EP 245: The Hospitality Industry Is About to Split in Two (And Most Hosts Aren't Ready) with Gil Chan

For the first time, I'm pulling back the curtain on what our first full peak season actually looked like at Cabins on the Cumberland. There are so many conversations online about buying boutique hotels, building micro resorts, and creating passive income, but very few people are willing to talk about the numbers behind the scenes. In this episode, I'm sharing ours. I break down our June and July performance year over year, where our ADR and occupancy landed, how a completed guest experience changed everything, and why branding, revenue management, direct bookings, and thoughtful hospitality all worked together to produce our strongest season yet. I also talk honestly about the realities that don't make it into Instagram posts: construction delays, unexpected expenses, cash flow, saving for slow season, and why a profitable hospitality business is about so much more than big revenue months. If you've ever wondered what it actually looks like to build a hospitality business from the ground up, or you're trying to increase revenue at your own property, I think you'll find this episode refreshing, practical, and hopefully encouraging. If you're ready to build a hospitality brand that drives more direct bookings, stronger guest loyalty, and long-term growth, I'd love to help. Learn more about working with my team at theweberco.com. Curious about the property behind today's numbers? Take a look at Cabins on the Cumberland and see how we've built the guest experience from the ground up at cabinsonthecumberland.com.

What separates a hotel that's simply beautiful from one that guests can't stop booking? In this episode, I sit down with hospitality designer Courtney Petrovich, founder of Deanery Designs, to talk about the role design really plays in the success of a hospitality brand. We dive into why boutique hotel design is so much more than selecting furniture and finishes, how thoughtful design can help attract investors before a project is even built, and the operational decisions that can save owners time and money for years to come. We also talk about the shift we're seeing as more short-term rental investors move into the boutique hotel space, why creating a true sense of place matters more than following design trends, and how the smallest details often create the most memorable guest experiences. If you're developing a boutique hotel, planning a micro resort, or simply want your hospitality brand to stand out in a crowded market, this conversation is full of practical insights you won't want to miss. Connect with Courtney: Website: https://www.denoridesigns.com/ Instagram: https://www.instagram.com/denoridesigns/  Connect with Steph: Website: https://www.theweberco.comInstagram: https://www.instagram.com/theweberco Podcast: https://www.theweberco.com/podcast

We're officially recording our first podcast episode from the camper, and after more than two weeks on the road, it's safe to say this adventure has already taught us more than we expected. In this episode, I'm sharing an honest behind-the-scenes look at what it's been like transitioning into full-time RV life with our family. From unexpected truck delays and finding a long-term tenant for our home to exploring South Dakota's national parks, navigating tiny living with two little boys, and discovering just how much lifestyle freedom entrepreneurship can create, this episode is a candid update on what this season has looked like so far. I also share one of the biggest mindset shifts I've had since leaving: realizing that building a business isn't just about financial freedom. It's also about creating the freedom to experience life differently, and this trip has completely changed the way I think about that. Finally, I'm announcing something I've been incredibly excited to launch: my new On-Site Marketing Intensives. These application-only experiences combine brand strategy, guest experience consulting, content creation, and marketing strategy—all at your property. If you've been looking for hands-on guidance to elevate your hospitality brand while creating a library of intentional content that actually converts, this is exactly what I've built these for. To learn more about the new On-Site Marketing Intensives, view our travel schedule, and submit an application, visit theweberco.com/on-site-marketing. I can't wait to meet some of you in person as we travel across the country.  

Everyone wants more direct bookings. But what if the question isn't "How do I get more direct bookings?" What if the real question is, "How do I build a business that guests want to book from directly?" In this episode of Branded & Booked, I sit down with Rose Taika, founder of Your Family's Place, a vacation rental company in Ohio's Amish Country that generates roughly 70% of its bookings through its own website. Rose is a homeschooling mom of six, a best-selling author, and a hospitality entrepreneur who has built a portfolio of family-focused vacation rentals by thinking differently about branding, guest experience, and long-term business value. Throughout our conversation, Rose shares why direct bookings are the result of years of intentional business building—not a software, funnel, or marketing hack. We talk about how Your Family's Place reached approximately 70% direct bookings, why most hosts focus on the wrong metrics when trying to increase direct reservations, and the role branding, email marketing, content creators, advertising, and repeat guests have played in their growth. Rose also shares why she believes hospitality is ultimately a relationship business and how that mindset has shaped everything from their guest experience to their long-term growth strategy. One of the most powerful moments in the episode comes when Rose says, "Real businesses market." It's a simple statement, but one that challenged the way I think many of us approach direct bookings. In an industry where Airbnb can bring us reservations, it's easy to forget that direct bookings don't happen by accident. They are often the result of years of building a brand, nurturing guest relationships, and consistently showing up. We also discuss the mindset shift from owning vacation rentals to building a hospitality business, creating value beyond the real estate itself, and why scaling a successful hospitality company requires consistent effort over time. Whether you're a vacation rental owner, boutique hotel operator, property manager, or hospitality entrepreneur, this episode is packed with insights on branding, marketing, guest relationships, and building a business designed for the long term. Connect with Rose Instagram: @yourfamilysplace_ Instagram: @hostinginthemotherhood Connect with Steph Website: TheWeberCo.comInstagram: @theweberco  

