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Get Paid For Your Pad | Airbnb Hosting | Vacation Rentals | STR Revenue Management
AI Gives STR Hosts Unfair Advantage Over Competition
👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/report
Find out how much money your portfolio is leaving on the table. Risk-free.
What happens when a Head of Marketing rebuilds an entire company website in just one week... without knowing how to code?
In this episode of Get Paid For Your Pad, Eric Moeller and Kaye Putnam pull back the curtain on the AI revolution happening inside Freewyld Foundry right now, and explain why STR operators who don't adopt AI in 2026 will be left behind by competitors who do. From Claude bots creating their own social networks to revenue managers building fully functional client-facing tools in three hours, this episode reveals how artificial intelligence is fundamentally changing what's possible in short-term rental operations.
Eric and Kaye share their experience using AI in marketing, sales, and revenue management, including the tools they rely on, mistakes they’ve made, and the impressive results they’re already seeing. This episode offers a clear roadmap for spotting bottlenecks, learning AI without technical skills, and building internal solutions that save 15–20 hours per week while improving outcomes.
Kaye explains how she rebuilt a website in 10 days with no coding experience using Claude Code, while Eric highlights why leaders must understand AI now. They break down why “human-led, AI-powered hospitality” is the future of short-term rentals, how to avoid distractions with new tools, and why those who direct AI strategically will dominate their markets.
You will discover:
- Why STR operators must adopt AI now or fall permanently behind
- How to rebuild an entire website in one week without coding skills
- Why revenue management bottlenecks can be solved with AI in days, not months
- How to identify repeatable tasks in your business that AI can automate
- Why Claude Code is the #1 tool every STR leader should learn
- How AI agents are making decisions 24/7 and what that means for your business
- The difference between AI tools you buy vs AI solutions you build internally
- Why pattern recognition is the most valuable skill in the AI era
- How to hire AI engineers who direct tools instead of traditional developers
Eric and Kaye also explore the dangers of AI going rogue, why Freewyld Foundry is building proprietary revenue management tools that don't exist in the market, how AI enables real-time dashboards that pull data from multiple sources, and why the future belongs to operators who lead with human expertise but execute with AI power. They discuss market intelligence, proactive decision-making, and why small operators can now compete with large companies using the same technology.
đź’ˇ Topics Covered:
- AI adoption strategies for STR operators
- Claude Code tutorial and implementation guide
- Building internal automation tools without developers
- Revenue management AI and data analysis
- Identifying business bottlenecks and solving them with AI
- Pattern recognition and strategic thinking
- Hiring AI engineers vs traditional developers
- The future of short-term rental operations
- Human-led, AI-powered hospitality model
- Real-time dashboards and business intelligence
- Competitive advantage through early AI adoption
đź”— Relevant Links:
Learn more about Freewyld Foundry → https://www.freewyldfoundry.com
Follow Eric Moeller → https://www.linkedin.com/in/ericdmoeller
Follow Kaye Putnam → https://www.linkedin.com/in/kayeputnam
Follow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundry
Keywords: AI for Airbnb, artificial intelligence, short term rentals, Claude AI, Claude Code, STR automation, revenue management AI, vacation rentals, AI tools for hosts, property management automation, Airbnb operators, STR business growth, coding without developers, AI implementation, hospitality technology, competitive advantage, business automation, Freewyld, Freewyld Foundry, Eric Moeller, Kaye Putnam, AI revolution, STR profitability, operational efficiency, pattern recognition, AI agents, website development, revenue optimization
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735. STR Conferences: Are They Worth It and How to Get the Most Value
16:32||Ep. 735Short-term rental conferences are a big investment of time, money, and energy. Are they worth it? And if you go, how do you actually get the most out of them?Jasper shares 12 years of conference experience, from Airbnb Open in 2014 to GuestyVal Madrid and VRMA Nashville, with practical advice on how to maximize the value of any STR conference you attend.Want to outperform the market? Freewyld Foundry's Revenue and Pricing Management service is driving an average 19% performance lift for $1M+ STR operators, even in down markets. If you are managing 15+ listings and want a free pricing audit, apply here: freewyldfoundry.com/get-startedYou will learn:Why the operators who get the least value from conferences are the ones who show up without a plan, and what to think through before you book your ticketHow getting on stage or joining a panel changes the entire conference experience, saves you money on the ticket, and gives you automatic credibility before you say a wordWhy most operators underestimate how much value they have to share, and why you should apply for a speaking slot even if you are not sure you will get itHow to use the conference app to book meetings before you arrive, and why protecting your open time from aggressive vendors is just as important as who you scheduleWhat Freewyld Foundry is doing at VRMA Nashville: a workshop on building an AI revenue management agent (Tuesday 11:30 AM), a surprise in-person event Monday night, and a booth with free revenue auditsWe also talk about:The real value of going to a conference is not the sessions, it is the personal connections, and most people are too passive to make themHow VRMA compares to IMN and regional conferences, and which type fits your goalsWhy traveling with a baby has kept Jasper to two conferences in 2026, and what the European conference calendar looks like for 2027The energy and motivation from being around other operators is underrated, and why getting out of your day-to-day once or twice a year is worth it on its ownMentioned in the Episode:Freewyld Foundry Free Revenue Report: freewyldfoundry.com/get-startedVRMA Nashville: October 4-6, stop by the Freewyld Foundry boothEmail Jasper: jasper@freewyldfoundry.comSubscribe for new episodes every Monday on YouTube, Spotify, and Apple Podcasts.
