Investor Meeting Preparation: What Questions VCs Actually Ask in First Meetings

Every founder prepares for "what's your market size?" But the questions that determine whether you get a second meeting are more specific. These catch founders off guard.

Walk me through one customer

This is the unit economics question disguised as a casual ask. If you can't answer with specific numbers, acquisition cost, lifetime value, payback period, you're not ready. Pre-revenue founders should have a model based on comparable companies and reasonable assumptions.

Why now?

This separates good founders from great ones. Why is this moment the right time? Is there a technology shift? A regulatory change? A new platform? "AI is getting better" is not an answer. "Open source LLMs crossed a quality threshold six months ago that now makes our product possible at a price that didn't exist before" is.

What's the hardest part?

This tests honesty and self-awareness. Don't say "nothing." Name a specific challenge and what you're doing about it. Founders who can name their weaknesses are more credible. Pitch an AI investor to practice answering these questions before your real meeting.