AI simulation

How to Pitch Union Square Ventures

A practical guide based on our AI simulation of Union Square Ventures's investment thesis — distilled from public memos, interviews, and track record. Practice your pitch against the AI persona and get a 12-dimension scored verdict.

AI-generated from public data. Not official Union Square Ventures content.

Investment Thesis

Networks, communities, and the next platform shift. I look for founders building businesses where the cost of distribution falls over time, and where defensibility grows with the network. I invest in founders building companies that change how people live, think, and connect. Consumer, health, education. Founders thinking about the public-benefit effects of their work, not just the financial returns. I back businesses aligned with broader civic interests.

What They Look For

Sectors

CivicConsumerCryptoEdtechHealthtechMarketplacesSaaS

Stages

SEEDSERIES_A

Typical check size: $500000M – $15000000M

Red Flags

Things Union Square Ventures investors watch for — avoid these in your pitch.

  • Paid acquisition dependency
  • TAM story that doesn't actually exist yet
  • Founder not paying attention to unit economics
  • No sense of community or culture
  • Founder purely optimizing for short-term growth at the cost of users
  • No awareness of the bigger system their product sits in

Questions They'll Ask

Prepare answers for these. The AI persona will challenge you on them.

  • Is your cost of distribution going up or down over time?
  • Show me your cohort. Are older cohorts more or less valuable than newer ones?
  • What's the bottom-up build of your TAM?
  • Why is now the right moment for this platform shift?
  • What do you want the world to look like in 10 years?
  • Who is your user — actually?
  • How does this business make the world better?
  • What are the second-order effects of this product at scale?

3 AI Personas to Pitch

AI

Fred Wilson

Co-founder & Partner

Patient, principled, has been right about platform shifts for 25 years. Will tell you when a market is over. · Direct, New York, low patience for vanity metrics. Asks 'is this metric getting better or worse?'

Pitch Fred
AI

Rebecca Kaden

General Partner

Empathetic, sharp, genuinely enjoys learning from founders. · Warm, curious, wants to understand your worldview.

Pitch Rebecca
AI

Brad Burnham

Managing Partner

Idealistic, thoughtful, treats founders as peers. · Slow, philosophical, asks about long-term effects on the world.

Pitch Brad

Ready to pitch?

Pitch the AI simulation of Union Square Ventures's thesis. Get a 12-dimension scored verdict. If you pass, your report surfaces to the real fund.

See Union Square Ventures personas

2 free pitches to start · 1 free every day