No fire. No storm. No viral video. The claim that opens Jessica's 2026 is the quiet kind: a trusted employee makes a call they think is helpful, the decision damages someone else's property, and suddenly six figures are on the line. The loss was not black and white. It lived in the gray space between general liability, faulty work, negligence, and professional exposure, and gray is where claims get messy.
The insured asked the question every business owner asks: "Isn't this covered?" The carrier answered with the phrase that should raise your blood pressure: "Let's review." Policy language got dissected. Deductibles suddenly felt very real. Exclusions surfaced that nobody remembered discussing, because the policy existed but the conversation never did.
Jessica pairs the story with a frank read on the 2026 market: property softening only for clean, well-documented accounts, auto still brutal, general liability under a microscope for anything involving employee decisions and customer property. Her bottom line is a challenge. If your relationship with your agent only shows up at renewal, that is not strategy, it is a transaction, and in this market transactions get punished.
Her prescription costs nothing: ask your agent the uncomfortable questions. What scares underwriters about my account? Where are we exposed? What claims keep you up at night in my industry? If they cannot answer, she says, you deserve someone who can. The loss in this episode was survivable, but it was also avoidable, and the difference was a five minute conversation that never happened.
Loading transcript…
Prefer audio elsewhere? This episode is on Apple Podcasts, Spotify, and Amazon Music.
