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Don’t Read the Policy… Just Ask Better Questions (And Pray Your Adjuster Can See)

Don’t Read the Policy… Just Ask Better Questions (And Pray Your Adjuster Can See)

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Should you read your insurance policy?

Dennis and Stephanie say no—and then spend the next 40+ minutes explaining exactly why.


In this episode of Insurance Gone Wild, the duo dives headfirst into the confusing, lawyer-written, comma-dependent world of insurance policies—where “herein” still exists, endorsements giveth and taketh away, and two adjusters can look at the same roof and see completely different realities.


They break down what consumers actually need to care about (hint: it’s not just price), why deck pages lie by omission, how underinsurance can quietly wreck your life, and why trusting the right agent matters more than trusting five-star internet reviews. Along the way, they share real-world stories—from brand-new homes burning down to $200,000 coverage gaps that make absolutely no sense.


Bottom line: insurance isn’t about reading 80 pages of legal jargon—it’s about asking the right questions, understanding the three C’s (Coverage, Cost, Claims), and making sure your house can actually be rebuilt from literal dirt.


Also discussed: bad adjusters, new agents learning the ropes, why “short episodes” are a lie, and why Dennis probably shouldn’t promise timelines ever again.


⏱️ Chapters


00:00:00 – Welcome to Chaos (a.k.a. “This Will Be a Short Episode”)

00:01:20 – Why Consumers Keep Asking the Same Insurance Questions

00:04:35 – Should You Read Your Insurance Policy? (Hard No.)

00:06:00 – Stephanie’s Airport Reading Story (and Public Humiliation)

00:07:52 – Are Policies Confusing on Purpose? Lawyers, Commas & ‘Herein’

00:10:30 – Core Policy Language vs. Endorsements That Ruin Everything

00:12:41 – Good Companies Pay Claims… Bad Ones Get Billboards

00:15:15 – The Three C’s: Coverage, Cost, and Claims

00:17:17 – Why Online Reviews Lie (and Roofers Know the Truth)

00:20:44 – Adjusters: The Wild Card Nobody Warned You About

00:23:23 – New Agents, Old Mistakes, and Learning the Hard Way

00:25:49 – Success, Failure, and Why Most People Ignore Good Advice

00:32:20 – The $200,000 Coverage Gap That Should Scare You

00:35:33 – Can Your Policy Rebuild Your House… From Dirt?

00:38:45 – Debris Removal, Ordinance Coverage & Commercial Nightmares

00:40:48 – “We Said This Would Be Short” (Final Lies & Wrap-Up)


Email: Contact@IGWpodcast.com

Facebook: https://www.facebook.com/InsuranceGoneWild


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