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the rob interview

Stewart Butterfield, Slack co-founder and CEO, seen at the company’s office in Vancouver on Feb. 16,Rafal Gerszak

On arrival at the Vancouver office of Slack Technologies Inc. – in a Yaletown warehouse that was home to rum runners back in the 1920s – visitors are greeted by a bright white fluorescent sign on the brick wall. "Welcome to Slack," it says in loose cursive script. Beside the front desk, a small plastic sign posted on a wood beam asks: "What good shall I do this day?"

The question may feel a little airy, but make no mistake: Slack co-founder and chief executive Stewart Butterfield is a serious capitalist. Mr. Butterfield believes his upstart software company, four years old in February, could become one of the largest such firms in the world. Slack makes software for business that is designed to help workers better communicate and collaborate. Instead of e-mail, users of Slack can chat and share information in what are known as "channels". This forum for teamwork, Mr. Butterfield argues, will change the way we work, lead to greater happiness among employees and make companies more productive.

Slack is among the most promising new names in tech. The company, whose main office is in San Francisco, has raised close to US$800-million in venture capital. Its latest round, US$250-million last fall, valued the firm at about US$5-billion. Slack is an unusual enterprise software company, and its character is infused with that of its boss, Mr. Butterfield. The 44-year-old is at turns irreverent and philosophical, the latter rooted in his education at the University of Cambridge, where he graduated with a masters degree. His studies focused on the philosophy of biology, cognitive science and the philosophy of mind.

In a recent interview, Mr. Butterfield, who hails from Lund, B.C., spoke of Slack's chance to rival the likes of Microsoft, about empathy and about his outspoken criticisms of U.S. President Donald Trump.

On Twitter in mid-February, when you appointed Edith Cooper of Goldman Sachs to the Slack board of directors, you talked about Slack's potential, that the company could be 50 times larger in a decade, or out of business. In 2014, when Wired asked about your ambition, you said: "Be the next Microsoft." But then of course there are the rumoured takeovers, such as Amazon reportedly offering US$9-billion last year. How big could Slack be?

I think it could be US$100-billion in revenue.

That would make it one of the biggest public companies in the world. I don't know that it will be. There's a lot of things that have to go right. Things that we have to do, but a lot of external conditions that have to go right. And not just meteors not striking the earth.

We certainly believe that everyone in the world will be using Slack or something like it over the next five to 10 years. It just seems inevitable. We have tens of thousands of customers, all over the world and they're not all idiots. They didn't get tricked into buying this product. It's worth it for them to pay for it because it makes a real difference for how their team operates, how their company operates, how their big organization operates – whatever it is – and that thing that they're buying is also something that everyone else will need. They just don't know it yet.

You've raised a lot of money and have said a lot of it hasn't been tapped. What's the company's financial position?

It all goes into one bank account. It's like breathing the air. I don't know which air I'm exhaling. We still have a huge amount of money in the bank.

You appointed your first chief financial officer in early February. And in the announcement of Ms. Cooper as a new director, you wrote about preparing for "accelerated growth at scale." How close are you to be going public? How much do you want to be public?

Well, I feel like – [exhales] – we have a lot to do already. It will probably be good for us in the long run. It can be, in the short term, kind of rocky. You know that phrase, in the short term the markets are a voting machine, in the long term they're a weighing machine. So it can take a while for people to recognize how the company actually works and its unique dynamics and stuff like that. When we announced Edith's appointment to the board, of course it was a question that reporters asked.

Putting a long-time Goldman Sachs executive on the board – that will happen.

Yes. But my reaction – and this didn't work so well – is I don't feel like it's news. We're a very successful enterprise software company. We're private now. It's almost inevitable that we will go public. There's certainly no scoop about the fact that we will eventually go public and we don't have any kind of timeline. And that's not being coy. It's just the truth.

How does Slack use Slack? How does your software help your company?

I'll give you an example. Every single tweet any customer sends to us gets pumped into our Slack. It can be scanned by a really large number of people and a really large number of people can search it, but it also means people can pick out one complaint about something that wouldn't be that hard for us to change. We call those Beef Tweets. I don't know exactly why. The idea that designers, product managers, engineers, marketers, all have this visibility into what's going on in the heads of our customers in a really direct way allows us to operate in a way that's fundamentally different.

What does fundamentally different mean?

One of the inhibitors of successful organizations often is a feeling of disenfranchisement that individuals have, which often comes from feeling like they don't know what's going on, or they can't trust people.

There's always a meeting with 10 people in it and someone walks past and they know a bunch of the people in the meeting and they're suspicious why they aren't there, or what's being discussed, but if you're in the meeting, it's like, "This is another stupid meeting, I'm wasting my time." [Our software can] break down some of the walls in between different parts of the company, whether that's between sales and marketing, or legal and sales.

Slack gives people a tool. IBM is our biggest customer and their former CIO Jeff Smith talked about using Slack as an instrument to effect the kind of change they were trying to make. In IBM's case, they have 380,000 employees. One of the ways was shaping the conversations that were happening at the company through Slack and increasing the transparency. Most conversations were previously private in e-mail threads and got moved into channels that were accessible to a much wider range of people. It's a really big change, as trivial as it might seem.

How has the Slack persona developed? The sign here in the room, "We're all in this together," or when you log on to Slack, sometimes there are user tips but other times pithy lines like "Be cool, but also be warm" and they're all signed "Your friends at Slack."

Playful.

Exactly. How did that emerge?

