, my name is Leo Walton. I’m the One of the co founders and I’m the chief of staff at SIPPOG. Um, we’re a trust and safety risk management toolkit, providing protection and, uh, risk management solutions to the short term rental space. I’m a short term rental junkie as well. Leo: I’ve been in the industry since 20. 11 not to age myself too much, but yeah, 2011 I was part of one of the, um, part of one of the businesses that kind of property management businesses that grew up and was sold to one

In our latest podcast episode, we had an insightful conversation with Katie Wanzer, co-founder of Wisco Hosts and a co-owner of a boutique motel in Door County, to explore pivotal strategies for boosting direct bookings. Katie shares how she believes that a well-defined brand identity is crucial for driving success in direct bookings. Discover how establishing a clear and compelling brand can streamline your marketing efforts and content creation, ensuring that every aspect of your strategy aligns seamlessly with your brand’s vision. Summary and Highlights In our latest podcast episode, we had an insightful conversation with Katie Wanzer about the essential strategies for enhancing direct bookings. We’ve broken down her key advice into actionable steps that can help you strengthen your brand and drive more direct bookings. Katie highlights the importance of establishing a clear brand identity as the foundation for increasing direct bookings. Begin by defining your brand, including your ideal brand avatar and the specific experience you want to offer guests. This clarity will guide your marketing strategies and content creation, ensuring that your efforts are cohesive and aligned with your brand’s vision. To enhance your brand and attract more direct bookings, leverage a variety of marketing channels. Blog content, social media, and email marketing are effective tools for highlighting the local area and unique experiences you provide. Engaging content that showcases these elements can help you stand out from the competition and appeal to potential guests. Katie stresses the need to prioritize a direct booking website before listing on OTAs. Having your own booking platform allows you to manage the booking process and build a direct relationship with guests. A well-designed website not only strengthens your brand’s credibility but also offers a smoother booking experience. Starting something new often involves facing uncertainties. Katie advises embracing these challenges and viewing them as opportunities for growth. Strive for progress rather than perfection, and use the lessons learned from overcoming obstacles to become a better entrepreneur. Knowing your target guest avatar is crucial for tailoring your offerings. Understanding their needs and preferences allows you to design amenities and experiences that resonate with them, ultimately driving more direct bookings. Utilize tools such as PriceLabs and conduct competitor analysis to optimize your pricing strategy. Effective revenue management helps ensure that your rates are competitive while maximizing your potential for direct bookings. Implement a robust email marketing strategy that includes segmentation, A/B testing, and automation. These tactics can help you engage with past guests and potential leads, encouraging repeat bookings and boosting your direct business. Conclusion: Building a Strong Brand for Long-Term Success Katie Wanzer’s insights underscore the significance of developing a strong, unique brand identity and exceptional guest experience for driving direct bookings. By focusing on these areas and strategically employing marketing tools, you can reduce reliance on OTAs and pave the way for sustained business success. For more tips, tune into our podcast, and start applying these strategies to elevate your brand and increase direct bookings! Follow Katie and Wisco Hosts’ Social Media Accounts Here Transcription Katie: We have stay fi at our properties. So anybody who stays there and logs into the internet, we capture that email right away. I think our email campaign and strategy was very low the first few years that we started this. Mostly from a standpoint of we were relying so heavily on OTAs, you know, Airbnb, VRBO, and then once we had that ability to book direct. Katie: We really wanted to focus a lot of our time and energy to get people to book direct with us versus the OTAs. Cause I think the biggest thing is to this gas don’t realize, I think how much the service fees are on both OTAs and how it can really skyrocket a bill. But also to them as owners, as part of this brand journey is you really then get to decide the touch points that your guests have with you and what those touch points look like. 