Investment Memo for Any Opportunity

What it does

Generates a structured investment memo for evaluating any significant resource commitment — venture investment, internal project funding, acquisition, major vendor selection, or strategic partnership. The format works for a $50k project budget request and a $5M acquisition decision. The key discipline: it forces you to articulate the thesis, anti-thesis, and what would change your mind.

The Prompt

Write an investment memo for the following opportunity.

Opportunity:
[DESCRIBE THE OPPORTUNITY — company, project, acquisition target, vendor, partnership. Include what's known: revenue/traction, team, market, technology, competitive position.]

Decision context:
- Decision type: [VC INVESTMENT / INTERNAL PROJECT FUNDING / ACQUISITION / VENDOR SELECTION / PARTNERSHIP]
- Investment size: [AMOUNT OR RANGE — or "TBD, help me think about this"]
- Decision timeline: [WHEN THE DECISION NEEDS TO BE MADE]
- Decision makers: [WHO READS THIS MEMO — board, leadership team, single exec]

What I know so far:
[DUMP EVERYTHING — pitch deck notes, call notes, financials, competitive intel, gut feelings. Raw and unstructured is fine.]

Structure the memo:

## 1. One-Line Recommendation
Invest / Don't invest / Conditional invest (with conditions stated). One sentence with conviction. Put this first so the reader knows where you're headed.

## 2. Investment Thesis (Bull Case)
3-5 bullet points. Each bullet: one specific reason to invest.
Rules:
- Each reason must be falsifiable (if I can't imagine evidence that disproves it, it's not a thesis — it's a hope)
- At least one bullet must address "why now" (timing advantage, market window, competitive moat forming)
- No generic statements ("large market"). Quantify or be specific: "[$X]B market growing at [Y]% with no dominant player in [specific segment]"

## 3. Anti-Thesis (Bear Case)
3-5 bullet points. Each bullet: one specific reason NOT to invest.
Rules:
- Steel-man these objections. Don't strawman the risks.
- For each: how severe (existential / significant / manageable) and how likely (high / medium / low)
- At least one bullet must address the "what if we're wrong about the biggest thesis point" scenario

## 4. Key Metrics & Evidence
Table format:
| Metric | Current Value | Benchmark / Comparable | Signal |
Signal column: Is this metric a GREEN FLAG, YELLOW FLAG, or RED FLAG for the thesis?

Include: revenue/growth, unit economics, engagement/retention, competitive position, team, and any domain-specific metrics.

## 5. Deal Mechanics
- Proposed investment/commitment: amount, terms, structure
- What we get: equity %, deliverables, rights, access
- Key terms to negotiate (if applicable)
- Comparable deals/pricing (if known)

## 6. Scenario Analysis
Three scenarios with approximate probability:
| Scenario | Probability | Outcome | Return/Impact |
- Upside case: what goes right
- Base case: realistic execution
- Downside case: what goes wrong
- Zero case (if applicable): complete loss scenario

## 7. What Would Change My Mind
Two lists:
- "I would upgrade to higher conviction if:" [2-3 specific, observable triggers]
- "I would walk away if:" [2-3 specific, observable triggers]
These must be concrete and checkable, not vague sentiment.

## 8. Open Questions
Specific questions that need answers before the decision. For each: who can answer it and what answer would be concerning.

## 9. Recommendation (Detailed)
Expand on the one-liner from section 1. Include:
- Recommended action and size
- Key conditions or milestones to attach
- What to monitor post-investment
- Suggested review/check-in timeline

Usage Notes

• The “anti-thesis” section is where most investment memos fail. If your bear case is weak, your bull case isn’t challenged, and the memo is advocacy, not analysis.
• “What would change my mind” is the highest-signal section for decision makers. It shows intellectual honesty and gives them specific things to test.
• Dump everything you know into the “what I know so far” section, even gut feelings. The AI structures the analysis; your job is to supply the raw information.
• For internal project funding, translate: “investment thesis” = “why we should fund this,” “return” = “business impact,” “deal mechanics” = “resource requirements.”
• This pairs well with the Scenario Planning prompt for deeper analysis of the three scenarios.