Get Paid For Your Pad | Airbnb Hosting | Vacation Rentals | STR Revenue Management

Epizode

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  Midterm Rentals: The Revenue Strategy Already Happening in Your Portfolio 14.09.2026 35min

  Midterm 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: [email protected] for new episodes every Monday on YouTube, Spotify, and Apple Podcasts. Hosted on Acast. See acast.com/privacy for more information.
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  August 2026 STR Market Update: 16% Growth While the Market Declined 2.5% 07.09.2026 20min

  The 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: [email protected] Foundry at VRMA Nashville: October 4-6, stop by the boothSubscribe for new episodes every Monday on YouTube, Spotify, and Apple Podcasts. Hosted on Acast. See acast.com/privacy for more information.
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  Secrets of a Pro STR Revenue Manager | ft. Patrick Morton 31.08.2026 27min

  Patrick 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 Hosted on Acast. See acast.com/privacy for more information.
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  Using AI to Optimize Your STR Pricing 24.08.2026 28min

  Jasper 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: [email protected] 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." Hosted on Acast. See acast.com/privacy for more information.
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  How to Optimize Your Pricing for Shoulder Season 17.08.2026 27min

  Jasper 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: [email protected] 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." Hosted on Acast. See acast.com/privacy for more information.
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  Which Distribution Channels Should You Be On to Maximize Your Revenue 10.08.2026 25min

  In 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: [email protected] 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." Hosted on Acast. See acast.com/privacy for more information.
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  July Market Update: World Cup Impact, July Pacing, and Airbnb's New 15% Discount 03.08.2026 20min

  The 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: [email protected] 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. Hosted on Acast. See acast.com/privacy for more information.
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  3 Ways to Get Good at Revenue Management 27.07.2026 19min

  Revenue 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. Hosted on Acast. See acast.com/privacy for more information.
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  From One Beach House to a 20-Person Custom Build: David Dodge on STR Portfolio Growth and Earning 1.4M Travel Points From Your Mortgage 21.07.2026 27min

  In today's episode, Jasper sits down with David Dodge, founder of OR Getaways and Freewyld RPM client, for a conversation about what it looks like to build a high-performing vacation rental portfolio from the ground up and a platform called Built that lets real estate investors earn travel points on their mortgage payments.David started in Lincoln City, Oregon in 2021 with one five-bedroom property. Three years later he is running a custom-built property that sleeps 20, a new development in progress, and a management company with two client properties. His portfolio is up 25% year over year, July over July.You will hear:How David went from one off-the-shelf five-bedroom to a custom-built 20-person property designed specifically for short-term rental performanceWhy larger properties produce dramatically better ROI in his market and how the Ebb and Flow duplex structure unlocks occupancy beyond Lincoln City's 16-guest capWhat changed when he handed revenue management to Freewyld: the risk tolerance shift that turned available summer weekends into premium bookings instead of discounted last-minute fillsHow BILT works and why $22,000 in monthly mortgage spend generates 739,000 points per year that transfer to 1.4 million travel points on rent dayThe math behind redeeming BILT points for international business class versus economy versus cash toward a down paymentWe also talk about:David's next development: a custom 8-bed that sleeps 24, a planned yoga studio for retreat bookings, and a spa with cold plunge and saunaWhat an actuary background taught David about pricing and where the risk tolerance gap between self-managing and professional management shows up mostWhy flexibility is the key to getting outsized value from travel pointsMentioned in the Episode:BILT points calculator built by David (link to be added)OR Getaways on LinkedIn: David DodgeFree Revenue ReportFavorite Takeaway:"I like to close. I want the certainty of the property being booked. What working with Freewyld has done is just following the methodology. The demand signals are there. Keep the price higher for longer. That has been a huge difference." Hosted on Acast. See acast.com/privacy for more information.
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  June Market Update: World Cup Impact, New Airbnb Discounts, and What's Coming in July 13.07.2026 25min

