Vacation Rental Success

Heather Bayer, author of Renting Your Recreational Property for Profit, former CEO of a highly successful cottage rental agency, and a popular blogger, hosts the Vacation Rental Success podcast. With many years experience of owning and managing multiple vacation rental properties, Heather brings her knowledge and views on every aspect of the business, together with interviews with vacation homeowners and industry experts. Heather has appeared as a guest on CTV Canada, CBC Radio, Rogers TV, and Chex TV and is frequently interviewed on real estate and travel topics by magazines and daily newspapers.

VRS677 - Who Decides What Good Looks Like? 08/19/2026

VRS677 - Who Decides What Good Looks Like? This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ Most people in short-term rentals describe how they got started with a slight apology in their voice. They fell into it. They bought a place, put it online, and worked out the rest as they went. Jodie Odlin thinks that story has run its course, and this episode is about what replaces it. Jodie trained in hospitality management and worked in five-star hotels before she started a rental business in the Cotswolds. What she found when she arrived in short-term rentals was a lot of beautiful properties with very little behind them in the way of standards. She began collecting host stories in a book called Hospitable Hosts, and that first volume grew into five books, more than two hundred authors, a publishing house, a training academy, an accreditation system, and a three-day summit in upstate New York at the end of September. In this conversation Heather and Jodie work through what an industry standard would actually contain, why it has to leave room for the character of an individual property, how you hold standards together from eleven time zones away, and why the standards conversation has to include owners and guests as well as hosts. Key takeaways A workable industry standard sets a floor for cleanliness, safety, and communication, and then leaves room for everything that makes one property different from every other one. Setting guest expectations accurately in the listing and in pre-arrival communication protects a review more reliably than any amount of upgrading. Standards only survive the owner being absent if they live in a trained local team and a documented process rather than in the founder’s head. AI guest messaging works best as a hospitality tool that is read every day, with a clear route to a human at the point where the guest says the problem cannot wait. Owner standards matter as much as property standards, because a property nobody is willing to invest in reflects on the manager’s brand rather than the owner’s. Holding a standard runs in both directions, and calling out a guest who leaves a property in a poor state carries less risk than most operators assume. _______________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/42446880

VRS676 - My AI Tool Stack, and What It Actually Costs 08/12/2026

VRS676 - My AI Tool Stack, and What It Actually Costs This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ Five days before recording this episode, Heather added an AI agent called Viktor to her Slack workspace. Within the hour it had introduced itself to her entire team, worked out on its own that the podcast was central to the business, counted the back catalogue, audited which episodes had transcripts, and offered to fix the gap. It had also spent two thirds of her credit balance, and when she asked where the money had gone, the answer was not what she expected. That story is the way into a full account of the AI tools Heather is currently paying for: what each one does, what it costs, and whether it earns its place. The total comes to $329 a month, which is just under $4,000 a year, and it is a number she had never added up before preparing this episode. The second half is a practical method for auditing your own stack. Where duplication hides, what your existing property management software already does that you may be buying twice, why monthly subscriptions beat annual ones until you are certain, and how to hand the whole exercise to AI rather than building another spreadsheet. Heather also covers what is genuinely worth learning right now and what most operators can safely leave alone for another six months. Key Takeaways Most AI spending is not a decision. It arrives as a run of small, individually defensible choices, and it lands on top of a software bill that was already growing. When an agent runs on credits, the work you ask for is usually the cheap part. The expense sits in recurring background jobs and proactive activity nobody requested. Ask any metered tool, within the first week, where your credits went and what it does when you are not watching. A capable agent needs a scope brief before it gets access, not after. Decide what it can see, who can instruct it, and what it may do without asking. Per-seat pricing is where software bills quietly grow. A tool that costs $84 a year can cost $420 a year across a team. Audit by job, not by tool. Write down the job, then list everything you pay for that does it. Check what your existing platforms already do. Most PMS and operations tools have shipped AI features that operators are separately paying for elsewhere. Only take an annual plan once you are confident you will still be using the tool in a year. The discount is always offered when you are most enthusiastic and least informed. __________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/42382240

VRS675 - If You Don’t Own Your Guest, You Don’t Own Your Business 08/05/2026

VRS675 - If You Don’t Own Your Guest, You Don’t Own Your Business This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ Twenty-five years ago, Heather could get on the phone with every guest who booked her cottage in Ontario and ask one question: what would it take for you to leave saying this was the best vacation of your life? One answer led to a fishing rod, a tackle box, and a tub of live worms in the fridge for an eight-year-old visiting from England. That depth of guest knowledge became impossible once she was managing 200 properties. This conversation is about getting it back. Orlie Benjamin spent her corporate career in marketing at Victoria’s Secret, American Airlines, NetJets, and Scotts Miracle-Gro before buying 78 acres near Hocking Hills, Ohio, and building her own vacation rental business. What she found was an industry with almost none of the guest marketing infrastructure she had taken for granted, and distribution channels designed to keep operators and guests apart. So she built Lasoh, an AI-driven guest portal, CRM, and marketing platform for short-term rental operators. Listeners will come away with a clear picture of what it means to know an incoming guest before they arrive, why the anticipation phase is the most neglected stage of the guest journey, and how to think about direct booking as a business strategy rather than a wish. Key Takeaways Revenue has three levers: the number of guests you have, how often they transact, and what they spend each time. Most operators only ever work on the first one, and they rent it from the OTAs rather than owning it. The anticipation phase is the longest stage of the guest journey, and for most operators it sits empty. The window between booking and arrival is where guest knowledge is gathered and goodwill is built. Three plain, open-ended questions sent before arrival will tell you more than any polished survey. Orlie deliberately made Lasoh’s pre-arrival form look unsophisticated so it feels like a human is reading the answers. One is. AI removes three of the four steps: asking, capturing, and drafting the response. The human does the fourth, which is reviewing the reply and adding the judgement and flair that make it exceptional. Build the goodwill piggy bank before arrival. A guest who has been genuinely looked after in the weeks before their stay will forgive the thing that inevitably goes wrong. A guest arriving at neutral will not. If your business runs entirely through Airbnb, your customer is Airbnb, not the guest. Direct booking is a deliberate strategy that requires people, systems, and process, and it starts with deciding who your guest and owner ICPs actually are. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/42277315