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 Katie Wanzer. Katie, welcome to the show. Katie: Thanks for having me again. Gil: Yeah. How are you doing? How’s uh, how’s the heat right now? Katie: The Midwest is getting slammed. We got slammed with rain all spring and summer and now the heat’s coming. So, you know, just the typical Midwestern summer, but you know, it’s, it’s great. It’s warm. So here in the Midwest, we love that. Gil: That’s so foreign to me being in San Francisco. We never get any weather beyond like 50 degrees to like 60 degrees all year round. So it’s, I find, I actually find it very interesting to see like people actually having to, to change seasons. And I, I kind of, I wish I had a little bit more of that in my life, but maybe, maybe not during these. Gil: Yeah, Katie: No, no. I mean, it is beautiful to see the four seasons, but to think it’d be a consistent temperature, especially all the way up here in Wisconsin, it’s just, it’s a foreign concept. So I’m also envious of your, you know, your static weather all the time to say the least. Gil: I guess that’s why, why we travel, like for us, like we travel to go get the heat or get the snow. So, yeah, that’s, Katie: Come to the Midwest. We get both, we get ample amounts of snow and ample amounts of heat. So come visit and we have it all. Gil: Um, before you get too deep into it, Katie, do you mind giving folks a brief introduction to who you are and kind of a glimpse into your portfolio? Katie: Yeah. So I, I am Katie Wanzer. I am one of the co owners and co founders of Wisco Hosts. Uh, we are a co hosting, um, company that per,

In the 23rd episode of Direct Booking Simplified, military veteran and superhost Jessica Fernandez offers a fresh perspective on hosting. Instead of focusing on expanding her portfolio or managing numerous listings, Jessica zeroes in on providing an outstanding guest experience. She reveals how her focus on personalizing and perfecting each stay not only ensures memorable visits but also turns regular bookings into repeat ones. Join us as Jessica reveals how her dedication to exceptional service and personalized touches helps her build lasting guest relationships and drive repeat bookings Summary and Highlights Doing it all from being in active military service to civilian life can be a daunting task, but Jessica, a military veteran, has embraced this challenge with the same strategic mindset that defined her career. In our recent podcast, Jessica shared her inspiring journey of moving from the military to becoming a successful short-term rental (STR) host in Virginia Beach. Her story offers valuable insights for anyone looking to make a mark in the STR community. Strategic Property Selection: A Tactical Approach Jessica and her husband, both seasoned entrepreneurs, embarked on their post-military venture with a clear strategy. They chose to invest in real estate with a focus on short-term rentals, specifically targeting properties that would attract steady clientele. One standout example is their property in Annapolis, Maryland. This particular location was chosen for its appeal to midshipmen parents and alumni, ensuring a reliable flow of repeat customers. By zeroing in on this niche market, Jessica has successfully tapped into a consistent demand, which is a critical factor in her business’s success. Elevating Guest Experience: A Five-Star Commitment In the competitive world of short-term rentals, delivering an exceptional guest experience is paramount. Jessica’s approach to hospitality is reminiscent of high-end hotels, where the focus is on creating memorable stays. From luxurious touches to meticulous attention to detail, she ensures her guests receive a five-star experience. This dedication not only garners glowing reviews but also fosters repeat bookings, which are essential for sustaining a profitable STR business. Effective Communication: Building Trust and Comfort Jessica understands the importance of communication in enhancing guest satisfaction. She maintains a personal touch by reaching out with pre-arrival text messages and staying available throughout their stay. This proactive approach helps build trust and ensures that guests feel valued and well-cared-for, leading to positive reviews and increased likelihood of repeat stays. Harnessing Technology: Streamlining Operations Technology plays a crucial role in Jessica’s business operations. She utilizes tools like Market My STR and a virtual assistant to manage guest communications effectively. This not only helps her maintain high standards of quality control but also ensures that her guests receive prompt and attentive service. By leveraging these tools, Jessica can focus on growing her business while maintaining a high level of guest satisfaction. Ensuring Legal Protection: Clear Agreements A comprehensive rental agreement is part of Jessica’s strategy to protect both herself and her guests. By setting clear expectations through detailed agreements, she minimizes potential misunderstandings and legal issues, creating a smoother experience for all parties involved. Direct Booking Strategy: Encouraging Future Visits Jessica actively encourages guests to book directly for future stays, providing them with her direct booking information during their visit. This strategy not only helps her build a loyal customer base but also maximizes her revenue by avoiding third-party booking fees. Leveraging Referrals: The Power of Networking Referrals play a significant role in Jessica’s direct booking success. Many of her new bookings come from previous guests or her personal network. This word-of-mouth marketing is a testament to the quality of her service and the strong relationships she has built with her guests. Commitment to Continuous Learning: Staying Ahead Jessica’s commitment to professional growth is evident in her investment in coaching and attendance