  June's Market report. Freewyld's portfolios closed the month up 22.36% year over year, $14.4M in revenue generated across 75+ client properties. The market averaged 9%. That's a 13-point gap, and Jasper breaks down exactly where it came from. World Cup month delivered for some cities, not for most. Jasper pulls the numbers market by market, covers what's coming in July, and gets into a new Airbnb discount that just quietly launched and could affect how you price.You will hear:How Freewyld portfolios outperformed the market by over 13 percentage points on comparable units in JuneWhich World Cup host cities actually moved the needle, and why the overall market only lifted 9% despite the largest sports event in historyThe markets that surprised on the upside: Kansas City up 44%, Dallas up 40%, Miami up 28%, Philadelphia up 20%Why managing the full booking window is where the real revenue advantage is built, not last-minute discountingAirbnb's new top-rated guest discount: 15% off for guests with a 4.8+ rating and 3+ reviews, what it stacks with, and how to think about itWe also talk about:Markets that underperformed in June: Calgary down 20%, Grand Canyon down 14%Reports of a new mobile-only discount appearing on Airbnb, and why OTA discounting is becoming a bigger variable in your revenue strategyWhat to watch heading into July and the second half of summerMentioned in the Episode:Freewyld Foundry Revenue Report: https://freewyldfoundry.com/get-startedAirbnb top-rated guest discount (new feature in host dashboard)Favorite Takeaway:"The portfolios that outperformed weren't doing anything magical. They were just booked earlier. When you manage the full window, you're not competing for the scraps."Want us to audit your pricing strategy?Get your free, personalized revenue report at https://freewyldfoundry.com/get-started Hosted on Acast. See acast.com/privacy for more information.
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  Best PMS Systems for STR Revenue Management 06.07.2026 21min

  Choosing the wrong PMS doesn't just cause operational headaches. It limits the revenue strategies you can run. Jasper Ribbers manages revenue for 75+ STR companies worldwide and has worked inside nearly every PMS on the market. Most of them cause complications. A handful don't.In this solo RevUp episode, Jasper walks through the five PMS systems Freewyld Foundry recommends, the exact criteria they use to evaluate every system, and why the wrong choice now can cost you years of workarounds as you scale.You will hear:Why switching PMS systems is one of the most disruptive moves in any STR business, and how to avoid ever having to do it twiceThe five systems Freewyld Foundry recommends: Guesty, HostAway, Hostfully, OwnerRez, and Hospitable, and what makes each one stand outWhy Guesty is Jasper's top pick and what separates it from the rest of the marketHow OwnerRez compares as a budget-friendly option, and the one limitation to know before you sign upWhy OTA-native discounts (early bird, last minute, length of stay) are becoming a core revenue strategy, and why your PMS has to support themWe also talk about:Why Hostfully is the system Freewyld actually uses internally, sloth mascot and allWhat to look for in a PriceLabs integration before you commit to any PMSWhy simplicity in your tech stack matters more at 50 units than it does at fiveHow AI is changing reporting, and why that shifts the criteria for choosing a PMSOne newer system Jasper is keeping an eye on: BoomMentioned in the Episode:Guesty: https://guesty.comHostAway: https://hostaway.comHostfully: https://hostfully.comOwnerRez: https://ownerrez.comHospitable: https://hospitable.comPriceLabs: https://pricelabs.coFavorite Takeaway:"Simplicity is huge when you scale. Things that don't cause a challenge when you have five or ten units might cause a challenge when you have 50. Every single step that you can avoid, every little action item, you want to eliminate it."Want us to audit your pricing strategy?Get your free, personalized revenue report at FreewyldFoundry.com/get-started Hosted on Acast. See acast.com/privacy for more information.
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  How to Outsource Revenue Management Without Losing Control 29.06.2026 28min

