Jessica Livingston

•She invests in the founder, not the slide deck. She is asking one question the whole time: "Will this person survive the next three years of hell?"

•She looks for evidence of obsession. Do you live inside your users' problems, or do you just like the idea of starting a company?

•She values coachability over IQ. She wants founders who listen, adapt, and change their mind when shown new data.

•She bets on grit. She has seen thousands of founders. She knows what relentless looks like, and she can spot performative toughness instantly.

•**Giving up easily.** If you describe a setback as "frustrating" and moved on without a fight, she sees a quitter. Say instead: "We hit X, it nearly broke us, here is exactly what we did for three weeks to fix it."

•**Treating team or customers without empathy.** If you blame users for not understanding your product, or call early employees "difficult," you are done. Say instead: "We changed our process because our users told us we were wrong."

•**Vague answers about hardship.** If you have no story of a specific, painful moment, she assumes you have not been tested. Bring a real one.

1. Walk me through the hardest thing you've done. (Not in the company. In your life.) 2. What are you like when things aren't working? 3. Tell me about a time you changed your mind after listening to a user. 4. Why this problem, and why you? 5. Who is the one person you cannot lose on your team, and what have you done to keep them? 6. What did you give up to start this?

Be direct, be human, and do not pitch. She will ask about your life story, your family, your low points. Answer honestly. Warmth and vulnerability land. Arrogance and rehearsed answers create instant distance.

You are at PRE-SEED/SEED. Traction is not expected.

•Lead with a specific insight about a user that no one else has. Show you have talked to dozens of them.

•Lead with your personal story of obsession. Why this problem has had you in a chokehold.

•Lead with a clear vision of the market that is contrarian but defensible.

A PASS requires her to believe you will not quit when things get dark, and that you genuinely love users more than your own idea. She benchmarks you against the grittiest founders she has backed. If she senses fragility, she passes.