In this episode of Branded & Booked, I'm pulling back the curtain on the real booking and revenue numbers from May at Cabins on the Cumberland. If you've ever wondered whether investing in direct bookings is actually worth it, this episode provides the proof. I break down exactly where our bookings came from, how much revenue each channel generated, and why direct bookings continue to outperform Airbnb when it comes to profitability. I also share the pricing strategies, marketing tactics, and guest experience considerations that have helped us grow direct bookings into a meaningful part of our business. During the episode, I walk through our May booking breakdown, explain why 29% of our bookings generated 43% of our total revenue, and share how Airbnb and direct bookings compare from a profitability standpoint. I discuss the pricing strategy behind maintaining rate parity across channels, how promo codes and email marketing support direct booking growth, and why direct guests are often less price-sensitive than OTA guests. I also explore the psychological difference between booking on Airbnb versus a branded website, how simple upsells can increase guest value, why owning the guest relationship matters, and the hidden costs of relying entirely on OTAs. Most importantly, I explain why building a brand is one of the most valuable long-term investments a hospitality business can make. The numbers from May tell an interesting story. While 62% of our bookings came from Airbnb, those reservations generated approximately 47% of our total revenue. Direct bookings accounted for just 29% of reservations but generated approximately 43% of total revenue. Airbnb produced $12,943.26 in revenue while direct bookings generated $11,927.27, leaving only about a $1,000 difference between the two channels despite a significant difference in booking volume. If you're a vacation rental owner, boutique hotel operator, or hospitality entrepreneur looking to create a more profitable and sustainable business, this episode offers practical insights you can apply immediately. Apply to work with us at theweberco.com.  Follow along for more hospitality marketing and direct booking strategies on Instagram at @theweberco.

I genuinely think the hospitality industry is entering one of the biggest shifts we've seen in years — and the hosts who survive over the next 3–5 years are going to think very differently than the ones who thrived during the Airbnb gold rush. In this episode, I sat down with Gil Chan, founder of Crafted Stays, to talk about where hospitality is headed, how AI is changing the way guests search for stays, and why branding and direct bookings matter more than ever moving forward. We talked about why relying completely on Airbnb is becoming increasingly risky, how AI tools like ChatGPT are already changing trip planning behavior, what makes a direct booking website actually convert, why amenities alone are no longer enough to stand out, and the difference between "having an Airbnb" and building a real hospitality brand. One of my favorite parts of this conversation was talking about the "middle tier" of hospitality slowly disappearing — and why the brands that deeply understand their guests and intentionally create experiences are going to be the ones that win long-term. If you want to connect with Gil and learn more about Crafted Stays, you can visit craftedstays.co, follow along on Instagram @craftedstays, and listen to his podcast, Booked Solid. If you loved this episode, I'd love to connect with you too. You can find me on Instagram @theweberco or learn more about working with me and my team at theweberco.com. If you're ready to build a stronger hospitality brand, improve your marketing, increase direct bookings, and create a business that doesn't rely entirely on OTAs, you can apply to work with us directly through the website.

We're about 30 days away from leaving for a year-long camper trip with our boys… and honestly? Life feels a little chaotic right now. In this episode of Branded & Booked, I'm sharing a very real behind-the-scenes update on what's been happening as we prepare to leave "normal life" for a completely different season. From our disastrous first RV test trip to truck issues throwing a wrench into our plans, packing up our house, balancing explosive business growth, and preparing for Collin to leave his six-figure job… there's been a lot happening all at once. This episode is honest, messy, vulnerable, funny at times, and probably one of the most personal conversations I've shared in a while. We talk about entrepreneurship, lifestyle freedom, risk, pressure, intuition, parenting, and what it actually looks like when you start building a life outside the version everyone expects you to live. Because the truth is… I don't think entrepreneurship is just about making more money anymore. I think it's about creating a life you genuinely want to wake up inside of. If you've ever questioned whether you're building a business… or building a life you actually want to live, this episode is for you. Follow along on the journey: Instagram: @theweberco Personal adventures + camper life: @lifewiththewebers Work with us: theweberco.com 

