What does a lone sailor circling the globe have to do with the fall of empires, the Model T, and the rise of AI? Everything--because maintenance, the quiet act of keeping things going, turns out to be the hidden force behind success and failure in nearly every domain of human endeavor. EconTalk's Russ Roberts speaks with Stewart Brand --creator of the Whole Earth Catalog, founder of the Long Now Foundation, and one of the great connective thinkers of the last half-century--to explore why some people and civilizations thrive while others collapse. From the 1968 Golden Globe Race, where three sailors' radically different attitudes toward maintenance determined their fates, to the M-16's deadly design flaws in Vietnam, to the cultural reasons Israel excels at crisis response but struggles with prevention, Brand ranges across history, warfare, technology, and philosophy. Along the way, they discuss John Deere's war against its own farmers, the Model T as democratic revolution, and what AI might mean for human vigilance and connection. A wide-ranging, endlessly surprising conversation about the unglamorous work that holds everything together.