All Essays · 11 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
· August 28, 2026The Questions Before the Policy, Part 1: Why Underwriters Price the Company
With almost no loss history to price against, AI underwriters price the company instead of the risk, and the renewal questionnaire is where that judgment is made.
Read the essay →Series · New to insurance? Start here
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.
Part 1 · Live
August 12, 2026The First Claims, Part 1: What the Machine Said
The first AI liability claims are about what the machine said. A chatbot's false promise and a fabricated accusation show insurers where an old exposure now speaks in a new voice.
Read the essay →Part 2 · Live
August 19, 2026The First Claims, Part 2: What the Machine Did
The first AI liability claims are also about what the machine did. Biased hiring algorithms and the fight over training data show where the biggest exposures are, and where the exclusions are moving fastest.
Read the essay →The Questions Before the Policy · 1 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.
Part 1 · Live
August 28, 2026The Questions Before the Policy, Part 1: Why Underwriters Price the Company
With almost no loss history to price against, AI underwriters price the company instead of the risk, and the renewal questionnaire is where that judgment is made.
Read the essay →Part 2 · Scheduled
The Questions Before the Policy, Part 2: The Underwriter's File
Arrives September 2, 2026
Standalone essays
Essays that stand on their own, outside any series.