“Now operators are no longer just spending 3% of their business for lead gen from Airbnb. They’re now spending 15.5%.” Airbnb’s latest fee structure changes everything—but are you ready to take control? Orlie Benjamin, founder of Lasoh and former marketing leader, breaks down why now is the moment for vacation rental operators to build their own direct booking infrastructure. In this episode, you’ll discover why owning your guest relationships is no longer optional, how to think about your marketing budget differently, and the critical first steps to reducing platform dependence. Whether you’re just starting your direct booking journey or ready to scale your existing strategy, this conversation reveals the marketing mindset shift that separates operators who survive from those who thrive. Summary and Highlights Guest Bio 🎯 Orlie Benjamin is the founder and CEO of Lasoh, a marketing SaaS platform built specifically for vacation rental operators. Before launching Lasoh, Orlie spent her career leading customer-centric innovation at Fortune 500 companies including American Airlines (where she managed the Priceline channel and revenue optimization), Victoria’s Secret (omnichannel marketing strategy), and NetJets (designing digital experiences for high-net-worth clients). She’s also an active vacation rental operator, running The Acres in Hocking Hills, Ohio. This unique combination of enterprise marketing expertise and hands-on STR experience positions her to see gaps in the industry that others miss—and build solutions that actually work for operators at every stage. Why This Episode Matters 💡 The vacation rental landscape shifted dramatically in late 2024 when Airbnb restructured its fee model, moving from a 3% host fee to a consolidated 15.5% operator fee. This isn’t just a pricing change—it’s a fundamental shift in the economics of relying on OTAs for distribution. Orlie walks through what this means for your bottom line and why the $20,000 you might be paying annually in commissions could become your marketing budget instead. But this conversation goes deeper than just reacting to Airbnb’s changes. Orlie shares the marketing playbook she refined at companies where customer lifetime value and repeat purchase rates are foundational metrics—concepts that most STR operators don’t even track. She explains why fewer than 20% of operators monitor repeat booking rates, and why that single metric might be the most important indicator of business health. If you’ve ever felt like you’re cobbling together marketing tools that don’t quite fit your workflow, or wondered why the STR industry doesn’t have the kind of purpose-built marketing infrastructure that ecommerce platforms offer, this episode gives you both the context and the clarity you need. Key Takeaways From the Conversation 🔑 —- The Economics Have Changed Airbnb’s fee consolidation transforms a 3% cost of doing business into a 15.5% margin hit. For a single property generating $100,000 annually, that’s the difference between paying $3,000 and $15,500. Orlie puts it plainly: “That can turn a whole business upside down depending on what sort of margins things are running with.” Marketing Budget vs. Commission Fees Instead of viewing that 15.5% as a fixed cost, Orlie suggests reframing it as your available marketing budget. In her own direct booking business, she spends significantly less than that percentage driving traffic to her properties—and owns the customer relationship in the process. This mental shift changes everything about how you evaluate direct booking investments. The LTV Blind Spot In retail and ecommerce, customer lifetime value is fundamental. Yet most vacation rental operators calculate value based on a single stay. Orlie explains: “The number of customers you have multiplied by the number of visits they have multiplied by the average spend per basket—those three things multiplied by each other equals value of a customer.” When you start tracking repeat booking rates and guest spend across multiple stays, your entire revenue strategy shifts. The Ownership Imperative OTAs deliberately disintermediate the host-guest relationship. They mask contact information, control communication channels, and own the data. Meanwhile, when you capture guest information from the entire travel party (not just the booker), you create opportunities to improve the stay, sell additional services, and build relationships that generate repeat bookings without additional acquisition costs. Purpose-Built Tools Matter Generic CRMs are designed for salesforce workflows, not nurture marketing. Email platforms like MailChimp weren’t built with vacation rental use cases in mind. Orlie’s background in enterprise marketing showed her what’s possible when technology is purpose-built for an industry—and she’s building Lasoh to fill that gap for STR operators. The Marketing Stack You’re Missing 🛠️ One of the most striking revelations in this conversation is how operators are trying to force-fit technology from other industries into vacation rental workflows. Orlie has seen operators using Airtable as a makeshift CRM, running into limits with Zapier integrations, or spending heavily on consultants to hand-code campaigns because the software doesn’t anticipate their needs. She draws a comparison to buying a Ferrari with a stick shift but not knowing how to drive