How to Price Your STR Without Leaving Money on the Table

From One Beach House to a 20-Person Custom Build: David Dodge on STR Portfolio Growth and Earning 1.4M Travel Points From Your Mortgage

I 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 [https://freewyldfoundry.com/get-started] 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." ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

June Market Update: World Cup Impact, New Airbnb Discounts, and What's Coming in 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: * 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 [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 [https://freewyldfoundry.com/get-started] ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

Best PMS Systems for STR Revenue Management

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 [https://guesty.com/] * HostAway: https://hostaway.com [https://hostaway.com/] * Hostfully: https://hostfully.com [https://hostfully.com/] * OwnerRez: https://ownerrez.com [https://ownerrez.com/] * Hospitable: https://hospitable.com [https://hospitable.com/] * PriceLabs: https://pricelabs.co [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 [https://acast.com/privacy] for more information.

How to Outsource Revenue Management Without Losing Control

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 ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

7 Hidden PriceLabs Features Most Hosts Are Not Using

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 [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 [https://acast.com/privacy] for more information.