734. Midterm Rentals: The Revenue Strategy Already Happening in Your Portfolio
35:49||Ep. 734Midterm rentals are already happening in your short-term rental portfolio. Most operators just are not being intentional about it yet. Frank Bosie, Senior Director of Partnerships at Hostfully, joins Jasper to break down the data, the economics, and the strategy behind adding midterm rentals as a revenue lever, without giving up your short-term rental business.Want to outperform the market? Freewyld Foundry's Revenue and Pricing Management service is driving an average 19% performance lift for $1M+ STR operators, even in down markets. If you are managing 15+ listings and want a free pricing audit, apply here: https://freewyldfoundry.com/get-started/39% of STR operators have already received at least one 30+ night booking. Midterm rentals represent only 1.7% of reservations but 20% of booked nights. You do not need many of them for them to meaningfully move your occupancy numbers, especially during low season.You will learn:Why midterm rentals are not a separate business model but a natural extension of what is already happening in most STR portfolios, and how to become intentional about itThe hybrid strategy that works better than going exclusively midterm: keep STR open, add long-stay discounts, and let demand self-selectHow to think about the occupancy crossover: why 100% MTR occupancy at $160/night generates roughly the same gross revenue as 53% STR occupancy at $315/nightWhich properties and markets are best suited for MTR, including proximity to hospitals, universities, military installations, and employer hubsWhat MTR guests actually need that vacation guests do not: fast wifi, a real workspace, full kitchen, laundry, storage, and the ability to live comfortably for 45 to 60 daysWhy new listings should not prioritize MTR first, and when the timing makes sense to add itWe also talk about:Hostfully's Furnished Finder integration: the first PMS to connect with Furnished Finder, currently in beta, with calendar sync, guest communication, and payment management coming through the same systemHow MTR nightly rates vary dramatically by market: California averages 95% of STR rates, while Connecticut and Pennsylvania average around 30 to 35%The tenancy regulation risk in some markets where a guest staying 30+ nights may gain renter rights, and how smart operators are navigating itFrank's data on portfolio size and MTR activity: 7.3% of single-property operators have MTR bookings, jumping to 69% for operators managing 6 to 20 properties and over 80% for larger portfoliosTop MTR operators averaging 8 active distribution channels compared to 4.8 for non-MTR operators, and why fragmented demand requires broader distributionJasper's personal experience staying in his own Colombian Airbnb for three months and the improvements he made for long-stay guests, including a standing deskWhy the operational cost savings of MTR (fewer turnovers, fewer cleanings, fewer check-ins) matter as much as the nightly rate when evaluating the economicsMentioned in the Episode:Freewyld Foundry Free Revenue Report: https://freewyldfoundry.com/get-started/Hostfully: https://www.hostfully.comFurnished Finder: https://www.furnishedfinder.comFreewyld Foundry at VRMA Nashville: October 4-6, stop by the boothEmail Jasper: jasper@freewyldfoundry.comSubscribe for new episodes every Monday on YouTube, Spotify, and Apple Podcasts.
