If you’re the kind of person who bitches incessantly about your corporate job, Stewart Butterfield has no sympathy for you. But he does have a remedy. His San Francisco-based start-up, Slack, has built a billion-dollar brand by alleviating the pain of workplace culture. A software application that allows teams to collaborate through group messaging, file sharing, and person-to-person chat, Slack replaces the most soul-deadening rituals of the information economy: the reply-all e-mail thread, the daily status meeting, and the conference call. (It also supports custom emojis.) Butterfield, 41, knows from soul-deadening. He sold his last company, the photo-sharing service Flickr, to Yahoo, working there for three brutal years while the Web behemoth bled the life from his creation - and then quitting with a now legendary e-mail. It’s no accident that using Slack can feel more like play than work: Like Flickr, it grew out of a doomed video-game launch. Fortunately, as every gamer knows, you can always respawn and try again. Here’s how he pulled it off.

For the first five years of my life, I grew up in a log cabin in coastal British Columbia in a very small town, like 300 people, mostly hippies. No running water, no electricity. When I was 12, I changed my name from Dharma to Stewart. At that age, you just want to be normal.

Flickr and Slack both started out as games, but they were more about trying to build a certain kind of context for social interaction. There are a lot of people in Silicon Valley who say that your execution matters a lot more than your idea. The fact that both the initial game ideas failed but something else worked is nice evidence for that position.

There’s a lot that’s wrong with the way we work—bad habits that develop around control of information, people hoarding information as a means of preserving their own power. When you’re using Slack, everyone can see what’s going on because the default mode is public.

From the outside, Yahoo was extremely successful. It was making money; it was still bigger than Google. But when I got there, I learned what a disaster of a company looks like from the inside. There were a lot of vice presidents, and it was basically a turf battle between them. Most of the energy went into politicking and infighting. As we scale Slack now, I’m very conscious of avoiding those things.

I’m not living like Jesus Christ, but once you get to the point where it doesn’t matter financially what you order when you go out to dinner, I don’t think getting richer makes a huge difference in your level of happiness.

I went to grad school to become a philosophy professor. A friend of mine finished his Ph.D. in philosophy and ended up getting a terrible job in Kentucky, not where he wanted to live. That was my future. This was 1998, the early days of the dot-com stuff. I had a lot of friends who knew how to make Web pages. They were moving to San Francisco, making twice as much money and having lots of fun. So I dropped out.

I tend to be a lot more honest and transparent with employees than most bosses are. But I’ve had people tell me, even those who love working with me, that I’m terrifying, which is hard for me to imagine.

We launched Slack at exactly the right moment. If we had started this product three years ago, it would not have taken off like this. I can’t tell you exactly why that’s true. In 10 years I’ll be able to. These things are not obvious at the moment, but they’re obvious in retrospect.

You see people in all walks of life who are great, and then you see people who don’t care and are inconsiderate. To all the people who happily do a good job, I am grateful, and to all the people who do a terrible job of simple things, I hate you. If you don’t care about what you’re doing, find something else to do.

Photos by Carlo Ricci