Episode · Lenny's Podcast · 2026-05-24

Lenny Rachitsky & Dan Shipper: books mentioned on Lenny's Podcast

The AI paradox: More automation, more humans, more work | Dan Shipper

4 books · With Dan Shipper · Listen · Watch on YouTube

Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work.

Dan Shipper recommended The Writing Life by Annie Dillard, The Second World War by Sir Winston S. Churchill, and The Rigor of Angels by William Egginton. Lenny Rachitsky discussed The Power Broker by Robert A. Caro.

Books mentioned, in the order they came up

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  1. The Writing Life

    Annie Dillard · at 1:25:36

    The Writing Life is a collection of essays by Annie Dillard that offers poetic reflections and practical insights into the solitary, often grueling craft of writing.

    Recommended
    “Everyone at Every has to read The Writing Life. Like when you join you get a copy and you have to read it. Uh you only have to read the last chapter though. I think the last chapter is incredible”
    Where to get it
  2. The Second World War

    Sir Winston S. Churchill · at 1:26:19

    The Second World War by Sir Winston S. Churchill is a monumental multi-volume historical account that combines rigorous documentation with personal memoir, detailing the global conflict from the perspective of one of its most pivotal leaders.

    Recommended
    “Churchill's a really good writer. And he has a whole history of World War II that he wrote, and it's like a combination history and memoir. And I think that's so cool because he was there, you know, he did it.”
    Where to get it
  3. The Rigor of Angels

    William Egginton · at 1:27:01

    The Rigor of Angels by William Egginton is an ingenious history of ideas by a humanities scholar that explores the ultimate nature of reality by connecting the thoughts of Immanuel Heisenberg, Jorge Luis Borges, and Immanuel Kant.

    Recommended
    “And there's this book called The Rigor of Angels that I just finished, which is um, it's like a it's a history of ideas that relates uh, Heisenberg, who has the his uncertainty principle, um, Borges”
    Where to get it
  4. The Power Broker

    Robert A. Caro · at 1:27:58

    The Power Broker by Robert A. Caro is a massive, highly acclaimed biography detailing the life and immense influence of urban planner Robert Moses, who shaped the physical landscape of New York more than any other figure in American history.

    Discussed
    “My current obsession is The Power Broker. I don't I think we talked about it when I was visiting you. It's just never ends, but it's uh, surprisingly compelling to read through the history of New York.”
    Where to get it
Other mentions in this episode (1) — ad reads, self-promotion and passing references, never counted
Passing The Golden Compass
“It's like if you ever Did you ever read The Golden Compass? Um it's like having a little daemon on your shoulder. You know, it's a little part of your soul.”