VRS674 - What Hyperlocal Really Means, and Why the Owner Is the Real Customer 07/29/2026

VRS674 - What Hyperlocal Really Means, and Why the Owner Is the Real Customer This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ This episode started on LinkedIn. Gil Chan posted about hyperlocal property management, using VueStay Vacations, a newly launched company with 4,500 homes across eight states, built on centralized revenue management and marketing through the Casago franchise network, as his example. Richard Vaughton replied that hyperlocal is as much about owner relationships as local market knowledge, and that the relationship piece is increasingly getting forgotten. That comment is where this conversation begins. Heather's guest is Richard Vaughton, a short-term rental consultant with close to thirty years in the industry and a career built on starting, scaling, and selling companies: an Italian rental business grown to roughly 800 properties, a UK company in Torquay, a PMS technology startup, and a VP role at Stay Alfred during its collapse in the pandemic. The two have known each other for more than twenty years, and this is an unscripted, fireside-style conversation rather than a structured interview. Listeners will come away with a clearer, more operational definition of hyperlocal, a look at why some of the industry's best-known roll-ups have failed while others have scaled successfully by staying local, and a reminder that the piece of this business that most often determines a guest's review, and an owner's trust, is not technology or marketing. It is cleaning. Key Takeaways Hyperlocal is an operating decision, not a marketing word: it means real local staff, a genuine local reputation, and a company culture rooted in one place, not a national brand run by a distant account manager. The owner, not the guest, is the most important person in the ecosystem. Without a well cared-for owner there is no polished product to offer a guest in the first place. Large-scale roll-ups have historically broken at the point where they centralize everything beyond accounts and revenue management, while UK consolidators like Sykes Cottages, Awaze, and Travel Chapter have grown large by staying hyperlocal at a national scale, keeping local offices and local staff as they expanded. AI is freeing up enough staff time that teams can spend it on relationship-building rather than admin, such as calling every guest and owner after checkout with nothing to sell, just a thank you. Culture, trust, and local relationships are the parts of this business that resist mechanization. Reporting, revenue management, and communication can be automated; the relationship at the center of it still has to be built by a person. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/42204985

VRS673 - When the Work Comes First, the Magic Follows 07/22/2026

VRS673 - When the Work Comes First, the Magic Follows This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ Paul Anderson first appeared on the Vacation Rental Success Podcast in 2021, when he was running a guest house in Oxford and building a following on Instagram. Five years on, he returns as a coach and strategist working across dozens of short-term rental operators, and now a commissioned officer in the Royal Air Force reserves. That mix of experience gives this conversation its shape: what the military taught him about briefing, decision-making and slowing down, and how those same lessons apply to the way operators are using AI in their marketing. The central argument is one Paul delivered on stage at Scale in Brighton, and it is worth sitting with. AI did not break marketing, it exposed the people who were never really marketing in the first place. When content becomes cheap and fast to produce, the operators who understood their audience all along pull ahead, and the ones who mistook activity for strategy get found out. Heather and Paul talk through his 10-80-10 protocol, his SMERLAC briefing structure borrowed from military planning, and why the real work in AI happens before you ever ask it to write a word. It is a practical, funny and genuinely useful conversation for any operator who has looked at their AI-generated captions and felt that something was missing. Key takeaways AI has not broken marketing. It has exposed the operators who were producing content without ever really marketing, because publishing posts, writing blogs and appearing in magazines are not the same as moving a guest from “I might visit” to “I want to stay there.” The real work happens before you prompt. Paul’s 10-80-10 protocol puts the first 10 percent into defining exactly who you want and briefing the AI properly, lets AI do 80 percent of the heavy lifting, then reserves the final 10 percent for inspecting and personalising the output. Define your perfect potential guest in granular detail. Go beyond age and income to how many cars they have, where they shop, even the colour of their hair, so you can picture one real person on the other side of the screen rather than a demographic. Use a proper brief, not a wish. “Write me 10 captions about my holiday cottage” is a wish. Paul’s SMERLAC structure (Situation, Mission, Execution, Resources, Limitations, Ask questions, Check understanding) gives the AI what it needs to produce something useful. Followers are not the same as money. A client with 28,000 followers built through giveaways had almost no buying intent, while 52 people who genuinely want to book beat 52,000 who just think you are funny. Feed AI your real voice. Heather uploaded the handwritten manuscript of a book she wrote in 2005, unedited, and it changed everything the AI produced. Your idiolect, the phrases only you use, is what cuts through the sameness. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/42058135

VRS672 - Direct Bookings, AI Websites, and the Search That's Changing Everything 07/15/2026

