Insurance Gone Wild

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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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 classic “tree limb smashed my tenant’s car” drama without turning a question into a claim. Come for the sarcasm, stay for the free advice your broker should’ve given you.

Chapters

00:00:00 – Feral Season: Kids, cameras, and chaos

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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 employer (not you, champ). We break down business-use vs. personal policies for realtors, agents, foremen, and trades, when a personal policy might say “LOL nope,” why companies love allowances more than fleets, and the legal circus where lawyers sue everyone with a pulse. You’ll also hear the infamous pee-break truck-rolls-into-a-house claim, a subcontractor vs. clearly marked gas line drama, and the trailer-full-of-tools tale that ended a business—plus a detour into curling-iron warning labels because of course. Bottom line: ask questions, disclose changes, and get the coverage that actually covers you—because our two immutable laws still apply: It depends and Insurance sucks.

 Chapters

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If you have questions, comments, concerns, strong opinions, or spicy rude remarks (we welcome those):

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We’ll answer your insurance questions whether or not you ever give us a dime.

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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 cry, you’ll probably check your deductible halfway through. Whether you’re an employee wondering why your premiums rival your mortgage, or a business owner trying to keep your sanity (and your staff), this episode will make you feel slightly better about it all.

Call it therapy, call it education — just don’t call your agent without listening first.

Chapters:

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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 require filing a claim, and the maddening truth about medical billing vs. cash pay. It’s practical help wrapped in humor—with one legendary six-banana intermission.

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Chapters

00:00:00 - Lights Up, Mics Hot

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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 with “appendectomy” (adorable), and somehow they map out how small businesses can save real money without summoning an HR demon. If you’ve wondered whether a $400 stipend can cover a whole family, why maternity waits a year, or whether your weekly “mom juice” voids coverage (it depends, breathe), this episode is wild, witty, and weirdly practical. 

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00:00 - Pop Quiz, Hotshot: Health Sharing 101

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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, and why endorsements are the dollar-store version of a real policy—this episode is your slightly sarcastic, very practical tour of why EPLI belongs in every business’s toolkit. Think of it as paying a retainer for an attorney you hope you never need… except it actually shows up.

Chapters

00:00 - Names Are Hard, Lawsuits Are Easy

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