Insurance Gone Wild

Life insurance gets misunderstood… a LOT.

In this episode of Insurance Gone Wild, Dennis and Stephanie break down why life insurance isn’t about “getting rich when someone dies”… and why that mindset is completely missing the point.

From the classic “buy term and invest the rest” debate to the controversial topic of life insurance for kids, this episode tackles the real questions people ask—but don’t always understand.

The...

The holidays are supposed to be magical…

but apparently they’re also peak season for fires, theft, water damage, and questionable life choices.

In this episode of Insurance Gone Wild, Dennis and Stephanie are joined by the one and only Policy Pete—who literally shows up uninvited—to quiz them on the most common (and most ridiculous) insurance claims during the holiday season.

Spoiler alert:

🎄 Your Christmas tree might be plotting agai...

You’re in a car accident.

It’s clearly not your fault.

The other driver has insurance.

So why is your insurance company getting involved?

In this episode of Insurance Gone Wild, Dennis and Stephanie break down a viral clip featuring a frustrated driver dealing with a “not at fault” accident — and the confusion that followed when the at-fault driver carried low state minimum limits.

video reference: https://www.instagram.com/...

What does it actually take to insure an event as massive as the Super Bowl?

In this episode of Insurance Gone Wild, Dennis Settle Meyer and Stephanie Lynchoni pull back the curtain on the wild world of large-scale event insurance — using the Super Bowl as the ultimate case study.

Spoiler alert: it’s not just one policy.

From general liability and excess coverage to cyber liability, terrorism coverage, assault and battery e...

In this episode of Insurance Gone Wild, hosts Dennis and Stephanie break down some of the most misunderstood — and expensive — areas of health and dental insurance.

If you’ve ever been confused about HSA vs FSA rules, wondered why doctors push year-end spending, or been shocked by a dental insurance max benefit, this episode is for you.

Dennis and Stephanie explain:

Why FSAs are truly “use it or lose it” while HSAs work ve...

Insurance feels modern, complicated, and overpriced — but here’s the plot twist: it’s actually been around for thousands of years, and the core idea has never changed.

In this episode of Insurance Gone Wild, Dennis and Stephanie take a surprisingly entertaining trip through the history of insurance — from ancient merchants spreading risk across ships and camels, to London coffeehouses full of underwriters (yes, possibly drunk), ...

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 brea...

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 unpac...

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? Abs...

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...

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...

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 i...

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 i...

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 ...

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 f...

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.

Are they insurance? (No.)

Do they act like insurance? (Kind of.)

...

It’s open enrollment chaos and Dennis and Stephanie are in rare form—part parenting therapy (“kids = feral”), part insurance intervention. They roast the industry’s favorite hobby—feelings masquerading as facts—then walk through why “coverage vs. cost” isn’t a slogan, it’s survival. Restaurants learn why a sewer backup can be a $20k cleanup, GCs learn “products-completed” isn’t optional, and everyone learns how to handle the classi...

Welcome back to Insurance Gone Wild—the show where we won’t fix the insurance industry, but we will absolutely roast it while helping you avoid accidentally bankrupting yourself. This week we tackle the Great Company Vehicle Mirage (“We’ll give you a $500 allowance—just use your car 🙂”), why that “sweet deal” can implode if you don’t ask your carrier the right questions, and how Non-Owned Auto Coverage (Symbol 9) protects your emp...

Tis the season for… open enrollment! Dennis and Stephanie dive into the thrilling, gut-wrenching world of health insurance like it’s the season finale of a reality show you didn’t know you were starring in. From why every employer seems to pick the most random renewal dates, to why your “perfect plan” doesn’t exist (sorry), they break down the madness with humor, sarcasm, and a sprinkle of “I told you so.”

You’ll laugh, you’ll c...