Lost Debate

Primary Takeaways + Free Speech & Boycotts

Lost Debate

Show Notes

Ravi Gupta unpacks a volatile primary season, where ideological insurgents are gaining ground, independents are being sidelined, and both parties’ youngest voters appear increasingly drawn to political extremes. He also examines Alaska’s surprising electoral possibilities and a radically reshaped Democratic presidential calendar designed to test candidates across a broader coalition. Then, acclaimed novelist and former PEN America president Dinaw Mengestu explains why he resigned over the organization’s approach to Israel, Gaza, and the boycott movement. Their probing conversation confronts a defining free-speech question: When does a boycott constitute legitimate political expression—and when does it become discrimination?

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Show Notes - ⁠https://thelostdebate.substack.com/⁠

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More from Lost Debate

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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.

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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?

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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.

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