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

Freewyld Foundry
  • 4.7 (180)
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Get Paid For Your Pad is the go-to podcast for Airbnb hosts, short-term rental operators, and vacation rental entrepreneurs who want to scale smarter, earn more, and stay ahead of industry shifts. Hosted by Jasper Ribbers, Eric Moeller, and Kaye Putnam from Freewyld Foundry, this podcast delivers actionable tips on Airbnb pricing strategies, revenue management, direct bookings, listing optimization, and guest experience. You'll hear from real hosts, property managers, and industry pros who share behind-the-scenes insights, lessons learned, and the systems they use to grow profitable STR businesses. Whether you're managing one property or one hundred, you'll walk away with practical strategies to increase occupancy, boost profits, and build a sustainable short-term rental brand. Tune in weekly to learn how to thrive in today’s competitive Airbnb market, and get paid what you’re worth. Freewyld Foundry offers revenue and pricing management (RPM) services to the top 1% of STR hosts. Learn more and request a free Revenue Report: https://www.freewyldfoundry.com Hosted on Acast. See acast.com/privacy for more information.

  1. 3D AGO

    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 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 seats We 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 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.coFree 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 Hosted on Acast. See acast.com/privacy for more information.

    19 min

  2. MAY 18

    3 Mistakes Short-Term Rental Operators Make That Leave Money on the Table

    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 curve We 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/report Favorite 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.

    13 min

  3. MAY 11

    How to Price Your STR Without Leaving Money on the Table

    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 function We 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 system Favorite 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.

    1h 15m

  4. MAY 4

    Why Your Cancellation Policy Is Costing You Bookings (And How to Fix It)

    Airbnb just rolled out seasonal cancellation policies - the feature hosts have been requesting for years. But there's a catch: implementing it requires manually selecting dates in every single listing's calendar. No bulk editing exists. Jasper Ribbers breaks down the fundamental trade-off that most hosts get wrong: flexible policies drive more bookings (revenue up), but strict policies prevent painful cancellations (risk down). The problem? You never see the bookings you gained from being flexible, but you absolutely feel the sting when someone cancels your New Year's weekend two weeks out. This psychological mismatch causes most hosts to over-protect their calendars and leave money on the table. The solution isn't choosing one blanket policy - it's strategically protecting only your highest-value dates (holidays, peak summer weekends, local events) while staying flexible everywhere else to maximize conversion. But with Airbnb's current implementation, applying this strategy across a 50+ listing portfolio could take days of manual work. You will hear: Why booking window matters more than bedroom count when choosing your cancellation policyHow to calculate whether firm and moderate offer the same protection in your marketWhat the revenue versus risk range looks like for each policy type (and why property managers should bias stricter than owner-operators)When flexible policies generate more revenue than strict ones despite occasional cancellationsHow to implement seasonal policies step-by-step in Airbnb's new calendar interfaceWe also talk about: The four recommended cancellation policy types (and which two to avoid)Why most hosts have policies that are too strictReal client story of losing thousands when a guest canceled and rebooked at a lower rateStrategic framework for protecting Memorial Day, July 4th, and other high-value weekendsHow to set expectations with owners about the flexibility-conversion trade-off Favorite Takeaway: "The conversion and visibility boost that you get from flexible policies, it's not very visible because you don't really know if you would have gotten that booking if you had a more strict policy." 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.

    17 min

  5. APR 27

    Prevent the Insurance Disaster Threatening Your STR Business with Darren Pettyjohn

