The long and affectionate piece from Wired's Mat Honan details Butterfield's pattern of founding unsuccessful whimsical games companies (Game Neverending, Glitch) that spawn innovative, beautifully functional tech startups (Flickr, Slack).
I was an advisor to Game Neverending/Flickr, and Stewart's kind enough to namecheck me in the piece. He's one of the genuinely nicest people I know — a rare combination of brilliance, humor, compassion and drive.
Stewart can be compulsive. That same day, on the same block, a woman in her late 40s or maybe early 50s, clearly not part of the trendy tech set, stops him and asks if he can tell her how to get to the ballpark. Yes! Of course! Just follow Second Street all the way to its end and take a right. It's probably a 10-minute walk. But then she asks if he's heard of Dropbox (um, yes) and how far the Dropbox office is from the ballpark. She's actually on her way to a job interview. Stewart immediately wants her to get the job. He asks what time she is meant to be there. He grabs his phone from his pocket, looks up the address, and gets walking directions. Turns out it is more like a 19-minute walk.
He becomes visibly concerned. She needs this job! He suggests she take a bus, and looks that route up for her, too. It turns out the 10 isn't running from its regular stop (road construction), so he looks around and helps her find the temporary stop. She asks if he can change a twenty. He looks in his wallet, there are a few singles, and some tens and twenties, but he can't make change. The bus is coming. It's all happening too fast. He looks indecisive for a second, staring down at the cash. Two bucks—exact fare—stare back at him. He hands it to her, he hugs her, and he wishes her luck. She makes the bus.
But back to coffee. Stewart is spending a lot of time getting coffee and sandwiches and beers with the media these days. These are morsels of obligation. The press loves him because he's both successful and incredibly frank. Ask him a question and he tends to speak in answers, rather than statements. He curses freely. It's a little bit shocking. He shrugs it off. "It's easy to be forthcoming when everything is good," he says. (Someone should tell Tim Cook.)
(Image: http://www.wired.com/wp-content/uploads/2014/08/20140730-SLACK-BUTTERFIELD-094-frontback.jpg"> Ariel Zambelich/Wired)