Insurance Gone Wild

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 deduct...

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...

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...

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 sa...

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...

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...

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 undeniab...

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.)
Can they save people thousands and make hospitals rethink their billing nonsense? (Oh… absolutely.)

From $180,000 hospital bills cut down to $53,000 to the infamous duplicate billing game...

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...

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...

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 busi...

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.

Contact: contact@IGWPodcast.com
 • 817-753-0093
Hosts: Dennis...

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 w...

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 ho...

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 art. It’s chaotic, educational, and—somehow—still makes you want to check your endorsements.

Questions or horror stories? contact@igwpodcast.com
 • 8...

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 wildly overestimate life insurance (spoiler: a lot), and why urban drivers meet deductibles like they’re old friends. It’s equal parts wake-up call and cheat sheet—snark included—so you can stop letting...

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 insure anything except their anxiety.

Come for the consumer-first straight talk; stay for the lovingly sarcastic therapy session on health insurance, the myth of “it gets...

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 “parts” cover (A, B, C, D…yes, it’s a lot), and why timing your enrollment matters more than you might think.

Whether you’re approachi...

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, to millions potentially losing coverage, Dennis and Stephanie break it all down with humor, storytelling, and the kind of honesty you wish your insurance agent had...

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 entertained. Whether you’re a small business owner, a startup dreamer, or someone who just wants to avoid costly insurance mistakes, this one’s for you.

👉 Don’t just skim your policy...

Think your homeowners insurance is just about the house? Think again. In this episode of Insurance Gone Wild, Dennis Settlemoir and Stephanie Lencioni blow the dust off liability coverage and show you why it’s the unsung hero of your policy. From backyard fireworks disasters to trespassers who somehow end up suing you, Dennis and Stephanie unpack real-life “you-can’t-make-this-up” scenarios that prove liability insurance is worth way more than its modest price tag.

You’ll hear how liability extends far beyond your front porch—covering rogue golf balls, party mishaps, and even your kid’s science project gone w...

This week, Dennis and Stephanie pull back the curtain on what your homeowner’s insurance really covers—and more importantly, what it doesn’t. 🏠💥

From misleading premiums to missing ordinance and water backup coverage, they break down real-life examples of claims gone wrong. If you’ve never looked at “Page Two” of your policy, this episode might just save your financial future.

Whether it's hail, theft, water leaks, or fire damage—this is what every homeowner needs to know before disaster strikes. Don't let a cheap premium cost you everything.

🔑 Key Takeaways:

Cheap premiums = skim...

🎧 If You Fail to Plan… You Might Just Flood the Living Room | Insurance Gone Wild

What happens when disaster strikes and you realize your “emergency plan” is just yelling “Grab the dog!” and running for the door? In this episode of Insurance Gone Wild, co-hosts Dennis and Stephanie  dig deep into the uncomfortable (and critical) truth: you probably aren’t as prepared as you think.

From flash floods in Keerville to house fires and heart-stopping kid chaos, Dennis and Stephanie bring the hard facts—sprinkled with humor, real-life experiences, and just enough tough love to get you thinking...

🎧 Insurance Gone Wild | Health Sharing Programs: Too Good to Be True?
Hosts: Dennis Settlemoir  & Stephanie Lencioni
🎙️ Episode Title: “Health Insurance Alternatives That’ll Make You Rethink Everything”
📍Contact: 817-753-0093 | ✉️ contact@igwpodcast.com

What if we told you there’s a way to ditch your high premiums and still get covered without jumping through hoops of a traditional insurance plan? Well, buckle up — because in this episode of Insurance Gone Wild, Dennis and Stephanie dive headfirst into the world of health sharing programs — the not-quite-insurance, budget-friendly alternative you’ve probably never fully understood.

Stephanie L3nchoni, our in-h...

🎙️ Think your insurance policy has you covered? Think again. In this episode of Insurance Gone Wild, co-hosts Dennis Settlemoir and Stephanie Lencioni pull back the curtain on the surprising (and often hilarious) ways insurance can go sideways — especially when you don’t read the fine print.

From jewelry riders that vanish faster than a diamond in a drain to health insurance options you didn’t know you had, Dennis and Stephanie break it all down with straight talk, real stories, and a little tough love. Whether you're a business owner, landlord, or just trying to figure out if your wed...

Is Your Contractor Insurance Actually Covering You… or Just Paperwork Pretending to Help? 🧐

In this wild ride of an episode, Insurance Gone Wild hosts Dennis Settlemoir and Stephanie Lencioni break down the often-confusing jungle that is contractors' insurance. Whether you’re swinging a hammer, managing a crew, or just trying to keep your business from burning down financially — this one's for you.