stick. The system is only as valuable as your ability to use it. This is why she’s focused on building Lasoh as a platform, not a consulting agency—the goal is to create technology that either empowers operators directly or makes consultants dramatically more effective with their clients. The conversation around SaaS versus services is particularly relevant for operators trying to decide whether to build their own direct booking infrastructure or outsource it. Orlie makes a compelling case that software scales, services don’t—and that the right platform creates compound value over time. When Strategy Meets Execution ⚡ Orlie’s tactical advice is grounded in clarity: “Be really clear on your strategy.” If you’re going all-in on Airbnb, make sure the math works with the new fee structure. But if you’re committed to diversifying distribution and going direct, you need to know exactly what your next step is. For some operators, that’s launching a direct booking website. For others, it’s selecting a PMS. Some need to start capturing guest contact information. Others are ready to activate that data through email campaigns and relationship marketing. The key is not trying to do everything at once. Identify where you

“The goal is to automate the annoying so you can focus on the amazing.” In this episode, Gil sits down with Sean McGregor, founder of NoCodeSTR.com, to explore how vacation rental hosts can reclaim their time without sacrificing guest experience. Sean has hosted over 5,000 groups on Airbnb while maintaining a 4.98★ rating since 2018—all while traveling through 40+ countries with his family. What’s his secret? A powerful combination of no-code automation tools and AI that handle the repetitive tasks most hosts dread. From guest communication to review management, Sean shares exactly how he maintains a 100% five-star rating even during a 3.5-week road trip through the Balkans. If you’ve ever felt chained to your phone answering the same guest questions or wondered how to scale without burning out, this conversation will show you a better way. Sean breaks down the tools, mindset, and systems that let hosts run professional operations from anywhere in the world. Summary and Highlights 🎯 About Sean McGregor Sean McGregor is the founder of NoCodeSTR.com, where he teaches vacation rental hosts how to automate the tedious parts of their business using no-code tools like Zapier, Airtable, and AI. Since 2018, he’s maintained a remarkable 4.98★ rating on Airbnb while hosting more than 5,000 groups—proving that automation and exceptional guest experience aren’t mutually exclusive. What sets Sean apart is his 5★ Guarantee: he doesn’t take commission if a guest leaves anything less than a five-star review. This bold promise reflects his confidence in the systems he’s built, which handle everything from pre-arrival communications to post-checkout follow-ups. Sean’s approach isn’t theoretical. He’s built his business while working remotely from over 40 countries with his family, demonstrating that proper automation creates true location independence. His free 5-day course at NoCodeSTR.com has helped hundreds of hosts discover what’s possible when they stop doing everything manually. 🔑 Key Highlights: Building a Five-Star Business on Autopilot The “Automate the Annoying” Philosophy Sean’s entire approach centers on one principle: identify the repetitive, time-consuming tasks that drain your energy and automate them. For most hosts, this means the same guest questions, check-in instructions, and review requests that repeat with every booking. “The goal is to automate the annoying so you can focus on the amazing,” Sean explains. This isn’t about cutting corners—it’s about redirecting your limited time toward high-impact activities like improving your property, building relationships with direct booking guests, or actually enjoying the lifestyle that drew you to hosting in the first place. The mindset shift happens when hosts realize that guests don’t care how they get information—they just want it quickly and accurately. Whether an answer comes from you personally or a well-designed automation makes no difference to guest satisfaction. No-Code Tools That Cost Nothing Per Listing One of the biggest misconceptions Sean addresses is that powerful automation requires expensive software or technical expertise. The tools he relies on—Zapier, Airtable, and Make—can be implemented at zero cost per listing for most hosts. These platforms connect your existing systems (PMS, email, calendar) and create workflows that run automatically. For example, when a new booking comes in, an automation can instantly send personalized welcome messages, add the guest to your communication sequence, and update your team’s task list—all without you lifting a finger. Sean emphasizes that the learning curve isn’t as steep as most hosts imagine. “If you can set up an Airbnb listing, you can build these automations,” he notes. The key is starting with one annoying task and building from there, rather than trying to automate everything at once. For hosts focused on growing their direct booking channel, these same no-code tools integrate beautifully with website forms and inquiry systems, creating a seamless guest experience from first contact through checkout. AI as Your 24/7 Guest Experience Manager The real game-changer in Sean’s