Teaching an AI to research stocks and poke holes in my ideas

I had a trade idea. To evaluate it properly I needed: current price action, historical bars for technicals, macro context, and whether the company filed anything interesting with the SEC recently. Four different sources. Four different formats.

That's a lot of context switching for one question: "Is this idea actually any good?"

The research agent

Give it a ticker, it goes to work. It pulls market data, computes technicals, fetches filings, and puts it all into a structured report. Technicals, fundamentals, recent filings, preliminary thesis assessment.

No single piece of the output is amazing on its own. The technical analysis mostly tells me what I can already see on the chart. The value is seeing everything in one place. Instead of switching between six tabs and trying to hold the full picture in my head, I get a structured starting point.

Is it as good as a professional analyst's report? No. Is it better than what I was doing before, which was "glance at a chart and go with my gut"? By a lot.

The thesis interviewer

This might be my favorite thing I've built. Almost didn't build it because it sounded gimmicky.

You describe a trade idea and it asks hard questions. What's your exit plan? What if the catalyst doesn't materialize? How much are you willing to lose?

It surfaces things I hadn't considered. Not because the AI is smarter. It's just methodical in ways that humans, especially humans excited about a trade idea, aren't. It asks the obvious questions you forgot to ask yourself because you were busy being convinced you were right.

I haven't had a dramatic "gotcha" moment where it saved me from a terrible trade. It's more subtle than that. It forces me to articulate my reasoning, and sometimes the act of articulating it reveals how thin it is.

The workflow

The two tools together create a loop: start with an idea, run the research agent to build context, then run the thesis interviewer to stress-test the idea against that context. What comes out the other end isn't a recommendation. It's a clearer picture of whether the idea is worth acting on.

Some ideas don't survive the process. That's the point.

What I've learned about AI in trading

If I've learned anything, it's that AI is best at synthesis and worst at judgment. Give it five sources about a company and ask for themes, and the results are solid. Ask "should I take this trade?" and it can't answer that. It doesn't know my risk tolerance or portfolio context.

As a devil's advocate it's surprisingly effective, because it doesn't care about being right. It just pokes at your reasoning until it finds weak spots. Humans get attached to ideas. AI doesn't.

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