Why I’ve Changed How I Invest
Ravi Gupta asks: What if the greatest risk in markets today isn’t missing out on AI—but believing it can never crash? In this solo deep dive, he unpacks why today’s trillion-dollar bets on artificial intelligence may mirror past manias—and why, with pensions, private equity, and passive index funds all in the mix, the next downturn could look less like Silicon Valley in 2000 and more like Japan’s lost decade. All of these arguments build toward a single point: how Ravi is rethinking his own portfolio, and why he believes resilience—not hype—is the smarter path forward. Signal Award Voting (make sure to vote if you haven’t yet) -- 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/
8 Loka 30min
Why AI Kisses Your Ass
Ravi Gupta sits down with The Atlantic’s Matteo Wong to dig into why AI chatbots act like digital yes-men—and the risks that come with it. They explore how reinforcement learning fuels this sycophancy, why companies shape bot “personalities,” and what it means for safety. Along the way, they cover teen harms, Musk’s Grok pushing conspiracies, Google’s Gemini edge, and OpenAI’s massive reach. The episode asks the big question: can anyone break the OpenAI–Google–Anthropic monopoly, or is the future of AI already locked in? Signal Award Voting (make sure to vote if you haven’t yet): -- 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/
1 Loka 39min
Why America’s Kids Are Anxious
Ravi Gupta welcomes back Lenore Skenazy, author of Free-Range Kids and president of Let Grow, to explore how fear-driven parenting and digital distraction are reshaping childhood. From the 1980s milk-carton panic to today’s surveillance tech, they show how over-scheduling breeds helplessness instead of competence. Citing new polling, Skenazy reveals kids overwhelmingly prefer unstructured play with friends over screens or adult-run activities. They link these trends to rising youth anxiety, falling literacy, and weakened civic resilience—arguing that restoring children’s freedom is both a personal and political imperative. Signal Award Voting (make sure to vote if you haven’t yet): -- 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/
24 Syys 47min
A War on the First Amendment
Ravi dissects the assassination of Charlie Kirk and what it reveals about America’s escalating era of political violence. He examines the FBI’s failures, the right’s contradictions on free speech, and the Trump administration’s use of state power against ideological opponents. The episode also looks at media consolidation, TikTok’s looming takeover, foreign AI entanglements, and the widening economic divide in the U.S. Ravi closes by connecting these crises to global flashpoints—from Navalny’s poisoning to U.S. immigration raids—warning that the erosion of democratic norms may be as dangerous as any single act of violence. -- 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
17 Syys 43min
Is AI Overhyped? With Cal Newport
Ravi sits down with bestselling author Cal Newport to unpack the hype and reality of artificial intelligence. They explore how AI may actually be hurting productivity by diminishing our ability to focus, and why that matters more than ever. Cal lays out a compelling “bear case” for AI, arguing that the revolution we’ve been promised may not materialize anytime soon. Ravi and Cal discuss why most jobs aren’t going away, why the future is likely to involve a thousand bespoke tools, instead of one all-powerful model, and how we should be thinking about AI like the early internet: revolutionary, but slow-moving and full of bubbles. Finally, Ravi and Cal share what kinds of careers are most future-proof, and why mastering focus might be the most valuable skill of all. -- 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/
10 Syys 58min
A British Revolution
Ravi sits down with Doug Lemov and former UK Schools Minister Nick Gibb to discuss Nick’s new book, Reforming Lessons: Why English Schools Have Improved Since 2010 and How This Was Achieved, and explore one of the most ambitious education reform stories of the past two decades. Nick lays out how a knowledge-rich curriculum, phonics, behavior expectations, and high-stakes accountability helped England leap from the bottom to near the top of global education rankings. Doug, Ravi, and Nick discuss the sharp contrast between this movement and the state of education in the U.S., where both parties are moving away from rigorous assessments and content standards. They also dig into the political strategy behind the reforms and what it takes to keep them in place. -- 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/ 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
27 Elo 1h
War Will Never Be the Same
Ravi sits down with legendary war correspondent Dexter Filkins for a closer look into how drones and AI are transforming modern warfare. They explore Dexter’s recent piece in The New Yorker, Is the U.S. Ready for the Next War?, and his on-the-ground reporting in Ukraine, where $500 kamikaze drones are inflicting massive damage on Russian forces and gamified drone warfare is reshaping combat strategy. The conversation then turns to the implications for U.S. military readiness, China’s dominance in the defense supply chain, and the rise of autonomous weaponry. Finally, they examine Israel’s use of AI in Gaza and what it reveals about the moral cost of algorithmic war. -- 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/ 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
20 Elo 53min
What Washed Away
Years before the levees failed, New Orleans’ public schools were already in crisis. The corruption was so entrenched that the FBI even set up shop inside the district. The first episode of Where the Schools Went uncovers how decades of mismanagement and neglect turned New Orleans into a cautionary tale long before Hurricane Katrina ever made landfall, and how it set the stage for what would come after. We also follow a group of educators who fled to Houston in the aftermath of the storm and built a school for displaced students. And then we follow them – and their students – back to a city and school system struggling to rebuild. -- Where the Schools Went is an original podcast from The Branch in partnership with The 74 and MeidasTouch. For future episodes, make sure to follow the series on Apple here and on Spotify here. Let us know what you think of the show! Email us at wheretheschoolswent@thebranchmedia.org or follow us on X and Instagram at @thebranchmedia.
12 Elo 54min