systems is how he’s integrated AI—not as a replacement for genuine hospitality, but as an enhancement. His AI-powered tools handle routine questions, provide instant responses outside business hours, and even anticipate guest needs based on patterns in previous conversations. During his recent Balkans road trip, Sean’s automations and AI systems maintained a 100% five-star rating without any human intervention. Guests received immediate answers to questions about WiFi passwords, local recommendations, or check-in procedures—all delivered in a natural, helpful tone that reflected his brand. “The technology has reached a point where guests genuinely can’t tell they’re interacting with automation,” Sean shares. But he’s quick to clarify that AI works best when it’s trained on your voice, your property’s unique features, and your approach to hospitality. This is particularly powerful for hosts managing multiple properties or building a portfolio. Instead of multiplying your workload as you scale, properly implemented AI and automation mean your systems scale without requiring proportional increases in your time. The Five-Star Guarantee: Confidence Through Systems Perhaps the most striking aspect of Sean’s business model is his willingness to offer a 5★ Guarantee—he only collects commission when guests leave five-star reviews. This isn’t just a marketing gimmick; it’s a direct result of the confidence he has in his automated systems. “When you’ve systematized every touchpoint in the guest journey, you know exactly what experience they’re getting,” Sean explains. His automations ensure consistent communication timing, complete pre-arrival information, and timely follow-up after checkout—all the factors that influence whether a guest leaves a glowing review. This approach also creates a virtuous cycle: because Sean’s systems are designed to generate five-star experiences, he attracts clients who are serious about quality and willing to invest in proper automation. The guarantee becomes a filter that aligns everyone’s incentives toward excellence. For hosts considering professional website implementations or upgrading their booking systems, this principle applies equally: when your infrastructure is solid, you can make bold promises about the experience you deliver. Location Independence Without Compromise Sean’s lifestyle proves that automation isn’t just about saving time—it’s about creating genuine freedom. He’s worked from 40+ countries with his family while maintaining his 4.98★ rating, demonstrating that the right systems let you run a professional operation

“As long as you’re providing value, hopefully your marketing will be mostly perceived generously and people will want to receive it.” What if the key to competing with major OTAs wasn’t just about building a better website—but capturing data from every single guest who stays at your property? Arthur Colker, Founder & CEO of StayFi, discovered this truth while helping a New Orleans property manager escape 99% OTA dependency. In this episode, he shares how a WiFi-based data capture solution evolved into a full guest marketing platform powering direct bookings across vacation rentals, boutique hotels, and hospitality brands. Arthur reveals why guest data ownership is the biggest missed opportunity in short-term rentals, how diversifying channels matters more than eliminating OTAs entirely, and the groundbreaking StayFinder meta-search tool launching soon that will let travelers compare direct booking prices against major platforms. Whether you’re managing 2 properties or 200, Arthur’s insights on guest data strategy and the evolving hospitality tech landscape will reshape how you think about building an independent brand. Summary and Highlights 🎯 Meet Arthur Colker Arthur Colker is the Founder and CEO of StayFi, a guest marketing platform that started as a WiFi data collection tool and evolved into a comprehensive solution for vacation rentals, boutique hotels, and independent hospitality brands. Since 2018, Arthur has been helping property managers capture guest data and build independent booking channels that reduce reliance on major OTAs. Before StayFi, Arthur worked as a marketing consultant across various industries. His entry into short-term rentals happened almost accidentally when he took on a vacation rental operator as a client and discovered they had zero guest data despite managing 200 properties. That gap became the genesis of StayFi—a platform now used by thousands of operators who understand that guest data ownership is the foundation of a resilient, profitable hospitality business. Arthur is passionate about helping independent operators compete with major platforms, not by undercutting them, but by building their own brands and creating direct relationships with guests. His latest project, StayFinder, aims to make direct booking discovery as easy as booking through an OTA—while delivering real savings to travelers. 