Stewart Brand, Silicon Valley’s Favorite Prophet, on Life’s Most Important Principle
with Stewart Brand
4/24/2026
Stewart Brand might be the most influential philosopher of the internet – at least in its more idealistic era. In the 1960s, Brand was the central bridge figure between the San Francisco counterculture and the emerging technology scene. He created the legendary Trips Festival with Ken Kesey in 1966, and was there at “the mother of all demos” in 1968. And he created and edited the Whole Earth Catalog, which Steve Jobs called “one of the bibles of my generation” and “Google in paperback form, 35 years before Google came along.”
Brand has seen Silicon Valley evolve in the decades since. And along the way, he has written many brilliant books about our relationship to technology, the built environment and the natural world. His latest book is “Maintenance: Of Everything, Part One.”
In this conversation, we discuss everything from dropping acid to the genesis of the Whole Earth Catalog, what he thinks A.I. will reveal about humanity, the 40 years he’s spent living on a tugboat and the importance of maintenance in a culture that prizes novelty and disposability.