    Most property managers believe they have business insurance. They filled out a form online, got a policy, threw it in their desk drawer, and moved on with life. But here's the problem: that policy likely excludes coverage for the very thing they need most - property damage liability at the properties they manage. Darren Pettyjohn built Proper Insurance from his spare bedroom to 160 employees and 150,000+ policies before selling to Hub International, the world's largest private insurance group. Now he's back with Wister Insurance, the only company focused exclusively on business insurance for vacation rental managers and co-hosts. And what he's discovered is shocking: the majority of STR operators are exposed to million-dollar lawsuits with zero coverage. In this episode, Darren pulls back the curtain on the massive insurance gaps plaguing the industry, shares real examples of wrongful death settlements his team has paid out, and explains why Airbnb's Air Cover won't protect you when things go wrong. You will hear: - Why most business insurance policies specifically exclude property damage liability at managed properties (the CG2270 problem that could cost you $100,000+ in a single water damage claim) - What changed in March 2025 with Airbnb's Air Cover that every co-host with 6+ properties needs to know immediately - How the "air traffic controller" co-host model creates massive professional liability exposure that standard CGL policies don't cover - Why you should call your insurance company for every incident, even minor ones, and how small settlements prevent massive lawsuits years later - What it took to sell a company to the world's largest private insurance group (14 months, 16 companies, and lawyers on lawyers) We also talk about: - The four categories of STR insurance and which ones actually apply to your business - Real wrongful death lawsuits Darren's team has settled in Florida (multiple million-dollar drowning cases) - How sobriety and redirected energy became Darren's competitive advantage in building Proper - The "reasonable person test" for property safety that could save you in court - Why premium pricing won (Proper was the most expensive product in the industry with a 33% close ratio) Mentioned in the Episode: - Wister Insurance: https://www.wister.insure - Darren's LinkedIn: https://www.linkedin.com/in/darren-pettyjohn-1708925/ Favorite Takeaway: "Right now, you're a manager. Oh, I got insurance. I feel good. It's in my desk drawer. And you have no idea that you have no coverage for property damage liability at any of the properties you manage." 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.

    54 min

  6. APR 20

    33% of Booking.com Is Now STRs: The Discount Strategy Driving 29% More Bookings

    Relying only on Airbnb just became a lot riskier. With the platform suspending listings after just a couple of four-star reviews, thousands of operators are scrambling to diversify. But Booking.com, the world's largest OTA with 29 million listings, isn't as simple as uploading your property and waiting for bookings to roll in. In this episode, Jasper Ribbers breaks down exactly how to navigate Booking.com's complex discount system, why your listings look "empty" without the right badges, and the strategic markup math you need to maintain profitability while offering multiple discounts. He reveals why getting your first five reviews is critical, how the Genius loyalty program drives 29% more bookings, and why accepting price inconsistency across channels is the only way to win on this platform. You will hear: Why Airbnb's binary review system (five stars = perfect, four stars = suspended) makes platform diversification mandatory nowHow to stack Genius discounts and mobile rates while maintaining your minimum pricing through strategic 20-25% markupsWhat the five-review checkpoint means for Genius eligibility and why you must proactively incentivize Booking.com users to leave feedbackHow properties using the Genius program see 29% more bookings and 24% more revenue compared to those without itWhy listings without visible discount badges automatically look broken to guests and how to fix that perceptionWhat the Property Page Score reveals about your listing optimization and why 100% is mandatory for maximum visibilityWe also talk about: How Booking.com's 1-10 rating system protects your revenue better than Airbnb's binary systemThe merchant payment model that solved Booking.com's notorious chargeback problemWhy paying 18% commission for Preferred status is worth it versus the standard 15%Mentioned in the Episode: Free Revenue Report: https://freewyldfoundry.com/reportFavorite Takeaway:"Being just on Airbnb is really not a viable option anymore. Airbnb is removing and suspending listings pretty quickly. Because technically, if you get a couple four-star reviews, your listing might be suspended." 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.