VRS672 - Direct Bookings, AI Websites, and the Search That's Changing Everything This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ Gil Chan came at the short-term rental industry from a direction most operators never consider. After 15 years in Silicon Valley, working with brands like Gap, Sephora, and Home Depot on their post-purchase e-commerce experience, he became an STR host - and immediately spotted a gap that his industry background made obvious. The tools that e-commerce businesses took for granted simply did not exist for vacation rental operators who wanted to build a direct booking website worth having. Crafted Stays is Gil's answer to that gap: a purpose-built direct booking platform that works the way a proper commerce site should, not as feature number 40 in a property management system's marketing materials. But what makes this conversation particularly timely is where Gil has taken the platform over the past year - deep into AI-powered search, website building, and the kind of content strategy that gets operators found in places Google's traditional search results simply can't reach. This episode covers direct booking strategy, how search is changing (and what SEO, AEO, and GEO actually mean for property managers), the Aria AI assistant Gil built into Crafted Stays, and how operators can start thinking about their online presence in a way that serves both guests and the AI systems that are increasingly mediating how people find places to stay. It's a practical, technically grounded conversation - and one that will stay relevant for some time. ‍KEY TAKEAWAYS‍ Direct booking websites built on WordPress and plugins were never designed for the live data demands of vacation rental commerce. Purpose-built platforms handle PMS connections, checkout, and mobile experience in a fundamentally different way.‍ SEO, AEO, and GEO are three different things. Traditional search engine optimization gets you on page one of Google. Answer engine optimization gets you into the snippet at the top of the page. Generative engine optimization gets you cited when someone asks ChatGPT, Perplexity, or Claude for a recommendation. Operators need to think about all three.‍ AI-powered review analysis is an underused tool. Most operators check a five-star review and move on. Mining reviews for recurring themes - a screened porch that guests keep mentioning, a location detail that keeps coming up - surfaces the specific things guests value most, and those become the content anchors for the entire website. The Sightline Report that Aria generates combines property data, review sentiment, and third-party SEO keyword research to produce a strategic playbook for each operator. It tells them which keywords to target, which landing pages to build, and which guest personas to write toward - without requiring any marketing expertise from the operator. Building your AI business brain before you start using AI tools is not optional - it is foundational. Gil has been giving every new team member at Crafted Stays the same 40-page document about the business since he built it a year ago. The quality of AI output is directly tied to the quality of context you give it. The divide in AI adoption is getting wider, not narrower. Some operators are building sophisticated automated systems; others have barely touched ChatGPT. The window to build a real advantage by getting in early is still open, but it will not stay that way indefinitely.‍ ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41847400

VRS671 - 10 Things I'd Do With AI If I Was A Property Manager Again 07/08/2026

VRS671 - 10 Things I'd Do With AI If I Was A Property Manager Again This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ This episode almost wasn't the one you're hearing. Heather had already recorded, edited, and prepared social media for a different episode when a morning of reflection sent her down a different path instead. The trigger was rereading her own contribution to Brooke Pfautz's book Vacation Rental Secrets, written a few years back - an unusually honest account of the mistakes she made running CottageLink Rental Management, the property management company she sold four years ago. Reading it back, Heather noticed a pattern. None of the mistakes came from working too little or caring too little. Every one of them came from not having the tools to see clearly, document what she knew, or build systems that didn't depend on her being at the centre of everything. That reflection became this episode: ten specific, practical things she would do differently if she were running a property management business today, with the AI tools now available. This is a solo teaching episode, released the week the second cohort of the AI Ambassador Program opens. It is aimed squarely at operators who want to know, in concrete terms, what using AI well in a property management business actually looks like - not in theory, but from someone who has run the business, made the mistakes, and now has the tools to fix them. Key Takeaways Build a brand voice document before writing a single word of copy. Capture your tone, values, and the phrases that are distinctly yours before you ask AI to write anything on your behalf - otherwise inconsistency creeps in and your team, guests, and owners start to feel it. Stop letting every vendor demo convince you a new platform will fix your business. Your PMS is the one system that genuinely needs a professionally built, purpose-designed solution - but beyond that, a lot of what operators buy off the shelf could now be built to fit their specific business instead. Document every process before it only exists in your head. Talk a process through, out loud, while you're doing it and let AI structure it into a living SOP - the knowledge that only lives with the founder is a liability, not an asset. Build a genuine owner communication system, not just good intentions. Work through frameworks for the hard conversations in advance, and use AI to generate genuinely personal quarterly owner reports at scale, not a mail merge with names swapped in. Use AI to keep direct booking relationships warm, not just to build them. The follow-up sequences that go quiet the moment peak season hits are where most operators lose ground - AI can keep that infrastructure running consistently even when you're buried. Analyze reviews instead of just reading them. The most useful information is often buried inside five-star reviews as an aside - patterns that only become visible when reviews are aggregated and analysed rather than read one at a time. Build a real owner acquisition pipeline instead of relying on referrals. Referrals are a result, not a strategy - a proper follow-up sequence and a clear sense of the right-fit owner prevents leads from going cold. Build an institutional knowledge base, not just a folder of SOPs. Capture the reasoning behind decisions, not just the steps, so that judgement can travel with the business even as people move on. Treat AI as a thinking partner, not just a writing tool. The most valuable use of AI is stress-testing decisions before you commit to them, not just producing first drafts. Start with clear values and strategy, and let AI help you communicate them. Clarity about what you're building and who it's for makes every daily decision easier - and AI can help both articulate that strategy and communicate it consistently across a team. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41956445

VRS670 - When Hospitality Leads and Tech Follows 07/01/2026

VRS670 - When Hospitality Leads and Tech Follows This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit and use code VRSUCCESS for 50% off 3 months of StayFi service. ________________________________________________________________________________________________________________________________________ Sab Mulligan came into the short-term rental industry from a decade in media production and another in tech education, and she arrived with a beginner's mind that turned out to be an advantage. What she noticed in those early industry conversations wasn't the passion for hospitality she'd expected. It was burnout, worn almost as a badge of honour. People competing over who'd taken the most 3am calls. She found that troubling, and it drove the approach she'd go on to build at Zzzing, a fast-growing property management company based in Malta. Three and a half years later, Zzzing has grown from 50 properties to 650, and their AI agent Zoe handles 90% of all guest communications across the portfolio. But what makes this conversation interesting isn't the scale or the technology. It's the philosophy behind it: that tech should be silent, and hospitality should be loud. That AI doesn't replace the human side of this business, rather it gives people more time and energy to deliver it. Sab and I talked about her TRT framework for designing AI policies, the seven guest moments that anchor everything Zzzing does, how they handled team resistance to AI adoption, and what she'd say to property managers still watching from the sidelines. Key Takeaways Tech should be silent, hospitality should be loud. The goal of AI in guest communication isn't to replace the host's voice. It’s there to deliver that voice consistently, at any hour, across every conversation. AI amplifies what you already have in place. If your policies aren't documented, AI won't fix that. It will amplify the mess. Getting your foundations right before deploying AI isn't a delay,it's the work. Sab's TRT framework makes policy design accessible. Trigger (what initiates this communication), Reaction (how you would genuinely respond), Tone (the warmth, the friendliness, the examples), and Guardrails (when does the AI stop and hand to a human). The seven guest moments give you a map. Discovery, booking, arrival, access, during-stay, checkout, and come-back. Everything you need from AI slots into one of those seven buckets. Humanising the AI agent internally matters as much as externally. Naming Zoe and giving her a clear job description helped Zzzing's team understand where the AI started and stopped, which reduced resistance significantly. Test your own policies. Don't experiment on real guests. Make a test booking and run your AI through every scenario every few days. You are in the driver's seat and AI isn't taking over. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41804690