at industry conferences. By staying updated on best practices and emerging trends, she ensures that her business remains competitive and adaptable to changing market conditions. Mindset and Long-Term Vision: Building for the Future A key element of Jessica’s success is her mindset. She focuses on controlling what she can and letting go of what she can’t, which helps her navigate the challenges of the STR industry with resilience. Additionally, Jessica views her STR business as part of a broader financial and tax strategy. Instead of seeking immediate cash flow, she aims to build long-term wealth and legacy assets, reflecting a thoughtful and strategic approach to her investment. Jessica’s journey from military service to becoming a successful short-term rental entrepreneur is a testament to the power of strategic planning, exceptional guest service, and continuous learning. Her story provides valuable lessons for anyone looking to thrive in the world of real estate investment. For more insights into Jessica’s successful strategies and to hear her full story, be sure to check out our latest podcast episode. Follow Jessica on Instagram Transcription Jessica: I get their phone numbers and their emails. And I also have a card that I made up with like a little like gift that basically says like, Hey, here’s our website. You know, if you ever want to come back, just email us or, or go on to the website and you can book through there and get a discount. So we’ve had multiple people while they were there. Message us and say, Hey, like we want to book for these other weekends because there’s specific like parents weekends and football games and alumni weekends that they already know those dates for. So I can book those out in advance and I can just fill in with everything else. 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 Jessica Fernandez. Jessica. Jessica: Yeah, Gil: good. It was, uh, really good bumping into you at, uh, STR Nation. Uh, this was a week ago. I feel like it was a week ago. Jessica: I, I’ve lost track of time. Like I’m quasi

Join us as we dive deep with Al and Elissa of Rather Be Properties. From 4 to 30+ properties in just a year, they share their journey of rapid growth while maintaining a focus on five-star hospitality. Learn about their innovative approaches to direct bookings, influencer partnerships, and balancing business scaling with family life. Discover how they’re playing the long game in the short-term rental space, one ‘rather be’ experience at a time. Summary and Highlights In the ever-evolving world of short-term rental management, few stories shine as brightly as that of Al and Elissa from Rather Be Properties. On our latest podcast, we had the pleasure of witnessing their journey, which has seen their business skyrocket from managing just four properties to over 30 in under a year. And they’re not stopping there—aiming to expand to 50-75 properties by really soon, their story is both inspiring and instructional for anyone in the industry. From 4 to 30+ Properties in Just a Year Al and Elissa’s rapid growth is a testament to their strategic approach and relentless drive. Their success didn’t come overnight; it’s the result of meticulous planning and execution. They’ve invested significantly in building robust systems and processes, enabling them to scale efficiently without compromising quality. Balancing Five-Star Hospitality with Profitability One of the key insights from our conversation was their focus on delivering “five-star hospitality” while also maximizing owner profits. This dual objective often presents a challenge, as exceptional guest experiences can sometimes conflict with profitability. However, Al and Elissa have found a way to harmonize these goals, creating a model that serves both their guests and property owners effectively. Investing in Systems and Team Expansion Scaling a business demands more than just increased inventory; it requires solid infrastructure. Al and Elissa have recognized this need and have heavily invested in systems and processes. This includes expanding their team, which is crucial for maintaining high standards across their growing portfolio. Their proactive approach to team building and process optimization has been instrumental in their rapid expansion. The Importance of KPIs Data-driven decision-making is another cornerstone of their success. They closely monitor various Key Performance Indicators (KPIs), such as guest review scores, response times, maintenance costs, and revenue targets. This meticulous tracking allows them to make informed adjustments and ensure their operations remain efficient and effective. The Power of Direct Bookings While Online Travel Agencies (OTAs) like Airbnb are valuable for visibility, Al and Elissa place significant emphasis on direct bookings through their website, social media, and email marketing. They view direct bookings as a vital component for fostering long-term guest relationships and mitigating some of the challenges associated with OTA platforms. This strategy not only helps in building a loyal guest base but also in enhancing their overall brand presence. Playing the Long Game Al and Elissa embody the essence of playing the long game in business. They understand that success involves continuous iteration and process