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August 13, 2025 37 mins

What makes smart, principled people work for the worst leaders? In this conversation, historian and author James Romm and Ryan dig into the timeless trap that’s snared some of history’s greatest minds, from Plato and Seneca to modern politics. They talk about the seduction of access, the slow erosion of integrity, and why walking away from a tyrant’s court is so much harder than it looks.


James Romm is an author, reviewer, and a Professor of Classics at Bard College in Annandale, NY. He specializes in ancient Greek and Roman culture and civilization. His reviews and essays have appeared in the New Yorker, the Wall Street Journal, the London Review of Books, the Daily Beast, and other venues. He has held the Guggenheim Fellowship (1999-2000), the Birkelund Fellowship at the Dorothy and Lewis B. Cullman Center for Writers and Scholars at the New York Public Library (2010-11), and a Biography Fellowship at the Leon Levy Center of the City University of New York (2014-15).


Follow James on Instagram @James.Romm and check out more of his work at his website, www.jamesromm.com


 📚 Get signed copies of James' latest book Plato and the Tyrant, and his other books Dying Every Day, How To Die, and How To Give, at The Painted Porch | https://www.thepaintedporch.com/


🎙️ Listen to James Romm’s first episode on The Daily Stoic Podcast:  https://dailystoic.com/romm/


📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work


🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast


🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast


✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail


🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/


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