Why making things work is hard

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

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Transcript: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield

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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/178320649/my-biggest-takeaways-from-this-conversation

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Where to find Stewart Butterfield:

• X: https://x.com/stewart

• LinkedIn: https://www.linkedin.com/in/butterfield

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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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

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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

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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

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.