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.
Read →How institutions, markets, and individuals navigate information under conditions of compression. The architecture mediating between data and judgement.
Every institution runs on an architecture sitting between data and judgement: what gets escalated, what gets filtered out, who is permitted to decide, what evidence a decision has to survive before it counts. The architecture is usually undocumented and almost never designed. It is inherited.
Under compression — more inputs, less time, higher stakes — the inherited architecture is what fails first, and it fails quietly. The information was available; the structure that would have surfaced it was not. A striking number of decisions that look like judgement failures turn out on inspection to be routing failures.
Private capital is the clearest case. The scarce input in venture was never capital, which is abundant and periodically oversupplied. It was the ability to separate the assumption carrying the whole story from the one that merely sounds good — and that ability has stayed artisanal, held inside individuals, resistant to being examined or transferred.
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.
Read →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.
Read →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.
Read →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.
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