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), agree (occasionally), roast carriers for not knowing their own appetite, and somehow end up with Stephanie defending AI and Dennis yelling at bots. If you’ve ever been told “yes,” then “no,” then “well… maybe” by underwriting—this one’s for you.

Human touch still matters. AI still guesses. And no, the robot cannot answer your question.

Chapters

00:00:00 - Welcome Back to Chaos (It’s Been a Week, Again)

00:01:11 - AI Is Affecting Everything… Including Our Patience

00:02:46 - Financial Advisors, Algorithms, and Following Politicians’ Trades

00:04:05 - Why Insurance Companies Tried to Kill Agents (And Failed)

00:06:19 - Where AI Actually Touches Agents Today

00:08:11 - New Construction, Bad Data, and AI Saying “No” for the Wrong Reasons

00:11:36 - Weather Prediction: Why 45% Rain Means Nothing

00:13:15 - Actuaries, Guessing, and Why Rates Keep Going Up

00:17:05 - Claims Without Adjusters (What Could Possibly Go Wrong?)

00:18:39 - Fraud, Roof Photos, and Why Your Neighbor’s House Matters

00:20:32 - Fender Benders, Fake Damage, and the Serpentine Belt Incident

00:23:28 - When AI Should Flag Claims (But Not Decide Them)

00:26:19 - Chat Bots, Phone Bots, and Dennis’ Deep Hatred of All Bots

00:29:48 - Underwriting Appetite: Restaurants, Alcohol, and Dance Floors

00:33:56 - Calling Back Until You Get the “Right” Answer

00:38:54 - Human Error vs Automation (The Real Problem)

00:41:12 - Stephanie Accidentally Defends AI

00:42:40 - The Future of AI, Human Touch, and Why This Argument Isn’t Over