The Unsupervised Learning Book List

I’m currently reading over 50 books a year, and I get a lot of questions about what I recommend.

UL Membership includes access to the book club, where we pick a book a month and talk about it live!

Below I’ll give one sentence about what each book is about, but I won’t try to sell it to you. The sell is simply that I’ve consumed a few hundred titles over the last several years, and these are my few recommendations from all of them.

It’s now the official Unsupervised Learning book list.

  1. Spent: Sex, Evolution, and Consumer Behavior — My favorite book on the merging of Evolutionary Psychology with marketing and personality.

  2. The Red Queen: Sex and the Evolution of Human Nature — This book taught me more science about human evolution and human nature than any other.

  3. Behave: The Biology of Humans at Our Best and Worst — An unbelievably broad and entertaining overview of how various factors effect human behavior.

  1. Homo Deus: A Brief History of Tomorrow — An unmatched look at the history, present, and future of humanity.

  2. The Dictator’s Handbook: Why Bad Behavior is Almost Always Good Politics — A stunning education into real-world politics that you can’t unlearn once you are exposed to it.

  3. Hamilton — A remarkable biography that taught me more about America than I’d learned any other way.

  1. The Real Internet of Things — My book on the future of the Internet of Things and how it’ll merge with society.

  1. Naked Economics — This book completely changed what I understood economics to be, and I’m now fascinated with it as a result.

  1. The Subtle Art of Not Giving a F*ck — A short, spectacular work on the most important lesson of all: worry less about what others think of you.

  2. The Sense of Style: The Thinking Person’s Guide to Writing in the 21st Century — Less of a dating book about women and more about becoming comfortable with yourself in any situation.

  1. Superforecasting: The Art and Science of Predicting — A stunningly brillant book on how to become good at predicting things, told through true stories of the actual experts, with clear descriiptions of their shared attributes.

  2. Algorithms to Live By — A fantastic overview of the various algorithms you can use to optimize your daily life.

  1. The Dichotomy of Leadership — My all-time favorite book on leadership, because it focuses on the management of extremes.

  1. Name of the Wind — My favorite fantasy series of all time.

  2. The Graveyard Book — Supposedly a children’s book, but enough fun for 10 adults put together.

  1. Ready Player One — An unspeakably fun journey for anyone who lived through—or is a fan of—the eighties geek scene.

  2. The Metamorphosis of Prime Intellect: A Novel of the Singularity — My long-time favorite story around the singularity and its fantasy-injected possibilities.

  1. Kill Decision — A novel-based exploration of numerous non-fiction concepts, with miniature drones being the centerpiece.

  1. Lexicon — A brilliant blend of hacking, psychology, and fantasy.


  1. If you don’t like my fiction selections because they’re not as refined as my nonfiction selections, I agree with you. Let me know what I should do to improve the list.

  2. It’s harder than you think to put books in order like this, especially as you start going down in the list. If it helps, consider it a recommendation of what order to read them in, not a hard statement of ultimate objective quality.

  3. Please send any recommendations. I’d love to improve the list!

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