Want to outperform the market?
Freewyld Foundry’s Revenue & Pricing Management service is driving a 24.6% performance lift for $1M+ STR operators, even in down markets.
If you’re managing 15+ listings and want a free pricing audit, apply here
Revenue management isn’t just about plugging numbers into a pricing tool. In fact, most STR operators are leaving money on the table because they’re chasing the wrong metrics and relying too heavily on “smart” algorithms.
In this episode of Get Paid For Your Pad, Eric Moeller (CEO of Freewyld & Freewyld Foundry) and Kaye Putnam (Head of Marketing at Freewyld) break down the real strategy behind pricing, pacing, and outperforming your market, without burning out or overcomplicating your business.
If you’ve ever wondered why occupancy rate isn’t telling you the full story, why booking windows matter more than you think, or how minimum night rules could be limiting your revenue, this conversation will give you the clarity (and practical playbook) you need.
You’ll hear:
- Why pricing tools often mislead STR operators
- The real metric that matters: MPI (Market Penetration Index)
- How pacing reveals future demand (and what to do with it)
- Why flexibility with minimum nights can drive more bookings
- How booking windows signal when to adjust pricing
- The power of last-minute discounts for visibility and conversion
We also talk about:
- Why cancellation policies can win you early bookings
- How comp sets get overrated (and what to focus on instead)
- The mindset shift from “occupancy” to “profitability”
- A framework for monitoring revenue without losing focus
🎯 Mentioned in the Episode:
- Freewyld Foundry: Revenue & Pricing Management for Professional STR Operators
- STR Mastermind: Community for 7- & 8-Figure Hosts
- Tools like AirDNA, Pricelabs, Beyond Pricing (and their limitations)
🔥 Favorite Takeaway:
“Tools don’t think, humans do. The best revenue strategy comes from reading signals, not chasing occupancy.”
📍 Ready to get serious about your pricing strategy? Apply for a free revenue audit or learn more about Freewyld Foundry’s Revenue & Pricing Management services at FreewyldFoundry.com
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Kaye Putnam:
All right, Jasper, complete this sentence. Tools are great, but they will never tell you blank.
Jasper Ribbers:
Pricing tools are great at saving you time, but they will never tell you what to price at.
Kaye:
Why not?
Jasper:
You give a tool inputs and it gives you outputs. If your inputs are wrong, your outputs will be wrong. It is not thinking for you. It is not artificial intelligence. It is just a tool that executes instructions.
Kaye:
Right. We do not have self-driving pricing tools yet.
Jasper:
And some things would be impossible to do manually at scale, like dynamic minimum night stay settings. For example, allowing a one-night gap to be bookable even if your standard minimum is two nights. You could do it by hand on your calendar every day, but it is not practical. A pricing tool can automate that kind of rule.
Kaye:
Welcome back to Get Paid for Your Pad. This is a Rev Up episode. I am Kaye Putnam, Head of Marketing at Freewyld Foundry. Today I am interviewing Jasper Ribbers, our resident revenue management geek. Our team manages just shy of 40 clients and over 65 million dollars in annual bookings across the world. We are diving into where pricing tools end and real revenue management begins for pro operators generating millions in bookings.
Jasper:
You, the human, do revenue management. The tool is only a tool. Think of mowing the lawn. You can cut every blade with scissors or use a machine. The machine does not mow by itself. You still push it and decide where to go. Tools do what you tell them. If you put nonsense in, you get nonsense out. If I set a base price at ten thousand dollars, no one will book. The tool will dutifully follow the bad input.
Kaye:
Exactly.
Jasper:
I like talking with you about this because it shows me how people outside the discipline think about revenue management. It helps me explain what we actually do.
Kaye:
Same here. Our clients know a lot, but your team’s depth shows in the results. My goal is to translate this into plain language. You mentioned dynamic minimum nights and orphan gaps. What else do pricing tools do reliably well in your workflow?
Jasper:
Tools provide settings and automation. A good example is a last-minute discount curve. You can start, say, 20 days before check-in and lower the price a small amount each day from 0 to 20 percent. It saves time and it nudges OTAs to surface your listing because a price drop is a fresh signal. Versus holding a static price at 200 dollars with no traction.
Another advantage is market data. If you price manually in your PMS, you lack context. Tools give you competitor pricing, market occupancy, and comp sets. They also let you execute strategies you could not do daily at scale, especially across 50 units.
Kaye:
We said garbage in, garbage out. Even if you had the right price once, that changes. What do you adjust day to day for our portfolio and clients?
Jasper:
Our job is to price correctly for each date. There is no way to compute the single optimal price in advance. Guests decide with their bookings. So we watch signals. If we are getting multiple early bookings in May, June, and July while the market shows little activity, that suggests we are too attractive and likely underpriced.
