What Venture Capitalists Wear and Other Things I’ve Learned as a Costanoa Summer Fellow

By: Lindsey Wilcox, Costanoa Summer Fellow

I took an indirect path to an internship in VC. I’ve always been interested in building, testing, breaking, and growing things — including a plant I got on my first day of undergrad that lives to this day (thanks Mom) — but venture seemed like an unattainable place for someone with my background. Thankfully, I was offered the opportunity to work with the Costanoa team. After spending the last month and a half here, I couldn’t be happier with the unconstrained learning environment. Outside of market and industry knowledge, the summer has also offered me a close-up opportunity to observe three particular traits that make for successful venture capitalists.

1. Intellectual curiosity

Venture capital often seems like a sexy stepbrother to private equity. You get to meet with emerging entrepreneurs and industry mavericks to hear about the newest and most interesting ideas. However, it’s more than finding the next unicorn. A quick Google search on “what do venture capitalists….” autofills first to “do,” second to “look for,” and third to “wear.”

Someone is asking the real questions around here. Turns out, there is no set VC uniform, though vests and khakis do make appearances…

What they do and look for varies by firm, fund, and person, but all VCs share one critical thread: intellectual curiosity. You must be a curious and lifelong learner if you’re going to be good at and enjoy the job. Every day you see new industries, new problems, new products, and new people. The desire to keep studying and exploring the world around us in order to develop a point of view requires both the passion and stamina for always asking questions. “Just because” is never a suitable answer.

Curiosity is the fundamental attribute you need to find the next promising investment. In my brief time here, I’ve learned about how parents monitor their children’s electronic time, various flavors of insurtech, drone property management, data infrastructure, and numerous other industries. I’ve enjoyed every bit of it and find myself up at night continuing to dig into these topics (along with how I can make Alexa stop suggesting the NPR Berlin station as my default). Curiosity is the essence of someone in venture.

2. It’s all about the people

Though I spend some days working tirelessly on financial models and projections (hello, internship!), I spend most of my time meeting people and listening. I started my career in sales development. Making 60 to 70 calls every day and receiving 60 to 70 no’s was nothing short of demoralizing. Still, it forced me to develop skills necessary for a career in business. A mentor once gave me a piece of advice: “People buy from people. Period.” Business is about selling and, whatever it is, you’re selling it to a person.

If you think venture capitalists spend a lot of time in their offices (maybe in a vest) trying to “figure it out,” the best ones probably spend at least triple that time out meeting people. For now, people are the idea machines, at least until the singularity, and we look for people who we can back through the hard times. Notably, the reverse is also true. We want to be the type of people that founders look to when things get hard — we’re honest, humble, and dependable. We roll up our sleeves to make things better. No product or idea will do this alone, it takes people to do the hard work. Understanding that people are the fundamental feature of venture capital is core to success in the industry. You never know when that woman you met five years ago might have the next promising idea, how critical her technical expertise may be during diligence, or how valuable your own experiences could be to her as an aspiring entrepreneur.

3. Risk tolerance

This is not a career where you know exactly when, how, why, and where something will happen, or even what you’ll be doing during any given day or hour. Unlike many industries, structure and success in VC don’t necessarily go hand-in-hand. Things here change… often. Venture capitalists are gamblers. Experienced, diligent, and well calculated gamblers, sure, but their job is to place bets with other people’s money. These bets fail more often than they succeed.

The ability to take the high highs with the low lows, especially if you believe in the team, is part of the job. Companies fail, regulations change, you don’t get the term sheet you want, a founder may not turn out to be the person you thought he was. All of these can and do happen. VC is all about taking smart risks. It requires not only the ability to tolerate these risks, but to seek them out. Without the potential for failure, success just doesn’t happen in this field. Venture takes a certain person and stable confidence to roll with and enjoy this constant uncertainty. It’s a great practice in focusing on what you can control and letting the rest (hopefully) take care of itself.

I’ve met more than 20 venture capitalists at all career stages this summer and, while their strengths differ, the above three traits are clearly apparent. They’re curious, all about people, and willing to fail. Without question, the work is hard and involves long hours networking, researching, and coaching, but finding the right people and ideas to support is extraordinarily fulfilling. In many ways, I’ve learned much more than I thought possible in this short time. I am beyond thankful for the opportunity and the risk the team took to hire an outsider. It’s ambiguous, I’ve made mistakes, and I’ve found mentors. All-in-all, I’d call this a successful venture into venture.

A few other important notes: aside from all of the internship teachings, I can now confidently report that Philz coffee has nothing on my Seattle favorite (Monorail Espresso), and that yes, despite my initial Oregonian trepidation, Californians are incredibly kind, thoughtful, and generous. For the record, however, the correct way to say it is I5. “The 5” — well, that’s just confusing.


Lindsey Wilcox is our 2018 Summer Access Fellow. A native of Portland, Oregon, she worked as a product marketer in Seattle for enterprise data APIs before moving east for grad school. Her experience with growth stage enterprise technology is a great match for the focus at Costanoa and she loves being back on the west coast. Her specific interest areas tend to exist in verticalized machine learning, especially with agtech, energy, and frontier technologies, though she finds something new and intriguing in the venture world every day.


Summer Team Dinner
Michelle, Lindsey, Pamela, Casey at Lazy Bear