💡 Key Takeaways ✅ Guest data is the most overlooked asset in short-term rentals — Most operators collect names and emails only from bookers, missing everyone else in the reservation✅ Direct booking isn’t about replacing OTAs — It’s about channel diversification and building a resilient business that isn’t dependent on one platform✅ Marketing works when it delivers value — Position direct booking as a “secret” that saves guests money, not just a way to avoid fees✅ Your property needs to rank on Google — If someone searches your listing name and can’t find your direct site on page one, you’re losing bookings✅ Unique property names matter for SEO — Generic names like “Cozy Creek Cabin” make it nearly impossible to rank and be discovered✅ Founders need conviction, not just optimism — Arthur calls it “delusional self-belief,” but you also need to listen when customers tell you what’s not working🏠 How StayFi Started: Solving One Client’s Problem Arthur didn’t set out to build a hospitality tech company. He was doing marketing consulting for various businesses when he landed a short-term rental operator called Heirloom, managing around 200 properties across New Orleans, Boston, and Scottsdale. Their goal was simple: build a brand identity and figure out how to get guests to book directly. The challenge? They were 99% dependent on Airbnb for bookings and had zero guest data. No names, no emails, no phone numbers. Arthur realized that acquiring new guests is expensive and trust-dependent. The easiest path to direct bookings would be marketing to people who already stayed and loved the properties. But how do you market to ghosts? He looked for existing solutions—captive portal systems used in cafes, airports, and hotels. Nothing worked well for single-family vacation rentals. So he built a custom solution using white-labeled hardware and a basic splash page that collected marketing consent when guests logged into WiFi. V1 of StayFi was scrappy. No customer portal. No self-service. Arthur manually configured everything for each client. But it worked. And when he looked around the industry, he realized the problem was universal. That’s how StayFi was born. 📈 The Evolution: From WiFi to Full Guest Marketing Platform The early years were a grind. Through 2019, StayFi was still a part-time project. Then Arthur went full-time—right as the hardware partner got acquired and pricing became unfeasible. He had to rebuild the tech stack while simultaneously dealing with COVID shutting down his 10-15 paying customers overnight. But instead of folding, Arthur used the downtime to build StayFi’s first self-service portal and flash page builder. By the time short-term rentals roared back in 2021, the platform was ready to scale. Timing couldn’t have been better—hosts were angry at Airbnb for how they were treated during the pandemic, and the industry was hungry for tools that reduced OTA dependence. Fast forward to today, and StayFi has evolved far beyond WiFi data collection. The platform now includes: 🔹 Homepage Tool — A link-tree-style page for guests that consolidates all the resources they need during their stay🔹 Email Marketing Software — Purpose-built for vacation rentals, not generic tools like MailChimp🔹 PMS Integrations — Pulling data from property management systems to create a unified guest database🔹 Upsell Amplification — Helping operators present offers like early checkout, mid-stay cleans, and local experiences to all guests, not just bookers The guiding principle? Collect guest data from every touchpoint, then help operators monetize that data—whether through rebookings, upsells, or entirely new revenue streams. For property managers who also run real estate businesses, tour companies, or retail shops, StayFi has become a powerful cross-marketing engine. Guests who stay in vacation rentals are often the same people who later buy properties in that market. The data becomes invaluable. 🔍 StayFinder: The Next Frontier in Direct Booking Discovery Arthur’s newest project, StayFinder, tackles a different problem: guest discovery. Most direct booking tools focus on converting existing traffic

Technology is transforming short-term rentals—but are we losing the heart of hospitality in the process? In this episode, Jessica Gillingham, CEO of Abode Worldwide and author of “Tech-Enabled Hospitality,” challenges the notion that automation and personalization can’t coexist. As a strategic advisor to transformative technology companies across the global hospitality sector and host of the Pillow Talk Sessions podcast, Jessica brings a unique perspective on building category leaders. From revealing why 90% of hosts only use 30-40% of their PMS capabilities to explaining how Netflix-style personalization could revolutionize guest experiences, Jessica shares insights from interviewing over 30 industry leaders. Whether you’re managing one property or a hundred, you’ll discover why the future of hospitality isn’t about choosing between technology and human connection—it’s about using one to amplify the other. Summary and Highlights 👤 Meet Jessica Jessica Gillingham is the CEO of Abode Worldwide, a strategic public relations agency specializing in elevating the profile of transformative technology solutions across the global hospitality, lodging, and living sectors. Abode sits at the heart of the developing intersection between work, life, and play in real estate and hospitality, partnering with brands playing a lead role in this transformation. A regular industry speaker, author, and adviser, Jessica is also the host of the Pillow Talk Sessions podcast and author of “Tech-Enabled Hospitality” (Kogan Page, August 2024). Drawing on interviews with over 30 industry leaders, her book examines how technology is transforming every aspect of hospitality operations and the guest experience. She’s also the creator of the Abode Worldwide Short-Term Rental Index, now in its third edition, which catalogs over 200 tech companies and trends shaping the STR industry. 