improvement. Their willingness to adapt and refine their approach over time underscores their commitment to long-term success rather than short-term gains. A Family Business with a Personal Touch What makes their story even more compelling is their ability to scale a thriving business while raising young children. They view Rather Be Properties not just as a business but as a family venture, adding a personal touch to their professional achievements. Leveraging Complementary Skills for Growth Al and Elissa’s journey highlights the power of leveraging complementary skills. Al’s focus on systems and efficiency pairs perfectly with Elissa’s background in hospitality, creating a dynamic duo that drives their business forward. Their synergy is a key factor in their impressive growth and continued success. Their story is a testament to what can be achieved with dedication, strategic planning, and a shared vision. For those looking to make their mark in the short-term rental industry, Al and Elissa’s approach offers valuable lessons in scaling, balancing priorities, and building a brand that resonates with both guests and property owners. Follow Rather Be Properties on Instagram Transcription Gil: Hey folks. Welcome back to direct booking. Simplify it. We break down the strategies and tactics to win direct bookings on today’s show. I have Al and Elissa. Welcome to the show, Al and Elissa. Thank you. Yeah. It’s great to have a power couple on the show. I’ve had a couple, but I always enjoyed, I kind of enjoy the dynamic there. Al: We like to think so too.  Gil: Yeah. Do you guys mind giving an introduction to yourself?  Al: Sure. Okay. Sorry. Um, cool. So my name’s Al. Um, I’ve been in tied to a residential real estate for probably the last 15 years. I was in the mortgage industry for quite some time. I retired out of that about a year ago. We bought and flipped homes in residential real estate, Southern California. Al: Um, we’ve done, uh, some, you know, property syndications, both multifamily, residential, short term rentals. Um, we started investing in short term rentals about four years ago, almost three and a half, four years ago. And, uh, really it was just an avenue for us to invest into a couple of properties, have some passive income. Al: Um, Elissa’s background is in hospitality. I’ll let you share your background.  Elissa: Um, so I was a massage therapist and an esthetician, and I was involved in some day spas and some five star resorts in Australia. And then Dubai where Al and I met. Uh, I’ve spent like 10 years in the hospitality industry, doing really fun stuff. Elissa: Fine five star hospitality, I guess. Um, I love that side of things. Um, the hospitality anticipating guest needs. Yeah. So with us love of real estate and my hospitality, I feel like we  Al: made a good combo. Yeah. So that’s why we just started to decide to start the company. Um, and then we started co hosting probably two years ago. Al: Uh, basically first property owner just reached out

In this episode, let’s join DJ Fornelli as he shares his unconventional path to success, including the risks he took, the mindset shifts he made, and the power of building the right team. Let’s discover how his 10-key boutique hotel, Yara Palm Springs, achieved 65% direct booking rate through strategic branding and influencer partnerships. Whether you’re a seasoned investor or just starting out, DJ’s insights on perseverance, personal growth, and work-life balance will inspire you to reach new heights as a host and entrepreneur. Summary and Highlights In our latest podcast episode, we had the pleasure of speaking with DJ Fornelli, a trailblazer who made a remarkable transition from archaeology to real estate investing and hospitality. DJ’s story is a testament to how passion and perseverance can lead to extraordinary career shifts and successes. Here’s a deep dive into our conversation and the valuable insights DJ shared about his journey. From Archaeology to Real Estate: A Career Pivot DJ Fornelli’s career began in archaeology, a field where he unearthed the past. However, after some reflection, DJ realized that his financial potential could be significantly higher in real estate. This epiphany led him to dive into the world of property investment and hospitality, where he quickly discovered the lucrative opportunities that flipping houses presented. DJ and his partners took a strategic approach to their new venture by investing in a real estate education program. This investment in knowledge equipped them with the skills needed to navigate the complex world of property investment. They started by flipping houses in Joshua Tree, California, a location that allowed them to capitalize on both the real estate market and the burgeoning short-term rental trend. From Flipping Houses to Boutique Hotels DJ’s real estate journey didn’t stop at flipping houses. His team’s success with short-term rentals led them to a new venture: a 10-key boutique hotel named Yara Palm Springs. This move marked a significant milestone in their hospitality endeavors. The hotel’s success is largely attributed to their focus on building a strong brand and creating a cohesive aesthetic across all platforms. Remarkably, about 65% of Yara Palm Springs’ bookings come through direct channels like their website. This