Investment Memo Devil's Advocate
Stress-test an existing investment thesis by arguing the strongest bear case and exposing weak links in the logic.
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
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
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
Run it, then refine. Ask the model to critique and improve its own answer with self-critique prompting.
Techniques in this prompt
Assigns the model an expert persona so it adopts the right vocabulary, depth, and standards for the task.
Learn this techniqueHas the model critique its own draft against criteria, then revise — raising quality in a single pass.
Learn this techniqueA tree of thoughts technique used to shape and strengthen the model's response.
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