It's who we are. I got online first in 1992 and most of the people who were early at Slack, certainly the co-founders, were on the internet really early. And being on the internet really early, especially preweb, was about creating some kind of identity or self-expression in a really limited palette. We wanted [Slack] to have a distinct identity. Because most enterprise software doesn't. It all kind of looks the same and sounds the same. Standing out helps.

How important are emojis? People like to use them in Slack – but normally they wouldn't be part of a corporate thing.

You know the shrug guy? It's not technically an emoji, it's a series of characters.

Your guy, in your Twitter bio.

It can be really nice shorthand. You can use it in ways that you couldn't use words. As weird or unimportant or trivial as it might have sounded to someone 10 years ago, or to someone today who doesn't use Slack, emoji reactions are incredibly powerful.

I was intrigued to see the unusual list of the Slack corporate values: empathy, courtesy, thriving, craftsmanship, playfulness, solidarity. How did you land on empathy as your No. 1 value? I've seen you talk about Slack building "empathy at scale." Google might have said "Don't be evil" in 2004, but capitalists aren't known for empathy.

It's certainly consistent with a capitalist outlook – because if you're able to produce something that people really love, then you're successful. We haven't effectively figured out how to turn out our giant piles of money into future customers yet, although we're getting better and better at that, [but] the reason Slack is successful is because people love it and the reason people love it is because we pay attention to their needs and the way you get that is empathy.

I tell this story to new employees. Yaletown sidewalks outside here are pretty narrow. I was with our creative director for product design. We were having a conversation, going for a walk. It started raining. We didn't have umbrellas with us. Maybe three-quarters of the people had umbrellas. And you know how when someone's holding an umbrella and walking at you, the pokey parts of the umbrella are right at your eye level.

Yeah, all the time.

It's a very narrow sidewalk and most of the people with umbrellas didn't move their umbrellas out of the way to not poke us in the eye. It became kind of a joke, we were guessing whether this woman coming towards us was going to do it, or this guy was going to do it. And it struck me after, why wouldn't they move their umbrella? There's only really two explanations. One is they just don't see it's happening.

A lack of awareness.

Yeah. Despite the fact that it must have happened to them, they must have been on the other end of that transaction. Or they see that it's happening and they're just like, "I can't think of what I can do." Even though what you can do is – [he motions a tilt of an umbrella] – a hundredth of a calorie worth of effort.

We talk internally at the company about tilting your umbrellas. People think that just means exhibiting courtesy. For us, there's a real opportunity, in that most people can't tell there's a negative impact on others, or if they can tell, they're not sure how to solve it. They're not sure how to make things more pleasant, simpler, more convenient – or in our case, more productive. Empathy is a real pathway to doing that. You have to be able to understand someone else's perspective in order to be able to serve them well.

How has your education shaped you as a business person?

It better prepared me for me some of the more complex decision making. There can be a huge number of competing voices and concerns. And I think that education, and probably more philosophy than anything else, is good for finding what the bedrock is, the most foundational, important goal for the company and being able to build off of that.

You are outspoken on Twitter. In January, 2017, you called the U.S. President's actions "gratuitously … evil." Most CEOs would be more conservative, quieter. What's your approach to your tweets?

I was on Twitter before I started the company. It doesn't feel right to give that up, or to silence myself. It would seem inauthentic. There are definitely things I don't say on Twitter.

I also don't joke around nearly as much as I used to, because my humour is idiotic and very obscure and almost no one ever gets it. I don't tweet 80 to 90 per cent of the things that occur to me to tweet.

You've never tweeted the name "Trudeau," I saw when I searched.

No.

But you're a dual citizen, right, American and Canadian?

Yes.

So, no desire to talk about Canadian politics?

I don't have anything interesting to say. I've been watching obviously the reaction to the verdict in Saskatchewan but I don't have that much to add to the conversion.

You were at Davos, the World Economic Forum this year, on a panel about the universal basic income. It's something you've talked about on Twitter. On the panel, you highlighted the vast untapped productive capacity of people who are low income, all the people so strapped they could never take an entrepreneurial risk. How would you sell a basic income to a skeptic?

There's a couple lines of skepticism that I've heard. One is there's no dignity in getting free money and people should have to work. I don't think we should be giving people $80,000 a year. It's more like $1,000 a month. I, and anyone else who had a sufficiently middle-class upbringing, got that, and we still work. We still go to work. I don't think there's a disincentive to work.

How would you present the upside?

What are we trying to do, being a species? Is it just GDP growth, or the Dow, or is it how happy people are? I think I said it at that panel, the John Adams quote ["I must study war and politics, so our sons can study mathematics and philosophy, and their children can study painting, poetry, music."] We would prefer that people are happy and safe and creative and expressing themselves.

Canada hasn't really launched a lot of tech companies. Why isn't the tech business in Canada bigger?

You could say the same thing about Chicago or Atlanta or Minneapolis, cities which are economically healthy and have most of the same advantages. However, I think it is going to matter less over the next 10 years because there will be less of a tech industry as opposed to what we have considered technology becoming a part of every single business. Is Airbnb a tech company or is it a hospitality company? Maybe right now you could answer either one and you'd probably be right. Ten years from now, that won't be true. So, Air Canada had better be a tech company. And Royal Bank had better be a tech company.

You've been talking about an AI idea Slack is working on, something of a personal daily assistant for everyone. What is Slack trying to do?

To give people some additional time. To delegate to someone else – in this case, an AI – the task of reading everything and synthesizing it and ensuring that you're not missing anything important. It would be a huge victory. More holy grail, than something we're going to launch next month.

This interview has been edited and condensed.

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