achievement underscores the importance of a well-executed branding strategy and a user-friendly booking experience. The Power of Influencer Marketing DJ shared that working with influencers has been a game-changer for marketing the hotel. Influencers have helped amplify their brand’s reach and credibility, contributing to a substantial increase in direct bookings. However, this approach hasn’t been as effective for their individual short-term rentals, highlighting the need for tailored marketing strategies for different types of properties. Key Mindset Insights Throughout our conversation, DJ emphasized the importance of mindset in achieving success: The Value of a Strong Team One of DJ’s biggest takeaways from his journey is the significance of having a strong, well-rounded team. He highlighted how having team members with complementary strengths and clearly defined roles and responsibilities has been pivotal in their success. A cohesive team not only enhances operational efficiency but also drives innovation and growth. Balancing Work and Family DJ’s transition to real estate and hospitality has also provided him with the flexibility to spend quality time with his young daughter. He expressed deep gratitude for the balance he’s been able to achieve between his professional pursuits and family life. Final Thoughts DJ Fornelli’s journey from archaeology to real estate and hospitality is a powerful reminder that career transitions, while challenging, can lead to fulfilling and profitable ventures. His insights into mindset, team-building, and branding offer valuable lessons for anyone looking to embark on a similar path. Tune in to the full podcast episode for more detailed insights and inspiration from DJ’s incredible journey. Whether you’re considering a career shift or looking to enhance your current business strategies, DJ’s experiences and advice are sure to provide valuable guidance. Follow DJ Fornelli on Instagram @davidjfornelli & @yarapalmsprings 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 DJ Fornelli. DJ Fornelli. DJ, welcome to the show.  DJ: Oh, thanks so much for having me, Gil. It’s awesome to be here, bro. Gil: Yeah, it was great meeting you at Nation. What it last week? It felt like much longer than that.  DJ: Yeah, yeah, it was awesome. We got to have lunch, uh, about two days in a row. We got to chat, learn more about each other, each other’s businesses. We talked about kids, man. So it was great meeting you.  Gil: Yeah. Gil: I really liked the more intimate, uh, conferences. I was at Wellcon earlier this year and it was just really, really big. And you, you feel like you’re speed dating with pretty much. All the attendees, whereas this one, we did get a chance to sit down and have lunch together multiple times and like have a real conversation and get to know each other and like, get to talk about our kids. Gil: Like you really don’t have that experience at a much bigger conference. Yeah.  DJ: Yeah. I agree, bro. I agree. And I feel like at the bigger ones, people are kind of sizing each other up. Right. Like everyone’s looking at each other, like, Oh, what does this guy have? What’s his portfolio? And then you kind of like judge someone, like, if you’re like, Oh, this guy’s a medium operator onto the next one. DJ: Um, whereas the smaller ones, a lot more intimate, like you said, we can get to know each other, everyone’s guards down just a little bit more. So thank you, Patrick and Stephanie for, for putting on a great event and allowing me to meet awesome people like Gil.  Gil: Yeah. Yeah. Hopefully they, uh, they pull back on their words and they bring it back for it in the year. DJ: Yeah, let’s convince him, dude. I’m gonna text Patrick after this

In this episode, we learn which tactics work for Dave to drive direct bookings. After trying many different tactics, Dave figured out how to reliably get a steady stream of direct bookings by using one simple tactic: calling the guest. He’s able to build relationships, understand the guest’s visit frequency, and secure the next stay should they come back to the area. Join us on this episode to dive deep into how Dave grew his portfolio and how he’s able to win in direct bookings. Summary and Highlights In our latest podcast episode, we had the pleasure of sitting down with Dave, a seasoned property investor who has navigated through various sectors of the industry over the past 14 years. Here’s a recap of Dave’s journey, insights, and strategies that have propelled his business forward, especially during challenging times like the COVID-19 pandemic. Dave’s Background Dave began his career in property investing with fix-and-flips and long-term rentals. However, six years ago, he pivoted towards short-term rentals and serviced accommodations. Today, he manages a diverse portfolio of 75 properties, including owned properties, rental arbitrage units, and properties managed for others. Dave is also expanding into building small hotels and apart-hotels, showcasing his dynamic approach to scaling his business. Business Evolution During the COVID-19 pandemic, Dave’s business saw rapid growth by catering to NHS staff and key workers, expanding his portfolio to nearly 100 properties at its peak. However, as the landscape evolved, Dave strategically scaled back on managed