The Proof

Rebecca Kaden, Partner at USV


Rebecca Kaden is a General Partner at Union Square Ventures, one of the leading VC funds in the country with investments in Twitter, Behance, Tumblr, Coinbase, Soundcloud, Stripe, and Kickstarter. Rebecca began her career as a journalist and, prior to USV, was a Partner at Maveron, a consumer-focused early stage fund in SF. Rebecca studied English & American Literature at Harvard and holds an MBA from Stanford.


On her morning routine. A year ago I would have said a loud alarm, one-eye-open email scanning in bed, and iced coffee with an open laptop. But now I have a 9-month-old, Max, which means I wake up to him letting us know he’s ready to start the day. My husband and I rush into his room - he’s usually sitting up with the biggest smile and starts clapping (his newest trick) when he sees us. Your day gets off to a pretty great start when it begins with a round of applause.

Then we read books, play with his toys, and I try ceaselessly to make him laugh as much as possible until I have to run out the door. Max has taught me a lot of things in a short time, but one is a new lens on time management and prioritization. Email and iced coffee come next, but the whole day is cast in a happier, brighter light when it starts with him.

On forging her own path. There is sometimes a tendency to believe there’s a “right” way to build a career in venture: you have to be the biggest tweeter, the most active conference goer, the schmooziest, the immediate thought leader. I think that’s a dangerous road. There isn’t one way to do it.

If big events aren’t your thing, figure out how to create intimate settings. If you express things best in words, start blogging (and if that gives you nightmares, don’t!) Careers aren’t any more likely to be quick hits than seed stage startups are - so take your time to figure out what feels right. The relationships and position you create from that will be worth it.

For me, a small group of other investors and entrepreneurs I met early on and spoke to often have become critical to many of the deals I’ve worked on (and also valued friends and advisors.) That circle started small but, over time, it grew. Same goes, by the way, for deploying capital - deals feel fun but they last a long time. Resist the urge to do them because you’re antsy.

On choosing mentors. A huge part of my career thus far has been access to great mentors and models. There is often a debate as to whether venture is an apprenticeship business, but one of the best things about this industry is how varied the paths are that the greats we all admire have traveled into it. As a result, there isn’t one way to do it or to learn.

But, for me, watching and engaging with those whose careers I look up to, both inside and outside partnerships I’ve been a part of - and having the access to ask the questions around non-obvious decisions - has been critical in getting up a learning curve as quickly as I can.

Venture is an industry based on repeatable processes (sourcing, analyzing, winning, managing investments) with a goal of reaching outlier outcomes that often take a long time to play out. So learning how others have navigated tricky moments that will likely repeat themselves lets you create a toolset broader than your own experience.

On the power of network. Building a network is different than building a rolodex. A strong network of great entrepreneurs and talent is one of the most critical pieces of venture. Create one in a way that feels authentic to who you are and how you like to operate with people. Go into every meeting thinking as much about how you can help - whether or not you’re interested in the business - as what you can learn about the founder and company.

Even if it’s not obvious how that will help you, eventually it will. This is an industry where it pays to think in a long timeframe. Pushing yourself early on to consider what you can give to it dramatically increases the chances that, eventually, it will give back to you.


On wellness trends. The current USV thesis across categories involves broadening access - how can businesses increase value, often by decreasing cost, and make products and services previously hard to reach accessible for mass consumers. Health & wellness is a category with lots of opportunities here, largely because of two developments.

One, consumers’ priorities are shifting and that’s reflected in shifting spend. We have an unprecedented amount of accessible data about our own wellness and we are willing to put our dollars behind it in new ways. Companies like Modern Fertility are great examples here.

Two, technology allows companies to simplify a healthcare value chain that’s long been opaque and difficult to navigate, allowing consumers to feel newly empowered and take increasing ownership over their own care. Nurx is a great example of this. We believe these trends are still in early innings and are excited to continue to invest behind them.

On her keystone habits. The first is morning playtime with Max. He’s an early to bed kind of guy and I don’t always make it home in time to say goodnight so those morning moments are extra important to me.

Second, at some point in the day, I like to walk to a meeting or part of the way home and get lost in thought. It helps me work through whatever is getting lost in the busy shuffle of the day and collect my thoughts. Growing up in NYC, I used to walk through the park when I needed to think. Walking through the city has always been my best tactic to think through a tricky problem, come up with new ideas, mentally draft something I need to write or shake off a bad day.

The third habit is my end of day debrief with my husband, Scott. Talking through highlights of our days, what we’re excited about tomorrow, or that funny thing Max did that morning is the best wind-down. Even after long days or work events that run late, we both try to carve out that time to pause before it all starts up again.

On her sleep ritual. I’m a big list maker. My mind rests easier if I know I’ve written down the highest priority items for the next day — whether its review a deck or respond to an email, or order the diapers on Amazon. So I often end days by making lists on my phone. But, beyond that, my nights usually end with a call to a friend on the west coast on a post-event walk home, peeking in on a sleeping (fingers-crossed) baby, meandering sleepy debriefs with my husband, and, admittedly, some bad reality TV.

Rebecca Kaden, General Partner at Union Square Ventures