S2 Ep51: Leaders Without Character Break Democracies (w/ Ryan Holiday)

John Avlon sits down with Ryan Holiday for a deep dive into virtue, character, and what ancient wisdom can still teach a country drowning in cynicism. They trace the Stoic roots behind Holiday’s bestselling series, unpack the dangers of America’s “wisdom deficit,” and explore how applied history can ground us in a moment when the loudest voices are often the least serious. Holiday opens up about his writing process, the influence of Robert Greene, and the books he returns to when he needs clarity. It’s a conversation about courage, justice, self-discipline, and why these old virtues feel newly urgent.

The Last Lion (William Manchester)
The Old, Weird America (Greil Marcus) 
The World of Yesterday (Stefan Zweig)
Montaigne (Stefan Zweig)
The Moviegoer (Walker Percy)
The Nightingale’s Song (Robert Timberg)
Stoicism (Ryan Holiday)
The Obstacle Is the Way (Ryan Holiday)
Ego Is the Enemy (Ryan Holiday)
The Daily Stoic (Ryan Holiday)
Perennial Seller (Ryan Holiday)
The 48 Laws of Power (Robert Greene)
Mastery (Robert Greene)
The Laws of Human Nature (Robert Greene)