properties, focusing more on owned properties and rental arbitrage. This shift allowed him to maintain greater control over operations and adapt to changing market conditions effectively. Direct Booking Strategy One of Dave’s standout achievements is his direct booking strategy, which currently accounts for 50% of his bookings, with a goal to increase this to 65%. His approach revolves around personalizing guest experiences through a “mid-stay customer care call” conducted the day after check-in. This not only ensures guest satisfaction but also encourages repeat bookings and referrals, especially from business and contractor guests who appreciate personalized service. Systems and Processes To streamline operations, Dave leverages technology such as Monday.com for tracking inquiries and follow-ups. Integration with his Property Management System (PMS), MailChimp, and Monday.com through Zapier has automated many processes, allowing Dave to focus more on enhancing customer experience and nurturing high-value repeat clients. Advice for Others Dave’s success is rooted in understanding his client base deeply and actively engaging with them. He emphasizes the importance of networking with industry leaders and investing in continuous education to stay ahead. His top recommendation for fellow property managers and investors is to prioritize direct customer interactions to convert OTA bookings into direct bookings, thereby building a loyal customer base. Conclusion Dave’s journey from traditional property investing to innovative hospitality solutions during the pandemic offers valuable lessons for anyone looking to thrive in the property sector. His strategic adaptations and focus on direct customer relationships underscore the importance of agility and customer-centricity in achieving sustained business growth. Follow Dave Goodfellow on Instagram @nokistays & @davegoodfellowofficial Transcription Gil: Hey folks, welcome back to Direct Booking Simplified, where we break down the tactics and strategies to win in direct bookings. On today’s show, I have Dave Goodfellow. Hey Dave, welcome to the show. Hey, thanks for having me. Really  Dave: appreciate you having me and giving me this space to talk. Gil: Yeah, you’re all the way across the sea. One of my furthest guests that I had so far. Um, so it’s welcome. Welcome. Welcome. Welcome to the show. Um, yeah. Why don’t you, uh, introduce yourself to, to our listeners?  Dave: Yeah. Happy to. So I’m Dave Goodfellow. I’m the owner of Nokia stays over here in the UK. We are a serviced accommodation, Airbnb, short term rental, whatever you want to call it, kind of operator. Dave: Um, I’m a property investor at heart. Um, I kind of got into property about 14 years ago and was, you know, Refurbishing properties and selling them and had a small buy to let portfolio or a rental prop, um, a rental business, um, and then six years ago, I decided that I wanted to get into the short term rental market and switched my, my property portfolio into this. Dave: And then I’ve grown, uh, A nice business over the last six years where we, we, we rent or rental arbitrage, you call it in, in the state. Um, we manage for other people and we build our own stuff and we’re now building kind of small hotels and apart hotels and stuff like that too.  Gil: So you’re, you’re, you’re now building your own hotels. Gil: Yeah. Uh, what’s, what’s, what’s been the journey through that? Have you launched your first, uh, build yet?  Dave: Uh, so I’m in the process of building one at the moment. Uh, it’s called what we call, it’s a concept called an apart hotel in the uk. So yeah, we’ll purchase a, an old sort of hotel. Um, yeah. We’ll then take out all the operational space, like the, the bars and the restaurants, and we’ll put rentable space in there by changing them into apartments. Dave: Um, so I’ve got one at the moment over in North Wales, a little town called Llandudno. Um, and that’s 11 apartments under one roof, uh, in this old sort of Victorian, uh, building that’s, uh, been now made into an apartment hotel.  Gil: And that one’s already live.  Dave: No, no. It’s in the process of  Gil: being built right now. Gil: Oh, okay. When, when do you, when do you plan to complete and start having your first few guests in there? So it should have been may just gone, Dave: but as with all developments, they all run over, they’re all over budget and they’re all a nightmare. Um, this one should be, we should be opening kind of back end of August, beginning of September. So we totally missed

