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

Because we had a relatively big user base who were very engaged, but we had a really, like a leaky bucket. It was very difficult to add new users to the game that we were working on, which is called Glitch. I felt very stuck in this position because on the one hand, you have a 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, prove people wrong, keep going even when times are dark. On the other hand, there's a morning when I woke up and I was just like, I can't do this anymore. I am the CEO, I'm the chairman of the board. I'm sure that this is not going to work. And it's actually hard to convince everyone else.

I think that's one of the hardest things about evaluating an idea is saying when this one's not going to work. So do you remember what it was about that morning when you woke up and said, you know what, it's time to move on?

I don't. I mean, I think people have very little introspective access to their own cognitive processes to begin with. So anything I say would be kind of making it up. But I think it was. I had exhausted all of the ideas we had to fix the problems. So we focused on new user experience. And we really wanted to teach people what this was and what the possibilities were and get them excited about it because we were okay at attracting people into the top of the funnel, but had a hard time retaining them.

That's always when I tell people to give up an idea. When you're out of ideas about how to make it.

Yeah, exactly. So we would have an idea, we'd try, it didn't work, have another idea, and then at first you can fill up post it notes like those giant boards. You can fill up whiteboards with ideas and you'll argue about which ones are the highest value, and then one by one, you kind of eliminate them. Months go by, a year goes by, another six months goes by and it's like, shit. These are all of the ideas that we thought were the worst ones to begin with. And we only had have three left, so this is probably not going to work.