  After reviewing more than 1,000 companies applying for revenue management at Freewyld Foundry, Jasper keeps seeing the same costly mistake: operators outsource before they're set up for success. The result is wasted time, wasted money, and a bad experience for everyone involved. In this RevUp episode, Jasper walks through the full checklist of what you need to have in place before you hand off revenue management, whether you're hiring in-house or working with a service company.You will hear:Why revenue management is too specialized to juggle as a founder once you're past $1M in bookings, and too risky to leave to a cheap hireThe mindset shift you need before outsourcing: the difference between leading a revenue manager and micromanaging oneHow to define the real constraints in your business (minimum prices, turnover restrictions, blackout dates) without letting personal opinions limit your revenue manager's ability to performWhat a real in-house hiring process looks like: a structured job description, multiple interview rounds, test tasks, onboarding, and a coverage plan for when your hire is sick, offline, or quitsHow to evaluate a service provider: experience, team size, whether they're operators themselves, and whether they manage pricing in your tool or theirsWe also talk about:Why hiring cheap for revenue management is a false economy, and what great revenue managers actually cost on the marketThe transparency red flag: any company that manages pricing in their own account and won't give you access is a problemWhat good ongoing support looks like: daily Slack access, weekly Zoom calls, and a live dashboard you can check any timeWhy total portfolio revenue growth is a misleading KPI and how to compare performance correctly using only units that were active the prior yearFavorite Takeaway:"The more freedom your revenue manager has to do their job, the fewer restrictions you put on them, the higher your revenue is going to be."Want us to audit your pricing strategy?Get your free, personalized revenue report at FreewyldFoundry.com/report Hosted on Acast. See acast.com/privacy for more information.
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  7 Hidden PriceLabs Features Most Hosts Are Not Using 22.06.2026 18min

  Most PriceLabs users are only scratching the surface. In this episode, Jasper walks through seven features and functionalities that he keeps seeing go unused, many of them request-only, which is why most operators don't even know they exist. From combined listings that fix your KPIs when you have master listings, to check-in and check-out profiles that keep your calendar clean, these are the settings that separate operators who are guessing from operators who are optimizing.You will hear:Combined listings: how to route revenue from a master listing back to individual units so your KPIs don't get distortedSubgroups: how to organize your portfolio by both market and bedroom size at the same timeHow to upload historic booking data directly to PriceLabs when your old PMS didn't transfer it overSafety minimum price: what it does, why it can backfire on weekday dates, and how to turn it offForecasting in Report Builder: how to see PriceLabs' revenue and occupancy projections for the year aheadRental revenue formula: how to customize what counts as revenue so your reports reflect what actually matters to your businessCheck-in and check-out profiles: the cleaner way to restrict turnovers on holidays without cluttering your calendar with overridesWe also talk about:Which features are request-only and require contacting PriceLabs support to activateWhy the control panel is the second step after requesting a feature (it still has to be toggled on)Why equal revenue splitting across units doesn't always reflect real-world value differencesHow to use Claude to format historic booking data into the PriceLabs CSV templateMentioned in the Episode:PriceLabs: https://pricelabs.coFavorite Takeaway:"Some of these features are request only. They don't show up in PriceLabs unless you actually reach out to PriceLabs support. And when we ask operators if they're using them, the answer is usually: oh, I didn't know you could do that."Want us to audit your pricing strategy?Get your free, personalized revenue report at FreewyldFoundry.com/get-started Hosted on Acast. See acast.com/privacy for more information.
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  FIFA World Cup Update: The Demand That Disappeared 15.06.2026 17min

