“The first 10 minutes of a guest’s stay set the tone for everything that follows.” That single insight from luxury hotel research changed how Katie Cline operates her short-term rentals, and it might change how you think about yours, too. In this episode of Booked Solid, Katie sits down with Gil to share what years inside the boardrooms of Ritz-Carlton, W Hotels, and St. Regis taught her about hospitality, and how she now applies those five-star principles to her growing portfolio of vacation rentals in upstate New York. From the psychology of confirmation bias to why your welcome note probably shouldn’t include the guest’s name, this conversation covers the small, often free gestures that turn first-time guests into repeat bookers. Whether you manage one property or forty, Katie’s hotel guest experience strategies for short-term rentals will give you a fresh perspective on how to serve your guests and strengthen your brand. Summary and Highlights 👤 Meet Katie Cline Katie Cline is an award-winning publicist, hospitality veteran, and short-term rental operator. She led global PR and communications for iconic hotel brands, including The Ritz-Carlton, W Hotels, St. Regis, and The Luxury Collection in both New York and London. Today, she hosts two podcasts — Second Home First, focused on helping people turn vacation homes into wealth-building investments, and Suite Success: Masters of Hospitality, a Hospitality.FM original, where she interviews the brightest minds in the hotel and hospitality industry. Katie owns and operates three short-term rental properties in upstate New York — Trout Landing (near Lake George), Gallant Fox (in Saratoga Springs), and The Lazy Oar (on Seneca Lake) — and co-hosts a fourth. She also publishes a free weekly newsletter at BuyYourSecondHomeFirst.com, helping readers turn vacation home ownership into a practical strategy for building long-term wealth. ✨ The First 10 Minutes That Make or Break Your Guest’s Stay One of the most memorable takeaways from this episode comes from Katie’s time working with Le Méridien. Research conducted during her tenure found that the first 10 minutes of a guest’s stay determine the tone for everything that follows. If those initial moments go well — the directions were clear, the lights were on, the door code worked, the place was clean and comfortable — guests spend the rest of their stay looking for evidence that they made a great choice. That’s confirmation bias working in your favor. But if those first moments go sideways — a missed turn, a dark entryway, a missing key — the guest will spend the remaining days noticing every cobweb and slow response time. For short-term rental operators, this means auditing your arrival experience from the guest’s perspective. Are your directions foolproof? Does the porch light stay on long enough for a family to unload a car at night? Is the temperature set right when they walk through the door? These are zero-cost, high-impact details that shape how your property gets reviewed, remembered, and recommended. 🏨 What Hotels Get Right (And What Short-Term Rentals Can Do Better) Katie brings a rare perspective to the short-term rental world because she’s spent years sitting in hotel boardrooms where guest experience was dissected and refined. She watched brands like Ritz-Carlton build systems around every guest touchpoint, from reservation confirmations to concierge outreach. But she also sees something hotels struggle with that short-term rental operators have as a natural advantage — humanness. When a guest books two nights at a hotel, they receive a polished but formulaic confirmation email. When someone books with Katie, she can respond as a real person. She can say she celebrated her own dad’s 70th birthday at the property and share what he enjoyed. She can mention that she’s a parent too and offer to have the pack-and-play set up before they arrive. That personal connection is something hotel brands spend millions trying to replicate. Independent hosts already have it — they just need to use it intentionally. If you want to build a brand that stands out, leaning into your humanity rather than hiding behind automation is one of the most effective things you can do. 🤝 Hospitality That Costs Nothing but Pays for Everything One thread running through the entire conversation is that the most impactful hospitality gestures are often free. Katie referenced a story from behavioral scientist Rory Sutherland about a cafe that set up comfortable chairs outside its entrance. The chairs didn’t generate direct revenue, but they communicated something powerful to everyone walking by: we care more about your experience than about squeezing every dollar out of you. That same principle applies to short-term rentals. Katie challenges the common mindset she sees in host forums — the idea that providing “enough shampoo to get them started” or “a few garbage bags” is sufficient. If a guest is paying $1,300 a night, needing to run to the grocery store for garbage bags on day two feels like a miss. It goes back to knowing your guest. If your property commands a premium ADR, the expectations for basics such as supplies, cleanliness, and amenities should match. And the good news is that stocking up on garbage bags and providing quality toiletries is one of the cheapest investments you can make, given their impact on reviews and repeat bookings. 🐾 Surprise and Delight Without the Risk Katie shared a fascinating hotel story about personalization gone wrong. A colleague was traveling to a hotel property, and the team had pulled photos from her Instagram to create a custom welcome featuring her dog. The problem? The dog had passed away the week before. The lesson isn’t to avoid personalization altogether — it’s to balance surprise and delight with risk management. Katie applies this through small, thoughtful gestures that carry very low downside. When a guest mentions they’re traveling with a baby, her cleaner knows to set up the pack-and-play, place the high chair in the kitchen, and have a baby gate ready. When someone brings their dog, bowls and a treat appear upon arrival. She also

