Stewart Butterfield and Slack, his second accidental success story

I’ve been going through some archives of mine, and came across a story I wrote in February of 2014, almost exactly 10 years ago, when I was working for Gigaom in San Francisco. I interviewed a young Canadian guy named Stewart Butterfield about a new thing he had just launched called Slack — a kind of all-in-one chat and workflow discussion app. I freely admit that I was not sold on this app at first, despite Marc Andreessen’s excitement about its growth rate, and I blame that on my lack of interest in corporate productivity apps in general, which I’m sure are really important but in most cases are as boring as watching paint dry.

What really interested me about Stewart and Slack was that the development of Slack happened while Butterfield and his team were trying to launch an online game called Glitch — according to Stewart, they came up with Slack as a way of collaborating with each other while working on the game, because every other form of collaboration (email, MSN Messenger, etc.) didn’t have the features they were looking for. But the really interesting part of the story was that this was the second time Stewart had invented something successful seemingly by accident, while doing something completely unrelated.

The first time was a little app called Flickr, which more or less invented the online photo-sharing market. Flickr grew out of another attempt at an online game that Stewart and his partners (including Flickr co-founder and Butterfield’s wife at the time, Caterina Fake) were working on. This one was called Game Neverending, and it was a very cool exploratory open-world type of animated game — I played it a few times and quite liked it, but it never took off. As part of the game, you could upload an avatar of yourself, a picture or image of some kind, and that feature turned out to be really popular, so Stewart and the Flickr team wisely decided to focus on expanding that, and Flickr was born.

Flickr pioneered a lot of the things we came to associate with the social web, including open APIs, hashtags, and social networking. It also implemeted Creative Commons sharing, which was not widely used at the time. Unfortunately, Flickr was acquired by Yahoo (for about $22 million, which at the time was a lot), and while they didn’t ruin it, they certainly tried hard to do so. Mat Honan described it this way: “They sold out to Yahoo assuming that they’d be backstroking in rivers of money and terabytes of memory. Instead they had to fight for everything: servers, people, time.” When he left, Stewart sent the senior executives of Yahoo a legendary letter of resignation that went semi-viral, in which he talked about the company as though it was an old-time mining company, and he a tin-smith.

“As you know, tin is in my blood. For generations my family has worked with this most useful of metals. When I joined Yahoo! back in ’21, it was a sheet-tin concern of great momentum, growth and innovation. I knew it was the place for me. Over the decades as the company grew and expanded, first into dies and punches, into copper, corrugated steel, synthesized rubber, piping, milling equipment, engines, instruments, weaponry and so on, I still felt at home because tin was the core of the business… Since the late 80s, as the general manufacturing, oil exploration and refining, logistics and hotel and casino divisions rose to prominence, I have felt somewhat sidelined.”

Slack, of course (like so many things I never thought would amount to anything) took off and became massive, and was acquired by Salesforce for about $27 billion or so. I have no idea what Stewart is up to now, but I hope he has moved back to a cabin in the wilds of British Columbia, which is where he grew up — back when his name was Dharma Butterfield rather than Stewart (he said later that he didn’t much like having a hippie name, so when he changed it he tried to find the most boring and normal name he could think of, and came up with Stewart). Or maybe he really did retire to take care of a herd of alpaca. Update: No alpacas apparently — he and his wife, who runs a multibillion-dollar luggage business called Away, have spent about $140 million buying ultra high-end real estate, including designer Tom Ford’s 20,000-acre ranch.

Stewart and his mother behind the log cabin he grew up in

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