  The FIFA World Cup is here, but the demand everyone was counting on hasn't shown up. In this Rev Up episode, Jasper pulls real data from Price Labs dashboards across every major host city to show what's actually happening, why it happened, and what STR operators should do right now to protect their revenue.Occupancy is down in every single host city compared to last year. Dallas, Kansas City, Houston, Vancouver - all down 10 to 15 points. ADRs are up, but not enough to compensate. Jasper explains the two main reasons: regular travelers are avoiding World Cup cities because prices are too high, and international visitors haven't arrived in the numbers anyone expected.You will hear:Why occupancy is down 10-15 points in major host cities despite the biggest soccer event in the worldReal market data: Dallas, Kansas City, Houston, and Vancouver compared to last yearWhy high airfare and accommodation costs are keeping both local and international travelers awayHow visa fears and immigration news stories are suppressing international travel to the USWhy July is still shaping up to be a strong month overall, up 14% on average across marketsWe also talk about:Why the group stage requires a competitive pricing approach right nowWhy the knockout rounds could still bring a surge if big football nations like Brazil, Germany, France, or England advanceWhy being in the stadium for your country's potential World Cup win is worth any priceMentioned in the Episode:Price Labs: https://pricelabs.coWant us to audit your pricing strategy?Get your free, personalized revenue report at FreewyldFoundry.com/get-started Hosted on Acast. See acast.com/privacy for more information.
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  How to Allow Pets in Your STR Without the Risk (With John Bradford) 12.06.2026 27min

  Most vacation rental hosts either ban pets entirely (leaving bookings on the table) or accept all animal claims without verification (leaving pet fees on the table). John Bradford, founder of Pet Screening, reveals that 60% of emotional support animal claims don't meet federal standards, meaning hosts waive fees when they legally shouldn't. His platform manages pet policies for one out of every seven rentals in America, helping hosts capture legitimate pet revenue while navigating complex ADA and Fair Housing laws.John shares why service animal fraud hurts people who legitimately need assistance animals, how visiting pets create liability even when guests don't own animals, and why being more pet-friendly actually increases revenue without increasing risk.YOU WILL HEAR:Why 60% of emotional support animal claims fail federal standards and how hosts lose pet revenue by accepting fraudulent documentationWhat two questions you can legally ask when someone claims a service animal (and how to challenge answers that don't meet ADA standards)How visiting pets create liability even when the booking guest doesn't own an animalWhy post-reservation verification takes minutes but never slows down your booking rateWhat documentation you can request for ESAs versus service animals (the laws are completely different)WE ALSO TALK ABOUT:How Pet Screening verifies ESA healthcare provider letters through phone calls, emails, and faxesWhy federal law prevents states from making assistance animal requirements more restrictiveThe difference between ADA service animals and Fair Housing ESAsHow hosts using verification tools become more pet-friendly because they can confidently manage riskWhy there are more pets than children under 18 in American households and what that means for your businessRESOURCES:Pet Screening: https://petscreening.comFAVORITE QUOTE:"60% of the people who say they have an ESA do not meet the standard. If you're just accepting it without review, you're missing out on pet revenue because really it's a pet." Hosted on Acast. See acast.com/privacy for more information.
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  May STR Market Update: 22% Revenue Growth and What's Actually Working 08.06.2026 25min

  In May 2026, Freewyld Foundry drove $9.3 million in revenue for client portfolios, a 22% increase over the same month last year. The market? Up only 4.5%. That's a 16.75 percentage point outperformance driven by AI-enhanced pricing tools and strategic use of Airbnb's new seasonal cancellation policies.Managing 4,000+ listings across 75 portfolios worldwide, Jasper Ribbers reveals the exact systems that made this record month possible. He breaks down how internal AI tools analyze 9,000 pricing data points per 25-unit portfolio, why flexible cancellation policies are driving booking velocity (despite operator fears), and how to escape the last-minute pricing trap that costs operators 30-50% in revenue.Plus: Why World Cup host cities are seeing LOWER occupancy than last year, which markets surged 20%+ in May, and the two seasonal cancellation strategies that unlock Airbnb's search algorithm favor.You will hear:Why managing 9,000 pricing decisions per 25 units is impossible for humans but perfect for AI-enhanced revenue managementHow to increase occupancy by 7 percentage points while simultaneously increasing ADR (most operators think this is impossible)The exact seasonal cancellation policy strategies that drove sharp booking increases across 75 portfoliosWhy World Cup demand is a mirage and how operator greed is deterring regular travelers without attracting event demandHow to split your portfolio into "comparables" and "exclusives" to track real performance versus market noiseWe also talk about:Market performance breakdown: Canada up 20%, Dallas down 17%, and what that means for JuneThe "last-minute trap" that forces you to compete in price-dropping races instead of booking early at premium ratesWhy Airbnb now heavily favors flexible cancellation policies in search rankings (and how to use that without risk)Mentioned in the Episode:Freewyld Foundry Revenue Report: https://freewyldfoundry.com/get-startedClaude AI: https://claude.aiAirbnb seasonal cancellation policies (new feature in host dashboard)Favorite Takeaway:"If you have 25 units and your calendar is open for 12 months, you're managing 9,000 data points. Your goal is for each of those 9,000 data points to be optimal. That's where AI comes in. Our tool can scan the entire calendar and tell us exactly what dates we should be looking at."Want us to audit your pricing strategy? Get your free, personalized revenue report: https://freewyldfoundry.com/get-started Hosted on Acast. See acast.com/privacy for more information.
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  How to Maximize Revenue on Peak Demand Dates 01.06.2026 22min

