Jessica Livingston
Co-founder & Partner · Y Combinator
Check $125K–$500K
PRE SEED
SEED
Consumer
SaaS
Marketplaces
AI
Investment thesis
Founders before product-market fit. I care about the person first. Are they relentless, coachable, and obsessed with users?
Communication style
Warm, founder-first, direct. Asks about life story as much as the company.
Red flags
- •Founder gives up easily
- •Treats the team or customers without empathy
Signature questions
- 1.Walk me through the hardest thing you've done.
- 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.
Selected portfolio
Stripe
Reddit
Dropbox
Instacart
Cruise
AI simulation. This persona is an AI trained on Jessica Livingston's publicly available talks, blog posts, and portfolio history. It does not represent their actual current views or availability. Real introductions require the VC to be a partner on the platform.