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Episode 007: Folder Mania — When AI Comes to You
Every AI tool claims it can read your folders. We actually tested that claim — across ChatGPT, Claude, Gemini, and Microsoft Copilot — using a real-world 48-document Chapter 13 case file. The results were all over the place.
Ron introduces the "File Cabinet Test": a threshold check that tells you whether an AI tool is actually seeing what you're giving it, before you trust it with anything that matters. Because if the AI is faking it — cherry-picking by relevance, wandering outside your folder, or missing documents entirely — that's not an AI intelligence problem. That's a visibility problem…
The skinny
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