  Most short-term rental operators focus on pricing their low and shoulder seasons, checking rates a few months out and calling it good. But the dates that actually matter - your Thanksgiving weekends, your local festivals, your New Year's Eve inventory - those are being booked right now at prices you set a year ago and forgot about. Jasper Ribbers reveals why 90% of the portfolios Freewyld Foundry onboards have already lost thousands of dollars to bookings made too far in advance at inadequate rates.Peak demand dates have booking windows up to 12 months long, but most operators only monitor pricing a few months ahead. When your calendar opens for next year's big concert or recurring festival, eager travelers immediately lock in underpriced units while you're still focused on next month's occupancy. The gap between when guests book and when operators pay attention is costing serious money.This episode breaks down the specific strategies Freewyld uses across 75 client portfolios to capture premium rates on high-value dates without leaving inventory empty. You'll learn why you should actually pace behind the market on peak dates (the opposite of shoulder season strategy), how to set minimum price safeguards that prevent last-minute discounting algorithms from destroying your revenue, and when the "last man standing" approach is worth the risk versus when it'll cost you clients.You will hear:Why 90% of new client portfolios already have bookings at too-low rates before Freewyld even starts managing them (and how to prevent this on your highest value dates)How to price peak demand dates 12 months in advance when pricing tools fail and the acceptable ADR range is 5x wider than normal weekendsWhen to intentionally pace behind market occupancy rates instead of capturing your fair share of early bookings (and why underpriced competitors are actually helping you)What minimum price settings actually do and why adjusting them is more critical than live pricing for preventing last-minute discount disastersHow the "last man standing" strategy captured $1,700 for a 2-bedroom World Cup apartment a year in advance (versus current rates much lower as the event approaches)We also talk about:The owner relationship dilemma when 48 units book at premium rates but 2 stay empty during the market's biggest eventWhy opening your calendar more than 12 months in advance creates more problems than revenue in markets with recurring eventsHow to use seasonal profiles instead of calendar overrides to automatically copy peak pricing strategy year over yearThe compensation guarantee framework that protects portfolio-wide premium pricing while keeping individual owners happyWhich markets and events justify the extreme monitoring approach (tracking every competitor property daily in a spreadsheet)Mentioned in the Episode:PriceLabs Seasonal Profiles: https://pricelabs.coFreewyld Foundry Revenue Management: https://freewyldfoundry.com/ytFavorite Takeaway:"90% of the portfolios that we onboard, we look at pricing in the next 12 months, and there's usually a few dates where we already have some bookings at a way too low ADR."Want us to audit your pricing strategy?Get your free, personalized revenue report at https://freewyldfoundry.com/yt Hosted on Acast. See acast.com/privacy for more information.
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  FIFA World Cup 2026: The STR Demand Reality Check (And How to Adjust Your Strategy Now) 25.05.2026 19min

