Enron, WorldCom and the dotcom bubble. It definitely wasn't a time to be betting money in the online world.
Moving from a remote northern BC community to Vancouver and raised by hippie parents (his birthname was Dharma before he changed it), Stewart Butterfield had a vision: he wanted to bring together all of the early virtual communities to collaborate in the form of play. He wanted to evolve the world.
That's why he created Ludicorp, to build a world-changing, revolutionary game.
Called Game Neverending, it turned out to be hard to explain and not commercially viable. Also, no one wanted to invest in a tech company because of all the accounting scandals and the recent dotcom bubble burst.
Game Neverending was ironically coming to an end.
But there was hope. The game's embedded photo-uploading tool was popular among players. So popular that the tool, called Flickr, got bought by Yahoo in 2005 for well over $20 million.
After working in Yahoo for four years, Stewart and three employees left Flickr.
"Now's the time we'll succeed", they thought. Servers were cheaper, there were tons of open-sourced software, the network had spread and ubiquitous broadband gave them the ability to spend time building a new game, called Glitch.
His company raised over $5 million in Series A funding, and another $10.7 million in the next year. Glitch was growing fast.
While building Glitch, Stewart had a largely diverse staff consisting of artists, developers and marketing teams. With such a massive, cross-disciplinary team, sending individual emails weren't the best way to communicate.
So his team created an internal communication system that had a concept of a "channel", instead of sending individual messages via email. Channels can exist before and after a team member leaves, and link to other systems as well.
The great thing was that all of the information was archived into those channels, and as the game began to crumble at the end of 2012, Stewart realized he still had to justify the $17 million of money raised.
When dissolving the team, Stewart and his employees realized they would never want to work without a system like this and thought, "maybe that's what the world will want".
By accidentally discovering that there is a lot of demand, Slack came to be.
Now, Slack has over $200 million in revenue, and a rumoured acquisition by Amazon for over $8 - $10 billion.
Turns out, all you have to do is pivot a f*ck-up into something more.