What do you do when the thing you set out to build isn't the thing people actually want? Most founders wrestle with that question in theory. Stewart Butterfield has lived through it twice.

Before Slack became the workplace messaging platform used by tens of millions of people, Butterfield was co-founder of Flickr, the photo-sharing service Yahoo acquired in 2005. That outcome put him in a rare category founders with a real exit and a second act to figure out.

He didn't take the obvious path. Instead of moving into the enterprise software lane that might have been expected, he started a game studio. In 2009, Butterfield founded Tiny Speck with the goal of building Glitch, a whimsical online world with a handmade aesthetic and a distributed team spread across North America.

To hold the studio together across cities and time zones, the engineers built an internal messaging system a way to maintain real-time communication while building the game. It wasn't a side project. It was what kept the work from falling apart, a living archive of decisions, files, and context that the team couldn't afford to lose.

Glitch, meanwhile, struggled. The game launched and never found the scale it needed. By 2012, it shut down.

What Butterfield noticed in the aftermath was simple and important: the internal tool had worked. Every day, under pressure, while everything else was slipping, the messaging system had proven its value. The question was whether it could prove it outside the studio walls too.

That question became Slack, launched in 2013. Not as an abstract thesis about the future of communication, but as a product shaped by genuine friction the daily challenge of coordinating remote work, preserving context, and keeping a team's collective memory from leaking away.

The numbers that followed tell the rest. By early 2019, more than 10 million people were using Slack daily. Annualized revenue had passed $400 million. In December 2020, Salesforce acquired Slack Technologies in a deal valued at approximately $27.7 billion.

It didn't begin with a pitch deck or a market analysis. It began with a small studio's way of staying coherent and a founder who noticed, in the wreckage of a failed game, what had quietly worked all along.