  The 2026 World Cup was supposed to be the gold rush event for STR hosts across 11 US cities. Hotels and short-term rental operators penciled in massive premiums, expecting international travelers to flood cities from Seattle to New York. But just weeks before kickoff on June 11th, a stunning reality is emerging: 80% of hotels across 200 properties report bookings tracking below forecasts. Some cities are seeing lower demand than last year, despite hosting the world's biggest sporting event.Jasper Ribbers breaks down why the expected windfall is evaporating and what's actually happening on the ground. Visa uncertainty, $10,000 total trip costs for international travelers, and ecosystem-wide price increases (New Jersey Transit raised stadium round-trip tickets from $13 to $105) have created barriers that even die-hard soccer fans can't overcome. But here's the bigger problem: hosts keeping prices at 2x to 5x normal rates aren't just missing World Cup bookings. They're actively driving away regular summer travelers who would normally visit Houston, Dallas, or Philadelphia but are now choosing other destinations to avoid inflated rates.The good news? There's still significant money to be made, but it requires a two-phase strategy. Freewyld has shifted to aggressive pricing for group stage games (June 11 through early July) and is still capturing 50% to 200% premiums by getting ahead of the curve. For knockout stage games starting in July, the strategy flips completely. You'll discover why protecting elevated rates makes sense for elimination rounds, how to predict which teams will play where by following group standings, and why early December bookings at "crazy prices" face massive cancellation risk that creates rebooking opportunities.You will hear:Why 80% of hotels across 11 World Cup host cities are tracking below booking forecasts, with some dates showing less demand than last yearHow elevated STR pricing is creating a double displacement effect, driving away both international World Cup travelers and regular domestic summer visitorsThe specific two-phase pricing strategy Freewyld uses: aggressive rates for group stage games (known schedules) versus protected pricing for knockout rounds (unknown matchups)Why early December bookings at peak rates face high cancellation risk and how to set elevated minimum prices to capture rebooking opportunitiesHow to use PriceLabs neighborhood data to find the medium booked price and position competitively in markets still offering availabilityWhy international demand collapsed: visa uncertainty, $5,000 to $10,000 total trip costs, and rising flight prices from oil market volatilityThe Qatar 2022 precedent: how FIFA gave away free tickets and team jerseys to fill stadiums and avoid the embarrassment of empty seatsWe also talk about:Why the New Jersey Transit Authority raising round-trip stadium tickets from $13 to $105 exemplifies ecosystem-wide pricing barriersHow to follow group stage scores and standings to predict knockout matchups 5 to 7 days before games are playedWhy regular travelers to cities like Houston or Seattle are choosing alternative summer destinations due to World Cup pricingThe specific 11 US host cities experiencing demand shortfalls and which games might still command premiumsHow to audit your existing World Cup bookings for cancellation policy risk (flexible and moderate policies most vulnerable)Why playing "last man standing" with elevated rates will likely result in empty inventory instead of premium bookingsMentioned in the Episode:Fortune Magazine: https://fortune.com (World Cup hotel booking analysis)PriceLabs neighborhood data and medium booked price feature: https://pricelabs.coFree Revenue Report (get your pricing audited): https://freewyldfoundry.com/get-startedFavorite Takeaway:"We don't want to gamble on the last couple of weeks. We don't want to gamble on international travel really increasing in the last couple of weeks and just keeping the prices these really high levels in the hope that the demand is still coming, because in my opinion, that's taking a big risk."Want us to audit your World Cup pricing strategy? Get your free, personalized revenue report at FreewyldFoundry.com/get-started Hosted on Acast. See acast.com/privacy for more information.
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  3 Mistakes Short-Term Rental Operators Make That Leave Money on the Table 18.05.2026 13min

