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

Jasper Ribbers, Eric Moeller, and Kaye Putnam sit down two weeks after VRMA Nashville to recap everything that stood out: the AI conversation that dominated every booth, the wave of private equity rolling up property management companies, the booking channel changes already live or coming, and why the team is still betting on human judgment over full automation.

What you will hear:

• The two things that came up in nearly every conversation on the show floor: AI and private equity

• Why a client is getting approached by private equity firms "every single day"...

We were at VRMA Nashville 2026, talking to operators and vendors on the show floor about what's actually shaping the short-term rental industry right now. Jasper walks the floor of the largest event in the industry, catching conversations on AI, guest screening, private equity consolidation, and what it actually takes to get guests to come back.

What you will hear:

• Operators and vendors reacting live from the floor of VRMA Nashville, the largest event in the short-term rental industry

• PriceLabs announcing Athena, their new AI revenue analyst, just days before the conference

•...

Jasper covers the September 2026 portfolio performance update for Freewyld Foundry clients. September was the best month in the company's history: comparable units finished up 37% year over year while the average market was up 7.3%, putting Freewyld Foundry's measurable impact at 27%, the highest they have ever recorded. Jasper walks through the market breakdown, shares which markets were up and which were down, and explains why September showed such strong numbers year over year. He also shares observations going into October and Q4.

In addition to the numbers, Jasper shares takeaways from GuestyVal in Madrid, including what the industry is...

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...

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...

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...

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...

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:

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...

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:

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:

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:

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:

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...

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:

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:

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:

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.

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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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

What happens when you scale from 10 listings to 50+ properties? Most operators hit a wall where their pricing strategy completely breaks down. Portfolio metrics look healthy while individual properties bleed revenue. Owners start comparing themselves to neighbors. Identical condos perform wildly differently for no apparent reason.

This episode captures a live masterclass where three revenue management experts reveal why the biggest threat to your portfolio isn't market competition but your own listings cannibalizing each other. Kyle Driscoll from PriceLabs moderates as Austin Whitaker (Enrich Revenue Management) and Jasper Ribbers (Freewyld Foundry) expose the critical shift from listing-level...

If you launch an STR listing on Airbnb (or Booking.com or VRBO) the wrong way, it can cost you thousands and thousands of dollars. And most operators get this completely wrong.

In this episode, Jasper Ribbers breaks down the exact strategy Freewyld Foundry uses to launch new short-term rental units, drawing from our experience launching 500+ properties across 70 portfolios in just two years. You'll discover why chasing high ADR in the first 60 days tanks your long-term revenue, how four-star reviews can permanently kill a new listing, and the step-by-step process to maximize review velocity and visibility...

Want to outperform the market? Freewyld Foundry’s Revenue & Pricing Management service is driving an 18% performance lift for $1M+ STR operators, even in down markets. If you’re managing 15+ listings and want a free pricing audit, apply here.

Most property managers think owner acquisition is a price war. Lower your commission rate, undercut the competition, and the owners will come.

Annie Holcombe has seen this play out hundreds of times across her career as an operator, Marriott channel manager, and now consultant. The PMs who compete on price burn out fast. The ones who win p...

Want to outperform the market? Freewyld Foundry’s Revenue & Pricing Management service is driving an 18% performance lift for $1M+ STR operators, even in down markets. If you’re managing 15+ listings and want a free pricing audit, apply here →

Most STR operators track revenue religiously. They check their dashboards daily, celebrate when numbers go up, and panic when they dip. But here’s the problem: they’re often tracking the wrong metrics, tracking them incorrectly, or comparing numbers that can’t actually be compared.

In this episode, Jasper Ribbers pulls back the curtain on how Freewyld...

One Christmas Eve, Ela Mezhiborsky got a call no STR operator ever wants to receive. Toronto Deputy Police had confirmed a known gang member posting Instagram photos with automatic weapons in one of her properties. They were asking permission to raid the place.

What started as a gut-wrenching $20,000 loss became the catalyst for Autohost, a screening platform now protecting operators from an even scarier threat: AI-powered fraud. The same tools making marketing easier are making crime easier too. Voice bots that sound more human than humans. Fake IDs generated in seconds. Deepfakes that pass visual inspection...

Why do airlines charge $500 for a 40-minute flight while short-term rental hosts slash prices 70% at the last minute?

In this episode, Jasper breaks down the three most-asked questions about pacing strategy. He reveals why STR pricing follows the exact opposite model of hotels and airlines, how fragmented ownership forces operators into a race-to-the-bottom, and the surprising scenarios where pacing BEHIND the market actually maximizes revenue.

You will hear:

- Why STR operators cannot take the same pricing risks as hotels with 200 rooms

- How to calculate Market Penetration Index...

You're paying for Price Labs. But chances are, you're not actually using it.

After reviewing hundreds of Price Labs accounts through our revenue management service, we discovered something shocking: 90% of operators are leaving money on the table by ignoring features they already have access to. Not premium add-ons. Not expensive upgrades. Just functionality sitting right there in their account, untouched.

In this walkthrough, Jasper Ribbers reveals the seven most powerful Price Labs features that separate high-performers from everyone else. From the free market dashboard that shows exactly how your market is pacing, to...

Eric was at an industry event talking to a seasoned operator: someone with a huge portfolio, a brand everyone knows, and years of experience. He asked a simple question: "What are you doing for revenue management?" The answer? "Oh, I use PriceLabs."

Eric asked again: "Yeah, but what are you doing for revenue management?"

That disconnect between having a pricing tool and having a revenue strategy is costing operators with $1M+ portfolios anywhere from $200K to $2M annually. And most don't even know it's happening.

In this episode, Jasper walks...

Most STR operators want more direct bookings, but they're stuck in the OTA ranking battle, competing on price against every other listing in their market. The problem isn't demand. It's that everyone is fighting over the same search traffic.

Dustin Baker, founder of Hidden Gem Media, has built a systematic approach to breaking that cycle. His team helps property managers and unique stay operators drive discovery traffic through social media, capture leads via email, and convert them into direct bookings with trackable ROI. And his results are hard to argue with: one client with traditional homes...

👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/report

Find out how much money your portfolio is leaving on the table. Risk-free.

What happens when STR operators finally get clear, direct answers to the revenue management questions they've been asking for months?

In this episode of Get Paid For Your Pad, Jasper Ribbers tackles the six most common revenue management questions submitted by operators across the country. From choosing between PriceLabs, Wheelhouse, and Beyond Pricing to understanding how much time revenue management actually requires, Jasper delivers actionable answers based on managing over...