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

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

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

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