Wister Insurance + Freewyld Foundry: Protecting and Growing the Modern STR Operator
The short-term rental industry has evolved dramatically over the last few years. Operators are becoming more sophisticated; portfolios are getting larger, and the risks, both operational and financial, are increasing alongside the opportunity.
That’s why we’re excited to announce our new partnership between Wister Insurance and Freewyld Foundry.
At Wister, our mission is simple: help short-term rental property managers and co-hosts properly protect their businesses with insurance designed specifically for the STR industry. Freewyld Foundry helps operators maximize performance and revenue through hands-on revenue management and strategic growth support for top-tier STR businesses.
Together, the partnership creates something powerful for STR operators:
Better revenue optimization
Better operational strategy
Better business protection
Because growth without protection is risky, and protection without growth limits potential.
Why This Partnership Makes Sense
The reality is that many STR operators are scaling into legitimate hospitality businesses, but their insurance hasn’t caught up.
One of the biggest themes we discussed on the podcast was how many property managers believe they’re covered, only to discover critical exclusions after a claim happens. The most common gap? Liability coverage tied to the properties they manage.
At the same time, Freewyld Foundry works every day with operators who are aggressively growing revenue, improving RevPAR, and scaling portfolios through strategic revenue management.
As businesses scale, the stakes rise:
Larger teams
More owner relationships
More guest exposure
More contractual liability
More operational complexity
With Wister being the only comprehensive insurance solution on the market, and every other option leaving operators exposed through critical gaps in coverage, the choice is clear. For Freewyld's revenue clients to truly succeed, Wister isn't just a smart option; it's the only one that makes sense.
Freewyld helps operators grow smarter. Wister helps operators protect what they're building.
Listen to the Podcast Episode
To kick things off, one of our founders, Darren Pettyjohn, sat down with Eric Moeller on the Get Paid for Your Pad podcast to discuss one of the most overlooked topics in the STR industry: business insurance for property managers and co-hosts.
What came out of this conversation was a wake-up call.
Here's the core of what Darren shared: Most property managers think they have business insurance. They don't, not really.
You paid for a policy. It's in your desk drawer. You feel covered. But there's a strong chance that if your cleaner accidentally floods a managed property tomorrow, or a guest is injured and files a lawsuit, your policy won't respond. Not because of fine print — because of a specific exclusion called CG2270 that removes property damage liability at the properties you manage. It's in nearly every standard business policy sold to managers today.
And that's just one gap.
The episode covers:
Why the policy in your desk drawer probably has zero coverage for property damage liability at managed properties
The difference between CGL and E&O coverage, and why you need both
What Airbnb's March 2025 Air Cover update means for co-hosts
Multiple wrongful death lawsuits that Darren's team has written checks for
What to do in the first 10 minutes after an incident at a property
Freewyld also published an excellent companion article that expands on many of the topics we discussed: https://freewyldfoundry.com/blog/str-business-insurance
What This Means For You
If you're a vacation rental manager or co-host, here's the practical takeaway:
Check Your Coverage
Pull out your current business insurance policy and look for the CG2270 endorsement. Check whether you have E&O coverage listed. If you're unsure what you're looking at, we'll review it for free. We'd rather you understand your gaps than find out about them during a claim. Get a free consultation.
Get Your Free Revenue Report
If you're managing 15+ listings and not working with dedicated pricing expertise, you're likely leaving significant money on the table. Freewyld Foundry's team is worth a conversation. Get your free revenue report.
Freewyld Foundry is a revenue management and growth partner for high-performing short-term rental operators. Their team works with STR businesses generating $1M+ in annual revenue, helping clients optimize pricing, increase occupancy, and outperform their markets through hands-on revenue management and strategic support.
Watch the Episode
Even if you think you have your insurance handled, watch the episode. Darren has seen how this plays out from the other side of thousands of claims. Episode 713: STR Business Insurance Gaps to Fix Now →
And if you want to go deeper on the coverage specifics, read the Freewyld Foundry companion post here.
Frequently Asked Questions
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Commercial General Liability (CGL) covers bodily injury and property damage claims: a guest slips and falls, a cleaner breaks something, that kind of thing. Errors & Omissions (E&O) covers professional mistakes: bad advice, a missed booking, a maintenance issue you were responsible for that you didn't act on. You need both. Most policies sold to managers only include one.
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Longer than you think, and that's the problem. Statutes of limitations for personal injury vary by state but often run 2–4 years. For wrongful death claims, it can be longer. This means an incident you barely remember from two years ago can become a lawsuit today. That's exactly why your coverage needs to be airtight from day one, not patched after something happens.
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No. The sooner you call Wister after an incident (or even when you just suspect one), the sooner we can start investigating. Memories fade, stories shift, and details get muddled fast. Getting us involved early means we can document everything while it's fresh, which almost always works in your favor when it comes to the outcome and the cost of a claim. Waiting is what gets expensive.
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You pay out of pocket. A missed maintenance request that leads to a guest injury, a booking error that costs an owner revenue, a miscommunication that results in a dispute, these are all E&O scenarios. Without coverage, any settlement or legal defense cost comes directly out of your business. The average E&O claim in property management runs well into five figures.
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Yes. The number of properties doesn't change your legal exposure, it just changes the scale. If you're earning income by managing someone else's property, you have professional liability. A single incident at a single property can generate a lawsuit large enough to wipe out years of management fees. Co-hosts with 1 listing have the same legal vulnerability as managers with 100.
For more insights and tips for vacation rental managers and co-hosts, visit our Blog →
