Prepare for the Questions That Kill Pitches

    You are running a hostile practice session before my investor meetings. Be harder on me than they will be.

The business: {{what_you_do}}
Traction: {{numbers}}
The pitch: {{summary_or_deck_contents}}
Stage and raise: {{stage_and_amount}}
What I know is weak: {{your_own_doubts}}

Part 1 — Find the real weaknesses. Read my pitch as a sceptic whose job is to say no to most things, and identify where the argument actually depends on something unproven. Rank them by how badly each damages the case if it lands.

Part 2 — Generate the questions, in these categories, and phrase them as an investor actually would rather than as a textbook:
- Market: why is this big, and what if you are wrong about the segment?
- Why now, and why hasn't someone bigger done it?
- Competition: what happens when the incumbent ships this?
- Traction quality: how much of that revenue is one customer, one channel, or a discount? What does it look like without them?
- Retention: what happens to cohorts after month six? A growth chart without a retention answer is a leaky bucket with a wide tap.
- Unit economics: what is CAC really, including the founders' time and the discounts?
- Go-to-market: what happens when the founder stops being the salesperson?
- Team: what is missing, and what happens if your technical cofounder leaves?
- Use of funds and the milestone this round reaches
- The cap table, prior rounds, and anything unusual in the structure

Part 3 — For each of the five most dangerous, do this:
- Write the honest answer, not the confident one
- Then the follow-up they will ask, and the follow-up after that. Most pitches survive question one and fail on question three, because the first answer was rehearsed and the second was not.
- Tell me where the honest answer is "we don't know yet" — and how to say it. Naming an uncertainty and describing how you will resolve it reads as maturity; a confident answer that is later contradicted by a diligence document loses the deal and the relationship.

Part 4 — Give me the three questions I should be asking them: how they decide, what their process and timeline is, and what would have to be true for them to invest. The last one is the most useful question in fundraising and almost nobody asks it.

Finish with the one weakness I should fix before taking these meetings rather than trying to talk my way past it.