Silicon Valley loves its engineer-founders. They are members of the region’s highest caste, the entrepreneurs trusted to turn bits and bytes into the next hit digital products, and the people venture capitalists most like to back.
Stewart Butterfield, co-founder and chief executive officer of the workplace chat app Slack, is not one of them. He stands out as a philosophy major in a start-up world full of software engineers, a non-techie who has made it to the top of the tech heap.
Slack’s listing on the New York Stock Exchange this week has cemented his reputation as one of the Valley’s most creative product designers — and values his own stake in the company at $1.6bn.
“He is your quintessential, product-oriented founder-leader,” says Aaron Levie, chief executive officer of Box, a cloud storage company. In a nod to an unconventional streak in Butterfield’s personality that separates him from the herd, he adds: “He has just the right level of quirkiness.”
Coming up with a viral hit product, to use a metaphor often heard in Silicon Valley, is like catching lightning in a bottle: the odds against it happening are extremely long. Butterfield has managed the trick twice.
Flickr, the photo sharing site he created with then-wife Caterina Fake 15 years ago, flared brightly — though briefly — on the Silicon Valley firmament. Three years before the iPhone made its appearance and six years before Instagram, Flickr showed how uploading and sharing pictures could become a new focus for online activity.
One developer who saw Butterfield’s impromptu unveiling of the service at a tech conference summed up the effect: It was an “amazing combination of utilitarian, usable interface aesthetic and genuinely witty whimsy”.
Those words stand as a perfect description of the qualities that have turned Slack into a workplace hit. Mamoon Hamid, an early investor and Slack board member, credits a deeply humanistic streak for Butterfield’s success as a product designer. That makes him an heir to the late Steve Jobs — another non-engineer with a perfectionist’s eye who was able to look beyond the bits and bytes to mould products that people welcome in their lives.
“He’s the sort of person who, if he’d lived in the Middle Ages, would have produced the perfect leather bag, with just the right stitching — he’s a craftsman,” Mr Hamid says.
Only a year into its existence, Flickr sold out for less than $25m to Yahoo! Butterfield stuck it out for three years before leaving to try his hand at founding a new company. If he feels bitter about selling out too cheaply (Facebook later paid $1bn for Instagram) he has always done a good job of hiding it, retreating behind slightly doleful eyes and a very deliberate, whisper-like delivery.
In the often dog-eat-dog world of Silicon Valley, Butterfield has gained something of a reputation for being less cut-throat than many. Slack was carved out of a failed gaming company, in one of the start-up world’s more famous “pivots”. One investor recounts how the Canadian entrepreneur refused to ditch his first backers when switching horses to the new product.
Most would have left their early investors for dead, this person says: it’s the way of things with tech start-ups, where failures are quickly passed over in the race to make the next fortune. Not Butterfield. Instead, he insisted that his first backers be cut in on the new opportunity.
Salvaging good ideas from technology wrecks has become something of a trademark for Butterfield — as has failing to make it with gaming companies. Flickr was also carved out of a failed gaming start-up.
At the age of 46, Butterfield now has to remake himself again — this time as the boss of a large, publicly traded enterprise software company. He has been undergoing coaching for the last few years on how to lead a larger company, and according to Mr Hamid has had to learn how to run a large sales organisation for the first time.
It is a world away from his deeply unconventional background. He was born on a commune in the remote village of Lund, in British Columbia, where his American father had fled rather than serve in Vietnam.
A desire for normality showed itself early. At the age of 12 he changed the name he was given at birth, Dharma, for the more prosaic Stewart. He went on to get a philosophy degree at the University of Victoria, followed by a master of philosophy at Cambridge, before being bitten by the internet bug at the end of the 1990s and moving to Silicon Valley.
Butterfield has landed on Wall Street at the helm of a hot technology but with the world’s most valuable company breathing down his neck. Microsoft paid Slack the backhanded compliment of copying its idea for a chat application and is now bearing down on it.
Pressed on how he can withstand the Microsoft onslaught, Butterfield defaults to the quiet, analytical self-assurance. “There has been a long history of the small, focused start-up taking on the large incumbent with multiple lines of business and being successful” — starting, he added, with a small and scrappy Microsoft itself taking on the giant IBM.
If he can repeat the trick, Slack’s impact on the software world is only just beginning.