Dilemma Podcast

Jay Shapiro
Dilemma Podcast

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

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

    6D AGO

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

    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 coordination breakdowns like the tragedy of the commons and the free-rider problem, I argue that the neat equations of “freedom = good outcomes” just don’t hold up. Especially not in a world where your attention, your data, and your impulses are being auctioned off in real time.To ground it all, we finish with a short watch-along of Milton Friedman’s 1980 documentary Free to Choose—a kind of holy text for the neoliberal era. I’m not here to dunk for the sake of dunking. I’m here to challenge some assumptions, explore alternatives, and ask whether "just letting the market decide" is really the kind of future we want—or just the one we can’t escape. Let’s watch together and think out loud.For the full Dilemma Archive including the mentioned Episode "Do I Smell Donuts?" whatjaythinks.com00:00 Intro: What I mean by Libertarian01:47 The Worlds We Want and the Worlds We Can't Resist04:43 Can Advertising Ever be Too Effective?11:22 The Base Capitalist Libertarian Assumption12:54 Mass Coordination Problems14:04 MCP One / The Stag Hunt15:39 MCP Two / First Mover Problems18:19 MCP Three / Free Rider Problem19:13 MCP Four / Tragedy Of The Commons22:13 Darwinian Evolution Misconception and the Range of Survival29:58 Watch Along Intro to Milton Friedman32:50 Free To Chose 10 Minute Watch-Along51:39 The Totalitarian Big Market Liberal and the Deluded Free Market Capitalists

    54 min
  2. The Possibility of Anarchy with Sophie Scott-Brown

    6D AGO

    The Possibility of Anarchy with Sophie Scott-Brown

    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 step in as chaos—or as a natural form of human cooperation?More than just rebellion, anarchism is about rethinking power, human connection, and the structures we assume are necessary. We dig into direct action, mutual aid, the role of creativity, and even cryptocurrency—examining whether anarchism is best understood as a philosophy, an adjective, or a verb. If today’s systems are failing, what comes next? And could the answer have been here all along?00:00:00 Intro00:02:02 The Modern Collapse of Order and the Anarchist Lens00:05:45 Do We Have Democracy? Have We Ever?00:12:11 The Danger of Temporary Power00:24:23 The Structure And the Solutions00:32:19 Anarchy in a Disaster00:34:31 The Existential Purpose of Civilizations00:46:18 What Is Freedom To an Anarchist00:50:25 Anarchy And Human Connection00:58:59 Anarchy as Chaos and Anarchy as Possibility01:03:53 Nihilism Versus Anarchism01:10:24 The Radical Fifties and The First Cold War01:14:23 Cryptocurrency and Anarchy at Scale01:22:02 Is Anarchy a Philosophy or Adjective or Verb?01:24:03 Protest Versus Direct Action and When We Join The Conversation01:30:44 When Nihilism Burns Itself Out and The Necessary Anarchist Creativity

    1h 34m
  3. Who's Afraid of Anarchy? The Russian Revolution, Spanish Anarchy, Punks, and Today with Ruth Kinna

    6D AGO

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

    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 struggles, punk culture, and a quiet rekindling in academic and activist circles.But anarchism has always been more than just resistance—it’s a way of imagining and building beyond what exists. We explore how anarchist thought adapted in response to fascism, war, neoliberalism, and Cold War propaganda, and why its core principles—mutual aid, autonomy, and anti-authoritarianism—continue to re-emerge in times of crisis.whatjaythinks.com00:00:00 Intro00:00:27 Turn of the Century Anarchist Violence00:05:45 Artistry and Dreams of Anarchy and William Morris’s News From Nowhere00:12:30 The WWI Disaster for Anarchists00:15:13 The Anti-Colonial Anarchists and The Rise of Lenin00:19:54 Lenin Rebrands “Communism” and Eclipses Anarchism00:21:00 The Ideas Don’t Go Away, The Red Scare and Anarchy Is Outlawed in America00:23:09 Spain’s Temporary Anarchy Breakthrough00:31:33 WWII’s Destructive Demonstration and Anarchy’s Response through Alex Comfort00:37:42 The Leviathan, Moral Atrophy, and the Death Drive00:41:57 The Free Love and Civil Rights Anarchists Rediscover the Classics00:46:48 The Cold War Slander of Ideas00:51:16 Neoliberalism, Reagan, Thatcher, and Punk Anarchy00:57:20 The Anarchy Tradition and Identity01:01:04 Rallying Points, Headline Events, and a Rekindling of Anarchism01:06:55 The Journal of Anarchist Studies