“Be so good they can’t ignore you. That’s where you are.” What if there was an entire organization in your county — funded partly by your own lodging taxes — dedicated to driving visitors to your destination, and you’ve never once reached out to them? In this episode of the Booked Solid Show, Gil sits down with Jennifer Barbee, tourism strategist and creator of the Host Gap™, to uncover a massive blind spot for short-term rental operators. Jennifer has worked with over 400 destinations across the U.S. and reveals how DMOs (Destination Marketing Organizations) hold a goldmine of traveler research, event calendars, and visitor data that most hosts have never tapped into. You’ll learn how independent lodging went from 4% of the market to nearly 30%, why that shift is changing everything, and how building a relationship with your local tourism office could reshape your direct booking strategy from the ground up. Summary and Highlights 👩‍💼 Meet Jennifer Barbee Jennifer Barbee is a tourism strategist with 30+ years of experience working inside and alongside destinations. She is the Co-Founder and CEO of Destination Innovate and creator of the Host Gap™ — a framework that names the disconnect between destination marketing organizations and the short-term rental hosts who now deliver a significant share of the visitor economy. Jennifer got her start in the late ’90s, accidentally becoming a programmer when the very first destination websites were being built. Before she turned 30, she had worked with over 400 destinations — from Las Vegas and Miami to smaller regional markets. Her career spans web development, advertising, audience research, and civic tourism strategy. Today, she’s focused on bridging the gap between DMOs and STR operators through her upcoming Hosts & Home Teams™ summit and her ongoing essays on LinkedIn’s The Daily Destruptor. 📊 From 4% to 30% — The Shift That Changed Everything One of the most striking numbers Jennifer shared: before 2020, independent lodging (short-term rentals, boutique hotels, B&Bs) accounted for roughly 4% of the U.S. lodging market. Today, that figure sits at nearly 30%. That explosion happened fast, and most destination marketing organizations weren’t prepared for it. Jennifer pointed out that DMOs were originally created by hoteliers—specifically as Convention and Visitors Bureaus— and funded through lodging taxes paid by hotels. Short-term rentals weren’t part of that equation. In many cases, they still aren’t fully integrated into the system. This is why so many cities and counties are scrambling to figure out regulations, representation, and how to work with independent operators. Jennifer’s take? It’s not a moral problem. It’s a systems problem. And solving it starts with getting hosts into the conversation. 🔑 What DMOs Have That You Don’t (But Should) Here’s where things get practical for operators thinking about their direct booking strategy. DMOs invest heavily in traveler research — the kind of data most independent hosts never see. Jennifer broke down what that includes: Who is visiting your destination, what are their demographics, and what are their travel patterns? What types of events and groups are coming each year? How repeat visitation compares across markets (Pigeon Forge, for example, sees about 75% repeat visitors, while Miami sees roughly 12%). Seasonal trends, spending data, and group travel behavior. This research doesn’t just help with marketing your properties — it can inform investment decisions, amenity choices, and even how you furnish your spaces. If you know your market draws families with kids who visit four times a year, that changes everything from your guest avatar to your email nurture sequences. 🏷️ The SMERF Market — A Hidden Goldmine for STR Hosts Jennifer introduced one of the episode’s most interesting concepts: the SMERF market. It stands for Social, Military, Educational, Religious, and Fraternal — and it refers to unmanaged group travel. Think quilting competitions, car shows, soccer tournaments, family reunions, and small niche conferences. These groups typically bring 10 to 50 people at a time. They travel more often, spend more money, and represent a huge opportunity for short-term rental operators — especially those who can accommodate multi-room bookings. The challenge? Most hosts don’t know these groups are coming because that data lives with the DMO. Jennifer emphasized that building a relationship with your destination’s tourism office can unlock exactly this kind of intelligence, giving you an edge in preparing your properties and tailoring your content marketing to attract these travelers. 