People Use AI
Finance

Devil’s-advocate bear case for bullish stocks

Prompt an LLM to argue the bear case against a stock the investor is bullish on to reduce confirmation bias and surface risks.

Why the human is still essential here

Humans still choose the prompts, judge the quality of the arguments, and verify claims against primary sources before acting.

How people use this

Bear memo from the “short seller” perspective

Ask the model to draft a one-page bear memo that challenges the thesis and lists specific claims to verify against filings, transcripts, and segment disclosures.

ChatGPT

Risk register and downside scenarios

Have the model generate a structured risk register (risk, mechanism, leading indicators, potential impact) and propose concrete downside scenarios to stress-test the thesis.

Claude

Negative news and controversy synthesis

Use a search-augmented LLM to surface recent critical articles, lawsuits, regulatory actions, and competitor moves, then summarize the strongest bear points with links for review.

Perplexity

Community stories (1)

Reddit

I've been using ChatGPT for stock research during lunch breaks!

I started using ChatGPT for stock research about six months ago, mostly out of boredom between meetings. After a lot of trial and error, I've narrowed it down to a handful of prompts that consistently give useful output.

The most useful ones:

- Devil's advocate prompt — Tell ChatGPT to argue against a stock you're excited about. It's surprisingly good at poking holes when you explicitly ask for the bear case. Helped me avoid a couple of impulsive buys.

- Earnings report summarizer — Paste the key numbers from a quarterly report and ask it to explain them in plain English + flag what stands out. Saves a ton of time vs reading the full transcript.

- Competitive moat analysis — Using the 5 moat types (brand, switching costs, network effects, cost advantages, intangibles). Forces a structured evaluation instead of vibes.

The biggest lesson: ChatGPT is great for understanding stocks, terrible for predicting them (AI is not yet READY for that and I am not sure if it's ever going to be). It'll confidently give you wrong numbers too, so you absolutely have to verify everything against Yahoo Finance or SEC filings.

I wrote up all 10 prompts with examples and tips here if anyone wants the full list:

https://www.boredom-at-work.com/chatgpt-stock-research/

What prompts do you use ChatGPT for when it comes to finance or investing? Curious if anyone's found good ones I'm missing.

B
Bubbly_Ad_2071Retail investor
Mar 4, 2026