After many rounds on both sides of the negotiating table, I've seen these three questions come up almost unchanged.
1. Where does this number come from?
Investors aren't afraid of bad numbers; they are afraid of numbers that can't be traced. Forty percent growth that can't be attributed to new customers or to price increases gets discounted immediately in the listener's head.
2. If you left in six months, what would happen?
This is a question about dependency risk. The more tightly a business is tied to one individual, the thinner the share of its valuation that goes to the future. The best answer isn't a promise but an executive structure that has already run for a few quarters without the founder signing off on everything.
3. Where will this money go, and how will you know it's being misused?
The second half of the question is the part that matters. A use-of-funds plan with stopping points — milestones at which you pause and review — shows that management has thought about the unfavorable scenario.
Fundraising doesn't start at the investor meeting. It starts with the quality of the numbers six months earlier.
Preparing for these three questions doesn't require complicated advice. It requires clean numbers, a clear governance structure and honesty about where the business is still weak.