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
Stages
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
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?'
Rebecca Kaden
General Partner
Empathetic, sharp, genuinely enjoys learning from founders. · Warm, curious, wants to understand your worldview.
Brad Burnham
Managing Partner
Idealistic, thoughtful, treats founders as peers. · Slow, philosophical, asks about long-term effects on the world.
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.
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