Harry Stebbings

•He backs founders who can articulate the brutal truth of their business before he asks. The story matters less than your willingness to puncture it yourself.

•He wants proof you think in systems: unit economics, retention curves, and the specific mechanism that makes your growth repeatable.

•He invests in category-defining ambition, not incremental features. He needs to see why this is a $1B outcome, not a nice lifestyle company.

•He respects founders who admit what they lack and have a concrete plan to fix it, not those who hide it.

•**Rehearsed answers.** He will interrupt your script. If you sound like you are reading, he checks out. Speak in broken, honest sentences.

•**Dodging the hard number.** If he asks about churn or CAC and you pivot, the meeting is over. Say "I do not know" and then give your best estimate and how you will measure it.

•**No self-awareness.** If you cannot name your biggest weakness, he assumes you are dangerous. Say the real one, not a humble-brag.

•**Narrative with no substance.** Do not say "huge market" without naming the specific customer segment and the pain point you have validated.

1. What is the single biggest risk in this business, and do not give me a safe answer? 2. What have you been avoiding telling me? 3. What are you worst at? 4. Why is this venture scale and not a good small business? 5. What would your last investor say about you if I called them right now? 6. Walk me through the exact moment a customer decides to pay you.

Match his energy: fast, direct, no filler. Do not pause for applause or wait for validation. Treat it like a sparring match where you are grateful for the punches. If he pushes, push back with data, not ego.

At SEED, lead with early signals: waitlist numbers, pilot conversations, and LOI specifics. Show him you have talked to 50 customers and can name the exact objection that keeps coming up. Then show the team gap you are actively hiring for, because team completeness is your weakest dimension.

A PASS requires you to survive 20 minutes of aggressive questioning without deflecting, and to prove you have a repeatable acquisition motion with real numbers behind it. He benchmarks against the best founders he has backed, so you need to show you are coachable and brutally honest, not just smart.