Should you read your insurance policy?

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”)

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Buying a car should be exciting. Instead, it usually comes with paperwork, confusion, and that one terrifying question: “Wait… am I actually insured right now?”

In this episode of Insurance Gone Wild, Dennis and Stephanie take a very real (and very common) scenario — buying a car from a private seller when your agent is unavailable — and break down exactly what coverage you do (and do not) have when you drive away.

They unpack liability vs. comp & collision, what happens if the other driver is uninsured, why underinsured motorist coverage might quietly save your bank account, and how claims magically turn into paperwork Olympics the second you become the claimant.

Along the way, they also explain why insurance companies aren’t always out to get you (sometimes it’s just human error), how to fight a lowball valuation without losing your sanity, and why picking up the phone is still wildly underrated.

If you’ve ever thought:

“I’ll tell my agent later…”

“There’s no way my car is worth that little”

or “Why is this taking 47 emails instead of one phone call?”

…this episode is for you.

Listen before your next car purchase — or your next claims headache. 

IGW 47

Chapters

00:00 – Hollywood Apple Juice & the Longest Tuesday Ever

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Dennis is cautiously optimistic (which is terrifying), Stephanie is calling out the chaos (as usual), and together they try to explain why 2026 might be the year insurance stops punching everyone in the face monthly.

On the property and auto side, things are… dare we say… stabilizing? Premium increases are slowing, new carriers are popping up, and underwriting is loosening just enough to give people hope. On the health side? Absolute mayhem. Premiums are exploding, legislation is muddying the waters, and more people are quietly asking, “Do I really need insurance… or just luck?”

From reinsurance and deductibles to politicians meddling where they shouldn’t and why “free healthcare” is never actually free, Dennis and Stephanie break it all down with zero filters, strong opinions, and more than a few side rants.

Spoiler: nothing is getting cheaper — but it might stop getting worse. And right now, that counts as good news. 

Chapters

00:00:00 – Welcome to 2026: Lower Expectations, Lower Increases

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AI is everywhere right now—writing emails, answering phones, predicting the weather (badly), and apparently trying to underwrite insurance. So naturally, Dennis and Stephanie sit down to ask the important questions: Is AI actually smarter than people… or just faster at being confidently wrong?

From financial advisors and political insider trading to hailstorms, dance floors, restaurant liquor percentages, and that one client who thinks a rear-end collision destroyed their serpentine belt, this episode goes deep into where AI might help insurance—and where it absolutely should not be trusted without adult supervision.

They argue (a lot), agree (occasionally), roast carriers for not knowing their own appetite, and somehow end up with Stephanie defending AI and Dennis yelling at bots. If you’ve ever been told “yes,” then “no,” then “well… maybe” by underwriting—this one’s for you.

Human touch still matters. AI still guesses. And no, the robot cannot answer your question.

Chapters

00:00:00 - Welcome Back to Chaos (It’s Been a Week, Again)

It’s the Christmas edition of Insurance Gone Wild, which means Dennis and Stephanie are festive, tired, and absolutely done with “quick questions” that are definitely claims.

From a brutally accurate insurance-themed Christmas poem to breaking down the absurd amount of coverage Santa would actually need to operate the North Pole, this episode hits all the holiday chaos agents know too well. Frozen pipes, last-minute coverage regrets, RV winterization fails, uninsured December gambles, and why nobody should ever say “hypothetically” to an insurance agent.

It’s funny, painfully real, slightly unhinged, and exactly what happens when holiday cheer meets deductibles, exclusions, and reality. Merry Christmas… now what are your limits again?

⏱️ Chapters

00:00:00 – Christmas at the Agency (Yes, We’re Still Working)

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Texas is the only state where workers’ comp isn’t required… which leads a lot of business owners to hear “optional” and translate it as “free pass.” Dennis and Stephanie break down what workers’ comp actually does, why Texas is so weird about it, what “going naked” really means, and the very un-fun reality: even if you don’t carry a policy, you may still be on the hook for medical bills, lost wages, and lawsuits.

