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.

For a closed-captioned version of this episode, click here. For a transcript of this episode, please email [email protected] and include the name of the podcast.

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.

For a closed-captioned version of this episode, click here. For a transcript of this episode, please email [email protected] and include the name of the podcast.

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.

For a closed-captioned version of this episode, click here. For a transcript of this episode, please email [email protected] and include the name of the podcast.

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.

For a closed-captioned version of this episode, click here. For a transcript of this episode, please email [email protected] and include the name of the podcast.

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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Charlie Warzel, Atlantic staff writer and host of the "Galaxy Brain" podcast, joins Offline to break down the news of the week: how Elon Musk's negligence and the Epstein Files continue to corrode our society, whether we’ve reached The Singularity with new AI-only social media sites like Moltbook, and how phones—and neighborliness—have been the saving grace of Trump’s assault on Minnesota.

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Adam Friedland sits down with Jon to make sense of his unlikely rise from the self deprecating (and self defecating) cohost of Cum Town to…a public intellectual? "The Adam Friedland Show" has a knack for jolting politicians and celebrities out of their canned talking points, and its host shares what he thinks of the format he initially set out to skewer, the questions we need to be asking about the ICE crackdown, and his issues with Republicans and Democrats alike.

For a closed-captioned version of this episode, click here. For a transcript of this episode, please email [email protected] and include the name of the podcast.