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The Curious Magic Of Dropbox’s Culture-Building, Product-Inspiring Outdoor Hikes

A hiking tour of San Francisco, with Dropbox coder Dan Wheeler.

Dan Wheeler is a programmer for the file-sharing company Dropbox. Click around a little on Dropbox.com, and odds are Wheeler had something to do with a given product or feature (he and a colleague hacked together a prototype of Dropbox Chooser, for instance).

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But one of Wheeler’s greatest contributions to Dropbox isn’t a product at all. Rather, it’s an extremely simple idea for how Dropbox employees could take a break–a tradition that has gradually become institutionalized in the company, acquiring a curious name: “hillcore.”

Come, walk with us.

FAST COMPANY: What is “hillcore”?

DAN WHEELER: It’s a philosophy. I think you could say that. It’s basically the belief that you can get a group of friends and coworkers together, and climb a hill. And that’s about it.

That’s it?

That’s all you need for a great time. I recommend the simplicity of it. Especially for programmers, or anyone using a computer for hours on end. It’s really designed to be the polar opposite of programming. When you’re programming, you’re doing your job more effectively if your mind is going faster. When you’re hiking, you’re letting your mind wander.

How’d you get the idea?

San Francisco is one of the few very hilly cities. A lot of other Boston transplants and I were meeting up and checking out different bars and neighborhoods. I was thinking it would be great to get people outside instead and hang out on a hill. The first proto-hillcore was in December 2010. We officially coined the term “hillcore” on Strawberry Hill the night of February 17, 2011. It’s a combination of “hill” and “hardcore.” Some of these hikes are strenuous.

What are some other hills you climb?

There’s lots to choose from. On Twin Peaks, there’s not a lot of trees, and you get slammed with wind. Corona Heights is not the tallest spot, but it’s close to downtown, so it’s a great view of the city. Mount Sutro is very forested, and there’s lots of eucalyptus trees. We had a clear night on Mount Davidson with a great view of the stars. On Tank Hill you have a view of the Golden Gate Bridge. If you’re climbing on a clear night and the fog happens to roll in that night, you can watch it sweep by, and in the end, you’re completely immersed in fog, and the environment has entirely changed.

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Dan Wheeler

Do work-related insights strike while on a hillcore expedition?

There’s no kind of explicit agreement not to talk about work on hillcore, but it’s mostly about unwinding. But I can think of one example. I was in Champaign, Illinois with two other engineers. There’s no hills there, but there is a lot of corn. We did a hillcore variant called “hillcorn.” We hung out in a corn field. We had the first kernel of inspiration for a new approach to password strength estimation. That idea started out in a cornfield.

How many people participate in hillcore?

Average is probably 20-ish people. The smallest was three people, the night we coined “hillcore.” The largest was our intern hillcore last summer, with over 100 people. Our intern hillcore has grown exponentially, from one, to three, to nine, to 20, to over 100 people.

You may need multiple hills.

We might. We’re gonna have some scalability problems, which we handle all the time here at Dropbox, so we’ll find a way.

This interview has been condensed and edited. For more from the Fast Talk interview series, click here. Know someone who’d be a good Fast Talk subject? Mention it to David Zax.

About the author

David Zax is a contributing writer for Fast Company. His writing has appeared in many publications, including Smithsonian, Slate, Wired, and The Wall Street Journal.

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