From Drunk Sailors to AI Models: Insurance Has Always Been a Thing

Insurance feels modern, complicated, and overpriced — but here’s the plot twist: it’s actually been around for thousands of years, and the core idea has never changed.

In this episode of Insurance Gone Wild, Dennis and Stephanie take a surprisingly entertaining trip through the history of insurance — from ancient merchants spreading risk across ships and camels, to London coffeehouses full of underwriters (yes, possibly drunk), all the way to today’s AI models, parametric coverage, and rising premiums.

Along the way, they break down:

Why insurance exists in the first place (hint: it’s not to annoy you)

How “claims-made” vs. “per occurrence” policies can quietly ruin your day

Why prices keep going up — and why it’s not just insurance

How supply, demand, zip codes, and exposure really drive premiums

And why even the richest people in the world still carry insurance

At the end of the day, insurance isn’t about policies, paperwork, or marketing mascots — it’s about peace of mind, protecting your family, and not losing everything over one bad moment.

Same idea. New packaging. Still necessary.

⏱️ Chapters

00:00 – Why Mondays Hit Insurance People So Hard
03:46 – How Insurance Started With Ships (and Fear)
05:43 – London Fires, Coffeehouses, and the Birth of Modern Insurance
09:28 – Insurance Isn’t for You — It’s for Your Family
15:14 – Claims-Made vs Per Occurrence (AKA: Surprise!)
20:21 – Why Insurance Companies Hoard Money (On Purpose)
24:58 – AI, Analytics, and Parametric Insurance
26:31 – Why Everything Is More Expensive (Including Insurance)
33:57 – Supply, Demand, Zip Codes, and “Too Much Exposure”
38:48 – Lloyd’s of London and Why the Basics Still Work
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