733. August 2026 STR Market Update: 16% Growth While the Market Declined 2.5%
20:13||Ep. 733The August 2026 STR Market Update is here. Every month, Jasper shares exactly what we are seeing across 70+ client portfolios: which markets are up, which are down, what has changed on the platforms, and what we are doing about it. Real numbers, real portfolios, no fluff. Think of it as the monthly briefing you did not know you needed.Want to outperform the market? Freewyld Foundry's Revenue and Pricing Management service is driving an average 19% performance lift for $1M+ STR operators, even in down markets. If you are managing 15+ listings and want a free pricing audit, apply here: https://freewyldfoundry.com/get-started/August was the highest-impact month to date for Freewyld Foundry. Comparable client listings, meaning properties that were active in both August 2025 and August 2026, were up 16.3% year over year while the broader market averaged a 2.5% decline. Combined, that produced a 19.3% impact and just over $2.1 million in additional revenue for clients. One number worth noting: Labor Day weekend fell in August last year and in September this year. If your own August numbers are down 5-10%, that shift is likely the primary explanation. The flip side is that September is already pacing well ahead.You will learn:Why Freewyld Foundry clients grew 16.3% in August while the broader market declined 2.5%, and how comparable-unit tracking gives you a clear picture of true performanceThe OTA discount stacking problem that is quietly eroding effective rates across Airbnb and VRBO, and how to calculate the right channel markup to protect your floorHow to position your low season pricing right now to capture midterm rental demand before snowbird bookings dry upWhy Airbnb's new AI pricing model should be treated with skepticism, and what the 15.5% host-only fee rollout means if you are not on a PMSWhat VRBO's new sponsored listings feature is, how the bidding works, and why early movers may get the cheapest visibilityWe also talk about:The markets that declined the most in August: Branson MO (-25%), Chattanooga TN (-25%), Myrtle Beach SC (-20%), Fredericksburg TX (-20%), Kansas City MO (-16%)Markets that grew: San Antonio TX (+13%), Columbus OH (+12%), Milwaukee WI (+11%), Canada and select European markets (+15%)Airbnb's record Q2 earnings (revenue up 17%, hotel bookings growing 3x faster than homes) and what it signals about where the platform is headingHow VRBO discounts stack differently than Airbnb discounts, and why Booking.com is in a category of its own for complexityThe full fall conference calendar: GuestyVal Madrid, Skift Global Forum NYC, VRMA Nashville, Host Expo Bogota, Vacation Rental World Summit Lyon, Direct Booking Success Summit (online), Skillfest BarcelonaMentioned in the Episode:Freewyld Foundry Free Revenue Report: https://freewyldfoundry.com/get-started/Midterm rental episode with Frank at Hostfully: search Get Paid for Your PadEmail Jasper: jasper@freewyldfoundry.comFreewyld Foundry at VRMA Nashville: October 4-6, stop by the boothSubscribe for new episodes every Monday on YouTube, Spotify, and Apple Podcasts.
732. Secrets of a Pro STR Revenue Manager | ft. Patrick Morton
27:55||Ep. 732Patrick Morton capped one of his properties at $650 a night. He thought that was what it was worth. Then he joined Freewyld Foundry, removed the ceiling, and watched it book at $1,000.In this episode, Jasper sits down with Patrick, one of Freewyld Foundry's own revenue managers, for a look at what actually moves the needle: pricing, listing optimization, and the tactics the team has discovered by managing hundreds of properties together.You will learn:Why setting a maximum price on your listing is costing you bookings, and what Patrick found when he removed the ceiling on his own propertyHow Patrick grew one OR Getaways property from $39,000 to $55,000 in a single month by holding prices and trusting the dataWhy high ratings and strong reviews are no longer enough to rank at the top of Airbnb search, and what actually moves the needle nowThe single amenity Patrick added to a listing that moved it from page 8 to page 3 overnightWhy the answer when a listing is stuck at minimum price with zero bookings is sometimes to raise the priceWe also talk about:How Airbnb custom promotions can create visibility and urgency without actually lowering your effective priceWhat Jasper learned about hiring for values over skills after years of building the Freewyld Foundry teamHow the weekly team brainstorm with ten revenue managers in one room produces better strategies than any individual could find alonePatrick's full circle moment: from assembling furniture and listening to this podcast to sitting across from Jasper as a guestMentioned in the Episode:Free Revenue Audit: freewyldfoundry.com/get-startedCareers at Freewyld Foundry: freewyldfoundry.com/careersFavorite Takeaway:"It's not really up to us to decide what the property is worth. It's the person that books who decides."Want us to audit your pricing strategy?Get your free, personalized revenue report at freewyldfoundry.com/get-started