VRS669 - Connectors, Skills, and the AI Business Brain - with Jodi Bourne 06/24/2026

VRS669 - Connectors, Skills, and the AI Business Brain - with Jodi Bourne This Episode is Sponsored by StayFi Your ultimate tool for Vacation Rental WiFi marketing allowing you to collect guest emails automatically via custom captive WiFi login splash pages. Drive repeat direct bookings and convert your OTA bookings to book direct for their next visit. Visit and use code VRSUCCESS for 50% off 3 months of StayFi service. _________________________________________________________________________________________________________ Jodi Bourne is back for the latest installment of the new regular segment with Heather, built around a simple premise: AI is moving fast, and the two of them are going to keep working through it together, out loud, for listeners who want to come along. This conversation goes deeper into the practical mechanics of working with Claude. Heather and Jodi talk through connectors (MCPs that link Claude to tools like Gmail, Google Drive, Asana, and accounting software), skills (saved, reusable instruction sets that replace the old habit of copying and pasting prompts), and what both of them call their AI business brain - a structured foundational document that teaches Claude who you are, what you sell, and how you sound, before you ask it to produce anything. You’ll come away with a clear starting point: build the foundation first, connect the tools you already use, and create one simple skill - Jodi's suggestion is a daily “morning coffee” briefing - before trying to do anything more ambitious. Key Takeaways AI output defaults to generic. The fix isn't a better prompt - it's a structured foundation document (Jodi calls hers the Hospitality Brand Bible; Heather calls hers her Business Brain) that teaches the model your business, voice, and audience before you ask it to create anything. Building that foundation properly is not a five-minute job. Heather recommends setting aside the better part of a day and using reverse prompting - asking Claude to interview you, question by question, until it has a full picture of your business. Connectors (MCPs) link Claude directly to the tools already in use - Gmail, Google Drive, Google Calendar, Asana, accounting platforms - so requests can be carried out end to end instead of copying information back and forth manually. Skills replace the old habit of maintaining a library of saved prompts. A skill is a reusable, named instruction set that automatically pulls in the right reference documents and brand voice without being told to every time. The recommended first skill for anyone starting out is a daily briefing - a “morning coffee” routine that summarizes email, flags anything unanswered, and reviews the calendar - because it is simple, immediately useful, and teaches the basics of how skills work. AI will hallucinate and occasionally get things wrong with total confidence. Both hosts were emphatic that nothing goes out the door - a guest bio, an email, an Instacart order - without a human checking it first. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41729930

VRS668 - Purpose Before Polish: AI in Business and Hospitality 06/17/2026

VRS668 - Purpose Before Polish: AI in Business and Hospitality This Episode is Sponsored by Lodgify If you have been thinking about building your own direct booking channel and reducing your reliance on the OTAs, Lodgify is worth a serious look. It brings your booking website, channel management, guest messaging, and unified inbox into one place. VRS listeners can get 20% off yearly and bi-yearly plans with code VRS-20, valid through to the end of June. Visit Lodgify and use code VRS-20 to get started. ________________________________________________________________________________________________________________________________________ Heather has just returned from a week in the UK - visiting family, catching up with old friends, and speaking at the Scale AI Summit in Brighton. In this solo reflection episode, she weaves together two very different vacation rental experiences, a hospitality revelation on a delayed Virgin Atlantic flight, and the core teaching from her conference session to land on a single, unifying idea: purpose comes before polish, and foundation comes before execution. The episode moves from a functional but story-free farm conversion cottage, to a 300-year-old Hastings cottage that felt like it had been created specifically for her friends, to a conference room full of STR operators at every stage of their AI journey. The thread connecting all of it: knowing who you are, who you serve, and what you stand for before you pick up a single tool - whether that tool is a £200 kettle, a booking platform, or an AI assistant. Heather also walks through the core framework from her “Building Your AI Business Brain” session, giving listeners a practical, actionable foundation they can start building this week. Key Takeaways A pilot who told his delayed passengers “I am the host of this flight and you are my guests” changed the atmosphere of an entire departure lounge with one sentence. Purpose, clearly stated, changes everything. The difference between the two cottages wasn’t price or quality - it was whether the owner knew exactly who they were creating the experience for. One was built for a specific person; the other was built for anyone passing through. Before you touch a single AI tool, you need five foundational pieces in place: your vision, your mission and values, your business profile (including avatars, brand voice, and workflows). Without these, AI will produce generic output for a generic audience. The fastest way to capture your brand voice isn’t to write it - it’s to talk it through using voice-to-text. Most people think out loud more naturally than they write, and the result is closer to your real voice. At the Scale AI Summit, fewer than half the room had a documented client or owner avatar - which means their AI has no idea who it’s writing for. If it’s not documented, it doesn’t exist as far as your AI is concerned. Strategy before execution, every time. Paul Anderson’s RAF officer training insight maps directly to AI adoption: the operators who slow down to build a foundation first are the ones who get useful, consistent results. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41650675

VRS667 - Two Ways to Make More Money This Year: Private Chef Upsells and Smarter AI Use 06/10/2026

