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.
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