Decision Systems
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.
Reading Your Own Deck Like a Skeptic
Founders are structurally unable to read their own decks as a skeptic would. The fix is a method that locates the one assumption carrying the entire story.
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.
Why I Stopped Writing Checks and Built an Instrument
Four bets across twenty-nine years turned out to be one bet. The scarce input in venture was never capital — it was judgment. So I stopped writing checks and built the instrument.
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.