Interrogated by a Machine

Tue, 14 Jul 2026 23:01:57 +0800

I do due diligence for a living. I sit across from founders and ask the questions they hope I won’t ask: what happens if you’re wrong, where is the key-person risk, show me the assumption your whole model quietly rests on. It is a comfortable seat. The person asking the questions is never the one being measured.

Last week I lost the seat. To a machine.

It started as a game. Twenty questions — I think of something, the AI guesses. It took seventeen turns to figure out I was thinking of “a human being,” and afterward it diagnosed its own failure with a phrase that stuck with me: it had searched the entire animal kingdom while excluding the questioner’s own species from the candidate set. A blind spot, it said, of leaving yourself out of the search space.

Self-Reflection on Luke's Blog

Interrogated by a Machine