VRS667 - Two Ways to Make More Money This Year: Private Chef Upsells and Smarter AI Use This Episode is Sponsored by Lodgify If you have been thinking about building your own direct booking channel and reducing your reliance on the OTAs, Lodgify is worth a serious look. It brings your booking website, channel management, guest messaging, and unified inbox into one place. VRS listeners can get 20% off yearly and bi-yearly plans with code VRS-20, valid through to the end of June. Visit Lodgify and use code VRS-20 to get started. _________________________________________________________________________________________ Siddhi Mittal has one of those backgrounds that makes you wonder how a single person contains all of it. She grew up in Agra, studied computer science and AI at Columbia, landed on an asset-backed mortgage securities trading floor in New York, moved to London, spent six years in finance, had a full-blown existential crisis, quit to build a startup, stumbled into the vacation rental industry almost by accident, had a baby, got lost down an AI rabbit hole, nearly derailed her marriage, and is now running two businesses while teaching women worldwide how to use AI to earn more and work less. And it seems like all that happened without her taking a breath! Yhangry is a private chef booking platform she co-founded in the UK. It started as a consumer product for anyone who wanted a chef to cook at home. Then Siddhi discovered that 50% of her users were vacation rental guests and property managers, and everything changed. Yhangry is now one of the most interesting upsell opportunities in the STR space: property managers can generate a simple affiliate link, share it with guests, and earn commission whenever a chef is booked. No operational overhead. No coordination. The platform handles everything from booking to payment to quality assurance. The conversation covers all of that, and then it goes somewhere else entirely. Because Siddhi is also the founder of SheCompoundsAI, a live AI education event series focused on helping women build practical AI skills. She brings the same direct, jargon-free energy she uses on stage to this conversation, and what comes out is one of the most accessible explanations of prompting, agents, and reverse prompting I have heard anywhere. If you have been hovering at the edge of AI adoption and not quite sure how to get started, this episode gives you the simplest possible on-ramp. And if you are a property manager looking for a genuinely low-effort upsell revenue stream, the Yhangry conversation is worth your attention. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41495850

VRS666 - The Seven Deadly Sins of AI in Your STR Business 06/03/2026

VRS666 - The Seven Deadly Sins of AI in Your STR Business This Episode is Sponsored by Lodgify If you have been thinking about building your own direct booking channel and reducing your reliance on the OTAs, Lodgify is worth a serious look. It brings your booking website, channel management, guest messaging, and unified inbox into one place. VRS listeners can get 60% off yearly and bi-yearly plans with code VRS-60, valid through June 9th and 20% off yearly and bi-yearly plans with code VRS-20, valid through June 10 to end of June. Visit Lodgify and use code VRS-60 to get started. _________________________________________________________________________________________ Episode VRS666 arrives with purpose. Rather than sidestepping the number, Heather uses it as a frame for something worth naming: the very human patterns that undermine AI adoption in short-term rental businesses. Drawing on her own experience, conversations with property managers, and the collected wisdom of fifty experienced operators featured in Brooke Pfautz's book Vacation Rental Secrets, she maps seven recognisable failure modes onto the classical seven deadly sins. These are not abstract warnings. They are patterns that show up with remarkable consistency across different markets, business sizes, and experience levels. Heather has lived several of them herself. And because they are patterns, they can be recognised, named, and redirected. That is the point of the episode: awareness is the first step toward a different choice. If you have been accumulating AI tools without connecting them, automating your guest communications without thinking about what that does to the relationship, or chasing the latest model release without going deep into the one you already have, this episode is for you. And if you recognise yourself in any of the seven sins, Heather's message is not judgment. It is: now you can make a different choice. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41483520

VRS665 - Bionic Not Robotic: Steve Schwab on AI, Integration, and Community 05/27/2026

VRS665 - Bionic Not Robotic: Steve Schwab on AI, Integration, and Community This Episode is Sponsored by Lodgify If you have been thinking about building your own direct booking channel and reducing your reliance on the OTAs, Lodgify is worth a serious look. It brings your booking website, channel management, guest messaging, and unified inbox into one place. VRS listeners can get 60% off yearly and bi-yearly plans with code VRS-60, valid through June 9th and 20% off yearly and bi-yearly plans with code VRS-20, valid through June 10 to end of June. Visit Lodgify and use code VRS-60 to get started. _________________________________________________________________________________________ A year ago, Steve Schwab closed one of the most talked-about deals in the short-term rental industry - the acquisition of Vacasa by Casago. At the time, he described it as surreal and exciting. A year on, the headline has given way to the hard work: integrating systems, transitioning markets, reshaping a culture, and doing all of it while holding onto the belief that this is, at its core, a relationship business. In this conversation, Heather catches up with Steve to take stock of that year - what has worked, what has been harder than anticipated, and what the ongoing Casago-Vacasa integration has taught him about leadership at scale. They also get into AI: how Steve is approaching it inside a franchise organisation that spans everything from small, locally owned operations to private equity-backed enterprises, why he talks about making Casago bionic rather than robotic, and the very real challenge of bringing people along when the pace of change is so fast that even the most enthusiastic adopters are missing fundamentals. The episode closes with something genuinely new for the industry: a free, community-based AI learning network on Circle, built for STR professionals at every level of familiarity with AI. Steve and Heather are both actively involved, and this conversation is part of the launch. If you have been curious about AI but not sure where to start, or looking for a place to ask questions without feeling foolish, this community is worth knowing about. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41414850

VRS664 - Building Two Businesses With a Small Team and a Smart AI Habit 05/20/2026

