Slack CEO Stewart Butterfield on how a fear of failure helped make him successful

Stewart Butterfield, co-founder and CEO of Slack. Photo: supplied.

Stewart Butterfield knows what it feels like to pick yourself up, dust yourself off and start again.

He’s had to do it twice.

First with a video game called “Game Neverending”.

And then with another game called “Glitch”.

While both ventures did not succeed, the products of their failure made their lack of success worth it.

Butterfield’s underdog journey to become royalty of the global tech scene has been well-documented.

It’s almost folklore that he was “puking my guts out” with a bad case of food poising when the idea for Flickr came to him.

The lightblub moment for Slack isn’t as well known, probably because Butterfield says “it wasn’t as instanteous” as it was for Flickr.

“We started working on the game, we worked on it for three-and-a-half years. There were 45 people. At some point we realised it was never going to be the kind of business that would justify the $17.5 million in venture captial investment that it had taken, and therefore we were going to shut it down.

“Over the course of that three-and-a-half years there was a slow boil where we had a tool for internal communications that we kept making little additions to. But it was very much in the background… and we just let it sit — that’s the best way to do software design because there is no ego, theres no speculation, theres no ‘I can imagine that users would want to do whatever’, it was just whatever the most urgent problems were [we fixed].

“So, after we decided to shut down that game we decided that it would never work without a system like [Slack] again, so it was a petty short leap from there to ‘oh, maybe other people would like it as well’.

“It wasn’t one defining instant. It was a couple of defining weeks.”

But it’s for this reason that Butterfield is convinced it has been so successful.

“What’s amazing is right at that time I wrote a presentation for investors to say this is what were going to do… that was three years and three months ago, and we did exactly what it said. No deviation at all. With most startups… there’s usually a really wide deviation from what you set up to do to what you end up doing.

“The fact that it did so well for us in the years leading up to that gave a really crystal clear vision of what the product would be.”

Butterfield simply says there’s nothing worse than failing.

“If you are scared enough about the humiliation and failure you will do anything to avoid it,” he said.

“Shutting down Glitch was horrible for many reasons. Firstly, it’s just humiliating to fail because you’ve raised money from investors and you do all this press. We had hundreds and thousands of people playing it, and we had to say sorry we’re destroying this whole world that you’ve built and enjoyed.

“But the worst part was telling people that they don’t have their jobs anymore, it’s about the worst feeling as you can have, although I’m sure it worst to be on the other end of that.”

And although pivoting worked for him, Butterfield says he’s not too sure how well it generalises.

“Sometimes you should preservere and sometimes you shouldn’t, and it’s one of the harder determinations to make,” he said.

“There’s definitely an element of skill, but… most of the decisions you make you have to make before you have sufficient information. Sometimes you just get lucky too.”

* The writer travelled to Melbourne as a guest of Slack.

Now read why one of Slack’s first employees, and last employees of Glitch, still has “survival guilt” despite now being the head of customer experience.