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

Javier Vasquez, one of Freewyld Foundry's revenue managers, joins Jasper to walk through a pricing strategy he built from scratch for a portfolio of glamping dome units near Toronto. These units run at 97-98% occupancy year-round with booking windows of up to 212 days and a waiting list. Because they attract destination travelers who book specifically to stay in those units, standard PriceLabs market factors did not apply. So Javier turned them off entirely and built a custom Portfolio Occupancy-Based Adjustment matrix instead. The result: ADR jumped from $493 in July to $565 in August. Jasper and Javier walk through the full setup live, including the screen share.

You will learn:

• What Portfolio Occupancy-Based Adjustment is in PriceLabs, and why it is the right tool when your inventory does not follow regular STR market patterns
• Why Javier turned off both seasonality and demand factors entirely for this portfolio, and what that changes about how the base price works
• How the matrix calculates occupancy on a per-day basis rather than a date-range basis, and why that distinction is critical for high-demand destination inventory
• How to build separate matrices for different unit types and day-of-week patterns, including why Sundays need their own factor separate from weekdays and weekends
• What the Javier Effect looks like in the data: ADR from $493 in July to $565 in August within two months of implementing the strategy
• How to use the PriceLabs pacing dashboard to monitor whether a new strategy is working and where to adjust

We also talk about:

• How to tell when your inventory warrants a custom strategy versus following standard market factors: the main tell is that your occupancy and booking patterns do not look like the market around you
• Why last-minute discounts are built directly into the matrix for this portfolio, eliminating the need for separate last-minute discount settings in PriceLabs
• The difference between regular occupancy-based adjustments (date-range basis) and portfolio occupancy-based adjustments (per-day basis), and why the distinction matters
• How booking windows shaped the date range columns in the matrix: 212 days for Forest Domes, 140 days for the middle units, and why a 366+ day column was added after October 2027 bookings started arriving
• What the pacing report shows heading into October: ADR $30 higher than the same period last year with occupancy also ahead
• Why most of the measurable impact so far is coming from weekday dates, and why the weekend impact will be clearer next year when weekend inventory was not already sold out before the strategy launched

Mentioned in the Episode:

• Free Revenue Report from Freewyld Foundry: freewyldfoundry.com/report
• PriceLabs Portfolio Occupancy-Based Adjustment: enable through the PriceLabs control panel; requires a group to be set up before the feature appears
• VRMA Nashville October 4-6: Booth 1143, Tuesday workshop at 11:30 AM, Sunday mastermind for Freewyld Foundry clients
• Email Jasper: [email protected]

Subscribe for new episodes every Monday on YouTube, Spotify, and Apple Podcasts.

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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-started

You 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 ticket
• How 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 word
• Why 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 it
• How 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 schedule
• What 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 audits

We 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 them
• How VRMA compares to IMN and regional conferences, and which type fits your goals
• Why traveling with a baby has kept Jasper to two conferences in 2026, and what the European conference calendar looks like for 2027
• The 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 own

Mentioned in the Episode:

• Freewyld Foundry Free Revenue Report: freewyldfoundry.com/get-started
• VRMA Nashville: October 4-6, stop by the Freewyld Foundry booth
• Email Jasper: [email protected]

Subscribe for new episodes every Monday on YouTube, Spotify, and Apple Podcasts.

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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 it
• The hybrid strategy that works better than going exclusively midterm: keep STR open, add long-stay discounts, and let demand self-select
• How 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/night
• Which properties and markets are best suited for MTR, including proximity to hospitals, universities, military installations, and employer hubs
• What 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 days
• Why new listings should not prioritize MTR first, and when the timing makes sense to add it

We 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 system
• How 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 it
• Frank'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 portfolios
• Top MTR operators averaging 8 active distribution channels compared to 4.8 for non-MTR operators, and why fragmented demand requires broader distribution
• Jasper's personal experience staying in his own Colombian Airbnb for three months and the improvements he made for long-stay guests, including a standing desk
• Why the operational cost savings of MTR (fewer turnovers, fewer cleanings, fewer check-ins) matter as much as the nightly rate when evaluating the economics

Mentioned in the Episode:

• Freewyld Foundry Free Revenue Report: https://freewyldfoundry.com/get-started/
• Hostfully: https://www.hostfully.com
• Furnished Finder: https://www.furnishedfinder.com
• Freewyld Foundry at VRMA Nashville: October 4-6, stop by the booth
• Email Jasper: [email protected]

Subscribe 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 performance
• The 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 floor
• How to position your low season pricing right now to capture midterm rental demand before snowbird bookings dry up
• Why 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 PMS
• What VRBO's new sponsored listings feature is, how the bidding works, and why early movers may get the cheapest visibility

We 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 heading
• How VRBO discounts stack differently than Airbnb discounts, and why Booking.com is in a category of its own for complexity
• The 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 Barcelona

Mentioned 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 Pad
• Email Jasper: [email protected]
• Freewyld Foundry at VRMA Nashville: October 4-6, stop by the booth