We’re talking real talk on everything from:
✅ Subcontractor agreements that actually protect you
✅ Why fudging sales numbers could cost you later (don't do it!)
✅ The difference between a GC, a paper GC, a...

When Life Throws a Curveball: Are You Actually Prepared? 🧾💼⚡️

Dennis and Stephanie are pulling back the curtain on the “oh no” moments life loves to throw our way — from surprise ER visits to the “where’s the life insurance policy?!” panic. In this episode, they break down the must-know moves to keep your family prepared, not panicked.

They’ll tackle everything from:

Making sense of life insurance (no, it’s not just for old people) 💀

Organizing your financial & insurance info before it’s an emergency 🧠

Why your loved ones need access to everything (digital...

Join hosts Dennis and Stephanie as they explore insurance challenges for when you go on vacation, covering how auto and health insurance work during travel across states and with rental cars. They delve into essential coverage types, including liability and walk-away insurance, plus the nuances of PPO and HMO health plans. Discover insights on Medicare and international health coverage, ensuring you're informed about potential pitfalls and recommended precautions. Whether you're a road trip enthusiast or planning international travel, Dennis and Stephanie provide valuable advice to help you navigate your insurance needs.

Key Takeaways:
*   Understand how your a...

Who Gets Paid in a Claim?

When disaster strikes and you file an insurance claim, who actually gets the check? In this episode, we unpack the often misunderstood process of claim payouts. From homeowners and auto policies, we explain who the money goes to. 

We cover key concepts like lien-holders, service providers, and repair shops, and dive into how insurance companies decide who gets paid and in what order. Whether you’re filing a claim or just want to better understand your policy, this episode clears up the confusion and empowers you to ask the rig...

Dennis Settlemoir and Stephanie Lencioni delve into the current tumultuous state of the Texas insurance market in this episode of Insurance Gone Wild. They discuss premium spikes, particularly for homeowners, and the intricacies behind varying auto insurance rates. The duo also covers the challenge of navigating policy changes like scheduled roof coverage and the importance of understanding differences between insurance offerings. Listeners will gain insight into why insurance prices fluctuate so dramatically and the factors affecting these shifts, equipping them with knowledge to better manage

Key Takeaways:

*   The Dallas-Fort Worth area faces unique challenges i...

In this episode, we tackle a common but often overlooked question—how much insurance is too much? From health and life to home, auto insurance, we break down the different types of coverage and explore where peace of mind crosses into over-insuring.

We discuss how to assess your actual risk, evaluate your lifestyle and financial goals, and make sure you’re not paying for policies you don’t need. With expert insights and real-life examples, we help you find the right balance between being protected and being practical.

Whether you’re an insurance minimalist or a covera...

🎧 Welcome back to Insurance Gone Wild – the only podcast where decoding insurance lingo is actually fun

In this episode, hosts Dennis and Stephanie roll up their sleeves and dive headfirst into the wild world of insurance terminology — breaking down everything from "exclusions" and "deductibles" to the tongue-twisting "material misrepresentation" and the courtroom-favorite "estoppel."

💡 Whether you're an insurance newbie trying to understand your first policy, a small business owner protecting your assets, or a seasoned pro looking for a quick refresher, this episode will help you cut through the jargon and get to the good stuff: **what your...

In this  episode of Insurance Gone Wild, your favorite duo Dennis and Stephanie take you deep into the mysterious—and surprisingly strategic—world of captive insurance programs.

Forget what you thought you knew about insurance. We're talking **DIY insurance companies**—yes, businesses forming their own insurance entities to cover specific risks, protect assets, and (drumroll, please)... **legally lower their tax bill** under Section 831(b) of the IRS code.

If you're a business owner raking in $1M+ in revenue and you’re not exploring captive insurance... you might be leaving money (and protection) on the table.

✅ W...

In this dynamic episode of "Insurance Gone Wild," hosts Stephanie and Dennis unravel the complexities of commercial insurance, highlighting its stark differences from personal lines like home and auto coverage. They delve into the critical role of liability class codes—numeric identifiers that categorize businesses based on risk exposure—and emphasize why understanding these codes is paramount for business owners seeking adequate protection. Throughout their engaging discussion, Stephanie and Dennis share real-world insights, underscore the challenges inherent in managing commercial policies, and offer actionable advice on asking the right questions and consulting knowledgeable agents. This episode is a must-listen for...

Is insurance jargon making your head spin? You're not alone. In this fun and informative episode of Insurance Gone Wild, hosts Dennis and Stephanie cut through the clutter of confusing insurance terms with their signature blend of expert insight and light-hearted banter.

From “deductibles” that sound like math homework to “beneficiaries” that aren’t just something out of a soap opera, Dennis and Stephanie break it all down in plain English—no textbook required. They revisit popular insurance myths and dive into real-world examples that bring terms like “premium, “policyholder,” and “coordination of benefits” to life.

