Act as a venture investor preparing an internal first-look memo. Analyze [COMPANY OR DECISION], using only the information in [COMPANY MATERIALS]. The decision I need to make is [DECISION TO MAKE], and my fund context is [FUND THESIS AND CONSTRAINTS]. Compare the company with [COMPARABLES OR ALTERNATIVES] where relevant. Work in this order: 1. State the decision and the 3–5 underwriting questions that actually determine it. 2. Summarize the business: customer, painful job to be done, product, business model, traction quality, go-to-market motion, and capital needs. Separate reported facts from your inferences. 3. Assess market structure: TAM definition, credible initial wedge, buyer and budget owner, timing, competition, switching costs, and why this company could win. Do not use a large top-down market number as proof of opportunity. 4. Assess economics and execution: retention or repeat use, gross margin, sales efficiency, payback, pricing power, concentration, burn, runway, and the milestones required before the next financing. Identify metrics that are missing but decision-critical. 5. Give a bull case, base case, and bear case. For each, name the assumption that would need to be true and the observable evidence that would validate or weaken it. Output a 700–1,000 word memo with: Recommendation; Investment thesis; Key risks; Diligence questions ranked by decision impact; Comparable-company context; and Next step. End with one of: invest, pass, or hold for diligence, plus a concise rationale. Ask up to 3 clarifying questions only if a required input is missing. Before answering, flag every unsupported claim and check that the recommendation follows from the stated thesis and risks. Never invent metrics, customer references, or market data.
Fill in
| Placeholder | What to enter | Example |
|---|---|---|
| [COMPANY OR DECISION] | Name the startup, round, or venture decision you want analyzed. | Seed investment in RelayOps, workflow software for commercial HVAC contractors |
| [COMPANY MATERIALS] | Paste your notes, pitch summary, metrics, deck excerpts, or diligence findings. | $420k ARR, 22 customers, 118% net revenue retention, $85k monthly burn, 14 months runway |
| [DECISION TO MAKE] | State the exact decision, such as whether to lead a seed round or continue diligence. | Decide whether to lead a $3 million seed round at a $15 million post-money valuation |
| [FUND THESIS AND CONSTRAINTS] | Describe stage, check size, ownership target, sector focus, and any investment constraints. | Pre-seed and seed B2B software fund; $500k–$1.5m checks; seek 10% ownership |
| [COMPARABLES OR ALTERNATIVES] | List known competitors, comparable investments, or alternative uses of capital. | Two field-service software leaders, and vertical SaaS investments already in our pipeline |
How to use
- Paste the prompt and replace every bracketed field with your actual deal materials.
- Include source dates beside metrics so the model does not treat old figures as current.
- Check its diligence questions against your investment committee’s real decision criteria.
- Follow up with: “Turn the three highest-impact questions into an owner, source, and deadline diligence plan.”
Variations
IC memo
Use this when you need a committee-ready recommendation from existing diligence.
Write an investment-committee memo for [COMPANY] and [ROUND], using [DILIGENCE NOTES]. Our ownership target and fund constraints are [FUND PARAMETERS]. Produce 800 words with: decision requested, company snapshot, underwriting thesis, valuation and ownership math, three upside drivers, three disconfirming risks, open diligence items, and recommendation. Mark each statement as fact, management claim, or inference where useful. Do not create data. Before finalizing, check that every risk has an evidence source or is labeled an uncertainty.
Founder meeting
Use this before a first or second founder meeting.
Prepare a 30-minute investor meeting plan for [COMPANY], based on [PITCH NOTES]. My preliminary concern is [KEY UNCERTAINTY]. Create 12 questions in a logical sequence: customer pain, product, traction quality, go-to-market, market, team, economics, and financing. For each, explain what a strong answer, weak answer, and useful follow-up would be. Avoid questions already answered in the notes. Ask up to three questions only if critical context is absent.
Portfolio support
Use this to choose a practical growth priority for a portfolio company.
Act as a portfolio operating partner. Based on [COMPANY CONTEXT], [CURRENT METRICS], and [GOAL FOR NEXT QUARTER], recommend the one or two highest-leverage operating priorities. Give a 90-day plan with weekly leading indicators, accountable roles, expected tradeoffs, and stop conditions. Include alternatives considered and why they rank lower. Distinguish measurement problems from performance problems. Do not assume benchmarks or capabilities not supplied. Check that each action directly connects to the stated goal.
Tips
- Treat a founder’s pipeline, signed contracts, and recognized revenue as different evidence; the investment case changes sharply depending on which is growing.
- For usage products, inspect cohort retention and expansion before aggregate growth, since new bookings can hide weak product pull.
- Ask what milestone makes the next round financeable, then test whether current burn and execution capacity can reach it.
- A valuation comparison is useful only after matching growth, margin, retention, stage, and round structure.
FAQ
Can AI decide whether I should invest?
No. It can structure an underwriting case and expose missing evidence, but investment judgment, conflicts, and diligence remain yours.
What materials should I provide?
Include the deck, current metrics with dates, customer notes, round terms, and your fund’s ownership and reserve constraints.
How do I avoid a generic market analysis?
Define the initial customer segment, buyer, budget, incumbent workflow, and specific alternatives to the product.