Insurance Gone Wild

Nobody likes talking about death. But your family will have to. In this deeply personal episode of Insurance Gone Wild , Dennis shares what he's experiencing firsthand while helping settle the affairs of an elderly couple—and why it's convinced him that life insurance is only one piece of the puzzle. The conversation goes far beyond policies and premiums. Dennis and Stephanie discuss the emotional...

Is life insurance a scam? Is investing your money instead a better idea? And do you really need it if you're young and healthy? In this episode of Insurance Gone Wild, Dennis and Stephanie respond to real comments from listeners and tackle some of the biggest misconceptions surrounding life insurance. The conversation gets passionate as they explain why term life insurance is often far more afford...

It started as a conversation about insurance... And quickly turned into a therapy session for just about everyone living in 2026. In this episode of Insurance Gone Wild , Dennis and Stephanie tackle the growing frustration many consumers are feeling as prices continue to rise, health insurance becomes increasingly difficult to navigate, and information overload leaves people feeling stuck. From sk...

You set up the LLC. You bought the rental property. You got insurance. So you’re protected… right? Maybe not. In this episode of Insurance Gone Wild, Dennis and Stephanie welcome investment property insurance specialist Todd Burnell to break down one of the biggest mistakes real estate investors make: 👉 Your insurance policy might not actually match your property ownership. And if the deed, LLC,...

It’s time for the annual Airing of the Grievances… insurance edition. In this episode of Insurance Gone Wild, Dennis and Stephanie vent about the thing everyone in insurance secretly complains about: 📞 endless hold times 🤖 automated systems that solve nothing 📧 underwriting departments that disappear for days 📂 claims adjusters who never call back 💸 rising premiums with shrinking coverage Fro...

Storm season is here—and if you think a little wind or hail means a brand-new roof, you might be in for a rude awakening. In this episode of Insurance Gone Wild, Dennis and Stephanie break down what really happens when storms hit your home, your car, and your insurance policy. From wind vs. hail claims to the frustrating truth about partial roof replacements, they unpack the biggest misconceptions...

Most business owners think they’re covered… until they’re not. In this episode of Insurance Gone Wild, Dennis and Stephanie pull back the curtain on the wild world of commercial insurance—and yeah… it’s worse than you think. We’re talking: A jiu-jitsu gym classified as a building materials dealer (??) A 24-hour restaurant with zero liquor liability Claims that were approved… then mysteriously “dis...

What do a comedian, a fake deer accident, and a totaled car have in common? Apparently… a masterclass in what not to do with your insurance claim. In this episode of Insurance Gone Wild, Dennis and Stephanie break down a viral comedy bit that raises a very real question: 👉 Could you actually fool an insurance company with a “creative” claim? From staged deer collisions (yes… involving venison 😳)...

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 do...

d most ridiculous) insurance claims during the holiday season. Spoiler alert: 🎄 Your Christmas tree might be plotting against you 🕯️ Your candles are more dangerous than they smell 🚗 And your neighbors? Yeah… they might steal your Amazon packages From house fires caused by cooking and decorations to burst pipes during cold snaps, and the shocking truth about holiday theft and accidents, this epi...

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...

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 cover...

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 l...

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 unde...

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...

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 wh...

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 peop...

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 perc...

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...

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 wage...

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 rea...

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...

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 basi...

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 th...

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 every...