🤝 How to Actually Reach Your Local DMO Jennifer offered straightforward advice on making that first connection. Look for the community management or community steward role at your local DMO — not the chamber of commerce (which may try to sell you advertising instead). Your destination marketing organization is usually the entity that collects the bed tax and may be called Visit [Your City], Experience [Your Region], or something similar. When you reach out, Jennifer recommended framing it this way: Introduce yourself as a host who loves the destination. Ask what traveler research or data they can share. Find out how you can better align with the types of travelers they’re attracting. Request any printed materials or visitor guides you can keep on-site for guests. It sounds simple, but Jennifer noted that most hosts have never taken this step. And the DMOs? They often don’t even know who you are — especially when OTAs like Airbnb remit taxes as lump sums without identifying individual properties. 🔄 Repeat Guests, Destination Identity, and the Direct Booking Connection Jennifer and Gil explored how understanding your destination’s repeat visitation rate completely changes your marketing approach. In a high-repeat market, your biggest opportunity is email capture and guest nurturing. In a low-repeat market, the focus shifts to discovery, social proof, and first-impression marketing. Jennifer also shared a powerful insight about direct booking guests versus OTA guests. A book-direct traveler tends to be less sophisticated, more loyal, and craving personalization. If you serve them well — learn their favorite coffee, remember their kids’ names, leave a small surprise — they don’t just come back. They post about it on

“Hospitality is the North Star. If it doesn’t drive back to that, it’s probably not gonna work.” James Varley went from managing communications for the FIFA World Cup to building one of the fastest-growing educational platforms in the short-term rental space. In this episode of Booked Solid, James opens up about his unconventional path into hosting, the painful lessons he learned rebranding his company, and why consistency beats complexity when building an audience. Whether you’re a new host wondering where to start or an experienced operator looking to sharpen your direct booking game, this conversation delivers practical wisdom on brand clarity, local marketing tactics, and why the simplest strategies often produce the biggest results. James also shares the QR code tactic that keeps bringing guests back to his properties and why building your email list remains the single most important thing you can do for your business. Podcast Summary and Highlights 🎙️ Meet James Varley James Varley is the Founder and CEO of Host Planet, a multimedia educational platform dedicated to helping short-term rental hosts and property managers build successful, sustainable businesses. Before launching Host Planet, James spent over 20 years in media, including a decade leading corporate communications for the FIFA World Cup Qatar 2022 organizing committee. His journey into hosting began while living overseas in Qatar. Needing a place to stay during UK visits, James purchased his first holiday let—and quickly discovered how underserved the market was when it came to practical, accessible education for operators. That gap became the foundation for Host Planet. Today, Host Planet produces multiple podcast series, free ebook downloads, blog posts, and social content reaching property managers across more than 90 countries. In 2026, James is taking the show on the road with the Host Planet Roadshow—seven events across the UK designed to bring collaborative, hands-on education directly to operators. 🧭 Why Hospitality Must Remain Your North Star One theme ran throughout this conversation: the property managers who succeed long-term never lose sight of hospitality. James put it simply—if your business decisions don’t drive back to delivering an exceptional guest experience, they probably won’t work. Revenue matters. Systems matter. But the operators who thrive are the ones who genuinely care about the people staying in their properties. This perspective shapes everything from how you define your brand to the way you communicate with guests. As James noted, the property managers reaching 97% direct bookings—like Andy Easton at Beach Retreats—built their success on crystal-clear brand identity and unwavering commitment to guest experience. 🏗️ Building Host Planet: Lessons from the Trenches James didn’t get everything right from the start. His original company name—Holiday Cottage Handbook—was too long, too niche, and confusing to international audiences. The rebrand to Host Planet came after he realized the industry was global and his platform needed to reflect that. The lesson applies directly to property managers building their own brands. Getting clear on who you serve and how you want to be perceived matters more than perfecting every detail on day one. Sometimes you have to start accepting direct bookings before everything feels ready—and iterate as you learn. James also shared his approach to content creation. Rather than chasing trends, he focuses on answering the questions hosts actually have. He uses YouTube search data, explores what people ask large language models, and tracks industry news to ensure every piece of content delivers genuine value. 