His ground-breaking book, Everyday Chaos (2019, Harvard Business Press), shows how the Internet taught us how to succeed by holding back from anticipating the future, setting machine learning up to reveal the chaos of everyday life and business by enabling us to succeed by embracing it.

Too Big to Know (2014) examines how contemporary digital tech and culture have fundamentally altered the nature and role of knowledge. As the subtitle says, now the smartest person in the room is the room.

Everything Is Miscellaneous (2007) explores how digitalization has changed our ideas about how the world is organized, since digital things can be put into as many categories as we want. Ranging over science, business, entertainment, philosophy, and more, Cory Doctorow called it an "instant classic."

Small Pieces Loosely Joined (2002) has been called "the best book written about the Web." It shows how weird the web's structure is, and wonders if people have flocked to it because its weirdness shows us the true nature of the offline world.

The Cluetrain Manifesto (2000) was a best-seller and a cultural phenomenon. It was taken as the voice of the early Web denizens and pioneers who were trying to tell businesses and the press that the Web is not a marketing tool or even an info highway. It's a social space (years before FB)in which we could talk with others in our own voice about what matters to us.

⊚ Nuclear Dialogues (1981): Philosophical dialogues about nuclear weapons.
⊚ Adventurers Guide to Interleaf Lisp (1993) A Beginner's guide to programming online docs with LISP.
⊚ My $100 Million Dollar Secret (2007) Young Adult novel about a kid who wins the lottery but has to hide it from his parents.

For an organized look at David's articles, posts, and podcasts, the linked page has links to hundreds of his articles for the likes of HBR, Wired, Scientific American, CNN, NPR, and many many more.