With Pope Leo XIV stepping up his criticisms of the Trump administration this month, the president is out for blood...and not the transubstantiated kind. Christopher Hale, author of the Letters from Leo newsletter, joins Offline to explain the real threat this woke offline pope poses to MAGA. He and Jon discuss why the head of the Catholic Church is so obsessed with AI, how the Democratic Party should make space for more religious people, and the wisdom of Leo’s boomerisms like “an algorithm will never replace a hug.”

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New York Times journalist Noam Scheiber stops by the pod to talk to Jon about his new book Mutiny: The Rise and Revolt of the College-Educated Working Class, in which he argues that stagnant wages and rising student debt have changed the economic promise once offered by a college degree. The two discuss how college-educated workers are responding to this new reality, both individually and collectively; how AI may supercharge the pains already felt by new college grads; and how it's all reshaping — and may even break — our political system.

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New Yorker journalist Andrew Marantz joins Offline to break down his new investigation into Sam Altman, the CEO of OpenAI, the maker of ChatGPT. Over the course of hundreds of interviews, including over a dozen with Altman himself, Andrew and his coauthor Ronan Farrow unveiled a leader who tells people exactly what they want to hear, whether or not it’s true. Just like the AI model he created! Jon and Andrew discuss the contradictory narratives coming out of OpenAI, whether they could build portals that summon aliens, and how Altman’s resolve to go “founder mode” means he may be headed down the same well-traveled path as many tech oligarchs before him.

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Mark Zuckerberg is finally being held accountable–not by government regulators, board members or shareholders, but by two lawsuits. Tech journalist Casey Newtown, editor of Platformer, joins Offline to explain how a young woman in California beat Meta and Google on the grounds that Instagram and YouTube had destroyed her mental health. Jon and Casey discuss the strengths and weaknesses of the case, whether losing end-to-end encryption could lead to a surveillance state, and what happens if social platforms’ defensive shield, Section 230, is overturned. Then Jon speaks to New Mexico Attorney General Raúl Torrez about his successful lawsuit against Meta, how the social media company plans to appeal it, and whether the case he’s made could ultimately lead the Supreme Court to regulate this 21st century addiction.

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Why fight for a better future if we don't believe one is possible? Why organize, why vote? Dr. Deepika Chopra, the "Optimism Doctor," joins the show to talk about the dangers of cynicism, and to explain how optimism is a more rational and democracy-safeguarding response to this political moment. In her new book, The Power of Real Optimism, Dr. Chopra argues that the outlook is neither a trait nor mindset; it's a learnable set of skills that even the most pessimistic among us can incorporate. And it’s an essential safeguard against the paralyzing, numbing effect our media ecosystem has on our brains.

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Life or death decisions are being gamified for profit on online prediction markets like Kalshi and Polymarket. But these platforms may also have the potential to create a modernized—if morally questionable—method of opinion polling. Politico Magazine contributing writer Nancy Scola joins Offline to explain the rise of these markets, the argument for them, and the people in D.C. who stand to gain the most. But first! Senator Chris Murphy stops by the show to break down the brand new BETS OFF Act, which bans wagering on government actions, terrorism, war, assassination, and events where an individual knows or controls the outcome. He and Jon discuss the bill's prospects for passing, and discuss what happens to us spiritually when every moral question becomes a market.

Journalist and historian Anne Applebaum joins Offline to discuss America’s slide towards autocracy, as illustrated through Trump's war of choice in Iran. Anne is a staff writer at The Atlantic, an authoritarianism expert, and the host of the "Autocracy in America" podcast. She and Jon discuss how Trump and the White House are using propaganda to minimize the seriousness of this war, what our president has learned from other autocrats, and why Anne is still hopeful that American democracy can still prevail.

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Derek Thompson, journalist and co-author of Abundance, joins Offline to hash out some hard truths about AI: who it will actually replace, why we haven’t seen more labor market disruption, and why the Department of War’s battle with Anthropic spells the end of private property rights in America. Then Derek lays out his Postmanesque "Everything Is Television" theory of media for Jon, where politics becomes theater and news becomes performance. The guys wrap it up by discussing how becoming fathers changed their views on parenting—and on living.

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Imran Ahmed, CEO of the Center for Countering Digital Hate, joins Offline to talk about the horrifying trends his team has unearthed across social media platforms…and how it’s put him in the crosshairs of the Trump Administration. To date, Imran has weathered multiple lawsuits, stood up to Elon Musk, and won. But now, the State Department is trying to get him deported back to the UK—just for publicizing how platforms are hotbeds of bigotry and self harm content. He and Jon talk about how Section 230 of the Communications Decency Act is a cancer on our democracy, why Tech Oligarchs view the rest of us as NPCs, and how the “things" Silicon Valley is moving fast and breaking are actually our own children.

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Max Fisher returns to the show to podmaxx with Jon about the latest Offline-worthy news, including the landmark court case that's put Mark Zuckerberg on trial and internal drama at the AI giants that has the companies feuding with the Department of Defense, Hollywood, and their own employees. Plus, the two discuss the role citizens' social media videos have played in holding ICE agents accountable and attempt to make sense of Clavicular, a 20-year-old "looksmaxer" who has taken over their Twitter feeds.

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AI company Anthropic has a new, values-oriented “constitution” that they’re feeding their chatbot, Claude. Amanda Askell, the company’s in-house philosopher, joins Offline to talk about what it means to teach ethics to an LLM, whether the AI skews more human or more robot, and how she is training Claude to make its own judgements. Breaking with other AI models—and social media’s attention obsession—Amanda is trying to teach Claude not to be sycophantic or engagement-driven, but a kind soul who may, one day, be considered sentient.

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