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Lenny Rachitsky @lennysan
Thursday, November 20, 2025 import

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Stewart Butterfield (@stewart) rarely does interviews. After 2 years of trying, I finally convinced him to come on. In this special conversation, Stewart shares the frameworks and mental models that most helped him build two of the most important products in tech history (@Flickr, and @SlackHQβ€”which he sold for $28B, and which powers how basically every company collaborates these days). We discuss: πŸ”Έ "Utility curves" β€” his framework for prioritizing ideas πŸ”Έ "The owner's delusion" β€” why restaurant websites suck πŸ”Έ "Tilting your umbrella" β€” a hilarious Slack core value πŸ”Έ "Hyper-realistic work-like activities" β€” my new favorite concept πŸ”Έ "Don't make me think" β€” Stewart's foundational design philosophy πŸ”Έ The story behind "We don't sell saddles here" Listen now πŸ‘‡ β€’ YouTube: https://t.co/oNz7E3wfqB β€’ Spotify: https://t.co/Ppn137qaL1 β€’ Apple: https://t.co/dVnCe0U3RN Thank you to our wonderful sponsors for supporting the podcast: πŸ† @WorkOS β€” Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://t.co/XH3bKmeEkH πŸ† @getmetronome β€” Monetization infrastructure for modern software companies: https://t.co/63xKc64FsP πŸ† @Lovable β€” Build apps by simply chatting with AI: https://t.co/bWplROYkTe