VRS664 - Building Two Businesses With a Small Team and a Smart AI Habit This Episode is Sponsored by Lodgify If you have been thinking about building your own direct booking channel and reducing your reliance on the OTAs, Lodgify is worth a serious look. It brings your booking website, channel management, guest messaging, and unified inbox into one place. VRS listeners can get 60% off yearly and bi-yearly plans with code VRS-60, valid through June 30th. Visit Lodify and use code VRS-60 to get started. ________________________________________________________________________________________ It has been over two years since Kerri Gibson was last on the show, and a great deal has changed. The Chalets Hygge brand has expanded into Experience Hygge, an umbrella that now also covers a roadside motel four hours away from the original property. It is a seventeen-room hospitality business with daily turnover, walk-in guests, and an operational rhythm that has almost nothing in common with the chalets that built the brand. Kerri and her partner Philippe Pichette took on the motel in 2024 and have spent the past seventeen months renovating it while keeping it operational. In this conversation, Kerri talks honestly about what running two very different businesses with a small team actually looks like, how she has stepped back to let her chalet team grow into their roles, and where AI has earned a permanent place in her week. She also speaks plainly about her seven-year history with Lodgify, her direct booking strategy across both businesses, and the move she has been quietly making from ChatGPT to Claude. There is something here for anyone running a lean hospitality business who is curious about AI but does not want hype. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41349060

VRS663 - Building the Foundations Before the AI Storm Hits 05/13/2026

VRS663 - Building the Foundations Before the AI Storm Hits This episode is sponsored by Lodgify, the all-in-one vaction rental platform that will help you start, manage and grow your short-term rental business. You get your own professional booking website. A channel manager that keeps Airbnb, Vrbo and Booking.com, all in sync. Automated guest messaging and a unified inbox so you're not bouncing between six different apps, whether you've got one property or more. It makes running your business a great deal cleaner, and right now through June 30th, you can get 20% off with code VRS20 on all their yearly and bi-yearly Ultimate and Professional plans. _______________________________________________________________________________________________________________________________________ In August 1992, Hurricane Andrew tore through South Florida and damaged or destroyed more than 125,000 buildings. When investigators went through the wreckage, they found that the worst destruction wasn't always explained by the strength of the storm. It was traced to something far more mundane: the connectors, the joints, the foundations. The hardware that held the structure together when the pressure arrived. Out of that came the Miami-Dade construction standards, some of the most rigorous building codes in the United States. Heather opens this solo episode with that story for a reason. After spending months speaking at industry events, running the AI Ambassador Programme, and watching property managers at every scale wrestle with AI adoption, she sees the same pattern: businesses are buying tools without building the foundations that determine whether those tools will hold up. The AI storm is already here. The question is what your connectors look like. This episode is a candid, honest look at why the AI gap in short-term rentals is getting wider, where people are actually learning about AI and what each source is good for, why team learning matters more than individual effort, and a simple three-question filter for evaluating any new AI tool. It also includes a practical foundation idea borrowed from Will Guidara's Eleven Madison Park, and a story about an operator who finally got moving when she stopped trying to learn more and started building one small thing. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41239805

VRS662 - The Guests You Don't See Coming 05/06/2026

VRS662 - The Guests You Don't See Coming This episode is sponsored by Lodgify, the all-in-one vaction rental platform that will help you start, manage and grow your short-term rental business. You get your own professional booking website. A channel manager that keeps Airbnb, Vrbo and Booking.com, all in sync. Automated guest messaging and a unified inbox so you're not bouncing between six different apps, whether you've got one property or more. It makes running your business a great deal cleaner, and right now through June 30th, you can get 20% off with code VRS20 on all their yearly and bi-yearly Ultimate and Professional plans. _______________________________________________________________________________________________________________________________________ This episode started with an observation Heather made on LinkedIn - a post from Ela Mezhiborsky about her company's annual self-care day - and grew into a conversation that cuts to the heart of something most operators get wrong when they bring AI into their businesses. Ela is co-founder and president of AutoHost, an AI-powered guest screening and identity verification platform used by property managers around the world. But she came to it the same way most VRS listeners came to their businesses: through hands-on operation. Before AutoHost existed, she was running Quick Stay, a Toronto-based property management company that grew to over 100 properties. The tool was built because she was the operator who needed it. The conversation opens with a real incident - a Christmas 2016 call from Toronto police about a known gang member, which revealed months of undetected criminal activity running through Quick Stay's properties. That story explains why AutoHost exists, and it also explains Ela's unusually clear-eyed view of where human judgment fails and where systematic screening has to take over. But the episode is as much about people as it is about technology. Ela runs an AI-first company and is visibly thoughtful about what that means for the humans inside it. She talks about what happens to a team when AI arrives - the anxiety before the relief - and what operators can do to manage that transition honestly. The annual self-care day, which honours Ela’s late husband and co-founder, Anton Silberberg, is part of that story too. By the end, the episode covers AI-powered fraud: synthetic identities, voice cloning, and why gut instinct is no longer a reliable defence. If you've been thinking about guest screening as a nice-to-have, Ela makes a case that identity verification is now table stakes - not because fraud is new, but because AI has made it dramatically cheaper, faster, and harder to detect. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41127365

VRS661 - The Year He Stopped Growing and Built Something Better 04/29/2026

VRS661 - The Year He Stopped Growing and Built Something Better This episode is sponsored by Lodgify, the all-in-one vaction rental platform that will help you start, manage and grow your short-term rental business. You get your own professional booking website. A channel manager that keeps Airbnb, Vrbo and Booking.com, all in sync. Automated guest messaging and a unified inbox so you're not bouncing between six different apps, whether you've got one property or more. It makes running your business a great deal cleaner, and right now through April 30th, you can get 60% off with code VRS60 on all their yearly and bi-yearly Ultimate and Professional plans. _______________________________________________________________________________________________________________________________________ A lot of property managers feel the pressure to do something with AI, but struggle to articulate what an AI agent actually is, or how one would function inside a real business. This conversation with Alex Zemianek goes straight at that gap. Alex is the CEO and founder of JZ Vacation Rentals in St. Louis, a dual-model business running about 70 fully managed properties alongside a curated luxury OTA representing close to 2,000 properties across 14 states and three countries. He is not a technical operator. He came up through sales and leadership, not software. And that is precisely what makes his experience with AI worth paying attention to. Alex spent most of 2024 building what he calls his internal AI, deliberately pulling focus away from adding properties and concentrating instead on organizing his systems, cleaning up his data, and building agents that could work across his business. The result was a 168% improvement in his bottom line without adding a single property. The episode covers what that actually looked like in practice: how he thinks about prompting, how he defines agents for a non-technical audience, what his CEO assistant agent does every morning, and why organizing your data is not a nice-to-have but the foundation everything else depends on. This is one of those conversations that gives listeners both the clarity and the confidence to stop waiting and start doing. Alex offers a rare combination: operational credibility, genuine enthusiasm, and the kind of plain-language explanations that make AI accessible without making it feel trivial. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/41020765

