Mark Twain didn’t just write American classics, he lived one of the most powerful personal transformations in history. In Part 2 of this conversation, Pulitzer Prize-winning biographer Ron Chernow returns to join Ryan for a deep dive into Twain’s remarkable moral evolution. They discuss how Twain’s journey mirrors those of Ulysses S. Grant and John D. Rockefeller, reflect on the tragic cost of chasing fortune over purpose, and explore what makes a biography timeless and a life unforgettable.

Plus, a special moment: Ryan’s 8-year-old son jumps in to ask Ron about Hamilton, his favorite musical.

Ron Chernow is the prizewinning author of seven previous books and the recipient of the 2015 National Humanities Medal. His first book, The House of Morgan, won the National Book Award, Washington: A Life won the Pulitzer Prize for Biography, and Alexander Hamilton—the inspiration for the Broadway musical—won the George Washington Book Prize. He has twice been a finalist for the National Book Critics Circle Award and is one of only three living biographers to have won the Gold Medal for Biography of the American Academy of Arts and Letters. Ron’s latest book is on the fascinating and complex life of American writer Mark Twain.

Follow Ron Chernow on Instagram: @RonChernow

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