Flip side, if it is Friday and the weekend is empty while the market is 80 percent booked, we are overpriced. Pacing solves this. We compare our forward bookings to the market to see if we are on track.
Kaye:
Historical comps also help, right?
Jasper:
Yes. If last May we averaged 200 dollars ADR and we are currently far below that without a market reason, we may be too low. We also look at similar units. For standard product types, if most one-bedrooms are between 100 and 200 and you are at 80, you are probably too cheap. If you are at 250 and still booking, the market says the price is fine. The market decides, not our opinions. We had two cabins, Black Mountain and Ursus. We thought Ursus would crush it, but the market loved Black Mountain more. You have to listen to demand, not attachment.
Kaye:
So when signals say we are off, what do you change?
Jasper:
We want to participate in the entire booking window. If the median booking window is three months, we aim to be a reasonable option from the moment shoppers start looking. If two weeks into that window we are at zero while the market is 10 percent booked, we reduce prices for those dates. The idea is to win a fair share of bookings across the window.
Kaye:
You are previewing your VRMA analogy.
Jasper:
Yes. Imagine a shopping street open from nine to five. Zara and H&M open at nine. Mango opens at one. Mango will make less revenue because it misses the early foot traffic. If your prices make you uncompetitive in the early booking window, you are effectively closed for business until late. Early bookings usually pay more. Late bookings push you into price drops.
Kaye:
Sometimes operators book far earlier than the market. That can be a warning too.
Jasper:
Right. If almost no one is booking yet and you are getting lots of early reservations, your prices are likely too low. High occupancy can be a false win. Price everything at ten dollars and you will be 100 percent occupied, but your revenue will be poor. It is not about occupancy alone. It is about revenue.
Kaye:
What other misunderstood metrics do you see?
Jasper:
People watch 7, 30, and 60-day occupancy by default. That is fine, but most manage only last-minute inventory and ignore early window performance. I also track pickup, which is the direction of your bookings over time. Low forward occupancy does not always mean lower price if weekly pickup is strong and trending to fill the calendar. If forward is low and pickup is weak, then we adjust. You need to look daily or near-daily. Nuance matters, and the devil is in the details.
Kaye:
You mentioned comp sets. Biggest mistakes there?
Jasper:
Operators often overbuild custom comp sets and underwatch pacing. Standard tool comp sets are usually fine for common units. If your unit is unique, make a custom comp set, but ensure the sample is large enough. A comp set of seven units is too small and too random. A big group booking can distort the signal. Better to include more units for stability, then add filters for key features if needed. Do not obsess over micro-features like a ping-pong table if it shrinks the dataset too much.
Kaye:
Beyond price, what other levers affect revenue?
Jasper:
Many. Location, bedrooms, fees, length of stay, and cancellation policy all influence conversion. If I need a two-night stay, listings with three-night minimums do not even show. If
I am booking months ahead, a strict cancellation policy pushes me away. When units underperform, 70 to 80 percent of the time it is not price. It is listing quality, policy friction, or visibility issues. We diagnose and fix those with clients.
Kaye:
Walk me through your daily review inside the pricing tool.
Jasper:
First, I check MPI for the next three months and the average across them. Are we ahead, behind, or in line with the market? Next, I look at distribution across units. An account can average fine while hiding big outliers. Then I go to our three pillars: pacing, minimum night strategy, and OTA performance.
On minimum nights, a common profile increases minimums further out. If your median booking window is long and guests mostly want one or two nights, raising to three nights early closes you to demand. We have switched several portfolios to a two-night minimum across the board and one night last minute. In some cases, average length of stay went up. Allowing short stays can increase visibility, which brings more total demand, including longer bookings.
Kaye:
That is counterintuitive and helpful. For lagging units, what do you try first?
Jasper:
If we are behind, we lower prices. How we do it depends. Sometimes it is targeted date overrides. Sometimes the base price is wrong. Tools apply seasonality factors, but they can be too aggressive or too soft. We might create a seasonal profile, drop low-season levels, and lift high-season levels. If pickup is strong, we may hold price and let occupancy catch up.
Kaye:
Before we close, a quick VRMA plug. We will be at booth 1118 offering Turbo Revenue Reports. You and one of our revenue managers will run live audits.
Jasper:
Exactly. Our full revenue review takes 45 to 60 minutes. The turbo version takes about 15 minutes. It gives you the 80-20 of where to focus for more revenue.
Kaye:
If you cannot attend VRMA, we also do the full revenue report. Go to freewyldfoundry.com slash report. If you are at one million dollars or more in annual bookings, it is free. Or if you prefer to hand off revenue management, we can explore a partnership.
Jasper, thank you for the insights.
Jasper:
Thank you. Looking forward to the next episode.
Kaye:
Bye, everybody.
Jasper:
See you next time.
