• 46 minutes 34 seconds
    Can You Predict a Recession?

    What if everything you’ve been told about recessions is wrong? On this episode, Ravi Gupta sits down with economist Tyler Goodspeed to challenge the classic “boom and bust” narrative—arguing that downturns aren’t inevitable consequences of excess, but the result of unpredictable shocks like energy crises, policy mistakes, or global events. Drawing on data stretching back to the 1700s, Tyler makes the case: “economic expansions don’t die of old age—they’re murdered”—and that trying to time the next crash may be a losing game. It’s a sharp, perspective-shifting conversation that reframes how the economy actually works—and what truly puts it at risk.


    Tyler Goodspeed’s Recession


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    1 May 2026, 12:26 pm
  • 1 hour 2 minutes
    Nobody Lasts That Long

    Ravi sits down with legendary music biographer Bob Spitz, who pulls back the curtain on rock’s biggest icons and the forces that made them endure. From secret blues records on military bases to the calculated creation of the “anti-Beatles,” they unpack the hidden strategy behind the Rolling Stones’ rise. The conversation dives into chaos—addiction, ego, death, and disaster—and asks how the Stones survived what destroyed everyone else. A sharp, unvarnished look at what it takes to become—and remain—arguably the greatest rock band in the world.


    Bob Spitz’s The Rolling Stones


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    23 April 2026, 10:00 am
  • 51 minutes 39 seconds
    Cuba Libre?

    When Ravi Gupta was a struggling high school student, he pulled Jon Lee Anderson’s biography of Che Guevara off his mom’s bookshelf—and it became the first book that truly grabbed him, shaping how he saw the world. That personal connection sparks a wide-ranging conversation about how Anderson’s globe-trotting childhood led him to report from the frontlines of history and build trust with everyone from warlords to world leaders. The episode traces Cuba’s dramatic ups and downs—from the economic collapse of the 1990s to Barack Obama’s brief attempt at reopening relations—and why the country now feels closer to crisis again. And it ends with an unforgettable twist: Anderson’s own unlikely role in uncovering what happened to Che Guevara after his death.


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    16 April 2026, 7:41 pm
  • 46 minutes 10 seconds
    Iran Ceasefire, Hasan Piker

    Ravi Gupta breaks down what he sees as a major U.S. loss in Iran, arguing that Trump’s threats and ceasefire ultimately left Iran with more power and America with less. He also shares clips of Hasan Piker’s commentary, arguing that Democratic candidates and media outlets should stop treating him as a credible political voice. The episode also covers early reactions to Mayor Mamdani’s first 100 days, Anthropic’s warning about a powerful new AI model, and fresh questions about Sam Altman. It’s a sharp, wide-ranging take on politics, media, and the power struggles shaping the moment.


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    8 April 2026, 9:44 pm
  • 1 hour 6 minutes
    How to Make and Lose a Million Dollars

    Ravi Gupta sits down with Alexander Hurst, author of Generation Desperation, to unpack his journey from $300 to over $1 million—and the identity he built around the life that money seemed to promise. As his portfolio surged during COVID, meme stocks, and the rise of online trading culture, so did a vision of becoming financially free, creatively unbound, and finally ahead. When the gains reversed and turned into debt, it forced a reckoning—not just with risk, but with how deeply a sense of self can become tied to numbers on a screen. It’s a candid conversation about ambition, illusion, and what his story reveals about a generation pushed to gamble for a different life.


    Alexander Hurst’s Generation Desperation

    Ravi’s recent substack, Turning the Camera On


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    1 April 2026, 10:15 pm
  • 50 minutes 14 seconds
    Iran Quagmire + AI Politics

    What happens when Americans fear AI more than Trump, ICE, or either political party? In this provocative conversation, Catherine Bracy joins Ravi to unpack why voters are deeply skeptical of artificial intelligence — and why neither Democrats nor Republicans have seized the political opportunity. They explore the rising influence of tech billionaires, the possibility of regulating or even “nationalizing” AI, and the surprising new alliances forming across ideological lines. If you want to understand how AI could reshape jobs, democracy, and the next presidential election, this episode is essential listening.