Subscribe 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 property
• How Patrick grew one OR Getaways property from $39,000 to $55,000 in a single month by holding prices and trusting the data
• Why high ratings and strong reviews are no longer enough to rank at the top of Airbnb search, and what actually moves the needle now
• The single amenity Patrick added to a listing that moved it from page 8 to page 3 overnight
• Why the answer when a listing is stuck at minimum price with zero bookings is sometimes to raise the price

We also talk about:

• How Airbnb custom promotions can create visibility and urgency without actually lowering your effective price
• What Jasper learned about hiring for values over skills after years of building the Freewyld Foundry team
• How the weekly team brainstorm with ten revenue managers in one room produces better strategies than any individual could find alone
• Patrick's full circle moment: from assembling furniture and listening to this podcast to sitting across from Jasper as a guest

Mentioned in the Episode:

• Free Revenue Audit: freewyldfoundry.com/get-started
• Careers at Freewyld Foundry: freewyldfoundry.com/careers

Favorite 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

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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 today
• The problem with 365 price points per listing and why a human can only realistically review 5 to 10% per day
• How to download your neighborhood data from PriceLabs and the exact chart options to have selected before you export
• How to prompt Claude to identify dates where you are currently priced 20% or more above the highest price you have ever booked at
• How to refine that analysis to compare like-for-like days: weekdays to weekdays, weekends to weekends, and special events to special events

We also talk about:

• How to flip the question and find nights where you are priced below what similar days have historically booked at
• How to use pacing data to flag periods where the market is already getting bookings and your calendar has nothing yet
• How to use Claude's voice input mid-session and how to teach it the output format you actually want
• How Jasper's team runs this analysis automatically every day across the full portfolio

Mentioned in the Episode:

PriceLabs: pricelabs.co

Free Revenue Audit: freewyldfoundry.com/get-started

Email Jasper: [email protected]

Favorite 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."

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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 calendar
• How to read a future occupancy graph to identify exactly when your shoulder season starts and ends in your specific market
• The weekday vs. weekend swing that defines shoulder season, and why a one-size-fits-all minimum stay strategy usually leaves money behind
• How to set up custom seasonal profiles in PriceLabs: percentage vs. fixed pricing, minimum stay profiles by season, and check-in and checkout restrictions
• Day-of-week price adjustments Jasper's team uses in shoulder season, including typical ranges for each day

We also talk about:

• Why forcing longer minimum stays during shoulder season usually cuts demand without adding revenue, and what to do instead
• How to download a PriceLabs seasonal profile as a CSV, edit it, and upload it across multiple units without starting from scratch
• How Jasper's team used Claude to generate 20 seasonal profile CSVs for a client in a fraction of the time it would have taken manually

Mentioned in the Episode:

• PriceLabs: pricelabs.co
• Free Revenue Audit: freewyldfoundry.com/get-started
• Email Jasper: [email protected]

Favorite 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."

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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 today
• US market share data from 2024-2025: Airbnb at 43%, Direct at 28%, VRBO at 28%, Booking.com at 8%, and why Europe looks completely different
• The three factors Jasper weighs when advising clients on channel selection: risk, revenue, and operational complexity
• Why concentrating all bookings on Airbnb creates compounding momentum and search visibility, and when that tradeoff is worth it
• Why Jasper considers Airbnb and Direct to be must-haves for almost every operator regardless of market
• How to evaluate whether VRBO or Booking.com is worth adding in your specific market, and what to look for before making that call

We 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 booking
• Booking.com's growing push into the US market, its reputation for complexity, and how the platform has improved in recent years
• Why adding channels beyond the big four rarely moves the needle and almost always adds operational cost

Mentioned in the Episode:

• Free Revenue Audit: freewyldfoundry.com/get-started
• Email Jasper: [email protected]

Favorite 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."

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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 clients
• Why 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 late
• Why extending your booking window is where most operators leave money on the table

Also 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 math
• The mobile-only discount reportedly rolling out in select markets
• Why OTA discount strategy is becoming its own discipline within revenue management

Mentioned in the Episode:

• Free Revenue Report: freewyldfoundry.com/get-started
• Email Jasper: [email protected]

Get 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.

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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 situation
• Why there is no substitute for experience in revenue management and what blocking daily time for pricing actually looks like in practice
• How to evaluate resources and avoid learning from content that is marketing material disguised as education
• Why community accelerates learning and how to structure a mastermind with operators in non-competing markets
• Why switching between revenue management approaches too often is one of the most costly mistakes operators make

We also talk about:

• The full resource library at freewyldfoundry.com including workshops, guides, podcast episodes, and blog posts
• Why PriceLabs updates its tool constantly and why staying current on your pricing tool is as important as understanding the strategy
• Why 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 results

Mentioned in the Episode:

• Freewyld Foundry workshops and guides: freewyldfoundry.com/resources
• PriceLabs resource library: pricelabs.co
• Free Revenue Report: freewyldfoundry.com/get-started

Get 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.