We have the honor of interviewing Tracey Northcott from Tokyo Family Stays about how she delivers her guest experiences and how that translates to more direct bookings. Tracey walks us through how she thinks about the entire booking journey and how she can deliver the best guest experience beyond just a great place to stay. Her mindset has led to a sustainable book-direct business from repeat guests and strong word of mouth. Summary and Highlights In our recent podcast episode, we had the honor of speaking with Tracey Northcott, the visionary behind Tokyo Family Stays, an established vacation rental business in Japan. With over 12 years of experience in the hospitality industry, Tracey shared invaluable insights on how to create a successful and sustainable hosting business that prioritizes authenticity and guest satisfaction over mere profitability. 1. Emphasizing the Local Experience and Anticipating Guest Needs Tracey’s journey began with a simple yet profound principle: provide guests with an authentic local experience. Unlike impersonal stays, Tokyo Family Stays thrives on connecting visitors with the heart of Tokyo, enriching their travel experience through carefully curated local insights and services tailored to their needs. 2. Developing a Strong Brand Identity and Values Rather than being just another “Airbnb host,” Tracey advocates for hosts to establish a distinct brand identity and values. This strategic approach not only attracts ideal guests who resonate with those values but also fosters long-term guest loyalty. By embodying values such as hospitality, cultural immersion, and community engagement, hosts can create a memorable and meaningful stay experience. 3. Mapping the Guest Journey and Personalizing Services Central to Tracey’s success is her meticulous attention to the guest journey. From initial booking inquiries to post-stay follow-ups, every touchpoint is an opportunity to exceed expectations. By anticipating guest needs and preferences, hosts can deliver personalized services that leave a lasting impression. 4. Building a Direct Booking Presence and Nurturing Relationships While many rely solely on OTAs (Online Travel Agencies), Tracey advocates for building a direct booking presence. This not only reduces dependency on third-party platforms but also allows hosts to cultivate relationships with repeat guests through effective email marketing, SEO strategies, and collaborations with local businesses. 5. Core Values and Authenticity Tracey’s guiding philosophy revolves around defining core values and purpose (“why”) as the foundation for building a hosting business. By staying true to these values, hosts can authentically connect with guests and uphold the responsibility of hosting beyond mere accommodation. 6. Long-Term Strategy and Sustainability In a landscape often dominated by short-term gains, Tracey underscores the importance of a sustainable business approach. By focusing on guest satisfaction, community integration, and ethical business practices, hosts can build a resilient and thriving vacation rental business. Conclusion Tracey Northcott’s insights challenge conventional wisdom in the hospitality industry. Her emphasis on authenticity, values-driven business practices, and personalized guest experiences serves as a beacon for both seasoned hosts and newcomers alike. By embracing these principles, hosts can not only differentiate themselves in a competitive market but also create meaningful connections that transcend mere transactions. Follow Tracey on Instagram through @tracey.northcott 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 Tracey Northcott, all the way from Japan. Welcome on the show, Tracey.  Tracey: G’day, g’day, g’day, Gil. Sorry, I have to be really Australian when I, you know, when I come on podcasts, I’ve got to like, you know, wear my, wear my, um, uh, my nationality with pride. Tracey: So,  Gil: That’s awesome. Before we get too deep, Tracey, do you mind giving folks a brief introduction of who you are?  Tracey: Sure. No problem. So yes, I’m, my name’s Tracey. I’m CEO of Tokyo family stays. So yes, I’ve been in Japan for 24 years. I’m not Japanese clearly. Um, and, uh, I run a vacation rental business. Um, and, I love it. Tracey: And it’s, it’s brought my family a lot of financial freedom and also, you know, freedom to, to travel and also learn about ourselves. So it’s, it’s been a really, really interesting journey. So I wasn’t always in vacation rentals. I come from a background of science and technology. Um, I was a chemist and then, which is a different whole other story. Tracey: And then I actually came to Japan to work with my brother, who’s a software engineer, and we make actually language learning applications on mobile phones. So we’ve been doing that for 25 years and that’s still going, but it’s mostly passive at this point. So it lets us play and do passion projects and real estate was always one of my passions. Gil: Yeah. How did you first get into it?  Tracey: Well, it was kind of by accident. So we were playing around in real estate. So, um, we, as. as business owners, we were always sort of happy to take on, uh, help other people with their businesses. And we had a friend who was a real estate agent who, who didn’t have like a full paid up company and they wanted to do real estate. Tracey: They had the license, but didn’t know how to actually run a company. So then we said, all right, rent a desk from us and, um, use our infrastructure and our, you know, our tax accountant and all of those things that you need when you’re running a business. And you play in real estate and then we’ll share some, we’ll do some profit sharing. Tracey: And so that was fun because, you know, we’re able to, you know, play around with real estate and, and, um, not buying. So I was sort of helping people, um, with subletting, um, you know, the, the visa and, and things are fairly, fairly strict here. So actually getting an apartment when you’re, you know, when you’re working here is quite hard when you’re a foreigner. Tracey: So I was helping people