Chat_147 - Insuring the Uninsurable with Rob Hamilton

"One of the founding tenets of anarcho-capitalism [is] that in a world without a government, you would have insurance contracts as the means for negotiating, disputing things. This actually goes into the original fire
departments were actually insurance companies. You'd purchase fire insurance from a particular purveyor of fire insurance and you would actually stamp on the cornerstone of your building, the sigil of whatever insurance company was protecting your property.
If the fire burned the building, the insurance company's on the hook. It's the most skin in the game, risk aligned way to get different parties to align on an outcome as an insurance contract. It's so much cheaper just to have an on-call fire bucket brigade team than to rebuild a building. So in the world without a government, you have insurance contracts."
~ Rob Hamilton

In this conversation with Rob Hamilton of AnchorWatch, we dive deep into the evolving frontier of Bitcoin custody, multisig innovation, and the emergence of Bitcoin‑insured financial infrastructure. We explore how tools like Miniscript and MuSig are reshaping what’s possible with shared ownership, time locks, and key hierarchies, and why AnchorWatch’s partnership with Lloyd’s of London represents far more than just insured Bitcoin—it’s a preview of an entirely new risk and capital market built on Bitcoin.

We talk about turning legal contracts into programmable money, the bridge between Bitcoin and traditional insurance, and the future path from Lloyd’s underwriting to fully Bitcoin‑denominated coverage. Rob breaks down how multisig could transform the meaning of trust, and we even venture into the implications for Lightning, AI authentication, and the long‑arc future of custody itself.

How do we insure Bitcoin without fiat? Can multisig redefine the institutional model? And what might a Bitcoin‑native insurance industry look like when the world finally catches up?

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