📢 The Power of Billboarding Your Direct Booking Channel One of the most practical takeaways from this episode: guests who stay at your property through OTAs need to know you have a direct booking channel. James uses simple QR code posters inside his rentals. The message is straightforward—book direct and save. It’s not complicated technology or expensive marketing. It’s visibility. The same principle extends beyond the property itself. James attends local business meetings, connects with chamber of commerce groups, and reaches out to companies in nearby enterprise zones whose workers need temporary accommodation. Word of mouth and local partnerships remain underutilized by most hosts. If you want to explore this further, our guide on building trust on your direct booking site breaks down how to convert that visibility into actual reservations. 📧 Build Your Email List—Period When asked for one tactical tip for hosts looking to amplify their direct bookings, James didn’t hesitate: build your email list. Social platforms change algorithms. OTAs restrict guest contact information. But email remains something you own. Every guest who books through your property represents an opportunity to stay connected, nurture the relationship, and earn repeat business. This aligns with what we consistently see from successful operators. The hosts who treat their email list as an asset—sending valuable content, seasonal updates, and personalized offers—build businesses that compound over time. Our vacation rental email marketing guide walks through exactly how to structure these campaigns. 🎯 Defining Your Audience (Whether You’re a Host or Building a Platform) James made an interesting point about audience definition that applies whether you’re running a property management business or building a media platform like Host Planet. Too many hosts try to appeal to everyone. The result is messaging that resonates with no one. The operators who succeed—and James pointed to Beach Retreats as an example—get incredibly specific about their guest avatar, their property standards, and their geographic focus. This specificity actually makes marketing easier. When you know exactly who you’re serving, you can write content that speaks directly to their concerns. You can go niche and own a category rather than competing with everyone for generic search terms. 🔁 Consistency Beats Complexity The conversation kept returning to one theme: success in short-term rentals (and in building any audience) comes from doing simple things consistently over time. James compared it to investing. You won’t see dramatic results immediately. But week after week, month after month, the content compounds. The email list grows. The relationships deepen. Eventually you look back and realize you’ve built something substantial. This patience is especially important for direct bookings. Growing your direct booking

“I’d rather be small and personal and well known for that than just be a generalist.” What does it take to build a vacation rental business valuable enough for acquisition? For Lisa Roads, the answer wasn’t having the most properties—it was building an STR brand identity that attracted direct bookings, earned owner trust, and created systems that could operate without her constant involvement. In this episode of the Booked Solid Show, Lisa shares the strategies that took her from furnishing her first Cyprus property to managing 175 coastal villas—and eventually exiting during one of the most challenging periods in travel history. Her insights on niching down, building trust signals, and understanding your ideal guest avatar offer a masterclass for any host looking to grow beyond OTA dependency. Summary and Highlights 👤 Meet Lisa Roads Lisa Roads is The Holiday Property Coach and founder of the Women in Short-Term Rentals community. With over 25 years in hospitality, property marketing, and management, she built and scaled Lifestyle Assets Property Management in Cyprus from zero to 175 coastal properties before successfully selling in 2021. Starting her property investment journey at just 22 years old, Lisa developed a full-service model that handled everything from interior design and furnishing to marketing and guest management. Her approach attracted hands-off investor owners who wanted turnkey solutions—and her company became known as one of the most professional operations on the island. Today, Lisa works exclusively with female STR business founders, helping them develop growth strategies, build direct booking brands, and prepare their businesses for scale or exit. She lives in the Cotswolds with her partner Clive and their rescue dog Poppy—who, as you’ll discover, inspired some powerful insights about niche marketing. 🏗️ Building Infrastructure Where None Existed Lisa’s journey began with a problem most hosts never face: there was literally no support infrastructure for vacation rentals in her chosen market. When she invested in Cyprus property in 2003, the short-term rental ecosystem simply didn’t exist. No furniture companies. No established cleaning services. No property management support for overseas investors like herself. Rather than waiting for solutions to appear, Lisa created them. She shipped entire containers of furniture from the UK, built relationships with customs brokers, and assembled her own network of contractors, cleaners, and maintenance providers. That resourcefulness became the foundation of her business model. Her “Investor Complete Service” took empty properties and transformed them into performing investments—handling interior design, furnishing, marketing, and ongoing management. In one particularly intense month, her team furnished 25 properties from empty to guest-ready. This full-service approach attracted hands-off investor owners who valued professional management over DIY solutions, and it’s the same foundation that helps hosts today build direct booking brands that guests actually remember. 