For as long as there has been software we have had this collective hope -- maybe more of a desire -- that software will make all kinds of work easier, more productive, and more creative. Spreadsheets, computer-aided design tools, digital publishing platforms, though never perfect, are examples of software that have definitely changed how we work and what is possible. Still, you find very few people enthusing about Excel over cocktails. So what is going on with Slack? The messaging app crops up in conversation at dinner parties. It’s become a kind of cultural signifier of a tech savvy workforce that is always looking for better ways to connect -- inside and outside of work. In this segment of the podcast we discuss Slack with its founder Stewart Butterfield. Why Slack has resonated so well across all types of people, from engineers at NASA’s Jet Propulsion Lab to dentists, and what that says about how we work today and about our ongoing quest for the perfect tools and services to get the job done. The conversation happened as part of a16z’s Capital Summit.
You've heard the story: Slack began as a game. But almost exactly 1 year ago today, the internal tool the team built for its own use became a team communication app that anyone (and especially enterprises) can use -- and is now one of the fastest growing ones at that. It seems like collaboration is "something software should be helping us with” Slack co-founder Stewart Butterfield observes, yet it typically isn't. So what can an app like Slack tell us about how we work today, and how the nature of work will change (fewer meetings? less emails)? Butterfield is joined in this edition of the a16z podcast by a16z board partner Steven Sinofsky and a16z's Benedict Evans. The trio examines the origins of messaging and task management tools (many of which Sinofsky worked on at Microsoft) -- and how the advent of cloud-based services and mobile in particular have changed the requirements for modern workplace tools and information management.
Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principles that most contributed to his success. From “utility curves” to “the owner’s delusion” to “hyper-realistic work-like activities,” his thoughts on craft, strategy, and leadership apply to anyone building products or leading teams. *We discuss:* 1. Hyper-realistic work-like activities 2. The owner’s delusion 3. Utility curves 4. “Don’t make me think” 5. “We don’t sell saddles here” 6. Tilting your umbrella 7. When to pivot *Brought to you by:* WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny Metronome—Monetization infrastructure for modern software companies: https://metronome.com/ Lovable—Build apps by simply chatting with AI: https://lovable.dev/ *Transcript:* https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/178320649/my-biggest-takeaways-from-this-conversation *Where to find Stewart Butterfield:* • X: https://x.com/stewart • LinkedIn: https://www.linkedin.com/in/butterfield *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Stewart Butterfield (04:58) Stewart’s current life and reflections (06:44) Understanding utility curves (10:13) The concept of divine discontent (15:11) The importance of taste in product design (19:03) Tilting your umbrella (28:32) Balancing friction and comprehension (45:07) The value of constant dissatisfaction (47:06) Embracing continuous improvement (50:03) The complexity of making things work (54:27) Parkinson’s law and organizational growth (01:03:17) Hyper-realistic work-like activities (01:13:23) Advice on when to pivot (01:18:36) The importance of generosity in leadership (01:26:34) The owner’s delusion *Referenced:* • Slack: https://slack.com • Flickr: https://www.flickr.com • Cal Henderson on LinkedIn: https://www.linkedin.com/in/iamcal • Blok: https://blok.so • Brandon Velestuk on LinkedIn: https://www.linkedin.com/in/brandon-velestuk-6018721b • Magic Link: https://en.wikipedia.org/wiki/Magic_Link • Ticketmaster: https://www.ticketmaster.com • John Collison on X: https://x.com/collision • Patrick Collison on X: https://x.com/patrickc • Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai • Three Questions with Slack’s CEO: https://www.technologyreview.com/2014/11/21/170330/three-questions-with-slacks-ceo • Six Sigma: https://www.6sigma.us • What is kaizen and how does Toyota use it?: https://mag.toyota.co.uk/kaizen-toyota-production-system • John Collison’s post on X about passion projects: https://x.com/collision/status/1529452415346302976 • Parkinson’s law: https://www.economist.com/news/1955/11/19/parkinsons-law • We Don’t Sell Saddles Here: https://medium.com/@stewart/we-dont-sell-saddles-here-4c59524d650d • Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game) • IRC: https://en.wikipedia.org/wiki/IRC • This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke • The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins: https://www.lennysnewsletter.com/p/the-making-of-canva • Prisoner’s dilemma: https://en.wikipedia.org/wiki/Prisoner%27s_dilemma • Stewart Little: https://en.wikipedia.org/wiki/Stuart_Little • Dharma and Greg: https://en.wikipedia.org/wiki/Dharma_%26_Greg • Stewart’s post on X referencing “the owner’s delusion”: https://x.com/stewart/status/1223286626991796224 *Recommended books:* • Principles: Life and Work: https://www.amazon.com/Principles-Life-Work-Ray-Dalio/dp/1501124021 • Why Nothing Works: Who Killed Progress―and How to Bring It Back: https://www.amazon.com/Why-Nothing-Works-Killed-Progress_and/dp/154170021X • Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586 • Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996 _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.
You can listen to the full pod with Noah Weiss here: https://www.youtube.com/watch?v=XrRlVOWe5GE #startup #founder #vctok #tech #FAANG #slack best startup founder podcast, startup advice, most innovative tech companies
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“The fundamental challenge of leadership is that of being a human being: living with an open heart and not seeing other people as instruments that can be used to your advantage or as obstacles in the way of something you want.” Stewart Butterfield, the co-founder of Flickr and now co-founder & CEO of Slack, was interviewed by Tylon Garrett, MBA ’20, for the decade’s first View From The Top. During the event, Butterfield discussed his journey as a serial entrepreneur, and the learnings along the way. Slack, which now has more than 12 million active users in 150 countries around the world, is Butterfield’s fourth company and reached a valuation of $1 billion within eight months.
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