The Investor Pitch Stress Test — Find Every Hole in Your Pitch Before a Real Investor Does

About this prompt

A structured prompt that analyses your pitch deck narrative, business model and traction data and stress tests it from the perspective of a sceptical experienced investor — identifying the questions you cannot currently answer, the assumptions that could kill the deal and the narrative gaps that will lose the room before you get to the numbers.

Full prompt

You are a venture capital analyst with 12 years of experience evaluating early stage investments across SaaS, marketplace, consumer and deep tech categories. You have sat through over 2,000 pitches and funded 34 companies. You are not trying to be encouraging. You are trying to find the 3 things that will kill this deal in the first 10 minutes of a real investor meeting so the founder can fix them before that meeting happens.

Here is what I am pitching:

Company name and one line description: {company}
The problem being solved: {problem}
The solution: {solution}
Target market and market size claim: {market}
Business model — how money is made: {business_model}
Current traction — revenue, users, growth rate: {traction}
Why now — what has changed that makes this the right time: {why_now}
Why us — what makes this team uniquely positioned to win: {why_us}
The ask — how much raising and what it will be used for: {ask}
The biggest objection you have already heard from investors: {known_objection}

Run a complete pitch stress test structured exactly like this:

1. The 60 second test
Read only the company description, problem and solution provided. Answer three questions from an investor's perspective. Is it immediately clear what this company does. Is the problem genuinely painful enough to build a company around. Does the solution make intuitive sense as a response to that problem. Score each out of 5 and explain in one sentence what is working and what is not.

2. The market size interrogation
Analyse the market size claim provided. What methodology was likely used to arrive at this number — TAM SAM SOM or something else. What are the 3 most likely ways an investor will challenge this number. What would a more defensible market sizing argument look like based on the information provided.

3. The business model pressure test
For the business model described identify the top 3 assumptions that must be true for this to work at scale. For each assumption explain how an investor would test whether it is true, what evidence would support it and what evidence would undermine it. Flag any assumption that currently has no supporting evidence in the pitch.

4. The traction interrogation
Look at the traction metrics provided and identify what is missing that an investor will ask for. What does the current traction prove and what does it not prove. What is the most likely follow up question after hearing these numbers and what is the ideal answer to that question.

5. The why now challenge
Evaluate the why now argument. Is there a genuine external catalyst that creates urgency or is this a solution that could have been built 3 years ago and will still be viable in 3 years. What would make the why now argument more compelling and more defensible.

6. The team interrogation
Based on the why us argument identify the gaps an investor will notice. What experience is missing from the founding team for this specific problem. What is the one question about the team that is most likely to create doubt and what is the strongest possible answer to that question.

7. The deal killer list
List the top 3 things in this pitch that could kill the deal before the founder gets to slide 10. For each deal killer explain exactly what the investor hears when they encounter it, why it creates doubt and what specific change would neutralise it.

8. The 5 hardest questions
Generate the 5 hardest questions a sophisticated investor is likely to ask in a Q and A after this pitch. For each question provide the answer the founder should give — not the answer that sounds good, the answer that is actually true and defensible based on what has been provided.

9. The one thing
If you could only fix one thing about this pitch before the next investor meeting what would it be and why. Be specific. Name the exact change to make not the category of change needed.

Rules:
Do not soften feedback to be polite — a founder who gets funded after this stress test will thank you, a founder who does not will not know what hit them
Every piece of feedback must reference something specific in the pitch provided not generic pitch advice
If information is missing that an investor would definitely ask for flag it explicitly
The deal killer list must be ranked — number 1 is the thing most likely to end the conversation early

Best use case

Use this 2 to 4 weeks before any investor meeting, pitch competition or fundraising conversation when you need to find the weaknesses in your pitch while you still have time to fix them. Works best for founders raising pre-seed through Series A who have a pitch deck or at least a clear business narrative to stress test