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

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

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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 performance
• Why 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 cap
• What 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 fills
• How 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 day
• The math behind redeeming BILT points for international business class versus economy versus cash toward a down payment

We 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 sauna
• What an actuary background taught David about pricing and where the risk tolerance gap between self-managing and professional management shows up most
• Why flexibility is the key to getting outsized value from travel points

Mentioned in the Episode:

• BILT points calculator built by David (link to be added)
• OR Getaways on LinkedIn: David Dodge
• Free Revenue Report

Favorite 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."

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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 June
• Which World Cup host cities actually moved the needle, and why the overall market only lifted 9% despite the largest sports event in history
• The 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 discounting
• Airbnb'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 it

We 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 strategy
• What to watch heading into July and the second half of summer

Mentioned in the Episode:

• Freewyld Foundry Revenue Report: https://freewyldfoundry.com/get-started
• Airbnb 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.

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 twice
• The five systems Freewyld Foundry recommends: Guesty, HostAway, Hostfully, OwnerRez, and Hospitable, and what makes each one stand out
• Why Guesty is Jasper's top pick and what separates it from the rest of the market
• How OwnerRez compares as a budget-friendly option, and the one limitation to know before you sign up
• Why OTA-native discounts (early bird, last minute, length of stay) are becoming a core revenue strategy, and why your PMS has to support them

We also talk about:

• Why Hostfully is the system Freewyld actually uses internally, sloth mascot and all
• What to look for in a PriceLabs integration before you commit to any PMS
• Why simplicity in your tech stack matters more at 50 units than it does at five
• How AI is changing reporting, and why that shifts the criteria for choosing a PMS
• One newer system Jasper is keeping an eye on: Boom

Mentioned in the Episode:

• Guesty: https://guesty.com
• HostAway: https://hostaway.com
• Hostfully: https://hostfully.com
• OwnerRez: https://ownerrez.com
• Hospitable: https://hospitable.com
• PriceLabs: https://pricelabs.co

Favorite 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.

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 hire
• The mindset shift you need before outsourcing: the difference between leading a revenue manager and micromanaging one
• How 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 perform
• What 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 quits
• How to evaluate a service provider: experience, team size, whether they're operators themselves, and whether they manage pricing in your tool or theirs

We also talk about:

• Why hiring cheap for revenue management is a false economy, and what great revenue managers actually cost on the market
• The transparency red flag: any company that manages pricing in their own account and won't give you access is a problem
• What good ongoing support looks like: daily Slack access, weekly Zoom calls, and a live dashboard you can check any time
• Why total portfolio revenue growth is a misleading KPI and how to compare performance correctly using only units that were active the prior year

Favorite 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

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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 distorted
• Subgroups: how to organize your portfolio by both market and bedroom size at the same time
• How to upload historic booking data directly to PriceLabs when your old PMS didn't transfer it over
• Safety minimum price: what it does, why it can backfire on weekday dates, and how to turn it off
• Forecasting in Report Builder: how to see PriceLabs' revenue and occupancy projections for the year ahead
• Rental revenue formula: how to customize what counts as revenue so your reports reflect what actually matters to your business
• Check-in and check-out profiles: the cleaner way to restrict turnovers on holidays without cluttering your calendar with overrides

We also talk about:

• Which features are request-only and require contacting PriceLabs support to activate
• Why 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 differences
• How to use Claude to format historic booking data into the PriceLabs CSV template

Mentioned in the Episode:

• PriceLabs: https://pricelabs.co

Favorite 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.

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 world
• Real market data: Dallas, Kansas City, Houston, and Vancouver compared to last year
• Why high airfare and accommodation costs are keeping both local and international travelers away
• How visa fears and immigration news stories are suppressing international travel to the US
• Why July is still shaping up to be a strong month overall, up 14% on average across markets

We also talk about:

• Why the group stage requires a competitive pricing approach right now
• Why the knockout rounds could still bring a surge if big football nations like Brazil, Germany, France, or England advance
• Why being in the stadium for your country's potential World Cup win is worth any price

Mentioned in the Episode:

• Price Labs: https://pricelabs.co

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.

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 documentation
• What 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 animal
• Why post-reservation verification takes minutes but never slows down your booking rate
• What 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 faxes
• Why federal law prevents states from making assistance animal requirements more restrictive
• The difference between ADA service animals and Fair Housing ESAs
• How hosts using verification tools become more pet-friendly because they can confidently manage risk
• Why there are more pets than children under 18 in American households and what that means for your business

RESOURCES:

• Pet Screening: https://petscreening.com

FAVORITE 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."

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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 management
• How 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 portfolios
• Why World Cup demand is a mirage and how operator greed is deterring regular travelers without attracting event demand
• How to split your portfolio into "comparables" and "exclusives" to track real performance versus market noise

We also talk about:

• Market performance breakdown: Canada up 20%, Dallas down 17%, and what that means for June
• The "last-minute trap" that forces you to compete in price-dropping races instead of booking early at premium rates
• Why 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-started
• Claude AI: https://claude.ai
• Airbnb 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.

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 weekends
• When 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 disasters
• How 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 event
• Why opening your calendar more than 12 months in advance creates more problems than revenue in markets with recurring events
• How to use seasonal profiles instead of calendar overrides to automatically copy peak pricing strategy year over year
• The compensation guarantee framework that protects portfolio-wide premium pricing while keeping individual owners happy
• Which 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.co
• Freewyld Foundry Revenue Management: https://freewyldfoundry.com/yt

Favorite 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.