Union Square Ventures

Rebecca Kaden

Managing Partner

Rebecca Kaden is a Partner at Union Square Ventures. She began her career as a journalist and, prior to USV, was a Partner at Maveron, a consumer-focused early stage fund. Rebecca was born in New York City. She studied English and American Literature at Harvard and received her MBA from Stanford.

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Notable Investments

Outschool, Stash, Brave Health

Questions & Answers

Origin Story: In a couple sentences, how would you describe your path to becoming an investor?

Journalist gets interested in how content might make money in a new online world, weaves her way from editorial to digital media and eventually to business school. Doesnt know whats next--big tech co? start co?--when mentor suggests that early stage venture's people-oriented approach and rapid pace might fit her inclinations and curiosities. Makes intro to Maveron where she starts as an intern and becomes a GP over 6ish years of learning, listening, network and idea building, and investing in consumer technology businesses. Joins USV partnership (& moves home to NYC) where she focuses on early stage companies broadening access to knowledge, capital and well-being.

Investment Approach: What are the key factors you consider when evaluating a founding team?

1) Are they captivating story tellers (this will be a consistent need--investors but also team members, customers, partners, the press, acquirers or public markets) 2) are they talent magnets that can attract great people to join the journey 3) do they have a POV that makes them uniquely fitted to tackle the problem they've picked 4) are they customer-centric--is this where they start 5) are they able to simultaneously live in the big vision and the details needed to get there.

What's your style and approach when it comes to working with founders post-investment? What are the characteristics of founders you've worked well with?

Transparent, casual, and regular dialogue--we're now on the same team so let's be in it together. You be blunt, reflective, and hungry--I'll be the same & constantly available to discuss the big or small (in scheduled or unscheduled ways.) I'll be clear about where we can help and our network will add value and where it won't--and follow up and through on what we say we'll do. We'll be in it together (which very often means the first and last check into the business.)

If I'm coming to pitch to you or your firm, what's the one piece of advice you'd give me?

Lets keep it conversational--we're more into dialogue than leaning back and going through the deck (we usually wont make it past a few slides and thats a good thing.) we want to show what itll be like to be in it together which means you should judge us on the quality of our ideas not only the reverse.

How would you describe your own personal mission and values, and how do they impact the way you invest?

I admire talent but cherish character. I believe a life lived with loyalty, generosity, and kindness is more important than success. I think working with and around people who are transforming the previously unimagined into potential fixtures of our world is incredibly inspiring. I like to work on things that I believe can do both well and good, that are personally interesting, where I find myself constantly learning, and most of all are being built by people I admire and want to work with. And I believe that helping change the composition of our industry into one far more diverse and varied will massively amplify all kinds of outcomes.

What do you like best about investing in NYC, and what’s your outlook on the future of NYC tech?

I'm a native and proud New Yorker. We live in the best city in the world. It smushes together industries, backgrounds, perspectives, and dreams--it has built and rebuilt, proving that invention and reinvention are part of its DNA. It has so many of the ingredients needed to bring new fragments of possibilities to life, most of all New Yorkers themselves. It has grit, optimism, realism, imagination, and loads of talent. I'm long long long NYC tech (and just look at some of the recent outcomes to reinforce that!)