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

Short-term rental conferences are a big investment of time, money, and energy. Are they worth it? And if you go, how do you actually get the most out of them?Jasper shares 12 years of conference experience, from Airbnb Open in 2014 to GuestyVal Madrid and VRMA Nashville, with practical advice on how to maximize the value of any STR conference you attend.Want to outperform the market? Freewyld Foundry's Revenue and Pricing Management service is driving an average 19% performance lift for $1M+ STR operators, even in down markets. If you are managing 15+ listings and want a free pricing audit, apply here: freewyldfoundry.com/get-startedYou will learn:Why the operators who get the least value from conferences are the ones who show up without a plan, and what to think through before you book your ticketHow getting on stage or joining a panel changes the entire conference experience, saves you money on the ticket, and gives you automatic credibility before you say a wordWhy most operators underestimate how much value they have to share, and why you should apply for a speaking slot even if you are not sure you will get itHow to use the conference app to book meetings before you arrive, and why protecting your open time from aggressive vendors is just as important as who you scheduleWhat Freewyld Foundry is doing at VRMA Nashville: a workshop on building an AI revenue management agent (Tuesday 11:30 AM), a surprise in-person event Monday night, and a booth with free revenue auditsWe also talk about:The real value of going to a conference is not the sessions, it is the personal connections, and most people are too passive to make themHow VRMA compares to IMN and regional conferences, and which type fits your goalsWhy traveling with a baby has kept Jasper to two conferences in 2026, and what the European conference calendar looks like for 2027The energy and motivation from being around other operators is underrated, and why getting out of your day-to-day once or twice a year is worth it on its ownMentioned in the Episode:Freewyld Foundry Free Revenue Report: freewyldfoundry.com/get-startedVRMA Nashville: October 4-6, stop by the Freewyld Foundry boothEmail Jasper: [email protected] for new episodes every Monday on YouTube, Spotify, and Apple Podcasts. Hosted on Acast. See acast.com/privacy for more information.

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.

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.

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.

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.