In this episode, Stewart tells Slack’s origin story and the hard decisions it took to get there, elaborating on when to follow your dreams and when to "stop banging your head into the ground until you bleed out."

Stewart Butterfield is the co-founder and CEO of Slack. Over the last 20 years, Stewart has built a distinguished career as a designer, entrepreneur, and technologist. He co-founded Flickr in 2003, and was its CEO through its acquisition by Yahoo!. Among many other honors, he was named one of the 100 Most Influential People in the World by Time Magazine, one of BusinessWeek's Top 50 Leaders, featured on Vanity Fair’s New Establishment List, and was recognized as the 2015 Technology Innovator of the Year by the Wall Street Journal.