Old School with Shilo Brooks

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

Roald Dahl gave the world Matilda, James and the Giant Peach, and Charlie and the Chocolate Factory. He was also a vicious antisemite.

A Broadway play about Dahl’s legacy; the new Michael Jackson biopic; Kanye West’s attempted redemption arc; all of these have the culture asking again: How do we approach brilliant art produced by morally compromised artists?

Throughout history, some of the world’s preeminent literary geniuses have also been deeply bigoted, even monstrous people. In this episode, Shilo is joined by Eli Lake, host of Breaking History, for a conversation about these geniuses, from Voltaire to Norman Mailer, and why we should read their work despite their odious prejudices.

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. 

In this episode, Shilo sits down with sportswriter Wright Thompson to explore what the ESPN mainstay has learned from decades of covering elite athletes such as Tiger Woods and Michael Jordan. Does greatness require rage, dysfunction, or “daddy issues”? And what does GOAT culture teach young men about winning—and losing? 

They dig into why sports matter so deeply: tribal belonging, meritocracy, tradition, and the rare intensity of collective experience that borders on the religious. Thompson also explains why the most passionate fandoms often emerge in poor, deindustrialized towns. They also examine the controversies and contradictions of modern sports, from coaches and universities running de facto professional programs to the rise of gambling and debates over salary caps.

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. 

As he built Kind Snacks into a $5 billion company, ‘Shark Tank’s Daniel Lubetzky didn’t turn to startup gurus or business manuals—but to a 2,000-year-old Jewish text.

After the death of his father, a Holocaust survivor with whom he was deeply close, Daniel’s rabbi encouraged him to read Pirkei Avot, a collection of ancient wisdom on ethics, humility, and leadership.

In this episode, Daniel explains to Shilo how its teachings shaped both his leadership and Kind’s culture by reminding him to question his ego, resist yes-men, stay grounded, and learn from everyone.

More than moral philosophy, Pirkei Avot became a practical guide—anchoring his values while building an iconic brand.

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

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.

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. 

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