731. Using AI to Optimize Your STR Pricing
28:29||Ep. 731Jasper sits down at his laptop and shows you exactly how to use Claude to find pricing opportunities in your portfolio, from scratch, in under 30 minutes. No prior AI experience needed. Just PriceLabs and a question.He walks through a live working session: uploading a single CSV from PriceLabs, asking targeted questions to find overpriced and underpriced nights, and using pacing data to flag periods where the market is booking and you are not.Freewyld currently manages over 4,000 properties across 75+ clients worldwide and $200 million in annual bookings. That data set informs every recommendation in this episode.You will hear:Why AI should support a revenue manager's decisions, not replace them, and how Jasper's team uses it at Freewyld Foundry todayThe problem with 365 price points per listing and why a human can only realistically review 5 to 10% per dayHow to download your neighborhood data from PriceLabs and the exact chart options to have selected before you exportHow to prompt Claude to identify dates where you are currently priced 20% or more above the highest price you have ever booked atHow to refine that analysis to compare like-for-like days: weekdays to weekdays, weekends to weekends, and special events to special eventsWe also talk about:How to flip the question and find nights where you are priced below what similar days have historically booked atHow to use pacing data to flag periods where the market is already getting bookings and your calendar has nothing yetHow to use Claude's voice input mid-session and how to teach it the output format you actually wantHow Jasper's team runs this analysis automatically every day across the full portfolioMentioned in the Episode:PriceLabs: pricelabs.coFree Revenue Audit: freewyldfoundry.com/get-startedEmail Jasper: jasper@freewyldfoundry.comFavorite Takeaway:"We got to combine the AI and the human being, put them together. And as a team, they can make better decisions than a single human being or a single AI tool."
730. How to Optimize Your Pricing for Shoulder Season
27:55||Ep. 730Jasper breaks down one of the trickiest parts of STR pricing that most operators never fully figure out: shoulder season. Low season and peak season have clear playbooks. Shoulder season is different. The weekday-weekend gap widens, occupancy swings from week to week, and the wrong settings in your pricing tool can quietly cost you revenue all the way through fall.Freewyld currently manages over 4,000 properties across 75+ clients worldwide and $200 million in annual bookings. That data set informs every recommendation in this episode.You will hear:How to define your four seasons using occupancy thresholds: low (below 50%), shoulder (50-70%), high (70-90%), and peak (above 90%)Why shoulder season is harder to price than both low and peak season, and what makes it behave differently from everything else on the calendarHow to read a future occupancy graph to identify exactly when your shoulder season starts and ends in your specific marketThe weekday vs. weekend swing that defines shoulder season, and why a one-size-fits-all minimum stay strategy usually leaves money behindHow to set up custom seasonal profiles in PriceLabs: percentage vs. fixed pricing, minimum stay profiles by season, and check-in and checkout restrictionsDay-of-week price adjustments Jasper's team uses in shoulder season, including typical ranges for each dayWe also talk about:Why forcing longer minimum stays during shoulder season usually cuts demand without adding revenue, and what to do insteadHow to download a PriceLabs seasonal profile as a CSV, edit it, and upload it across multiple units without starting from scratchHow Jasper's team used Claude to generate 20 seasonal profile CSVs for a client in a fraction of the time it would have taken manuallyMentioned in the Episode:PriceLabs: pricelabs.coFree Revenue Audit: freewyldfoundry.com/get-startedEmail Jasper: jasper@freewyldfoundry.comFavorite Takeaway:"Be careful that you don't make your strategy too complicated. Only add complications if you're very confident it's going to increase your revenue. The challenge I see with some operators is they make it so complicated that their strategy becomes completely ununderstandable. You just don't know anymore why the prices are where they are."
