Diligence
6 pieces
The Halvard Dilemma: Why the Last Mile of AI Is Judgment
In 1999, capital underwrote dark fiber and Webvan by their existence, not their operating physics. AI infrastructure is repeating it with Paper Megawatts.
How Investors Stress-Test Market Sizing — and How to Catch Yourself First
Most sizing slides describe a market assembled for the meeting, not one that exists. The number that survives scrutiny is one whose every figure has provenance.
The Questions That Kill a Series A Deck
Most Series A decks die in the first meeting to four or five plain questions a disciplined partner asks — questions a founder can run on themselves first.
The First-Meeting Questions
The set of questions a partner asks in a first meeting, codified as a self-administered instrument — what each one tests beneath the surface, and how to read a strong answer from a weak one.
The Half-Life Curve
A reading instrument for AI system reliability — how to think about the gap between demo capability and deployment capability, and what flattens the curve.
Data and Signal in the 2023 Reset
The 2023 venture environment is materially different from the one that closed 2021. A reading of which signals matter most in the reset — and which are giving founders and investors false readings.