Insights & Analysis

The Grey Brief

Institutional perspective on origination, founder psychology, and strategic transitions.

Deal Sourcing Shivam Shirolawala Deal Sourcing Shivam Shirolawala

Structural Risk in AI-Driven Origination: The Plausible List Problem

AI-powered market mapping has reshaped buy-side origination, but the integrity of the target universe is increasingly in question. Classification systems built on large language models create plausible lists that appear comprehensive yet exclude companies investors never realize were missed. This article examines the structural risks embedded in AI-driven sourcing infrastructure and why coverage accuracy, not speed, determines mandate outcomes.

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Deal Sourcing Shivam Shirolawala Deal Sourcing Shivam Shirolawala

The 150,000 Company Problem

Most private equity CRMs are built to store companies, not to decide which ones matter. As databases scale, structure decays. What begins as thesis-driven coverage turns into undifferentiated accumulation, forcing BD teams to rely on sorting and filtering to answer a question the data was never built to answer: who should we call next.

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