Most short-term rental owners spend all their time thinking about branding, bookings, design, amenities, and guest experience… But almost no one talks about the legal side of this business until something goes wrong. In this episode, I sat down with STR attorney, host, and co-host Katie Johnson to talk about the legal mistakes we see owners and property managers making all the time and honestly, some of these are way more common than they should be. We talk about LLCs, insurance, rental agreements, safety compliance, co-hosting contracts, operating agreements, capital raising, and what owners need to think about before scaling into boutique hotels, glamping sites, or micro resorts. Katie shares why simply having an LLC is not enough if your property is not transferred correctly, what insurance companies are actually looking for when denying claims, why rental agreements matter more than most hosts realize, and the biggest risks she sees owners overlooking every single day. We also dive into safety inspections, reducing liability, protecting yourself as a co-host or property manager, partnership operating agreements, and the legal side of raising capital for STR investments. This conversation was eye-opening even for me, and if you own, manage, or are investing in short-term rentals in any capacity, this is genuinely one of those episodes you should not skip. Katie also shares details about her legal template shop, her podcast, and resources specifically created for short-term rental owners and operators. You can connect with Katie on Instagram at @strlaw.with.katie, through her website at strlaw.com, or by listening to her podcast, STR Law. If this episode helped you, send it to another host, investor, or co-host who needs to hear it. And if you're building a hospitality brand you want to grow beyond Airbnb, head to theweberco.com or connect with me on Instagram @theweberco.

Influencer marketing is not just about getting pretty content. It's about creating a moment people want to be part of. In this episode of Branded and Booked, I'm breaking down what boutique hotels, micro resorts, and short-term rental brands can learn from companies like Virgin Voyages, 818, COMFRT, and Colorescience when it comes to using creators in a way that actually drives attention, demand, and revenue. Because the brands doing this well are not treating influencer marketing like an afterthought. They are building entire experiences around it. I'm sharing why Virgin Voyages' recent creator cruise was such a smart marketing move, how brands are using groups of influencers to create FOMO and social proof at scale, and why hospitality brands should be thinking much bigger than "let's trade a free night for a Reel." I also walk through how I'd apply this strategy to a boutique hotel, micro resort, or even a single short-term rental, especially around launches, seasonal campaigns, and direct booking growth. If influencer marketing has felt confusing, expensive, or hard to measure, this episode will help you think about it differently. And if you want help sourcing, negotiating, and collaborating with creators the right way, grab my free influencer marketing guide in the show notes. You can also connect with me at theweberco.com or come hang out with me on Instagram at @theweberco.

I feel like everywhere I turn right now, someone is talking about AI…how fast it is, how efficient it is, how it can replace entire roles on your team. And while I do think there's a place for it (and we're absolutely exploring that on the operations side of our businesses), I've had this growing tension around how it's being used in marketing… especially in hospitality. Because here's the reality I can't ignore: so much content is starting to sound the same. Same captions, same emails, same listing language. And when everything feels templated and mass-produced, we lose the very thing that actually drives bookings, connection. This episode is me unpacking that in real time. The good, the bad, and honestly… the ugly of what I'm already seeing happen as more people lean on AI without a real strategy behind it. I talk through where I think AI actually makes a lot of sense (like supporting your team, reducing burnout, streamlining backend systems), but also where I think we need to be really careful. Because if your brand isn't clear, if your messaging isn't rooted in a real guest experience, AI is only going to amplify what's already broken. More content isn't the answer. Better, more intentional content is. We also get into what this means for trust. Because at the end of the day, hospitality is human. It's how your guest feels before they book, during their stay, and after they leave. And if your marketing starts to feel robotic, overly polished, or disconnected from reality, you're not just missing bookings… you're eroding trust. That's a much bigger problem. My hope with this episode is that it challenges you a little bit. Not to avoid AI, but to use it differently. As a tool, not the strategy. To double down on your story, your perspective, your brand voice… the things AI can't replicate. Because the brands that are going to win in this next season are the ones that feel real. If you want support building a brand and marketing strategy that actually converts to direct bookings, you can connect with us at theweberco.com. And if you're not already, come hang out with me on Instagram. I'm always sharing more behind the scenes there.