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    18 March 2026, 8:58 pm
  • 47 minutes 53 seconds
    The People vs. AI

    In this episode, Ravi Gupta talks with Time’s Andrew Chow about an unlikely coalition rising up against AI — from MAGA-aligned tech skeptics to democratic socialists pushing for data center moratoriums. They trace how local activism is already stalling major infrastructure projects, even as Big Tech prepares to flood elections with money to keep regulation at bay. The conversation zeroes in on the highest-stakes frontier: AI’s role in weapons and domestic surveillance, and whether any company will hold firm on its “red lines” when contracts and market pressure hit. Ultimately, Ravi frames it as a defining political fight of the decade: can everyday people set the terms, or will the machines — and the companies building them — decide for us?


    Andrew Chow’s The People vs. AI (Time, Feb 2026)

    Ravi’s recent substack post: The Melt-Up

    Join Squadra, Ravi's fitness community


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    25 February 2026, 9:16 pm
  • 37 minutes 20 seconds
    The Openclaw Revolution

    AI is shifting from something you prompt to something that can proactively work for you. Ravi Gupta sits down with technologist Michael Simon to unpack OpenClaw—an open-source, always-on AI agent that connects to your email, calendar, and other tools to function more like a chief of staff than a chatbot. They explore what this unlocks (from daily briefings to real automation), why it could be economically disruptive fast, and the new security and safety risks that come with always-on agents. The takeaway: the upside is real—but so is the need for boundaries, before the tech reshapes work and life faster than we’re ready for.


    Ravi’s recent substack post: The 50/50 Life

    Join Squadra


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    18 February 2026, 7:05 pm
  • 1 hour 15 minutes
    Wacky Economy, Epstein Fallout, Our Elders

    Ravi Gupta examines new data challenging the idea of a strong economic recovery and connects the week’s biggest political and cultural stories—from deficits, tariffs, and the Epstein revelations to immigration, schools, and AI—before asking a deeper question: what holds a society together when trust in institutions fades? In conversation with former Obama White House lawyer Jason Green, the focus turns to memory, community, and preserving elders’ stories, suggesting that rebuilding meaning may begin with humility, listening, and the people closest to home.


    Jason Green’s Too Precious to Lose 


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    12 February 2026, 12:00 am
  • 24 minutes 32 seconds
    More Epstein Revelations

    Ravi breaks down the week’s most important stories. He examines what’s wrong with the Epstein file release—and what it reveals about elite culture, status addiction, and moral drift. He then turns to an under-covered AI development: a bot-only social network powered by autonomous agents already behaving in unsettling ways. Plus: a striking Cato Institute report on immigration and deficits, a Texas special-election swing, election-system warning signs, and new reporting on foreign money and influence around Trump. The throughline: power without accountability distorts behavior—and the consequences are no longer theoretical.


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    5 February 2026, 11:00 am
  • 1 hour 19 minutes
    Pretti Killing, ICE Impunity, NVIDIA Dominance

    Ravi begins by explaining why this conversation matters to him: although he’s often skeptical of tech leaders, he sees Nvidia CEO Jensen Huang as a rare and genuinely consequential figure. He briefly reflects on the Pretti shooting in Minnesota and the broader questions it raises about accountability and transparency before turning to the interview. Ravi then speaks with author Stephen Witt about the forces that shaped Jensen’s leadership—from a punishing childhood and Nvidia’s early brush with failure to the high-risk CUDA bet that helped make modern AI possible. It’s an absorbing portrait of leadership, obsession, and the building of one of the most important tech companies of our time.


    Stephen Witt’s Jensen Huang, Nvidia, and the World's Most Coveted Microchip

    Ravi's Garbage Town

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    28 January 2026, 10:21 pm
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