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
In this episode of Get Paid For Your Pad, Jasper Ribbers (Co-Founder of Freewyld) breaks down the three most costly mistakes short-term rental (STR) operators are making when it comes to revenue management in 2026.
If you’re serious about growing your STR portfolio this year, even in a softening market, this episode is packed with high-impact strategies that top operators are using to stay ahead.
You’ll learn:
Jasper also shares real data and examples from Freewyld Foundry’s managed portfolios across the U.S., including markets in Wisconsin and Washington state, showing how proper pacing and pricing strategy led to over $20K in extra revenue in one low season alone.
We also talk about:
🎯 Mentioned in the Episode:
📍 Learn how to:
If you’re managing a portfolio of STRs, especially across multiple markets, this is a can’t-miss episode that could save (and earn) you tens of thousands.
For questions, email: jasper@freewyld.com
Subscribe for more episodes every Monday and Friday on YouTube, Spotify, and Apple Podcasts.
👍 Like, comment, and leave a review if this helped your hosting business!
A step-by-step guide to tracking and using pacing data to optimize your short-term rental pricing strategy.
Download Free Guide
Three revenue management experts reveal why growing from 10 to 50+ properties breaks traditional pricing strategies and how to shift from listing-level to portfolio-level optimization without sacrificing individual property performance or owner satisfaction.
Jasper Ribbers reveals why most STR operators lose thousands launching new units by chasing ADR instead of review velocity. Drawing from 500+ launches across Freewyld Foundry's portfolio, he shares the exact 60-day strategy to build momentum that lasts for years.
Annie Holcombe shares why trust beats price in owner acquisition, how to turn your entire team into brand ambassadors, and why telling owners hard truths upfront closes more deals than overpromising.
**Jasper Ribbers:**Welcome back to Get Paid For Your Pad. Today, I'm breaking down the three biggest mistakes short-term rental operators make with revenue management, and how to avoid them in 2025.
If you want better results this year, even in a flat or declining market, this episode is for you.
Also, stick around until the end. I'll be sharing a free training you can sign up for that walks you through everything we're learning across 30+ portfolios.
**Context:**We manage revenue for operators doing $1M+ per year in STR income. That includes 30 portfolios across the U.S., Canada, Europe, and Australia. With hundreds of listings under management, we see clear patterns, especially when onboarding new clients.
Mistake #1: Pricing Too High in Low SeasonDuring the off-season, many hosts set unrealistic prices and hope for last-minute bookings. But in most markets, demand simply isn't strong enough to support that strategy.
Instead:
Key takeaway: The low season is not the time to chase high ADRs. It's about securing bookings early and keeping listings active.
**Why It Matters:**Even low-paying bookings have long-term value:
In Wisconsin, for example, one of our portfolios generated $22K more in revenue during January simply by pricing correctly. That's $22K more bookings, reviews, and search visibility heading into summer.
**Mistake #2: Underpricing High Season (Pacing Too Fast)**We often see operators price too low in peak season, just to get early bookings. But when you book up too early, you leave a lot of money on the table.
Use pacing tools (like PriceLabs' Portfolio Analytics) to compare your occupancy and rates against the market. If you're pacing ahead too early, your prices are too low.
Real example:
Booking slower at higher rates beats early occupancy at low prices.
Mistake #3: Ignoring Peak Demand Events in AdvanceThis is the costliest mistake we see: not setting high enough rates for known peak events (like graduations, holidays, or major sports weekends).
Example: A university town in the Midwest
Solution:
Tip: Even if the calendar isn't open that far yet, set your override rules early. Protect your future revenue from early bookings at low rates.
Bonus Tip: Use Reporting to Track ADR Trends: With tools like PriceLabs, you can compare booked ADRs now vs. same time last year vs. final ADRs. This helps you catch underpricing before it's too late.
You'll learn:
**Final Notes:**If you have revenue management questions, email me at jasper@freewyld.com. I use real listener questions to guide these episodes.
We release new episodes every Monday and Friday on YouTube, Spotify, and Apple Podcasts. If this episode helped, leave us a like, review, or comment. It makes a big difference.
Until next time!