    1h 8m
  4. Who's Afraid of Anarchy? Part 1: From Proudhon to The Brink of War with Ruth Kinna

    6D AGO

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

    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 justify power today.What if anarchism isn’t chaos but a creative, practical response to domination? We track how anarchists challenged the state, capitalism, and even socialism itself, revealing a tradition that’s far more nuanced—and necessary—than its reputation suggests. This is Part 1, setting the stage for a deeper dive into how anarchism lives and breathes in today’s world.whatjaythinks.com00:00:00 Intro: A Renewed Interest in Anarchy and Libertarianism00:04:22 Intro: The Dark Shadow of Thomas Hobbes00:07:30 “Greed Is Good” and Human Nature00:15:18 Where Proudhon Begins and What Anarchy Isn’t00:20:00 Hobbes Builds the Sovereign Beast00:25:23 Proudhon Tries To Intellectually Slay the Dragon00:29:44 “Property Is Theft”00:33:17 The Enclosure Movements and The End of Free Shared Open Land00:38:14 Leo Tolstoy, “War and Peace”, and International Workers00:40:22 The Socialism Split, Marx vs. Bakunin00:46:04 The Paris Commune, Demise and Legacy00:50:25 How Should We Think About Marx00:55:56 Kropotkin Pushes “Anarchist Communism”01:01:45 What Is “Mine” Without Private Property?01:05:55 The American Interest in Anarchy01:10:55 Anti-Slavery Anarchy, Lucy Parsons and Emma Goldman

    1h 15m
  5. Surveillance For Sale and Threats To Pro-Palestine Protestors with Jack Poulson

    FEB 12

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

    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 mechanics of AI-powered repression, from facial recognition threats to the Pentagon’s hands-off approach to ethical oversight. Alongside this, I examine the philosophy of data capture—how the “front door” of willing consent and the “back door” of clandestine access have converged into a powerful system of control... with some important vulnerabilities and weaknesses.Jack Poulson's Site : https://techinquiry.org/Terms and Conditions May Apply (2013) : https://youtu.be/hRJEYmodC08?si=2vBOdOGIfa7C2yHSWrath of Zion Investigation on Dropsite : https://www.dropsitenews.com/p/israel-palestine-dox-new-york-facial-recognition-ai00:00:00 Intro: Jack Poulson the Google “Whistleblower”00:03:27 Intro: The Trackpad Dilemma and Ethical Surveillance00:08:30 Intro: The Open Front and Locked Back Door of Data Access00:27:30 Jack Poulson’s style of Journalism and the “Whistleblower Trap”00:33:30 How Surveillance Programs are Marketed00:37:47 The Wrath of Zion Investigation and Intimidation of Pro Palestine Protests00:47:35 Facial Recognition and What Can Be Done With Data00:52:26 Two Paths to the Data01:04:54 Apps and Terms and Conditions May Apply vs Direct Wiretaps01:13:25 Children’s Data and Zuckerberg’s Emojis01:16:42 Security and Privacy “Tradeoffs” and Advocacy to Journalism01:27:37 What Are They Trying to Build and Will Incompetence Save Us?01:39:07 U.S Tech Companies are Effectively Peers of the U.S. Government01:50:58 The Digital Dock Worker Who Refuses to Pass Along 1’s and 0’s01:57:42 Where Are the Vulnerabilities In This Digital Web02:04:47 What Constitutes a Contribution to a Bomb Being Dropped On Children?02:11:41 Keep Up With Jack

    2h 13m
    4.7
    out of 5
    67 Ratings

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

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