The Stacking Benjamins Show
Why Your Homeowners Insurance Bill Keeps Going Up (And What to Do About It) Special Episode SB1876
Homeowners insurance prices are up a whopping 24% since 2022. One in seven homeowners now has no insurance at all. In some parts of the country, companies aren't just raising rates -- they're refusing to write policies. Bob Litterman co-created the Black-Litterman model that the financial industry still uses to price risk, spent 23 years running risk at Goldman Sachs, and now chairs the Coalition for an Insurable Future. He joins Joe and OG on a special Thursday episode to explain what's actually happening, why it's not going to stop, and what you can do about it right now.
What You'll Walk Away With
- Why the insurance market breaks down when probabilities stop being stable -- and how billion-dollar weather events went from three per year in the 1980s to 23 per year today
- The domino chain: how rising insurance costs in one ZIP code can drive down home values, freeze bank lending, shrink local businesses, and quietly hollow out an entire community
- Why this isn't 2008 -- and the one important way it's actually worse than what the mortgage crisis taught us
- Why one in seven homeowners now carries no insurance at all -- and what that means for the next major weather event
- The 100-year flood problem: why homes built to withstand a once-in-a-century event are now getting hit every five to ten years
- What first-time homebuyers should ask that their realtor almost certainly won't bring up -- and why the insurance question is now as important as the mortgage rate
- How to actually read your renewal letter: what to look for beyond the premium, what hidden changes insurance companies are legally required to disclose, and why your deductible may have quietly doubled
- OG's Claude trick: how he uploaded both his old and new policy documents, asked for the differences, and found actionable savings plus a jewelry rider gap he didn't know he had
- Why Bob says the real mispricing isn't in the insurance market -- it's in the pollution market -- and what that means for how this eventually gets resolved
- The risk management reframe: why thinking about insurance is the wrong starting point, and what to think about instead
Why This Matters Now
This isn't an inflation blip. The risk is genuinely increasing, the models are being rewritten in real time, and the insurance companies pulling out of markets are the canary in the coal mine. The good news: there are specific things you can do right now -- at your house, with your policy, and in how you think about risk -- that most homeowners haven't done yet.
From the Basement
Bob Litterman joins Joe and OG on a special Thursday episode to walk through the home insurance crisis from the inside -- the pricing models, the domino chain, the reinsurance squeeze, and the difference between a tail event and the slow-moving sea level rise underneath it. OG's takeaway: upload both your old and new policy to Claude and ask it to find the differences before your next renewal. Doug arrives with flood insurance trivia tied directly to the episode content. The Coalition for an Insurable Future, a nonpartisan cross-industry group, made this episode possible. Stacking Benjamins received compensation for this episode.
Resources Mentioned
- Coalition for an Insurable Future -- nonpartisan cross-industry group on climate and insurance risk; coalitionforaninsurablefuture.com
- Black-Litterman Model -- referenced for Bob Litterman's background in risk pricing
- Climate Central -- tracks billion-dollar weather events annually; climatecentral.org
- National Flood Insurance Program -- referenced for the 1968 government backstop for flood risk; floodsmart.gov
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