VRS660 - Values First: Why What You Stand For Shapes Everything AI Does Next 04/22/2026

VRS660 - Values First: Why What You Stand For Shapes Everything AI Does Next This episode is sponsored by Lodgify, the all-in-one vaction rental platform that will help you start, manage and grow your short-term rental business. You get your own professional booking website. A channel manager that keeps Airbnb, Vrbo and Booking.com, all in sync. Automated guest messaging and a unified inbox so you're not bouncing between six different apps, whether you've got one property or more. It makes running your business a great deal cleaner, and right now through April 30th, you can get 60% off with code VRS60 on all their yearly and bi-yearly Ultimate and Professional plans. _______________________________________________________________________________________________________________________________________ This episode began somewhere else entirely. A few weeks ago, Heather appeared as a guest on The Art of Hospitality Podcast, hosted by Adam Norko and Conrad O'Connell, expecting to talk about AI. They ended up talking about values. That conversation planted a question Heather has been sitting with ever since: if you train an AI on your processes without first being clear on what your business actually stands for, are you just automating the wrong thing, faster? Adam returns to the show for a third time to help answer that question. He is the founder of VR Growth, a consultancy working with vacation rental and PropTech companies, and someone who has seen this industry from multiple angles - as a marketing director for a large management company, a vendor-side executive at Point Central and Breezeway, a Chief Growth Officer, and now an independent consultant. He is also, by his own admission, a small Airbnb host on the Outer Banks, running five properties with his wife. The conversation moves through the gap between values written on a wall and values that actually show up in daily decisions, the leadership behaviours that make the difference, how AI can help operators discover and articulate what they genuinely believe in, and Adam's emerging thinking about self-selected communities of like-minded operators as the industry's next meaningful structural development. The through-line is clear: values have to come before systems, and community has to come before scale. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/40961955

VRS659 - AI Safety for Short-Term Rentals 04/15/2026

VRS659 - AI Safety for Short-Term Rentals This episode is sponsored by Lodgify, the all-in-one vaction rental platform that will help you start, manage and grow your short-term rental business. You get your own professional booking website. A channel manager that keeps Airbnb, Vrbo and booking.com, all in sync. Automated guest messaging and a unified inbox so you're not bouncing between six different apps, whether you've got one property or more. It makes running your business a great deal cleaner, and right now through April 30th, you can get 60% off with code VRS60 on all their yearly and bi-yearly Ultimate and Professional plans. ________________________________________________________________________________________________________________________________________ Most short-term rental operators know how to manage the safety risks they can see: a broken step, a misplaced fire extinguisher, a pool gate that needs a new latch. What is far less well understood is the category of risk that doesn't show up on a property walkthrough - the AI workflows running inside your business right now, handling guest communications, triaging maintenance requests, and making small decisions at two in the morning when nobody is watching. In this solo episode, Heather Bayer draws directly from the AI safety module she developed for the AI Ambassador Program to examine what AI safety actually means for STR operators. This is not a conversation about rogue technology or science fiction scenarios. It is a practical look at four specific failure types that are already happening in real businesses, and a framework for assessing your own workflows before something goes wrong. The episode introduces two key tools listeners can apply immediately: the Review Ladder, a three-tier system for categorizing every AI workflow by the level of human involvement it requires, and six pre-launch questions to ask before any new AI tool or automation goes live. Think of it as the season-opening property walkthrough - but for your AI systems. ________________________________________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is also brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/40830405

