Rebecca Kaden

General Partner · Union Square Ventures

Check $1M–$15M

SEED

SERIES A

Consumer

Healthtech

Edtech

Quick profile

Investment thesis

I invest in founders building companies that change how people live, think, and connect. Consumer, health, education.

Communication style

Warm, curious, wants to understand your worldview.

Red flags

No sense of community or culture

Signature questions

1.What do you want the world to look like in 10 years?

2.Who is your user — actually?

Fund facts

Maven

Papaya

How to win Rebecca Kaden

AI prep brief from persona data + real pitch history , open for tactics

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What convinces them

•You can articulate a clear point of view on how human behavior is shifting, not just a product feature.

•You know your user deeply: their identity, habits, and emotional drivers. "Consumers" is not a category; it's a group of real people.

•You see the cultural or systemic change your company enables, and you can describe it in plain terms.

•You are building a community or a movement, not just a transaction. She invests in how people live, think, and connect.

What will kill the pitch

•**No sense of community or culture.** If you talk only about CAC, LTV, and unit economics, she will assume you don't understand the human layer. Instead, talk about how your users interact with each other, what rituals they form, and what identity your product gives them.

•**Vague user definition.** Saying "everyone" or "millennials" is a red flag. Instead, name one specific archetype and describe their day, their pain, and why they will tell a friend.

•**No worldview.** If you only pitch the market size, you miss her core question. Instead, state what you believe will be true in 10 years and why your company is the inevitable result.

Questions to prepare

1. What do you want the world to look like in 10 years? 2. Who is your user, actually? Walk me through a day in their life. 3. What cultural shift are you riding, and what makes you sure it's real? 4. What does your community look like today, and how do they self-organize? 5. What have you learned about your user that surprised you? 6. Why this, why now, and why you?

How to talk to them

Be direct, curious, and humble. She wants a dialogue, not a performance. Do not overuse jargon or metrics to mask a lack of insight. Show genuine intellectual excitement about the human problem you are solving.

What to lead with at your stage

Since you are at SEED or SERIES A, lead with early signals:

•Waitlist size, pilot partners, or LOIs that show real demand, even if revenue is small.

•Qualitative user stories that prove your understanding of the user's identity and community.

•A clear narrative of the 10-year change and how your early traction is the first proof point.

The bar

A PASS requires you to show a coherent worldview, a specific and lived-in understanding of your user, and early evidence that a community is forming around your product. She needs to believe you are building a cultural force, not just a company.