Episodes

  • Nobody Lasts That Long

    Nobody Lasts That Long
    Apr 23 2026
    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 ____________ Leave us a voicemail with your thoughts on the show! 201-305-0084⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow Ravi at @RaviMGupta Notes from this episode are also available on Substack: https://thelostdebate.substack.com/ Read more from Ravi on Substack: https://realravigupta.substack.com Follow The Branch at @thebranchmedia Listen to more episodes of Lost Debate on Apple: https://podcasts.apple.com/us/podcast/the-lost-debate/id1591300785 Listen to more episodes of Lost Debate on Spotify: https://open.spotify.com/show/7xR9pch9DrQDiZfGB5oF0F Listen to Where the Schools Went: https://thebranchmedia.org/show/where-the-schools-went/
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    1 hr and 2 mins
  • Cuba Libre?

    Cuba Libre?
    Apr 16 2026
    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. --> VOTE HERE for Where the School’s Went for Best Health, Science, or Education Podcast ------- Leave us a voicemail with your thoughts on the show! 201-305-0084⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow Ravi at @RaviMGupta Notes from this episode are also available on Substack: https://thelostdebate.substack.com/ Read more from Ravi on Substack: https://realravigupta.substack.com Follow The Branch at @thebranchmedia Listen to more episodes of Lost Debate on Apple: https://podcasts.apple.com/us/podcast/the-lost-debate/id1591300785 Listen to more episodes of Lost Debate on Spotify: https://open.spotify.com/show/7xR9pch9DrQDiZfGB5oF0F Listen to Where the Schools Went: https://thebranchmedia.org/show/where-the-schools-went/
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    52 mins
  • Iran Ceasefire, Hasan Piker

    Iran Ceasefire, Hasan Piker
    Apr 8 2026
    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. Vote for Where the School’s Went Best Health, Science, or Education Podcast - vote here _____________ Leave us a voicemail with your thoughts on the show! 201-305-0084⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow Ravi at @RaviMGupta Notes from this episode are also available on Substack: https://thelostdebate.substack.com/ Read more from Ravi on Substack: https://realravigupta.substack.com Follow The Branch at @thebranchmedia Listen to more episodes of Lost Debate on Apple: https://podcasts.apple.com/us/podcast/the-lost-debate/id1591300785 Listen to more episodes of Lost Debate on Spotify: https://open.spotify.com/show/7xR9pch9DrQDiZfGB5oF0F Listen to Where the Schools Went: https://thebranchmedia.org/show/where-the-schools-went/
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    46 mins
  • How to Make and Lose a Million Dollars

    How to Make and Lose a Million Dollars
    Apr 1 2026
    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 Vote for Where the School’s Went Best Documentary Podcast - vote here Best Health, Science, or Education Podcast - vote here -------------- Leave us a voicemail with your thoughts on the show! 201-305-0084⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow Ravi at @RaviMGupta Notes from this episode are also available on Substack: https://thelostdebate.substack.com/ Read more from Ravi on Substack: https://realravigupta.substack.com Follow The Branch at @thebranchmedia Listen to more episodes of Lost Debate on Apple: https://podcasts.apple.com/us/podcast/the-lost-debate/id1591300785 Listen to more episodes of Lost Debate on Spotify: https://open.spotify.com/show/7xR9pch9DrQDiZfGB5oF0F Listen to Where the Schools Went: https://thebranchmedia.org/show/where-the-schools-went/
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    1 hr and 6 mins
  • Iran Quagmire + AI Politics

    Iran Quagmire + AI Politics
    Mar 18 2026
    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. Catherine Bracy’s organization Tech Equity and book World Eaters Ravi’s recent substack post: Go To Camp ––––––– Leave us a voicemail with your thoughts on the show! 201-305-0084⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow Ravi at @RaviMGupta Notes from this episode are also available on Substack: https://thelostdebate.substack.com/ Read more from Ravi on Substack: https://realravigupta.substack.com Follow The Branch at @thebranchmedia Listen to more episodes of Lost Debate on Apple: https://podcasts.apple.com/us/podcast/the-lost-debate/id1591300785 Listen to more episodes of Lost Debate on Spotify: https://open.spotify.com/show/7xR9pch9DrQDiZfGB5oF0F Listen to Where the Schools Went: https://thebranchmedia.org/show/where-the-schools-went/
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    50 mins
  • The People vs. AI

    The People vs. AI
    Feb 25 2026
    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 –––––– Leave us a voicemail with your thoughts on the show! 201-305-0084⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow Ravi at @RaviMGupta Notes from this episode are also available on Substack: https://thelostdebate.substack.com/ Read more from Ravi on Substack: https://realravigupta.substack.com Follow The Branch at @thebranchmedia Listen to more episodes of Lost Debate on Apple: https://podcasts.apple.com/us/podcast/the-lost-debate/id1591300785 Listen to more episodes of Lost Debate on Spotify: https://open.spotify.com/show/7xR9pch9DrQDiZfGB5oF0F Listen to Where the Schools Went: https://thebranchmedia.org/show/where-the-schools-went/
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    48 mins
  • The Openclaw Revolution

    The Openclaw Revolution
    Feb 18 2026
    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 –––––– Leave us a voicemail with your thoughts on the show! 201-305-0084⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow Ravi at @RaviMGupta Notes from this episode are also available on Substack: https://thelostdebate.substack.com/ Read more from Ravi on Substack: https://realravigupta.substack.com Follow The Branch at @thebranchmedia Listen to more episodes of Lost Debate on Apple: https://podcasts.apple.com/us/podcast/the-lost-debate/id1591300785 Listen to more episodes of Lost Debate on Spotify: https://open.spotify.com/show/7xR9pch9DrQDiZfGB5oF0F Listen to Where the Schools Went: https://thebranchmedia.org/show/where-the-schools-went/
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    37 mins
  • Wacky Economy, Epstein Fallout, Our Elders

    Wacky Economy, Epstein Fallout, Our Elders
    Feb 12 2026
    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 ––––– Leave us a voicemail with your thoughts on the show! 201-305-0084⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow Ravi at @RaviMGupta Notes from this episode are also available on Substack: https://thelostdebate.substack.com/ Read more from Ravi on Substack: https://realravigupta.substack.com Follow The Branch at @thebranchmedia Listen to more episodes of Lost Debate on Apple: https://podcasts.apple.com/us/podcast/the-lost-debate/id1591300785 Listen to more episodes of Lost Debate on Spotify: https://open.spotify.com/show/7xR9pch9DrQDiZfGB5oF0F Listen to Where the Schools Went: https://thebranchmedia.org/show/where-the-schools-went/
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    1 hr and 16 mins