A Long Walk Through Brooklyn With Collaborative Fund Founder Craig Shapiro

How moving at a snail’s pace helps the venture capitalist work more efficiently.

A Long Walk Through Brooklyn With Collaborative Fund Founder Craig Shapiro
[Photo: Flickr user Jon Kristian Bernhardsen]

It’s easy to imagine the founder and managing partner of a Manhattan venture-capital firm speeding through the streets of New York in the back of a car with a driver, juggling two smartphones and multitasking like a madman. Craig Shapiro has the job titles, the company, and the tony Manhattan office address, but nothing could be further from the black-car scenario. Each day, Shapiro wakes up with the sun, and instead of diving into a flurry of calls, emails, and meetings, he laces up his sneakers and hits the pavement for an over six-mile walk to work.


Shapiro began Collaborative Fund, which provides seed capital to creative entrepreneurs, in 2011. Since then, they have invested in companies including Kickstarter, Lyft, and Blue Bottle Coffee. To juggle the demands of the dozens of firms they are working with while keeping up with trends in the areas he wants to get more involved in—from local food movements to children’s vitamins—Shapiro has turned himself into a pedestrian wunderkind. He walks through staggering humidity, snow, basically anything except walls of rain as a way to be a more productive, better businessman. Here are three lessons he learned for why slowing down is his best shot at keeping up.

Craig ShapiroPhoto: John Maeda

Take Meditation Where You Can Find It

“I’ve been doing the walking-to-work thing for a long time, starting when I lived in San Francisco. Now in Brooklyn, I get up super early, around 5:30 or 6 a.m., and go from my apartment [in the Lefferts Gardens neighborhood of Brooklyn] to the office in Soho. It’s about six and a half miles and takes two hours. My route is always the same—through Prospect Park, down Flatbush Avenue to the Manhattan Bridge and then west into Soho.

“Even though the city is so loud and construction is always happening somewhere, the time for me is like meditating. It allows me to gather my thoughts and centers me. There’s balance when I get to work, I operate better in meetings and with my coworkers. Also, on days when I take the subway or a car, I’m more jittery and anxious. It’s tougher to get in a good zone without having the physical and mental exercise of walking. All in all, it makes me a lot more productive.”

The Joy Of Monotasking

“I keep it pretty simple—no fancy sneakers or headphones. Just the regular iPhone earplugs so I can listen to podcasts, either political ones or on Mondays, the Meet the Press that aired the day before. I’m so busy, it’s basically the best way for me to get my news consumption. I can also use the podcasts to catch up on the latest technology trends, which might lead to investment ideas. Sometimes I steal my wife’s playlist as a way to discover new music. The main thing is to not use the time on the phone or texting.”

Find Time To Focus On The Big Picture

“Walking has opened my eyes to stuff that’s happening, not just in my [rapidly changing] neighborhood, but for the company. How it has translated into meaningful returns on Collaborative Fund is that this is the only time I have where I’m able to think about our future and our investment thesis more fully. I can see where we’re going in a holistic way. It’s 2015; what are the goals for this year? And what about 2016 and 2017? I have space to think on that scale. Once I get into the office, there’s an email, a phone call, pitches—all good and exciting things, but they leave no time to reflect. Walking down Flatbush Avenue is the chance to make sure my business’s compass is set in the right direction.”


About the author

Ayana Byrd writes about people, ideas and companies that are groundbreaking and innovative.