Jerry Cobb read The Odyssey in ninth grade, the same year he lost his father. Decades later, he tracked down the exact 1957 edition he read as a teenager, and opening it again felt like the book finally coming home to him.

Jerry is a Senior Business Management Consultant at Charles Schwab and helps lead the Schwab Executive Leadership Program. We trace the book forward into his own atypical path from journalism into wealth management, and what he only recognized as a through line once I asked him about it directly.

We also get into Grant, Ron Chernow's biography of Ulysses S. Grant, and what it taught Jerry about the loneliness of leading, the reading list behind Schwab's leadership curriculum, and John Kotter's eight-step framework for change.

If you're leading people through decisions that never feel entirely comfortable, and you want a reading list to go with it, this one's for you.

Spenser Segal spent sixteen months and 27 interviews writing the book behind a moonshot he's chased for two decades: closing the gap between the sliver of people who get world-class financial advice today and the far larger group who could, with AI.

He joins me for the first Author Chats episode to unpack his book, The AI-Enabled Future of Wealth Management: why a firm without clean data is building a skyscraper on sand, and what an agentic mesh of specialized AI agents can do to prep an advisor for a Friday meeting before they open a laptop.

But his real argument is that the AI is the easy part: the firms that win will be the ones whose leaders treat this as an organizational capability problem, not a technology decision, starting with the change management most firms underestimate. We get into what that looks like day to day, and the line his whole book builds toward: human-AI synergy at the speed and strength of trust.

In 2001, on vacation, Chip Munn finished The E-Myth at two in the morning and sketched his first org chart on the only paper he had: the back of a paper plate. He kept that plate for twenty years. He joins me to talk about the book that started it, and where twenty-five years of building on it took him: EOS, a hundred-year firm, and a plan to hand it all to the next generation.