Most property managers believe they have business insurance. They filled out a form online, got a policy, threw it in their desk drawer, and moved on with life. But here's the problem: that policy likely excludes coverage for the very thing they need most - property damage liability at the properties they manage.

Darren Pettyjohn built Proper Insurance from his spare bedroom to 160 employees and 150,000+ policies before selling to Hub International, the world's largest private insurance group. Now he's back with Wister Insurance, the only company focused exclusively on business insurance for vacation rental managers and co-hosts. And what he's discovered is shocking: the majority of STR operators are exposed to million-dollar lawsuits with zero coverage.

In this episode, Darren pulls back the curtain on the massive insurance gaps plaguing the industry, shares real examples of wrongful death settlements his team has paid out, and explains why Airbnb's Air Cover won't protect you when things go wrong.

You will hear:

- Why most business insurance policies specifically exclude property damage liability at managed properties (the CG2270 problem that could cost you $100,000+ in a single water damage claim)

- What changed in March 2025 with Airbnb's Air Cover that every co-host with 6+ properties needs to know immediately

- How the "air traffic controller" co-host model creates massive professional liability exposure that standard CGL policies don't cover

- Why you should call your insurance company for every incident, even minor ones, and how small settlements prevent massive lawsuits years later

- What it took to sell a company to the world's largest private insurance group (14 months, 16 companies, and lawyers on lawyers)

We also talk about:

- The four categories of STR insurance and which ones actually apply to your business

- Real wrongful death lawsuits Darren's team has settled in Florida (multiple million-dollar drowning cases)

- How sobriety and redirected energy became Darren's competitive advantage in building Proper

- The "reasonable person test" for property safety that could save you in court

- Why premium pricing won (Proper was the most expensive product in the industry with a 33% close ratio)

Mentioned in the Episode:

- Wister Insurance: https://www.wister.insure

- Darren's LinkedIn: https://www.linkedin.com/in/darren-pettyjohn-1708925/

Favorite Takeaway:

"Right now, you're a manager. Oh, I got insurance. I feel good. It's in my desk drawer. And you have no idea that you have no coverage for property damage liability at any of the properties you manage."

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