🎯 Why This Episode Matters Most property managers are sitting on goldmines of untapped potential. Jessica reveals a startling reality: operators typically use only 30-40% of their existing technology’s capabilities. This isn’t just about underutilization—it’s about missing the fundamental shift happening in hospitality. While other industries, such as e-commerce, have seamlessly integrated digital experiences into every touchpoint, vacation rentals remain “clunky” and fragmented. This episode cuts through the noise of endless tech solutions to address the real question: How do you leverage technology without sacrificing the warmth and personalization that defines true hospitality? Jessica’s perspective, informed by years working with both hotel and vacation rental technology companies, offers a rare bird’s-eye view of where the industry is heading and what operators need to do now to stay competitive. 💡 The Mindset Shift: Investment vs. Cost One of the most powerful insights Jessica shares is the divide she observed while researching her book: successful operators view their tech stack as an investment that enhances their business, while struggling operators view it as a necessary expense. This mindset difference determines everything—from which tools you adopt to how you implement them. Operators who treat technology as an investment actively seek to understand its full capabilities, integrate systems to create seamless experiences, and continuously optimize their digital guest journey. Those who see it as a cost often implement the bare minimum, leaving powerful features dormant. The gap isn’t just philosophical. As Jessica points out, guests now expect the same frictionless digital experiences they get from booking doctor appointments, ordering food, or shopping online. Everything in our lives has been digitalized—except, often, the hospitality booking journey. <a href=”https://craftedstays.co/blog/”>Property managers who fail to bridge this gap</a> risk being left behind as the industry consolidates and guest expectations continue rising. 🔍 The Education Gap: Why Hosts Aren’t Using Their Tools Jessica identifies a critical problem plaguing the industry: operators often lack awareness of their own knowledge gaps. Most hosts and property managers can’t identify where automation could help them because they haven’t clearly defined their operational gaps. Even more challenging, they don’t fully understand what their existing software can do. This creates a vicious cycle. Without understanding your problems, you can’t evaluate solutions effectively. Without understanding your solutions, you can’t leverage them to solve problems. Jessica compares this to any software we use—”We’re on Riverside right now,” she tells Gil, “I bet you don’t use the whole caboodle of what Riverside can do for you.” The solution? Strategic education. Before adding another tool to your stack, invest time in understanding what you already have. Map your operational pain points. Then systematically explore whether your current PMS, guest communication platform, or pricing tool already addresses those challenges. As Jessica emphasizes throughout the conversation, <a href=”https://craftedstays.co/blog/”>the most successful direct booking strategies</a> start with understanding your foundation before building upward. 🏨 The Accidental Entrepreneur Problem Jessica makes a crucial distinction that many hosts overlook: “Most hosts are accidental hosts. You don’t go to university thinking I’m going to be a professional property manager.” This creates unique challenges because running a short-term rental business requires three distinct skill sets that rarely come naturally together: Hospitality expertise – Understanding guest needs, creating memorable experiences, and maintaining service standards Business acumen – Managing finances, hiring teams, scaling operations, and strategic planning Real estate knowledge – Property selection, market analysis, and investment strategy Unlike long-term rentals or commercial real estate, which have established frameworks and educational pathways, vacation rental operators often stumble into the business without realizing they’ve started a 24/7 hospitality operation. As Jessica notes, “It’s always on. Property managers tend to be extremely hardworking, putting in a lot of hours into their businesses.” The path forward involves recognizing these gaps and actively seeking education. Whether through podcasts like Booked Solid, industry conferences, or peer mastermind groups, successful operators treat learning as a core business function rather than an occasional activity. 🤝 Technology + Hospitality: Not an Either/Or Perhaps the most important theme Jessica emphasizes is captured in a single quote from Ryan Killeen, CEO of The Annex in Toronto: “The future of hospitality is hospitality.” Despite all the discussions about AI, automation, and efficiency, the winners in this space will be those who use technology to enable hospitality, not replace it. “Hospitality doesn’t always have to be in person,” Jessica explains. “It can be delivered through digital methods. It’s