Stewart Butterfield (00:00:00): This is 2014. That was the year that Slack actually launched. I was interviewed by MIT Technology Review and asked if we were working to improve Slack. I said, "I feel like what we have right now is just a giant piece of shit. It's just terrible and we should be humiliated that we offer this to the public." (00:00:14): To me that was like, "You should be embarrassed." If you can't see almost limitless opportunities to improve, then you shouldn't be designing the product. Lenny Rachitsky (00:00:24): Slack was famous for being one of the early, consumerized B2B SaaS products. Stewart Butterfield (00:00:29): At more than one company all hands, I made everyone in the company repeat this as a chant. In the long run, the measure of our success will be the amount of value that we create for customers, and you can put effort into demonstrating that you have created this value and stuff like that, but there's no substitute for actually having created it. Lenny Rachitsky (00:00:45): Something else I heard that you often espouse is friction in a product experience is actually often a good thing? Stewart Butterfield (00:00:52): It became an assumption that it should always be trying to remove friction when the challenge is really comprehension. If your software stops me and asks me to make a decision and I don't really understand it, you make me feel stupid. If people could get over the idea of reducing friction as a number of goal or reducing the number of clicks or taps to do something, and instead focus on how can I make this simple? How do I prevent people from having to think in order to use my software? Lenny Rachitsky (00:01:15): You started two companies, both famously pivoted. I imagine many people come to you for advice on pivoting. Stewart Butterfield (00:01:20): The decision is about have you exhausted the possibilities? Creating the distance so that you can make an intellectual rational decision about it rather than an emotion...