🎯 Why Niching Down Beats Being a Generalist One of Lisa’s most transformative business decisions was deliberately shrinking her portfolio from 225 properties to 175. The reason? Focus. She identified that her best-performing properties shared common characteristics: period and character coastal properties within three kilometers of a beach, serving hands-off investor owners. Properties that didn’t fit this profile—regardless of their individual potential—diluted the brand and complicated operations. Lisa explains the math simply: “If you are a smaller business, you’ve got limited resources, limited marketing budget, limited time. You are better to focus what you do have and be niche and well known in a niche than the scatter gun approach.” This principle applies directly to building a direct booking niche that fills your calendar year-round. When you try to serve everyone, your marketing message speaks to no one. When you curate your portfolio around a specific guest avatar, everything aligns—your photography, your messaging, your amenities, and your direct booking website all tell the same story. Consider a property owner looking for management services. Would they choose a company with a mixed portfolio of studios, coastal villas, and mountain cabins? Or would they select the expert who specializes in exactly their property type and understands its unique requirements? The specialist wins every time. 🔑 A Logo Isn’t a Brand: Building Trust Signals That Convert Lisa sees a common mistake among property managers attempting to transition away from OTA dependency: they think having a website equals having a brand. “They think that having a logo is having a brand. It’s not,” Lisa explains. “Outside of the OTAs, they haven’t really proudly shouted about who they are, why people should come to them. Where’s the trust? None of that really exists.” Building a direct booking brand requires layers of trust signals that OTAs provide automatically but independent operators must create themselves. Lisa’s checklist includes team photographs showing real people behind the business, a clear story about why you do what you do, client and guest charters that communicate your standards, credentials and accreditations that establish credibility, and transparent policies that remove booking friction. These elements work together to answer the question every potential direct booker asks: “Why should I trust you with my money and my vacation?” The Direct Booking Quadrant framework breaks this down into four essential pillars: Branding, Presence, Channels, and Funnels. Lisa’s approach addresses each one, but she emphasizes that branding must come first. Without a clear identity, the other elements have nothing to amplify. 📸 Photography That Sells the Dream Lisa’s insights on property photography go far beyond “hire a professional.” She emphasizes staging your photos to tell a story that resonates with your specific ideal guest. The principle is simple: show prospective guests exactly what their experience will look like. For family-friendly properties, that means photographing the pack-and-play set up next to the master bed, the high chair at the dining table with kids’ utensils ready, and safety gates installed throughout the home. This approach transforms photography from documentation into aspiration. Parents scrolling through listings aren’t just looking for amenities—they’re imagining their family in that space. When they see a property clearly designed for families like theirs, the mental leap to booking becomes much shorter. Lisa experienced this principle firsthand when booking a dog-friendly cottage

“Your brand is the emotional connection that an organization has with its public.” In this episode of the Booked Solid Show, Gil sits down with Amber Hurdle—brand strategist, keynote speaker, author, and former Gaylord Hotels executive—to explore why personal branding isn’t just for influencers. It’s the foundation of trust that converts lookers into bookers. Amber breaks down how short-term rental hosts and property managers can leverage psychology and neuroscience to build authentic brands that attract ideal guests, command premium rates, and create lasting loyalty. From her celebrity event planning days with Sony Music and Jessica Simpson to leading the internal rebrand when Marriott acquired the world’s largest hotel property, Amber brings decades of hospitality expertise to help you stop hiding behind a logo and start building a business that books direct. Whether you manage two properties or two hundred, this conversation will shift how you think about showing up for your guests—and why it matters more than ever. Podcast Summary and Highlights 👤 Meet Amber Hurdle Amber Hurdle is a globally recognized brand strategist, multi-award-winning keynote speaker, and author of The Bombshell Business Woman. She brings over two decades of experience helping Fortune 100 companies, celebrities, and entrepreneurs build brands that connect deeply and drive measurable results. Her hospitality credentials run deep. Amber spent years at Gaylord Hotels overseeing internal communications and employee engagement—ensuring staff felt valued so they could deliver exceptional guest experiences. She later led the internal rebrand when Marriott acquired Gaylord Opryland, which remains the largest Marriott property in the world. Today, Amber runs Brand Edge Accelerator and the Vanguard Council, working with founders and executives to build personal