Jul 1, 2026 The Context Window with David Deming

Walter Isaacson went from a kid in New Orleans who didn’t yet know writing was a job to authoring the definitive biographies of Steve Jobs, Elon Musk, Albert Einstein, and Benjamin Franklin. In this conversation with Harvard Dean David Deming, the acclaimed biographer argues that the most innovative people are often difficult, with a more complicated relationship to empathy than the word suggests; that “We hold these truths to be self-evident” is not a factual description of America, but a promise the country has spent 250 years trying to keep; and that artificial intelligence will revolutionize education, but can never replace human reporting and emotion. Along the way: Walker Percy’s advice to be a storyteller, the time Albert Einstein was rejected from college, why Elon Musk believes empathy is sometimes just vanity, Michael Sandel’s “skyboxification” of America, and why he forces all his Tulane students to use three different AI models. Walter Isaacson is the bestselling author of biographies of Steve Jobs, Elon Musk, Leonardo da Vinci, Benjamin Franklin, Albert Einstein, and Jennifer Doudna. His latest book is The Greatest Sentence Ever Written (Simon & Schuster, 2025). He is the Leonard A. Lauder University Professor of History at Tulane University, and has been chairman and CEO of CNN, editor of Time, and head of the Aspen Institute. A native of New Orleans, he came to Harvard in 1970, concentrated in History and Literature, and later studied at Oxford as a Rhodes Scholar. Subscribe to The Context Window with David Deming: https://thecontextwindowpodcast.subst… CHAPTERS 0:00:00 Cold open 0:00:08 Introduction 0:01:30 Two kinds of Louisianans 0:02:35 How biography fell out of favor 0:04:25 Fingerprints on history 0:06:40 Is empathy a weakness? 0:08:35 Two kinds of genius 0:10:20 Staying objective 0:12:35 Would they have gotten into Harvard? 0:14:50 The greatest sentence ever written 0:16:05 A forcing mechanism 0:16:55 What are we getting wrong now? 0:21:35 Sacred to self-evident 0:24:20 The pursuit of happiness 0:26:35 The commons 0:29:00 Out of balance? 0:31:15 What would Franklin do? 0:33:35 Why his students must use AI 0:35:00 Boswell & Company 0:37:20 Don’t eat the seed corn 0:40:05 When intelligence is abundant 0:43:40 The cradle of liberty 0:45:15 Loving the country at 250 MENTIONED IN THIS EPISODE