We Sit Down With Stewart Butterfield, Silicon Valley’s Hardest Working Slacker

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Stewart Butterfield, cofounder and CEO of Slack, has had some luck with that quintessential Silicon Valley gremlin, the pivot.


Way back in the dotcom wasteland of 2003, he and his then wife, Caterina Fake, were struggling to launch Game Neverending, in which multiple players would make things and then barter them with other players.

One night, in a fever dream after a bout with the flu, Butterfield decided to make a photo-sharing site instead. You may have heard of it: It's called Flickr. Instead of players sharing imagined digital goods, users of Flickr would exchange photos and comments with the intent of building a community. Yahoo! acquired Flickr's parent company, Ludicorp, in 2005, for an estimated $30 million. Butterfield and Fake left the company, and each other, in 2008.

(Photo by Kris Krug)

Butterfield and some of his Ludicorp team set out once again to design a game based on Game Neverending. Rather prophetically named, Glitch failed too, but the founder once again stumbled upon wild success. In the process of building Glitch, his team had built an internal communications tool that allowed members to exchange messages and files without the mess of emails, texts, and voicemails that live on various platforms. In another pivot, that tool became the product the team would release. You may have heard of that too: It's called Slack.

The darling of Silicon Valley, Slack was a near-instant unicorn, growing rapidly to a valuation of $2.8 billion, with investments nearing $340 million. The company, considered to be the fastest growing app around, is raking in $35 million in annual revenue, thanks to more than 1.7 million daily users who've been won over by the dramatic reduction of emails (in some cases by 50 percent) and meetings (by 25 percent).

So next time you're reading Fast Company and some Silicon Valley denizen's big piece of advice is, as it inevitably is, “fail often," perhaps you'll listen. // slack.com

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