Lost Debate

Lost Debate is a weekly podcast from The Branch that brings you news, ideas, and arguments from around the political spectrum. We engage in the good-faith discussions that too much of our society and media miss. It's hosted by Ravi Gupta, a former Obama staffer turned school principal.

  1. What if the Iran War Never Ends?

    11H AGO

    What if the Iran War Never Ends?

    What if the Iran war never really ends—but instead settles into a dangerous, permanent limbo? In this episode, Ravi Gupta sits down with former Deputy National Security Advisor Jon Finer to unpack the confusing reality behind Trump’s Iran strategy, the collapse of diplomacy, and why the world may now be worse off than before the war began. Together, they revisit the Obama-era JCPOA nuclear deal, debate whether any future agreement is still possible, and explore how America’s shifting foreign policy has damaged trust with allies and adversaries alike. It’s a sobering conversation about war, power, diplomacy—and what happens when no one can clearly define what “winning” even means anymore. Jon’s podcast: The Long Game with Jake Sullivan and Jon Finer ____________ 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/⁠⁠

    43 min
  2. Cuba Libre?

    APR 16

    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. --> 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/

    52 min
  3. How to Make and Lose a Million Dollars

    APR 1

    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 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/

    1h 6m
4.6
out of 5
601 Ratings

About

Lost Debate is a weekly podcast from The Branch that brings you news, ideas, and arguments from around the political spectrum. We engage in the good-faith discussions that too much of our society and media miss. It's hosted by Ravi Gupta, a former Obama staffer turned school principal.

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