729. Which Distribution Channels Should You Be On to Maximize Your Revenue
25:42||Ep. 729In today's episode, Jasper tackles one of the most common questions STR operators ask: which distribution channels should you actually be on to maximize your revenue? He walks through the full picture, from the history of each major platform to a practical framework for deciding where to list based on your market, your stage, and your goals.Freewyld currently manages over 4,000 properties across 75+ clients worldwide and $200 million in annual bookings. That data set informs every recommendation in this episode.You will hear:How VRBO, Booking.com, and Airbnb each got started, and why the founding story of each platform still explains the type of guest using it todayUS market share data from 2024-2025: Airbnb at 43%, Direct at 28%, VRBO at 28%, Booking.com at 8%, and why Europe looks completely differentThe three factors Jasper weighs when advising clients on channel selection: risk, revenue, and operational complexityWhy concentrating all bookings on Airbnb creates compounding momentum and search visibility, and when that tradeoff is worth itWhy Jasper considers Airbnb and Direct to be must-haves for almost every operator regardless of marketHow to evaluate whether VRBO or Booking.com is worth adding in your specific market, and what to look for before making that callWe also talk about:Why a guest email list is the one asset no OTA can take from you, and how to start building it from your first bookingBooking.com's growing push into the US market, its reputation for complexity, and how the platform has improved in recent yearsWhy adding channels beyond the big four rarely moves the needle and almost always adds operational costMentioned in the Episode:Free Revenue Audit: freewyldfoundry.com/get-startedEmail Jasper: jasper@freewyldfoundry.comFavorite Takeaway:"Don't build your business on somebody else's land. If you're only using Airbnb, Airbnb can block your account, they can ban you as a user. If you built your business solely on Airbnb, you're taking risk because you have no control over what Airbnb decides to do."
728. July Market Update: World Cup Impact, July Pacing, and Airbnb's New 15% Discount
20:13||Ep. 728The July market update is here! The World Cup had less impact than expected, Airbnb just dropped a new discount every operator needs to understand, and there are moves you should be making right now for August.In this Rev Up episode, Jasper shares what happened across STR markets in July, breaks down which cities the World Cup actually moved, and covers the new Airbnb discount that changes how you think about OTA pricing strategy.You will hear:Portfolio results for the month: comparable listings up 22.36% year over year, $14.4 million in total revenue generated for clientsWhy the broader market only moved 9% during the World Cup, and which cities actually outperformed (Dallas +40%, Kansas City +44%, Miami +28%, Philadelphia +20%)July pacing: Freewyld portfolios currently up 29.8%, markets up 5%Why August weekdays are already softening and which weeks to reprice before it is too lateWhy extending your booking window is where most operators leave money on the tableAlso covered:Airbnb's new 15% discount for top-rated guests (4.8+ rating, 3+ reviews), how it stacks with other discounts, and how to think about the pricing mathThe mobile-only discount reportedly rolling out in select marketsWhy OTA discount strategy is becoming its own discipline within revenue managementMentioned in the Episode:Free Revenue Report: freewyldfoundry.com/get-startedEmail Jasper: jasper@freewyldfoundry.comGet Paid For Your Pad is the number one podcast for short-term rental operators who want to maximize revenue and run a professional business.New episodes every Monday.Subscribe on Apple Podcasts, Spotify, and all major platforms.
727. 3 Ways to Get Good at Revenue Management
19:19||Ep. 727Revenue management is a specialty skill set. If you do not invest in learning it, you are leaving 10 to 40 percent of revenue on the table every year.In this Rev Up episode, Jasper breaks down the three pillars of actually getting good at revenue management: experience, resources, and community. Whether you are doing it yourself, considering hiring in-house, or evaluating a third-party service, this episode gives you a clear framework for making the right decision and developing the skill the right way.You will hear:The three options for filling the revenue management seat in your STR business and how to think through which one fits your situationWhy there is no substitute for experience in revenue management and what blocking daily time for pricing actually looks like in practiceHow to evaluate resources and avoid learning from content that is marketing material disguised as educationWhy community accelerates learning and how to structure a mastermind with operators in non-competing marketsWhy switching between revenue management approaches too often is one of the most costly mistakes operators makeWe also talk about:The full resource library at freewyldfoundry.com including workshops, guides, podcast episodes, and blog postsWhy PriceLabs updates its tool constantly and why staying current on your pricing tool is as important as understanding the strategyWhy it takes a full year to truly learn a portfolio and why long-term commitment to any RM approach is the only way to see real resultsMentioned in the Episode:Freewyld Foundry workshops and guides: freewyldfoundry.com/resourcesPriceLabs resource library: pricelabs.coFree Revenue Report: freewyldfoundry.com/get-startedGet Paid For Your Pad is the #1 podcast for short-term rental operators who want to maximize revenue and run a professional business.New episodes every Monday.Subscribe on Apple Podcasts, Spotify, and all major platforms.