I've spent years building AI prompt systems for real investment research with real money behind it. Here are the 5 failure modes I see investors make and how to fix every one of them.

I manage a small private investment fund and I have been building AI-powered research systems for my own portfolio for years. Not hypothetical backtests. Not paper trading. Actual capital allocation decisions where being wrong costs real money. After running hundreds of analyses I started noticing the same five failure patterns in AI output. Once I learned to diagnose them, the quality of my research improved by an order of magnitude. Every single one of these failures is an input problem, not a technology problem. Failure Mode 1: The Confident Generalist This is the most common one.