Old School with Shilo Brooks

Neal Stephenson, the prophetic author of cyberpunk classics like Snow Crash and The Diamond Age, has shaped how we imagine the future, from the metaverse to crypto to AI. His science fiction has a way of becoming reality.

But Stephenson’s thinking is just as rooted in the past, returning to timeless questions of empire and decline. In this episode, he joins Shilo to discuss Edward Gibbon’s The History of the Decline and Fall of the Roman Empire, a sweeping work that has captivated readers from Winston Churchill to Iggy Pop.

Was Rome undone by barbarians, Christianity, decadence, or elite failure? And what do those patterns reveal about our own age of technological upheaval—and the risks of AI?

Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org.

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For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount. 

Life is short. How do we live it well?

Harvard professor Arthur Brooks has spent years studying happiness. In this episode, he joins Shilo to explore what neuroscience, faith, and philosophy reveal about how to live a happy life.

Most of us are caught up in either the pursuit of empty pleasures or the pursuit of great achievement—“slacker” and “striver” extremes that keep us in a doom loop, like addicts. 

The real keys to happiness are deepening relationships, cultivating faith, and committing to lifelong learning, without concern for external validation or reward. Above all, we must learn to love and be loved and to accept suffering and heartbreak as features, not bugs, of a meaningful life.

Arthur’s latest book, The Meaning of Your Life: Finding Purpose in an Age of Emptiness, comes out March 31, 2025, pre-order your copy today at the link!

Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org.

Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe.
Learn more about your ad choices. Visit megaphone.fm/adchoices

For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount. 

Richard Connell’s 1924 short story “The Most Dangerous Game” tells of a hyper-sophisticated aristocrat who hunts human beings for sport on his private island.

In this episode, best-selling author, screenwriter, and former Navy SEAL sniper Jack Carr joins Shilo to discuss the story’s enormous influence on the thriller genre, including on Carr’s own novels.

The conversation explores the thin line between killing and murder—and when violence becomes necessary for peace.

Carr also explains why he is skeptical of current U.S. operations against Iran and talk of regime change, and recounts his successful push to change the name of the U.S. Department of Defense back to the Department of War in 2025. 

Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org.

Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe.
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The perfect book to read around the Oscars this weekend? Joan Didion’s Play It as It Lays.

In this episode, Shilo sits down with Peter Savodnik to discuss Didion’s 1970 novel—a book that seemed to anticipate everything ugly about Hollywood, celebrity culture, and the spiritual emptiness that we now take for granted on the red carpet and on social media.

They break down why Didion’s story of an actress drifting through 1960s Los Angeles feels like it could have been written in 2026, how she saw the darker underside of feminist “liberation” long before it was fashionable to question it, and why the real problem with today’s young stars is that we hear from them constantly, leaving little of the mystique that once defined celebrity. 

Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org.

Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe.
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In this episode, Shilo Brooks sits down with New York City public defender Ben Schatz to discuss the novel True Grit–and the nature of justice in America.  

Ben founded the nonprofit Books Beyond Bars, which sends requested books (not just random donations) to  individuals locked in in New York jails and prisons, giving them dignity, mental escape, and intellectual stimulation. 

After discussing True Grit, Ben offers his critique of the U.S. criminal justice system itself: its coercive plea bargaining, racism, overburdened defenders and judges, and prisons that function more as warehouses than places of rehabilitation, especially for mentally ill and addicted people. 

Throughout, the conversation links the moral center of True Grit to real‑world questions about what justice is, who deserves mercy, and how to look past someone’s criminal history.

Old School is proudly brought to you by the Jack Miller Center. If you believe in the importance of civic education and want to help prepare the next generation to carry on our democracy, join us at JackMillerCenter.org.

Become a paid subscriber to The Free Press today to enjoy exclusive bonus episodes and reduced ads. Click here to subscribe.

The Free Press earns a commission from any purchases made through all book links in this article.
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