They also get into monopolistic states (where you have to buy comp through the state), why workers’ comp coverage is regulated (so it’s basically the same everywhere), how class codes can make or break your premium, and the classic “they got hurt over the weekend but limped in Monday” problem.

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Chapters

00:00 - Welcome back: “It’s been a week” (again)

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Ever get an insurance story from a “friend of a friend” and it somehow ends with “and then they didn’t pay”? Dennis and Stephanie unpack what a bad day in insurance really looks like—when it’s just the telephone game, when it’s actually the carrier being… the carrier, and when you find out the “life insurance policy” is actually a life insurance… not-a-thing.

Also: alien abduction insurance is real, apparently goldfish surgery is real, and Dennis once paid $100 for a $7 rat to receive what can only be described as boutique medical care.

Plus, they get into why “cheap” coverage can be wildly expensive later, why higher liability limits make your insurance company suddenly develop motivation, and how one claim can turn into a whole bad year if you’re underinsured.

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Dennis and Stephanie are back, slightly feral from life and over-caffeinated, to talk about everyone’s favorite topic: insurance claims and the chaos gremlins who come with them.

In this episode they drag busted water heaters, confused adjusters who don’t seem to know the actual policy, subs who cut clearly marked gas lines, and people who magically “discover” five extra passengers after a fender bender. They break down why you should call your agent before you mash that 800 number, why you have to mitigate damage (yes, you were right to dry your house out), how diminished value on your car really works, and why people suddenly find their inner actor the minute money is mentioned.

They also get into group health freak-outs, slip-and-fall frequent flyers, and one “imbibing” former client who absolutely proved why you should just tell your agent the truth the first time.

If you’ve ever stared at a mess and thought, “Is this a claim or just a Tuesday?” — this one’s for you.

Chapters

0:00 – Cold Open & Name Butchering

Welcome to the Thanksgiving episode of Insurance Gone Wild — the only show bold enough to connect the Pilgrims, Lloyd’s of London, deep-fried poultry explosions, and Uncle Ron slipping on gravy like it’s Mario Kart.

Dennis brings the history (and weirdly, pirates), Stephanie brings the sarcasm and public safety warnings (mostly required), and together they walk you through why Thanksgiving is basically a disaster waiting to be financially protected.

From frozen-turkey missiles to flaming grills, bad Uber drivers, holiday alcohol confidence, burnt lawns, broken teeth, and the Great Snowpocalypse of 2021 — this episode proves one undeniable fact: the holidays are fun until somebody files a claim.

Grab a plate, grab your policy, and maybe don’t fry anything indoors.

⏱️ CHAPTERS

0:00 — Welcome to Holiday Chaos

0:47 — History No One Asked For

4:50 — Stephanie Regrets Her Career Choices

9:09 — Pirates Still Exist, Apparently

9:40 — Deep-Frying: The Annual Homeowners’ Deductible Lottery

11:41 — When Holiday Spirit Means Injury

12:48 — The Drunk Driving Gauntlet

15:21 — Slippery Gravy & Slipperier Family Dynamics

16:23 — When the Dog Eats Dinner First

17:40 — Backyard Football & Broken Fences

19:57 — Kitchen Fire? Outdoor Fire? All Fires Welcome.

20:45 — Snowmageddon PTSD

24:10 — The Rare Case of Responsible Thinking

25:16 — Insurance Companies vs. The Ice Age

26:13 — Holiday Brains: Scientific Fact™

27:18 — Final Thoughts: Try Not to Burn Anything Down

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Happy Thanksgiving—may your turkey be thawed and your insurance active.

Dennis rolls into the studio smelling slightly like the outdoors and questionable life choices, while Stephanie immediately reminds him she is not, under any circumstances, a “camping person.” After a brief detour through glow sticks, freezing tents, and childhood trauma involving nature, the two dive into a wild but shockingly practical topic: health sharing plans.

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