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Is it still possible to grow a short-term rental business in 2025 when markets are soft, regulations are restrictive, and Airbnb’s review system has turned harsher than ever?
In this episode of Get Paid For Your Pad, Jasper Ribbers welcomes back Garrett Ham, founder and CEO of Weekender Management. Garrett is a unique guest because he wears three hats at once: short-term rental operator, investor, and attorney specializing in STR law. That perspective gives him a clear view of both the opportunities and the risks hosts face right now.
Garrett opens up about the reality of today’s market, from fighting a lawsuit before the Arkansas Supreme Court, to acquiring 10+ properties in the past year through creative financing, to protecting visibility on Airbnb when one bad review can cost thousands in lost bookings.
You’ll learn:
✔️ How Garrett reviews 100-200 properties to find just one worth buying
✔️ Why creative financing has become essential for STR acquisitions in 2025
✔️ The legal battle over Fayetteville’s restrictive ordinances and its potential impact on property rights
✔️ Why Weekender is expanding into Missouri and Florida when many operators are contracting
✔️ How stricter Airbnb review policies can wipe out performance even in quality listings
We also talk about:
- The decline in Airbnb performance across most U.S. markets
- How to avoid getting trapped by overly optimistic projections from tools like AirDNA
- Why knowing your bottom line is the most important skill when negotiating creative deals
- The hidden cost of four-star reviews and what you can do to protect your visibility
Mentioned in this episode:
- Weekender Management → weekendermanagement.com
- Pricelabs and AirDNA as examples of pricing and forecasting tools
- Arkansas Supreme Court case on short-term rental property rights
Favorite takeaway:
“A four-star review on Airbnb isn’t good. It can put your listing at risk and cost thousands of dollars in lost bookings.”
If you are an Airbnb host, investor, or property manager trying to make sense of the shifting STR landscape, this episode will give you practical strategies, cautionary lessons, and a candid look behind the scenes of one operator’s journey in 2025.
📍 Ready to build direct bookings with intention?
Apply for your free Revenue Review here → https://www.freewyldfoundry.com/report
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Jasper Ribbers | Freewyld
Welcome back to Get Paid For Your Pad. It’s Monday, which means another Rev Up episode where we dive into revenue management and give you a behind-the-scenes look at Freewyld Foundry. Today my guest is one of our revenue management clients, Garrett Ham. He’s been here before, and he’s the CEO and founder of Weekender Management out of Fayetteville, Arkansas. Garrett, welcome back.
Garrett Ham
Thank you, Jasper. It’s great to be back.
Jasper Ribbers | Freewyld
We used to meet weekly on Zoom when I was managing your account. Since then, one of our revenue managers took over, so it’s been a while. What’s new in the last six months?
Garrett Ham
It’s been eventful. My involvement in the short-term rental space is twofold. I run Weekender Management, managing properties for clients, and I also own and acquire my own properties. On top of that, I practice law exclusively in this area.
In the legal realm, my firm filed a lawsuit against the city of Fayetteville over short-term rental regulations. We argue the ordinances violate the Arkansas Constitution. After years in court, the case is now before the Arkansas Supreme Court, and I’ll be presenting oral arguments next week.
Jasper Ribbers | Freewyld
Regulatory challenges are a big issue in many markets. We’ll come back to that. I also know you’ve been expanding into new markets and acquiring properties. With prices holding steady while STR performance drops, how do you approach acquisitions?
Garrett Ham
Traditional deals are tough right now. Prices aren’t coming down, yet STR performance is trending lower. In the past year, we acquired about 10 or 11 properties, but only one was a traditional purchase. The rest were creative financing deals where sellers carried part of the note.
High-end homes are sitting on the market for 6-12 months, which creates opportunities. Sellers become more open to terms like owner financing. These deals allow us to keep growing even as the market adjusts.
Jasper Ribbers | Freewyld
How many properties do you typically analyze before closing on one?
Garrett Ham
For every purchase, we probably look at 100200 properties, make 10-20 offers, and close on one. It’s a big funnel. We use MLS, since I’m a licensed realtor, which also gives credibility when negotiating creative terms.
Jasper Ribbers | Freewyld
What’s the most important lesson from negotiating these deals?
Garrett Ham
Know your bottom line upfront. With creative deals, after many “no’s,” it’s tempting to compromise when someone finally says “maybe.” But stretching numbers or relying on overly optimistic projections can backfire quickly, especially now that tools like AirDNA often overestimate.
Jasper Ribbers | Freewyld
Let’s go back to regulations. What exactly happened in Fayetteville?
Garrett Ham
Fayetteville capped the number of STR permits and requires a conditional use permit from the planning commission. The standards are vague and arbitrary, which is part of our argument. We also believe the ordinances violate Arkansas’ strong protections of property rights. That’s what we’re fighting before the Supreme Court.
Jasper Ribbers | Freewyld
Airbnb has also tightened policies in the last year. How has that affected you?
Garrett Ham
We’ve maintained high-quality listings, so reviews haven’t hurt us much. But Airbnb is less host-friendly than before. Customer service is harder, and even a single bad review can trigger warnings. Competitors are working to reduce dependency on Airbnb, and I understand why.
We’ve seen cases of blackmail where guests demand discounts in exchange for avoiding bad reviews. In the past, Airbnb helped more in these situations. Now it’s harder. One review can linger at the top of your listing and cost thousands in lost revenue.
Jasper Ribbers | Freewyld
Exactly. I know a client with four identical units. One unit got a one-star review months ago, and it still performs 50% worse than the others. The review is stuck in the “most relevant” section, costing serious revenue.
Garrett Ham
We warn guests that four stars can hurt us, since many don’t realize it. People think four out of five is good, but on Airbnb, it’s not. That misunderstanding is one of the most frustrating parts of the system.
Jasper Ribbers | Freewyld
Do you think Airbnb will adjust?
Garrett Ham
I think the pendulum will swing back eventually. They went from tolerating bad hosts to being overly strict. Enough pushback from larger operators could force changes. For now, we’re focused on accuracy, hospitality, and diversifying where possible.
Jasper Ribbers | Freewyld
Tell us about Weekender Management and how people can connect with you.
Garrett Ham
We’re a full-service property management company. We manage our own portfolio and many client properties across Arkansas, Missouri, and Florida. If you want help managing your STRs, visit weekendermanagement.com.
Jasper Ribbers | Freewyld
I can vouch for Garrett and his company. Their operations are well-run, and I’ve seen firsthand how they manage revenue. If you’re looking for a trusted property manager, definitely check them out.
Thanks for joining, Garrett. And thank you all for listening. See you next time.