VRS658 - Who We Are, What We Do, and Where We’re Headed 04/08/2026

VRS658 - Who We Are, What We Do, and Where We’re Headed This is a reset episode. After months of working behind the scenes, Heather and Mike Bayer come together to do something they have not done for a while: reintroduce themselves, take stock of where the Vacation Rental Formula Business School is now, and talk honestly about what they are building next. If you have been a long-time listener, this is your update. If you are new, this is the best place to start. The conversation covers the full VRF ecosystem, from the just-completed first cohort of the AI Ambassador Program and what Heather has already learned from running it, to the newly launched THRIVE Essentials onboarding course, the opening of five consultancy slots, and the decision to build community through Substack rather than another standalone platform. What comes through clearly is that the focus has sharpened. VRF is no longer trying to serve everyone in the STR industry. It is building specifically for professional operators who are ready to bring AI into their businesses in a structured, responsible way, and who want experienced guidance rather than just another tool recommendation. About Heather and Mike Bayer Heather Bayer spent 20 years managing CottageLINK Rental Management in Ontario, growing it to nearly 200 properties before selling in 2022. She has hosted the Vacation Rental Success Podcast since 2014, making it the longest-running podcast in the STR space, and has spent the last two years building a focused AI education practice for property management professionals. Mike Bayer is CEO and co-founder of the Vacation Rental Formula Business School. He works across strategy, marketing, technology integration, and community, and joins Heather on the podcast periodically to discuss direction and new programmes. Key Takeaways The AI Ambassador Programme just completed its first cohort. Heather is already rewriting Module 2 because the tools she built the course around have shifted in the months since she wrote it. The second cohort launches in May and will include returning members alongside new participants. A knowledge base is the non-negotiable foundation for any meaningful AI adoption. Before touching any tool, operators need documented business context that gives the AI something real to work with. Without it, output is generic. The AI Ambassador role is not a tech job. It is the person in a company who understands the business well enough to see where AI can reduce friction, and who has the trust of the team to guide adoption without creating resistance. Think conductor, not programmer. THRIVE Essentials is a short onboarding course for new STR employees who may have no background in property management. It covers industry structure, operational roles, technology foundations, values, compliance, and a new AI-in-the-workplace module focused on ethics and safe use. The consultancy model is a 90-day intensive followed by nine months of monthly coaching. It is capped at five clients at a time, starts with a free hour-long discovery call, and is specifically designed around AI adoption and integration. It is not coaching in the general sense; it is bespoke problem-solving for a specific business. Community is now on Substack, specifically the Grounded in AI group. After trying several platforms over the years, Heather and Mike landed on Substack because it combines articles, short notes, and a chat forum in one place with a genuine mobile app, which has consistently been what makes community work for people who are managing a business during the day. Resources and Links Mentioned AI Ambassador Programme - vacationrentalformula.com/AI [TBC - confirm final URL] Thrive Essentials - link in show notes [TBC] Grounded in AI Substack community - free subscription, link in show notes Consultancy enquiry / free discovery call - link in show notes Shortcuts - vetted STR trainers, consultants, and coaches [TBC - confirm URL] VR Nation Conference - 28–30 April, Heather presenting on AI foundations Scale UK Conference — Brighton, 9 June, Heather presenting on AI adoption foundations Shortcuts webinar - 23 April, “What You Need to Know Before the Magic Begins” Connect With Heather and Mike Bayer The best place to connect is the Grounded in AI Substack Community, where Heather posts daily and responds to comments. If you are curious about the AI Ambassador Programme, Thrive Essentials, or consultancy, head to the show notes for the relevant links, or reach out directly through Substack. Heather’s Substack: groundedinai.substack.com [TBC — confirm handle] Vacation Rental Formula Business School: vacationrentalformula.com ________________________________________________________________________________________________________ 📣 The AI Ambassador Program This episode is brought to you in part by our . If you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/40737150

VRS657 - When the Calendar Looks Full But the Business Is Bleeding with Sarah Stahl 04/01/2026

VRS656 - How STR Businesses Are Using Claude for Smarter Marketing and Better Workflows 03/25/2026

VRS656 - How STR Businesses Are Using Claude for Smarter Marketing and Better Workflows In this episode, Heather sits down with returning guest Jodi Bourne to talk about how short-term rental professionals can use Claude in practical, business-building ways. Rather than focusing on AI hype, this conversation digs into what actually matters: saving time, improving clarity, supporting creativity, and using tools like Claude to strengthen both operations and marketing. Jodi shares why she moved toward Claude, what makes it so useful in her day-to-day work, and how features like Projects, Skills, and Cowork can help STR operators stay organized, create more relevant content, and reduce repetitive work. A big theme throughout the discussion is that AI works best when it is set up with clear inputs. Jodi and Heather talk about the importance of structure, brand voice, and organized information, rather than expecting AI to magically produce great results without context. They also explore how Claude can support better marketing, from messaging and keyword-informed content to blog refreshes and more strategic brand communication. The episode also looks at the bigger picture: how hospitality businesses can use AI to create more space for creativity and better decision-making, without losing the human side of hosting. ________________________________________________________________________________________________________ 📣 STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And if you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/40572700

VRS655 - The Shift from Collecting Prompts to AI That Actually Knows Your Business 03/18/2026

VRS655 - The Shift from Collecting Prompts to AI That Actually Knows Your Business In this solo episode, Heather explores one of the biggest shifts happening in the AI space right now: the move away from relying on prompt libraries and toward building systems powered by context. A couple of years ago, prompt engineering was everything. People were collecting prompt packs, saving templates, and searching for the “perfect prompt” that would magically produce the right result. And at the time that made sense. Early AI tools needed much more structure, narrower inputs, and a lot more hand-holding. But things have changed. Today’s AI tools are better at understanding natural language, asking follow-up questions, inferring structure, and working inside persistent environments like projects, custom assistants, and knowledge bases. That means the real advantage no longer comes from having a huge library of prompts, it comes from giving AI the right context. Heather unpacks why prompt libraries are becoming less central, what should replace them, and how short-term rental professionals can start building smarter AI systems that actually reflect their business, voice, standards, and guest experience. If you’ve been wondering why AI sometimes still feels generic, even when you use “good prompts,” this episode will help you see what’s missing - and what to build next. ________________________________________________________________________________________________________ 📣 STRAIT Chat & the AI Ambassador Program This episode is brought to you in part by the - an exclusive space for short-term rental pros who want deeper conversations, smarter systems, and more collaborative learning. And if you're curious about using AI in your business - whether it's for guest communication, operations, or even marketing - check out our . It's designed to help you learn, lead, and get hands-on with the tools shaping the future of hospitality. 🌐 Learn more and join us at Are you listening to this podcast on the move? Get to the show notes here: /episode/index/show/cottageblogger/id/40490250

VRS654 - VRNation, Education, and the Next Chapter of the Vacation Rental Industry 03/11/2026

VRS653 - The Authority Shift: What AI Agents Mean for STR Leaders 03/04/2026

VRS652 - Structure Before Speed: The Smarter Way to Bring AI Into Your Business 02/25/2026

VRS651 - Trust, Conversions & The Direct Booking Mindset 02/18/2026

VRS650 - Amber Hurdle – Keeping the Human in the Loop: Building a Strategic AI-Driven Brand 02/11/2026

VRS649 - Sewn in Soil and Spirit – Designing Guest Experiences with Heather Dunwoody - A Book Direct Day Special 02/04/2026

VRS648 - Lead Better, Clean Smarter: The Coaches and Consultants Behind Vacation Rental Growth 01/28/2026

Vacation Rental Success

TOPICS