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Slack founder Stewart Butterfield on when to give up on an idea

Stewart Butterfield is the founder of Slack, which he famously pivoted to from a failed gaming platform called Glitch.

In the clip below, he describes how he felt stuck trying to figure out whether or not it was time to give up on Glitch:

“On the one hand you have the narrative of: good entrepreneurs are resilient; when everyone else thinks it’s a bad idea, it’s probably a really good idea; you have to dig in and prove people wrong; keep going even when times are dark. On the other hand, there was a morning when I woke up and was like ‘I can’t do this anymore. I’m the CEO and Chairman of the Board, and I’m sure this is not going to work’”

What convinced him that the idea wasn’t going to work?

Basically the Glitch team had exhausted all of the ideas they had to fix the problems with the product.

And Sam Altman—who is conducting the interview—agrees:

“That’s always when I tell people to give up on an idea: when you run out of ideas for how to make it work.”

Stewart goes on to explain the process in more detail:

“At first you fill up whiteboards with ideas and argue about which ones are the highest value. And then you eliminate them one-by-one. Months go by. A year goes by. Another six months goes by. And then you’re like: ‘we’ve already gone through most of the worst ones and we only have three left. This is probably not going to work.’”

The good news is that coming to terms with the failure of Glitch allowed the team to move on to a more promising idea: Slack--which ended up being acquired by Salesforce for $27.7 billion.