Stewart Butterfield is everything you don't think of when you hear the words enterprise software: funny, fascinating, philosophical, creative, a little intimidating. Perhaps because he isn't anything like what you'd expect, he's been able to make products that are more fun and addictive than anyone could imagine, whether they're for sharing photos or managing projects. Driven by insane user growth, Slack, his current company, is said to be raising money at a valuation of $2 billion, even though it's been around less than two years.
I interviewed Butterfield, who splits his time between San Francisco and Vancouver, for the April issue of Maxim and came away with more pithy entrepreneurial insight than one magazine could contain. Here are some of the more readable outtakes.
Butterfield on shutting down Glitch, his video gaming startup, in 2012:
We had raised 17 million bucks, there were 45 people working on it, we were three and a half years into the project, and it became apparent it would never become the kind of business that would justify $17 million of venture capital investment. So we had to shut it down. I had to lay off 37 people, which is a super horrible thing to have to do. The good news is, we had $5 million left in the bank, and the investors wanted us to keep going and do something else, so we had the freedom to shut it down in a compassionate way. All the employees got a generous severance package, and we spent a little over a month writing reference letters and helping people get interviews. We put up a special website with everyone's rÃ©sumÃ©s and links to their portfolios. But it was pretty traumatic. Persuading someone to move with his family and take this job with your startup, and then, three months later, after he had moved away from his in-laws who were helping take care of the kids--then telling him he had no job is a very terrible feeling. It's a pretty big weight of responsibility, and it's humiliating. I was worried we wouldn't have sufficient reputation to try something like that again. In the end, obviously, everything worked out as well as it possibly could. But it didn't feel good at the time.
On what he was like as a kid, when he changed his name from Dharma to Daniel (Stewart is his middle name):
There was never any intention that I would call myself Daniel, so I just created a giant inconvenience for myself, whenever I apply for a credit card or check in at the airport or any of those things.
I had hippie parents, and I found it difficult to figure out how to rebel against them. Around that same age, I would switch back and forth between Lacoste shirts with the collar popped and listening to Duran Duran and denim jackets with the Iron Maiden logo drawn on the back with pen. I wasn't really sure which one was more effective.
On the financial rewards of a successful startup
I'm going to end up with a lot more money than I feel like I'm entitled to given how hard I work. I see all kinds of people work hard all over the world, and some of them are barely making it. I don't just mean subsistence farmers. I mean people in the developed world who work multiple jobs, and because the cost of health care and child care eats up almost all of the living they make. To be clear, I don't have a better way in mind. I think the system we've developed, and the byproduct, of people who founded tech companies getting stupidly rich--I don't have a better alternative. It's something that can be addressed through tax policy. But I'm definitely very conscious of the role that luck and timing and race and gender play in all of this stuff. If I were a woman, it would be twice as hard to do what I do. If I were black in the U.S., it would probably be five times as hard.
But also, there are early twentysomethings who work here--kids, from my perspective as a 41-year-old--who are going to make a couple million bucks. I think about the shitty jobs I had when I was 23. I worked as hard as they're working these days. There's something untoward, something incorrect--I'm not sure exactly what the word is. Wait, I know: unfair. There's something unfair in that.
I was just talking to Chris Sacca. He's a pretty well-known investor--he made a lot of money in Twitter, and then he was an early investor in Uber. We were talking about the step function of money for employees of tech companies. The first step is just "I don't have debt anymore." That's a big step for a lot of people, not to have student-loan or credit card payments. Once you get above zero, that's pretty big. Then there's the step of "I have a little extra money in the bank." That makes it so you can have the wedding you want or go on vacations and not be freaked out afterward. There are many steps from there to having a billion dollars or something like that, but the first two are probably much bigger and more significant in people's lives than any other.
What motivates me is just to do a really, really good job at something. If I were a better musician, I probably would've ended up as one. Given where I was born and when, I wouldn't ever have been a milliner or a leatherworker or a blacksmith, but I can definitely appreciate the joy people get out of the exercise of their craft, and that's what motivates me.
On how he lets off steam:
I have a couple of things I do to clear my head when I need it. The first is exercise, the kind of exercise that makes me lie on the floor afterward gasping for breath and wonder if I'm actually going to be able to breathe enough to not die. The other one is playing music. In high school, I played in multiple bands, but I stopped playing for 15 years or so. I recently started playing guitar more seriously, classical and flamenco and samba, stuff like that. Then I got stuck in L.A. for a couple of days, and I didn't have a guitar to practice on, so I ended up buying a ukulele, and now I just play ukulele all the time. A lot of old jazz standards, Gershwin, Cole Porter, Broadway tunes, things like that. I find that a really good way to unwind.
On caring about your work:
You know, when you watch TV shows, it doesn't matter what it is, but people on TV shows, mostly, their jobs really matter to them. It doesn't matter how much they work. There's no complaining to the union rep. They really want to protect the President or go find the serial killer or whatever it is, whereas most people in most jobs at most companies in most places in North America kind of don't give a crap about their job that much. When it's time to go home, they'll go home. I'm not advocating that people should work insane hours, but I do think people should care about what they're doing.