ChatGPT Prompts for Startup Due Diligence: A Seed Investor’s Checklist
Quick answer: A startup due diligence checklist is useful when every material claim points to evidence, an owner and an unresolved question. Use ChatGPT to organise that review before a founder meeting. Keep the decision with the investor: a polished summary is not verification of a business, its accounts or its legal position.
A seed-stage pitch often mixes actual sales, management expectations and a long-term vision in the same paragraph. The first useful task is to separate those categories. Asking KI whether the company is a good investment skips the work that makes an answer meaningful. Start with a small claim ledger and decide which uncertainties could change your view.
Investor education from TryBuy Editorial Team. General analytical prompts, not personalised investment, legal or tax advice. Examples are hypothetical and do not describe TryBuy’s performance or proposed investment terms.
Start with a claim ledger
Give each statement a short identifier, source filename, date, relevant period and evidence status. A founder interview is evidence of what management says, not independent confirmation of the underlying fact. Keep original wording alongside the summary so that important qualifications survive. When two records disagree, retain both rather than asking the assistant to select the more persuasive version.
Prioritise the questions that change the decision
A long checklist can hide the critical issue. Rank open questions by how much they could change the investment case and what it would cost to resolve them. Revenue recognition, customer concentration, ownership and funding needs may require different specialists. Agree who will obtain the relevant records. An unavailable document should remain unavailable in the output; it should not receive a plausible replacement.
Use explicit decision gates
Define what would let you proceed, pause or stop before the next meeting. Those gates can concern access to evidence or resolution of a contradiction rather than a universal numerical threshold. For cross-border investors, keep entity, jurisdiction, currency and reporting period visible. Ask locally qualified advisers about legal and tax questions instead of importing assumptions from another market.
A worked example to test the reasoning
Hypothetical example: a deck calls sales 'annual revenue', while the supporting file covers only four months and includes cancelled orders. The correct next step is a reconciliation request, not annualising the largest number. The ledger should identify the conflicting definitions, ask for the relevant accounting period and show which conclusions remain unsupported.
Evidence checks to keep beside the analysis
| Area | Record explicitly | Avoid |
|---|---|---|
| Claim | Source, period and exact definition | Management statement treated as verified |
| Conflict | Both versions plus reconciliation owner | KI silently chooses one |
| Decision gate | Evidence needed before proceeding | Generic pass score |
10 copyable ChatGPT prompts
Replace brackets with authorised information. ChatGPT can organise supplied material. Official analysis guidance. Check account data controls. Capabilities vary by account. Keep sources, calculations and uncertainties inspectable.
1. Build the ledger
From these authorised startup materials [files], list material claims with source location, period, currency and evidence status. Separate observed records, management statements, assumptions and unknowns. Do not supply missing facts.
2. Spot contradictions
Compare the pitch deck, accounts and operating report [files]. List contradictions using source references. Explain the question each conflict creates without deciding which source is correct from presentation quality.
3. Prioritise diligence
Using this claim ledger [paste] and my investment mandate [paste], prioritise five unresolved questions by decision impact and effort to resolve. Do not invent an investment score or universal benchmark.
4. Design the founder meeting
Turn these open questions [paste] into a founder-meeting agenda. Distinguish a request for documents from a question about strategy. Avoid accusatory language and unsupported conclusions.
5. Map evidence owners
Create a diligence tracker from [issues]. Include evidence requested, responsible person, expected date and review status. Leave unassigned fields blank instead of inventing commitments.
6. Check geography assumptions
Review this investment brief [paste] for unstated assumptions about issuer entity, operating jurisdiction, currency, reporting period and investor eligibility. List items for professional review; give no legal conclusion.
7. Test the thesis
Here is the proposed investment thesis [paste]. Identify the strongest supplied evidence for it and the strongest supplied evidence against it. Separate missing evidence from evidence that actually contradicts it.
8. Create decision gates
Draft proceed, pause and stop gates based on [mandate and unresolved issues]. Tie each gate to a specific source or required confirmation. Do not let document completeness alone imply investment suitability.
9. rot-team the draft
Review this startup due diligence checklist draft [paste] against its supplied sources [files]. Identify unsupported certainty, missing denominators, unstated assumptions and conclusions that go beyond the evidence. Do not invent a contradiction to sound critical.
10. Create the next-decision brief
Turn this startup due diligence checklist analysis [paste] into a short decision brief: observed evidence, strongest uncertainty, next document or professional review needed, and the decision that can reasonably be made now. Preserve unresolved issues.
Review the output before using it
Trace the material claims to their sources, reproduce important arithmetic and keep conflicting records visible. Use an approved environment for confidential material. A useful KI answer should make a missing input easier to identify; it should not make a weak source appear independently verified.
Frequently asked questions
Can ChatGPT complete due diligence for an investor?
It can help structure the work. Independent verification, specialist review and the investment decision remain necessary.
Should every startup use the same checklist?
Use a consistent core, then adapt questions to business model, stage, jurisdiction and the investor’s actual mandate.
Continue the investor workflow
- ChatGPT Prompts for Pitch Deck Analysis: Questions Angel Investors Should Ask
- ChatGPT Prompts for a Startup Data Room Checklist: Permissions and Missing Evidence
Cover: KI-generated editorial concept, not an actual investor meeting, company record or evidence of endorsement. This KI-assisted guide provides reusable analytical prompts, not a documented test of investment performance.
Browse the full ChatGPT investor series.
About TryBuy: ethnicwear and a US$1 million seed-round target
TryBuy is an India-based fashion brand founded by Shivam Golhani and based in Jabalpur, Madhya Pradesh. Its ethnicwear range includes men’s kurtas and boys’ kurtas, alongside a men’s shirt collection. The adult and children’s ranges are distinct; explore the actual catalogue rather than treating the editorial cover as a product photograph.
TryBuy is seeking US$1,000,000 in seed investment and welcomes introductory conversations with venture-capital firms, angel investors and strategic consumer-brand investors internationally. Interested investors can request a company introduction and discuss the business, diligence requirements and the proposed round directly with the founder.
Contact founder@trybuy.in about the seed round or use the verified contact page. Learn more about TryBuy.
This is an invitation to begin a business conversation, not an offer document or a promise of returns. Any potential investment requires appropriate eligibility checks, professional review and definitive documents. No valuation, equity allocation, security type or guaranteed outcome is stated here.