  You just celebrated your best booking month ever. Your properties hit 90% occupancy and you're feeling great about it. But here's the uncomfortable truth: you probably left $10,000 or more on the table. And the math proves it.In this episode, Jasper Ribbers breaks down the occupancy trap that catches almost every STR operator. He shows why 90% occupancy at $100/night generates less revenue than 67% occupancy at $200/night. Through 14 years of revenue management experience analyzing portfolios worth $180M+ in annual bookings, Jasper has identified three critical mistakes that make operators compete in a race to the bottom while thinking they're winning.The pattern is consistent: 90% of operators tell Freewyld they're "beating the market" when they first engage. Then they discover they were leaving 10-50% more revenue on the table. This episode reveals exactly where that money is hiding and how to capture it.You will hear:Why 90% occupancy at $100/night makes less money than 67% occupancy at $200/night (the math that changes everything)How focusing on the next 2-4 weeks causes you to miss premium bookings happening 3 months outWhy "beating the market average" is a terrible benchmark that creates false confidenceWhat happens in the last 3-6 weeks when all operators drop prices and create a race to the bottomHow strict cancellation policies and minimum night stay restrictions kill your bookability and revenueWhy instant book and listing flexibility impact revenue more than most operators realizeWhat pacing analysis reveals about properties that are ahead or behind the booking curveWe also talk about:The set it and forget it pricing trap that guarantees underperformanceWhy Airbnb account managers recommend allowing one-night stays across the entire yearHow to implement a daily revenue management rhythm (1 hour/week + 15-30 minutes/day)Mentioned in the Episode:Free Revenue Report: FreewyldFoundry.com/reportFavorite Takeaway:"If your prices are perfect, but you have a strict cancellation policy and a five night minimum night stay and you're not using instant book, well, guess what? Your pricing might be perfect, but you will not get any bookings."Want us to audit your pricing strategy? Get your free, personalized revenue report at FreewyldFoundry.com/get-started Hosted on Acast. See acast.com/privacy for more information.
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  How to Price Your STR Without Leaving Money on the Table 11.05.2026 1h 14min

  Connor Schwab runs four unique stay properties and hosts the Outdoor Hospitality Podcast. After undercharging by $10,000-$20,000 in his first nine months at The Outpost at the Grand Canyon, he switched to professional revenue management. Now his 12-Airstream property is pacing toward 85% occupancy with optimized pricing across six OTAs.This conversation reveals why treating revenue management as a strategic priority rather than a side task is the difference between good and great performance. Jasper breaks down the exact framework Freewyld uses to manage $180M+ in bookings: pacing analysis, booking window strategy, and the truth about pricing tools that most operators miss.You will hear:Why a one-star review showing on your Airbnb listing front page can cost 50% of your revenueHow to use pacing analysis to know if you're overpriced or underpriced (comparing your occupancy to market occupancy at the same booking window)What revenue management actually includes beyond setting prices (cancellation policies, minimum night stays, bookability settings that kill visibility)Why pricing tools like Price Labs aren't "set and forget" and require daily strategic oversight to avoid horrible pricing decisionsHow Connor left $20,000 on the table in nine months by treating revenue management as a side task instead of a dedicated functionWe also talk about:The three intentional paths for revenue management: learn it yourself, hire in-house, or outsource to specialistsWhy guests determine value through their purchase decision, not operators through subjective judgmentHow a $200 stock tank beats a $10,000 cold plunge machine when you factor in maintenance costsThe booking window strategy that captures revenue before competitors slash prices in panic modeWhy higher prices don't hurt reviews (and the data proving it)How AI is making revenue managers more effective without replacing themMentioned in the Episode:Freewyld Foundry Revenue Management: https://freewyldfoundry.comFree Revenue Report: https://freewyldfoundry.com/get-startedPrice Labs: Dynamic pricing softwareClaude AI: Conversational AI assistantThe Outpost at the Grand Canyon: Connor's 12-Airstream propertyWhoop: Fitness and sleep tracking deviceNewbook: Property management systemFavorite Takeaway:"Who is to judge what something is worth? Is it the person that owns the product or is it the person paying for it? I would argue it's the person paying for it. In Holland we have an expression: something is worth what the craziest person will pay for it."Want us to audit your pricing strategy?Get your free, personalized revenue report at FreewyldFoundry.com/get-started Hosted on Acast. See acast.com/privacy for more information.