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AI Is Taking Our Jobs… But Can It Underwrite a Dance Floor?
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
View all episodes
By Insurance Gone WildAI 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