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FIFA World Cup 2026: The STR Demand Reality Check (And How to Adjust Your Strategy Now)
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 year
- How elevated STR pricing is creating a double displacement effect, driving away both international World Cup travelers and regular domestic summer visitors
- The 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 opportunities
- How to use PriceLabs neighborhood data to find the medium booked price and position competitively in markets still offering availability
- Why international demand collapsed: visa uncertainty, $5,000 to $10,000 total trip costs, and rising flight prices from oil market volatility
- The Qatar 2022 precedent: how FIFA gave away free tickets and team jerseys to fill stadiums and avoid the embarrassment of empty seats
We also talk about:
- Why the New Jersey Transit Authority raising round-trip stadium tickets from $13 to $105 exemplifies ecosystem-wide pricing barriers
- How to follow group stage scores and standings to predict knockout matchups 5 to 7 days before games are played
- Why regular travelers to cities like Houston or Seattle are choosing alternative summer destinations due to World Cup pricing
- The specific 11 US host cities experiencing demand shortfalls and which games might still command premiums
- How 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 bookings
Mentioned in the Episode:
- Fortune Magazine: https://fortune.com (World Cup hotel booking analysis)
- PriceLabs neighborhood data and medium booked price feature: https://pricelabs.co
- Free Revenue Report (get your pricing audited): https://freewyldfoundry.com/get-started
Favorite 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
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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.
726. 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
27:43||Ep. 726In 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."
725. June Market Update: World Cup Impact, New Airbnb Discounts, and What's Coming in July
25:53||Ep. 725June'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
724. Best PMS Systems for STR Revenue Management
21:18||Ep. 724Choosing 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
723. How to Outsource Revenue Management Without Losing Control
28:42||Ep. 723After 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
722. 7 Hidden PriceLabs Features Most Hosts Are Not Using
18:56||Ep. 722Most 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