    24 min

  7. APR 13

    AI Built My Revenue Projections in 10 Minutes

    Most STR operators treat revenue projections like fortune-telling - last year's numbers plus a prayer. But when you're managing $1M+ in bookings, you need a system that accounts for market shifts, booking momentum, and realistic pricing decay. In this technical deep-dive, Jasper Ribbers walks through building a three-method projection framework from scratch, then shows how Claude AI can automate the entire process in under 15 minutes. Here's the problem: historical data ignores market changes, market seasonality ignores your specific performance, and forward-looking bookings require assumptions about conversion rates you probably don't have. Most operators pick one method, cross their fingers, and wonder why they miss their targets by 20%. Jasper demonstrates why using all three methods simultaneously creates a reality-tested range rather than a single-point guess, and how AI can flag discrepancies automatically. You will hear: - How to extrapolate annual revenue potential from just three months of data using market seasonality (divide monthly revenue by that month's typical % share of annual RevPAR) - Why "unbooked potential" in your PMS is a fantasy number (assumes 100% occupancy at current rates, reality is 75-85% occupancy at 15% lower prices) - What the seasonality math reveals about underperformance (if January extrapolates to $300K annually but March extrapolates to $260K, you underperformed market patterns in March) - How to build a weekly-updating projection system using Claude AI that remembers your portfolio context across conversations - When to manually adjust projections (owner stays, maintenance downtime, or market events skew individual months and need human judgment) We also talk about: - The three data sources you need from PriceLabs to feed Claude (historical trends, listing performance, market seasonality) - How Freewyld Foundry now uses AI to connect directly to the PriceLabs API and generate revenue reports in minutes instead of hours - Why voice-to-text tools like Whisper can cut your AI prompting time in half Mentioned in the Episode: - Claude AI: https://claude.ai - PriceLabs (revenue data and market analysis): https://pricelabs.co - Whisper (voice-to-text tool): https://whisper.ai - Freewyld Foundry Revenue Report: https://freewyldfoundry.com/get-started Favorite Takeaway: "You can now, once you have this, you could literally upload your bookings every week, new bookings, and tell Claude, 'Hey, here's some new bookings. How does this affect our projections?' And it will create an updated version for you." 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.

    35 min

  8. APR 6

    How to Forecast STR Revenue Without Coding Experience

    Most STR operators track total revenue, but that metric lies to you. When one unit books 10 three-night stays and another books a single 30-day reservation, both generating $3,000 in nightly rates, the total revenue numbers look completely different because of cleaning fees, OTA commissions, and other variables. You're comparing apples to oranges, and it's hiding which units actually perform. Jasper Ribbers breaks down the three-method projection framework that reveals the truth: historical comparison shows what happened last year, seasonality-based extrapolation tells you what should happen based on market patterns, and forward-looking opportunity analysis predicts what will happen based on current bookings and unbooked nights. When these three methods disagree significantly, you've found a problem that needs investigation. You will hear: - Why net rental revenue is the only projection metric worth tracking (and why total revenue creates false comparisons) - How to combine three complementary projection methods to catch unit-level problems before they compound - What happened when one client's unit appeared to underperform until data revealed last year's anomalous booking - How to build an automated projection system in under 60 minutes with zero coding background - Why the Ramp CEO worries when employees spend less on AI credits than their salary - When revenue projections function as red flag detection systems versus forecasting tools - How AI automation reduced client call follow-up from 10-15 minutes to 3 seconds We also talk about: - The difference between rental arbitrage cash flow planning and owner communication strategies - Why low season projections remain volatile while high season accuracy increases - How market seasonality percentages convert recent performance into annual baselines - What "unbooked opportunity" means and how to calculate expected capture rates Mentioned in the Episode: - Claude AI: https://claude.ai - PriceLabs Market Dashboard: https://www.pricelabs.co - Fathom AI Note Taker: https://fathom.video - Ramp CEO AI Interview (search: "Ramp CEO AI podcast") Favorite Takeaway: "I spent three hours and I built an entire web app. It calculates market penetration index for a portfolio and I have zero coding experience." 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.

    20 min
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4.7
out of 5
180 Ratings

About

Get Paid For Your Pad is the go-to podcast for Airbnb hosts, short-term rental operators, and vacation rental entrepreneurs who want to scale smarter, earn more, and stay ahead of industry shifts. Hosted by Jasper Ribbers, Eric Moeller, and Kaye Putnam from Freewyld Foundry, this podcast delivers actionable tips on Airbnb pricing strategies, revenue management, direct bookings, listing optimization, and guest experience. You'll hear from real hosts, property managers, and industry pros who share behind-the-scenes insights, lessons learned, and the systems they use to grow profitable STR businesses. Whether you're managing one property or one hundred, you'll walk away with practical strategies to increase occupancy, boost profits, and build a sustainable short-term rental brand. Tune in weekly to learn how to thrive in today’s competitive Airbnb market, and get paid what you’re worth. Freewyld Foundry offers revenue and pricing management (RPM) services to the top 1% of STR hosts. Learn more and request a free Revenue Report: https://www.freewyldfoundry.com Hosted on Acast. See acast.com/privacy for more information.

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