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 deductibles to politicians meddling where they shouldn’t and why “free healthcare” is never actually free, Dennis and Stephanie break it all down with zero filters, strong opinions, and more than a few side rants.

Spoiler: nothing is getting cheaper — but it might stop getting worse. And right now, that counts as good news.

Chapters

00:00:00 – Welcome to 2026: Lower Expectations, Lower Increases

00:10:33 – Home & Auto Rates: Still High, Just Less Insulting

00:12:49 – Reconstruction Costs vs. Reality (Spoiler: Math Ain’t Mathing)

00:17:34 – COVID, Freezes, and Why Everything Broke at Once

00:21:25 – Politicians, Insurance, and Why This Never Ends Well

00:25:06 – Health Insurance Premiums: Choose Your Own Financial Disaster

00:32:54 – Dropping Coverage, Going Bare, and Hoping Nothing Happens

00:37:39 – Preventative Care: Use It Before You Rage Quit

00:42:15 – Socialized Medicine: Great If You’re Healthy, Awful If You’re Not

00:43:05 – Taxes, Incentives, and Why Nothing Is Actually “Free”

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