Lost Debate

Cuba Libre?

Lost Debate

Show Notes

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/

More from Lost Debate

Oct 21, 2026

What happens when a government promises more than it can afford—and voters reject the changes needed to sustain it? Ravi examines France’s unrest, tracing the tensions between student demands, rising debt, and pension obligations that crowd out spending on public services. He explores how political leaders respond to rioting and looting, why Marine Le Pen stands to benefit, and what the turmoil reveals about Europe’s weakening political center. He also considers the parallels facing the United States, from growing retirement costs to public systems that spend more without delivering better results.

Oct 14, 2026

Nearly 2,000 claims of child sexual abuse reveal a devastating pattern: schools protecting adults while failing children. Ravi sits down with The 74’s investigative reporter Amanda Geduld to unpack her more than two-year investigation into sexual abuse across New York’s public and private schools. They examine how ignored warnings, quiet resignations, opaque disciplinary records, and legal gaps can allow accused educators to move between schools. The conversation exposes a broader failure in institutions entrusted with children—and what it would take to put their safety first.

Oct 7, 2026

Nikole Hannah-Jones’s essay about her daughter’s education has reignited the debate over school integration and parental choice. But are we learning the right lessons? Drawing on his experience as a school principal and superintendent, Ravi examines her account and challenges the idea that integration and more funding can fix what’s failing in public education. He explores charter school results, teachers’ unions, grade inflation, and the barriers to holding educators accountable—arguing for a system built around rigorous teaching, honest assessments, and families’ ability to choose schools where their children can thrive.

Sep 24, 2026

Ravi is joined by Jeremiah, host of the New Liberal podcast, for a wide-ranging conversation that starts with the seemingly endless things people blame on capitalism. Then they take on Nikole Hannah-Jones’s account of choosing a school that reflected her beliefs about integration—and realizing her daughter wasn’t getting the education that was best for her. They also discuss the White House’s restrictions on press access, the Trump administration’s ties to right-wing influencers, and the Ed Sheeran–Macklemore controversy: what happens when trying to silence a message only makes it louder?

Sep 22, 2026

To celebrate the launch of his new book, The Invisible List, Ravi shares an audiobook excerpt about his “skill sabbatical” learning to surf—an exhilarating, difficult, and at times terrifying pursuit. Along the way, he explains how he transformed his life by treating each year like a school year—and himself as his only student. But the chapter isn’t really about surfing; it’s about facing fear, embracing discomfort, and finally tackling the big thing on your invisible list—the one you’ve dreamed of doing since you were a kid.

See all episodes →