Dilemma Podcast

Mar 28 2025 83 ep. 77 mins 1.3k
Dilemma Podcast artwork

Solving the problems of what to do next with some of today's top thinkers and writers. Hosted by Jay Shapiro.

  Society & Culture
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When Is RESISTANCE Necessary? Where the Intellectual Dark Web go?

Mar 28 2025 49 mins  
I'm still waiting for a debate partner—so I've decided to start without one. In this video, I deliver my opening statement.Plus, I'm announcing a short break to focus on finishing my upcoming book about moral progress and technology.My essay "Be Careful In The Dark" is available here https://whatjaythinks.com/essays/2021... 00:00 Intro - My History with the

Libertarians HATE These Challenges Plus A Watch-Along Of Milton Friedman

Mar 25 2025 53 mins  
Capitalist Libertarianism sells itself as the champion of freedom and personal choice—but what happens when the very systems we’ve unleashed are shaping our desires, not responding to them? In this video, I dig into the fundamental blind spots that libertarians (especially the free-market capitalist kind) tend to ignore. From psychological manipulation in advertising to global

The Possibility of Anarchy with Sophie Scott-Brown

Mar 24 2025 93 mins  
In this conversation, Sophie Scott-Brown, historian and political philosopher, joins me to explore how anarchism isn’t just a theory, but a way of seeing, organizing, and acting in the world. We unpack the illusion of democracy, the dangers of temporary power, and what freedom actually means through an anarchist lens. When disaster strikes or institutions crumble, does anarchy st

Who's Afraid of Anarchy? The Russian Revolution, Spanish Anarchy, Punks, and Today with Ruth Kinna

Mar 24 2025 67 mins  
In Part 2, Ruth Kinna and I trace anarchism’s turbulent path through the 20th century—from early revolutionary violence to its erasure under Lenin, the Spanish Civil War, and the Red Scare in America. As anarchism was eclipsed by state communism and crushed by authoritarian forces, its ideas never disappeared. Instead, they resurfaced in free love movements, civil rights strugg

Who's Afraid of Anarchy? Part 1: From Proudhon to The Brink of War with Ruth Kinna

Mar 24 2025 75 mins  
In this conversation, I sit down with Ruth Kinna, historian of anarchism and professor of political theory, to explore the roots of anarchist thought—from Proudhon’s challenge to property to Bakunin’s clash with Marx to Kropotkin’s vision of anarchist communism. But first, we confront the towering figure of Thomas Hobbes, whose vision of human nature still shapes how we jus

Chosen People or Chosen Families: Judaism and The Destruction of Gaza with Peter Beinart

Feb 24 2025 70 mins  
In this video, I talk with Peter Beinart about Being Jewish After the Destruction of Gaza and the cracks forming in Zionism. But first, I share a personal reflection: What if Judaism’s survival isn’t about being the Chosen People, but about Chosen Families? Could the very thing seen as a threat be what actually saves it? We dive into power, myth, and the future of Jewish identi

Dear TRUMPERS: We have more in common than you think... from a LEFTIST

Feb 21 2025 42 mins  
Donald Trump is often mocked for his bluntness, but what if his “no more bullshit” approach is actually revealing something deeper—something that both leftists and Trumpers can recognize about the world order? In this video, I break down what Trump’s honesty really exposes, from his bizarre Greenland purchase idea to his “Gaza Riviera” plan, and how it all connects to t

Surveillance For Sale and Threats To Pro-Palestine Protestors with Jack Poulson

Feb 12 2025 132 mins  
In this video, I sit down with journalist and whistleblower Jack Poulson to uncover the hidden world of surveillance, data brokers, and the quiet war on dissent. We explore how pro-Palestine protesters are being tracked, the real-time auctions selling your personal data, and the murky alliances between Big Tech, intelligence agencies, and the military. Jack breaks down the mechanic

The CRISIS of Journalism with Anjan Sundaram

Jan 30 2025 137 mins  
In this video, I sit down with journalist and author Anjan Sundaram to explore the crisis of journalism, the emotional strain of witnessing trauma, and the uneasy coexistence of catastrophe and daily life. We discuss how the news is shaped, the search for the “perfect victim,” and the geopolitical narratives that demand palatable symbols of justice. Anjan’s insights are pair

Something WORSE THAN GENOCIDE with Dirk Moses

Jan 02 2025 135 mins  
In this video, I sit down with scholar and author A. Dirk Moses to unpack how the merging of the Holocaust’s specific history with the generic concept of genocide—and its elevation to the “crime of crimes”—has shaped our collective imagination in ways that blind us to potentially far worse horrors. Moses explains how the pursuit of permanent security by states and groups