Notes on Due Diligence & AI

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July 22, 2026

Finding AI opportunities in companies that have never used AI

Most of the businesses we look at have never used AI. They are profitable companies run for decades on paper, fax, and hard-earned judgment. Assessing them is the opposite of auditing a startup's AI claims: management can't tell you where AI would help, because they don't know what the technology can do, and there's no reason they should.

The new essay covers how I work in that situation: tracing the work itself before mentioning technology, splitting every improvement into an AI lens and a without-AI lens, and why the roadmap gets decided jointly with the management team rather than handed to them.

Read it here: Finding AI Opportunities in Companies That Have Never Used AI

It's part two of a pair. Part one, on diligence when a target does ship AI, is here.

Roy

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