Prevent the Insurance Disaster Threatening Your STR Business with Darren Pettyjohn

Prevent the Insurance Disaster Threatening Your STR Business with Darren Pettyjohn

April 27, 2026 · 54 min · Episode 713

About this episode

Darren Pettyjohn discusses the critical insurance gaps in the short-term rental industry and the risks property managers face.

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…

People in this episode

Guest: Darren Pettyjohn

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Mentioned in this episode

Organizations: Proper Insurance, Hub International, Wister Insurance, Airbnb

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