Insurance Gone Wild

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...

Dennis and Stephanie take the show live—and it gets delightfully weird, wonderfully useful, and wildly honest. From “can you insure a dominatrix?” (spoiler: yes) to small-biz health plans that actually make sense, they bust clickbait myths, decode the 60–65 pre-Medicare maze, and share real ways to cut premiums without upping your risk. Expect shrinkflation in policies, deductible-reimbursement hacks, wind/hail payouts that don’t r...

Dennis brings the pop quiz, Stephanie brings the receipts, and together they turn “wait, is this even insurance?” into your new favorite game show. They spar over health sharing vs. traditional plans, why “contribution” isn’t just a bougie word for premium, how faith-based commitments actually work, and when pre-existing conditions really are… pre-existing. Stephanie even vows to ditch her employer plan (spicy), Dennis wrestles wit...

Dennis and Stephanie stumble out of an HR presentation and straight into the wonderfully litigious world of Employment Practices Liability Insurance (EPLI). Between Dennis’ Ozarks charm and Stephanie’s “that really chaps my ass” energy, they skewer the myth that “we’ll just hire a lawyer” is cheaper than having coverage. From wrongful termination to TikTok-inspired “pranks,” vendor side-eye, retaliation, wage & hour landmines, ...

Dennis and Stephanie play Approved or Denied? with the weirdest claims on earth: a cow swan-dives onto a sedan, toilets go boom, a burglar sues after face-planting through a skylight, and a very good boy eats a very expensive diamond. Along the way you’ll learn why comprehensive isn’t just for deer season, when liability saves your bacon (and your neighbor’s fence), and how one stray golf ball can turn your windshield into modern a...

Medical bills that still bankrupt people who have insurance. Life insurance everyone swears is “too expensive” (until they actually check). Auto claims that hit faster than a Dallas hailstorm. In this spicy, stats-soaked episode of Insurance Gone Wild, Dennis and Stephanie drag the numbers into daylight and make them behave. You’ll hear why “I’ve got coverage” can still end in a five-figure out-of-pocket faceplant, how much folks w...

Broadcasting from the fiesta-friendly confines of Dos Amores in Hurst, Texas, Dennis and Stephanie take insurance out of the cubicle and into the cantina. With restaurant manager Jesús popping in between karaoke nights and Tejano Saturdays, this live episode leans into real questions from real people—why your premium jumped when you did nothing, whether bundling is a BOGO or a bozo move, and how a broke 21-year-old is supposed to i...

Confused about Medicare, Medicaid, and all the alphabet soup in between? You’re not alone—and that’s exactly why Dennis Settlemoir and Stephanie Lencioni are here to break it all down.

In this episode of Insurance Gone Wild, Dennis and Stephanie cut through the jargon and dive into what really separates Medicare from Medicaid. With their signature humor and honest takes, they’ll help you understand who qualifies, what the different ...

What happens when Congress names a law the One Big Beautiful Act? Spoiler: it turns into one big beautiful mess for health insurance. In this episode, Dennis (yes, the man with the hats) and Stephanie (the one who actually keeps things sensible) dive headfirst into the new legislation shaking up healthcare.gov, subsidies, and the future of insurance in America.From subsidies vanishing faster than free donuts in the office kitchen, ...

When it comes to protecting your business, is “cheaper” really better? In this lively episode, Dennis and Stephanie pull back the curtain on commercial insurance, breaking down the real risks of cutting corners and the hidden gold inside endorsements and classifications that too many business owners overlook.

They mix insider expertise with humor, real-life scenarios, and a little tough love, leaving you both informed and entertaine...