Fast Fails: Stewart Butterfield’s Detour to Slack
Our second Friday drop. Still failing forward.
Welcome back to Fast Fails—founder flameouts with comeback energy.
Every Friday, we dig up the story behind the stumble—because great founders don’t just launch. They reroute. Rebuild. Return.
Today’s feature? Stewart Butterfield.
Because before Slack took over work culture…
He failed. Twice.
And neither failure looked like failure—until it did.
Let’s get into it.
From Game Over to Workplace Ubiquity: The Stewart Butterfield Story
Before Slack was a $27 billion company, Stewart Butterfield wanted to build video games.
In 2002, he launched Ludicorp, a company that set out to build an ambitious online game called Game Neverending. It flopped. But inside the wreckage was a silver lining: a photo-sharing tool they’d built for the game.
That tool became Flickr.
Yahoo bought it in 2005. Stewart cashed out.
But he wasn’t done. He tried again.
This time with Tiny Speck, and a new game called Glitch.
It flopped again.
But once again, there was a spark inside the rubble: an internal chat system the team used to collaborate while building the game.
That tool?
Slack.
In 2013, Butterfield pivoted fully. No more games. Just Slack.
By 2021, Slack was acquired by Salesforce for $27.7 billion. And Butterfield—twice failed as a game founder—became a tech icon of the modern workplace.
📉 The Fail
Two failed gaming startups: Game Neverending and Glitch. Years of work, millions spent, and nothing to show… except tools hidden inside the wreckage.
💪 The Grit
He didn't cling to the dream. He pivoted hard, twice—first to Flickr, then to Slack—spinning gold out of abandoned ambitions.
✨ The Comeback
Slack became one of the fastest-growing B2B startups of all time—acquired for $27.7B by Salesforce. Stewart Butterfield went from failed game dev to founder of a work platform used by millions.
🗣️ Founder Quote
“Failure is simply the opportunity to begin again, this time more intelligently.”— Stewart Butterfield
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