Stewart Butterfield: evaluation

Transcript context

…You started two companies, both famously pivoted. I imagine many people come to you for advice on pivoting. 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 emotional decision is essential. And the reason I say you have to be coldly rational about it is because it's fucking humiliating. Today, my guest is Stewart Butterfield, a founder and product legend who rarely does podcasts. Stewart founded Flickr and then Slack, which he sold to Salesforce in one of the biggest acquisitions in tech history at the time. There is so much product and leadership wisdom locked away in his head. I feel like our conversation just scratched the surface. We chat about utility curves, something he calls the owner's delusion, a hilarious pattern he sees at companies he calls hyperrealistic work-like activities, what he's learned about product and craft and taste and Parkinson's law, why you need to obsess with not making your users think, the backstory on his legendary we don't sell saddles here memo, and so much more. A huge thank you to Noah Weiss, Chris Cordell, Ali Rael, and Johnny Rogers for suggesting topics and questions for this conversation. This is a really special one and I really hope to have Stewart back to delve even deeper. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my newsletter, you get 17 incredible products for free for an entire year, including Devin, Lovable, Replit, Bolt, n8n, Linear, Superhuman, Descript, Wispr Flow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, ChatPRD, and Mobbin. Head on over to lennysnewsletter.com and click Product Pass. With that, I bring you Stewart Butterfield after a short word from our sponsors. Here's a puzzle for you. What do OpenAI, Cursor, Perplexity, Vercel, Plaid and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, WorkOS. If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, SCIM, RBAC, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Whether you're a seed-stage startup trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise-ready and unlocking growth. They're essentially Stripe for enterprise features. Visit WorkOS.com to get started or just hit up their Slack support where they have real engineers in there who answer your questions superfast. WorkOS allows you to build like the best with delightful APIs, comprehensive docs, and a smooth developer experience. Go to workos.com to make your app enterprise-ready today. This episode is brought to you by Metronome. You just launched your new shiny AI product. The new pricing page looks awesome, but behind it, last-minute glue code, messy spreadsheets, and running ad hoc queries to figure out what to bill. Customers get invoices they can't understand. Engineers are chasing billing bugs. Finance can't close the books.…

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