In today’s episode, I sit down with Professor Richard Wolff for a raw, unscripted debate on capitalism, socialism, and the future of the American Dream. New York City’s election of a socialist mayor sets the stage, but the conversation quickly dives into the deeper forces splitting the country in two and the slow unraveling of a system that millions feel no longer works for them. We go back and forth on wealth, risk, entrepreneurship, worker power, and whether the U.S. is inching toward a historic transition far bigger than anyone realizes.

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00:00:00 — Why New York’s Election Matters

00:02:05 — The End of America’s Anti-Socialism Taboo

00:04:55 — Generational Anger and the Collapse of the American Dream

00:07:34 — The Country Is Splitting in Two

00:11:44 — Trump, Sanders, and the Politics of Rage

00:15:35 — Jay Pushes Back: “Hard Has Always Existed”

00:18:25 — Wealth, Elon Musk, and the Question of Fair Reward

00:23:55 — Capitalism, Choice, and Who Really Holds Power

00:28:38 — The Sandbag Parable & Unequal Rewards

00:33:12 — The Stories We Tell Ourselves About Markets

00:38:27 — Small Business Sacrifice vs. Public Perception

00:46:15 — Risk: The Entrepreneur vs. The Worker

00:53:55 — Why Workers Don’t Get a Fair Shot

00:55:48 — Are We Near the End of Capitalism as We Know It?

00:59:21 — Employee Ownership and the Coming Transition

01:03:20 — Leadership, Democracy, and What Actually Works

01:08:51 — Closing Thoughts & Invitation for Part Two

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