brands grounded in psychology, neuroscience, and authenticity. She’s been featured in Entrepreneur, Fortune, and Bloomberg Businessweek, and recognized as one of the top 30 brand professionals globally by Global Gurus. Connect with Amber: 🎯 Why Personal Branding Matters for Direct Bookings Most hosts think branding is about logos and color palettes. Amber sees it differently. A brand is the emotional connection your business creates with everyone who encounters it—guests, community members, even local government officials dealing with short-term rental regulations. When you build a direct booking website, you’re asking strangers to trust you with thousands of dollars and their vacation memories. Unlike Airbnb, which provides trust signals, your direct booking site must earn that trust from scratch. The hosts who succeed at direct bookings share something in common: they put themselves out there. They show their faces, share their stories, and communicate their values consistently across every touchpoint. 🪝 The Fishing Analogy That Changes Everything Amber explains positioning through a fishing metaphor that every host should memorize. If you want to catch a catfish, you don’t take a boat to the ocean with squid as bait. You find a murky pond, use something like chicken liver, drop your line, and wait. Knowing your lure and your body of water is essential. For vacation rental operators, this means understanding exactly who your ideal guest is before creating any marketing. Your brand promise answers three questions: What do you do? Who do you do it for? How do you do it uniquely? The “who” tells you what body of water you’re fishing in. The “how” becomes your lure. Without this clarity, you’re marketing to everyone and connecting with no one—the same trap that keeps many hosts stuck on the OTA treadmill. 📸 Why Your Face Matters More Than Your Logo Gil shared data from CraftedStays showing that websites with host photos and personal bios convert significantly better than those hiding behind company logos or property images. The psychology behind this is simple. Vacation rentals aren’t hotels. Guests want to feel they’re staying in a home, welcomed by a real person. Your prefrontal cortex—the part of the brain that makes values-based decisions—responds to human faces. It’s why putting a personal picture on your direct booking site isn’t vanity; it’s conversion optimization. CraftedStays now makes the host bio and photo a mandatory field during onboarding because the data proves it works. When guests see who they’re booking with, trust forms faster. 🏆 Case Studies: Hosts Who Built Brands on Their Backs Amber highlighted two examples of vacation rental operators who understood personal branding before it became trendy. Lance and Elaine Stitcher of Seaside Vacation Rentals built their company’s visibility through their own presence—appearing on podcasts, serving on the VRMA board, posting consistently on social media. When industry awards come around, voters already know them because they’ve shown up repeatedly over time. Robin Craig with Moving Mountains in Colorado followed a similar path. His visibility in advocacy and industry events helped position his company as the number one luxury vacation rental brand in Colorado according to Forbes. Neither started with sophisticated marketing budgets. They started with authenticity, consistency, and a willingness to be the face of their brand. 🛋️ Setting the Table for Your Guests Amber offered a hospitality metaphor that every host should remember. Think of your direct booking website as your home. You wouldn’t invite guests over without knowing their preferences, preparing thoughtfully, and creating a welcoming environment. Yet many hosts bury important information, make booking harder than necessary, or—the cardinal sin—charge more on their direct booking site than on Airbnb. If you expect guests to trust you with their vacation, show them you’ve prepared for their arrival from the very first click. This means clear pricing, easy navigation, mobile-friendly design, and content that speaks directly to your ideal guest’s needs. Everything on your site should signal that you understand who they are and why they’re traveling—the foundation of any strong email marketing strategy that turns one-time guests into repeat bookers. ✨ Different Is Better Than Better Sally Hogshead, one of Amber’s mentors and a two-time New York Times bestselling author, has a mantra that applies perfectly to vacation rental marketing: “Different is better than better.” The secret to success isn’t trying to out-Airbnb Airbnb. It’s becoming more of who you already are. When you lean into your authentic values,

“Brand is where trust is built. Brand is the reason people say yes.” In this episode of the Booked Solid Show, we welcome back our very first podcast guest—Steph Weber, CEO of The Weber Co. and co-owner of Cabins on the Cumberland, a 12-cabin micro resort in Kentucky. From building brands that emotionally connect with guests to navigating Airbnb’s 2025 fee changes, Steph shares raw insights from the trenches of hospitality marketing. Whether you’re managing one property or planning your first micro resort, this conversation covers the critical shifts every STR operator needs to embrace heading into 2026—including why your direct booking website matters only if a marketing strategy backs it. Summary and Highlights 👤 Meet Steph Weber Steph Weber is a branding and marketing powerhouse who has helped over 100 small businesses scale to six and seven-figure brands. As CEO of The Weber Co., she now focuses exclusively on the vacation rental niche, working with STR hosts, property management companies, boutique hotels, and micro resorts. Together with three other couples, Steph built Cabins on the Cumberland—a 12-cabin micro resort and event venue along the Cumberland River in Kentucky. She also runs Hosted by the Webers, a co-hosting company she and her husband scaled to six figures in just one year. With 10 years of experience in brand and marketing strategy, Steph brings fresh energy to the world of short-term rentals, helping investors and guests experience destination properties with rave-worthy experiences. She hosts the Branded & Booked Podcast and lives in Indianapolis with her husband, Collin, and their two boys. 