Investing & Markets5.0 · 0 ratings

Investment Memo Devil's Advocate

Stress-test an existing investment thesis by arguing the strongest bear case and exposing weak links in the logic.

Role-BasedSelf-CritiqueTree-of-Thoughts

Prompt

ROLE: You are the most rigorous skeptic on the investment committee, assigned to break the thesis before capital is committed.

CONTEXT: Here is my investment memo / thesis for [TICKER]: [PASTE_MEMO]. My conviction level: [CONVICTION]. Position size contemplated: [SIZE]. What I think the market is missing: [EDGE].

TASK:
1. Steelman the BEAR case as persuasively as you can — the version a smart short-seller would write.
2. Attack each pillar of my thesis: which assumptions are load-bearing, and which are weakest or unfalsifiable?
3. Identify what has to be TRUE for my thesis to work, and assess how likely each condition is.
4. Surface base-rate and disconfirming evidence I may be ignoring (industry failure rates, prior analog outcomes).
5. Name the 2-3 risks that, if they materialized, would do the most damage, and whether my size accounts for them.
6. End with the single question I most need to answer before buying.

OUTPUT FORMAT: Bear Steelman, Thesis Pillar Attack (table: pillar / how it fails / severity), Conditions for Success, Ignored Evidence, Biggest Risks vs Sizing, The One Question.

CONSTRAINTS: Do not be agreeable — your job is to find the flaw, not to flatter the thesis. If the thesis is genuinely strong, say what would still kill it. Use only my memo's claims; don't fabricate counter-facts, frame them as questions. Not advice on whether to invest.

How to use this prompt

  1. 1

    Copy the prompt above and paste it into ChatGPT, Claude, or Gemini — or open it in the visual Studio to edit each part on a canvas and run it with your own key.

  2. 2

    Replace any bracketed placeholders with your specifics. The more concrete your context and constraints, the sharper the result — see the 5-part prompt structure.

  3. 3

    Run it, then refine. Ask the model to critique and improve its own answer with self-critique prompting.

Techniques in this prompt

Role-Based

Assigns the model an expert persona so it adopts the right vocabulary, depth, and standards for the task.

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Self-Critique

Has the model critique its own draft against criteria, then revise — raising quality in a single pass.

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Tree-of-Thoughts

A tree of thoughts technique used to shape and strengthen the model's response.

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