Whether you're tryin...

In this episode of "Insurance Going Wild," Dennis and Stephanie delve into the multifaceted world of health insurance. With the Affordable Care Act (ACA) serving as a surrounding framework, the hosts dissect various insurance options available for individuals, especially those navigating career changes or lacking access to group benefits. The conversation unveils the complexities of ACA-compliant plans, short-term health insurance, and emerging health sharing alternatives, equipping listeners with valuable insights into finding the most suitable coverage.

Dennis and Stephanie explore key aspects of ACA plans, highlighting their significance for low-income households and potential drawbacks for higher earners...

Join hosts Dennis and Stephanie in this episode of "Insurance Going Wild" as they demystify the often-confusing roles of insurance agents, brokers, and carriers. With their signature wit and engaging banter, Dennis and Stephanie break down the unique responsibilities of each player in the insurance game, helping you understand who does what when it comes to managing your policies.

Key Take Aways
- Insurance Agents vs. Brokers: Discover the key differences between agents, who represent insurance companies, and brokers, who advocate for clients. 
- Captive Agents Uncovered: Learn about captive agents who exclusively sell products f...

In this episode, hosts Dennis and Stephanie dive deep into the intricate world of life insurance, exploring everything from the importance of life insurance to the different policy types available for families and individuals. This podcast is designed for anyone curious about how insurance works and those ready to enhance their understanding, particularly focusing on the critical need for life insurance.

Understanding life insurance can be daunting, but Dennis and Stephanie break it down using key concepts and acronyms like LIFE and DIME to assess insurance needs. Through a conversation that mixes practical advice with real-world examples...

In this captivating episode of "Insurance Gone Wild," hosts Dennis and Stephanie unravel the intricacies and misconceptions surrounding insurance policy cancellations, non-renewals, and coverage nuances, especially in high-risk areas like California and Texas. They debunk myths perpetuated by media and political figures, offering listeners a clearer perspective on the evolving insurance landscape.

California's Wildfire Woes:

Amid escalating wildfire threats, California has witnessed a surge in policy non-renewals. Dennis elucidates the critical distinction between non-renewals and cancellations, emphasizing the importance of understanding legal terminology. He highlights how political influences often distort public perception, leading to confusion...

In this engaging episode of "Insurance Gone Wild," hosts Dennis and Stephanie introduce their first guest, Steven Paris, a 24-year-old recent Finance graduate from Missouri State University. Steven candidly shares his experiences and concerns about entering the adult world of insurance, particularly with auto and renters insurance. Dennis and Stephanie provide expert insights and advice to not only guide Steven but also to assist other young adults facing similar transitions.

Listeners will gain valuable knowledge on how to navigate the intricacies of choosing the right auto insurance coverage. Key topics discussed include understanding liability limits, the importance...

In this eye-opening episode of Insurance Gone Wild, hosts Dennis and Stephanie delve into the misconceptions surrounding insurance. They tackle prevalent myths that consumers often fall prey to and clarify these with expert insights. The conversation covers everything from the importance of insurance for peace of mind to dispelling common misconceptions about health insurance, homeowners, and auto insurance policies.

As the discussion unfolds, keywords like "insurance myths," "homeowners insurance," "health insurance coverage," and "auto insurance claims" are expertly explored. The hosts provide real-world examples that shed light on the essential nuances of choosing the right insurance plan...

When disaster strikes—whether it’s a fender bender, a burst pipe, or storm damage—should you file an insurance claim or handle it out of pocket? In this episode of Instance Gone Wild we break down the factors you need to consider before making a claim, from deductibles and rate hikes to coverage loopholes and long-term impacts. We’ll share real-life scenarios, expert tips, and maybe a little nonsense along the way. Tune in to make sure your next insurance decision is the right one!

 Key Takeaways:
 - Contact your insurance agent before calling the...

Uncover the secrets of homeowners insurance in this episode of Insurance Gone Wild podcast. Don't let misinformation cost you big - tune in now!

Chapters: 
00:00  Home Sweet Hassle: Navigating the Homeowners Insurance Maze 
05:04  Up in Smoke: How Wildfires Are Torching Insurance Costs
06:50   Premium Panic: Solving the Rising Cost Crisis
13:05  Deductibles Demystified: Get Your Money Back (Kind Of)  
16:12  Insurance Hackathon: Creative Ways to Save Big 
23:58 Roofing Roulette: Shady Practices in Texas You Need to Know  
29:40 Deductible Drama: The Interest-Free Payment Plan That Wins Clients 
33:29 Twister Trouble: Tornado Insurance and the Buyback Lif...