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7 questions investors want you to have asked before you pitch
Most founders validate by asking customers if they would use the product. Most customers say yes. That answer is not validation — it is politeness. The questions below reveal whether a problem is real, urgent, and worth building a business around. Work through them before you build, before you pitch, and before you raise.
01 — Why haven’t you solved this already?
Reveals whether the problem is genuinely unsolved or just inconvenient enough to tolerate.
02 — What have you tried before, and why did it fail?
Prior attempts confirm the problem exists and that existing solutions are inadequate.
03 — How many people have this problem AND cannot work around it AND will pay to solve it?
The three conditions together define a real addressable market. Each one alone does not.
04 — Who else is solving this — and why are people still using them?
Proxy competition confirms the problem is real. Understanding why incumbents persist reveals your actual challenge.
05 — What would it take for you to actually change how you work today?
Surfaces the real switching cost — the invisible barrier between a founder’s solution and a customer’s decision.
06 — What is the strongest evidence you have that this problem is real — not that people said so?
Forces the distinction between stated interest (cheap) and demonstrated behaviour (expensive and rare).
07 — What assumption, if wrong, would invalidate your entire thesis?
The founders who have done genuine discovery can answer this immediately. The ones who haven’t will pivot to the vision.
Ask these questions in customer discovery interviews — not to your customers, but to yourself after each conversation. If you cannot answer questions 03, 06, and 07 with specific evidence, you are not ready to pitch. Go back to the market first.
The founders who raise are not the ones who pitch best. They are the ones who can answer these questions without reaching for a script.
DM & Associates works with pre-seed founders on validation, investor readiness, and go-to-market strategy. View the Founder Readiness Products at dmassociates.xyz/products.
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