Serendipity in Design & Entrepreneurship
Stanford interviews Stewart Butterfield
A podcast episode that comes from Stanford’s Entrepreneurial Thought Leaders Speaker Series
The Gist
Part autobiography, part philosophy lecture — Butterfield talks about his journey from being one of the first few thousand internet users to the twists and turns his life took through multiple startups, acquisitions and eventually founding Slack (currently valued at $3.8B).
The Gem
Stewart pulls absolutely no punches when it comes to the dirty work one must do as a CEO. He makes you feel the psychological and emotional weight of the position as he recounts, with painstaking detail, the layoff that occurred during the pivot to Slack.
Why I Chose this
Stewart is a trained philosopher who just happens to be working in tech. This training is apparent throughout the episode. Stewart’s unflinching intellectual honesty and vulnerability provide a rare inside glimpse into the not-so-glamorous underbelly of a unicorn startup. I have long suspected that despite all the rosy from-the-outside-looking-in perceptions of a “successful” startup, the crown weighs heavy for whoever is at the helm. This episode confirmed those suspicions while also leaving the door open to get excited about the possibility of building something that others use.