🏔️ From Construction Site to Micro Resort: The Cabins on the Cumberland Journey When Steph and her partners started building Cabins on the Cumberland, they were just seven weeks into their short-term rental journey. The timing made no logical sense—she was eight months pregnant with her second child, they had just spent most of their savings on their first STR, and they were pivoting an entire business. But when opportunity knocked, Steph answered. The build taught her invaluable lessons about letting a vision grow organically. When their builder questioned whether all 12 cabins needed hot tubs, Steph ran an experiment. The cabin with a hot tub tripled the bookings of the other two. The builder quickly got on board. By the end of 2025, Cabins on the Cumberland was maintaining 30-50% direct bookings every single month—a testament to the power of intentional branding from day one. Even when the property had nothing but mud, dirt, and porta-potties, Steph was building the brand story that would later drive those conversions. For operators considering their own micro resort or boutique hotel project, Steph recommends finding a mentor who has made the mistakes and can share them transparently. The underwriting, financing, and sweat equity requirements differ fundamentally from those of standard STR investing. 📢 2025: The Year Hosts Woke Up to Brand Ownership The short-term rental industry experienced a collective awakening in 2025. Between Airbnb’s 15.5% host-side fee, changes to cancellation policies, AI-driven review automation, and new experience programs, operators began realizing they had placed too many eggs in one basket. Steph noticed a significant shift in what her clients were asking for. Instead of social media management, hosts wanted deeper brand strategy work. They wanted to understand who they were beyond their Airbnb listings. This tracks with what industry experts have been emphasizing at conferences throughout the year. Brand was the recurring theme—not as a nice-to-have, but as the foundation for everything else. When Steph talks about brand, she means much more than logos and color palettes. Her process includes in-depth target audience analysis, competitive research, and core messaging that gets woven into every guest touchpoint. The visual identity comes after that strategic foundation is solid. Brand is how trust gets built. Brand is why someone chooses to book with you over a competitor. It creates the emotional connection that makes guests feel confident handing over their credit card to a stranger’s property. 💡 Why Your Direct Booking Site Means Nothing Without Marketing Here’s the hard truth Steph wants every host to hear: having a beautiful direct booking website is only the beginning. Too many operators launch their sites and expect bookings to roll in the same way they do on Airbnb. But that’s not how direct bookings work. You can’t set it and forget it. If your guests only know you as “another Airbnb property,” your direct booking site won’t matter. You need a marketing strategy that actively drives traffic and converts visitors into paying guests. The good news? Direct bookings compound over time. The energy you invest today pays dividends for years. Your email list grows. Your social following expands. Your messaging gets sharper. But none of that happens passively. Steph recommends starting with email marketing as the lowest-hanging fruit. It’s the foundation that makes everything else work. From there, you can layer in social media content, SMS marketing, and even paid advertising. The key is to be responsible for marketing your brand, whether you do it yourself or hire someone to help. 🤖 Using AI Without Losing Your Voice AI tools like ChatGPT have transformed how hosts create content. But Steph has noticed a troubling pattern: too many operators are copying AI-generated text verbatim, resulting in generic messaging that sounds like everyone else. Phrases like “unforgettable memories” and “your dream vacation awaits” mean nothing when every competitor uses them. This is why Steph advises clients to answer branding questions from their own perspective first, before bringing AI into the process. She recommends going directly to real humans who fit your guest profile. Ask them about their vacation experiences, their priorities, their best travel memories. That authentic research creates messaging that resonates in ways AI cannot replicate. Once you have that foundation, AI becomes helpful in refining ideas, generating variations, and speeding up execution. Steph’s team uses ChatGPT to visualize brand experiences for clients—creating images of proposed amenities and guest touchpoints that help operators see possibilities before they invest.