Episode · Lenny's Podcast · 2025-11-20

Lenny Rachitsky & Stewart Butterfield: books mentioned on Lenny's Podcast

Slack founder: Mental models for building products people love ft. Stewart Butterfield

4 books · With Stewart Butterfield · Listen · Watch on YouTube

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.

Stewart Butterfield recommended Positioning by Al Ries and others, discussed Don't Make Me Think! by Steve Krug and Thinking in Bets by Annie Duke, and criticized Why Nothing Works by Marvin Harris.

Books mentioned, in the order they came up

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  1. Don't Make Me Think!

    Steve Krug · at 36:57

    Don't Make Me Think! by Steve Krug is a prominent guide on web usability and human-computer interaction that focuses on intuitive navigation and user-friendly digital design.

    Discussed
    “And if there is one mantra that I would use to replace that, it's don't make me think. I don't know if you remember that that book. Absolutely.”
    Where to get it
  2. Why Nothing Works

    Marvin Harris · at 52:22

    Why Nothing Works by Marvin Harris explores systemic challenges in modern society and prompts critical reflection on organizational structures.

    Critiqued
    “There's a book called Why Nothing Works recently, which is like It's not an I'm sorry to the author if they They doubt they're listening, but just give It's not like an amazingly written book.”
    Where to get it
  3. Positioning

    Al Ries; Jack Trout · at 1:11:19

    Positioning: The Battle for Your Mind by Al Ries and Jack Trout is a foundational marketing strategy book examining how consumers perceive products, brands, and corporate messages in a crowded marketplace.

    Recommended
    “This is book positioning um which is an absolute classic. It's very short. I would recommend everyone read it. Where the the point of it is from my perspective it's almost impossible to create a net new idea in someone's head.”
    Where to get it
  4. Thinking in Bets

    Annie Duke · at 1:15:21

    Thinking in Bets by Annie Duke is a popular guide to decision-making under conditions of uncertainty, teaching readers how to separate the quality of their choices from the unpredictability of outcomes.

    Discussed
    “I think you have to really be coldly rational and Now you know, some of this shows up in the book um thinking about Some of it's in Andy second book. The title of which I'm forgetting right now, but I'm someone will will know it.”
    Where to get it