All Essays · 13 Published
Underwritten
Essays on insurance, risk, and the arrival of AI liability coverage. Long-form history and analysis from the team behind the buyer's guide, each piece a doorway into the data.
Newest essay
· September 16, 2026Guarantee or Indemnity
A performance guarantee pays when your AI fails to work. A liability policy pays when your AI harms someone else. Buyers lump the two together and end up holding the wrong one.
Read the essay →Series · New to insurance? Start here
The History of Insurance
01The Oldest BargainGenesis of insurance: pooling risk.July 22, 2026 →Also in brief · the 4-minute version →02Fire, Coffee, and MathematicsInception: from gamble to a discipline.July 23, 2026 →Also in brief · the 4-minute version →03Insuring the Machine AgePerigon: Insurance meets software.July 24, 2026 →Also in brief · the 4-minute version →Start with Part 1 →The First Claims · 2 of 2 parts published
A two-part reading of the earliest AI liability claims, split by how the machine caused the harm: what it said, and what it did.
The Questions Before the Policy · 2 of 2 parts published
A two-part guide to becoming insurable when there is no loss table: why underwriters price the company, and the nine-document file that makes you insurable.
Standalone essays
Essays that stand on their own, outside any series.