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.

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.

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.

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.

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.

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.

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.

Minneapolis isn’t just protesting ICE—it’s fully organizing against it. Lydia Polgreen, journalist and opinion columnist at The New York Times, joins Offline to explain the difference, share what she saw on the ground in the Twin Cities, and explain how it compares to other countries’ slides towards authoritarianism. As a former foreign correspondent in West Africa and India—and having grown up in Minnesota—Lydia breaks down this civil unrest and what it spells for the future of America.

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, blogger, and science fiction writer Cory Doctorow stops by the studio to talk to Jon about “enshittification,” his theory that explains how, sometime over the last decade, everything online became substantially worse. The two discuss how tech companies lure in, trap, and then extract as much capital as possible from users; how that process played out at Facebook and Amazon; and what it would take — from a Democratic-led FTC and Congress — to reverse the trend before it’s supercharged by AI.

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.

Does misinformation even matter if no one can agree on a shared reality? The New Yorker’s Jay Caspian Kang joins Offline to explain how the ICE shooting in Minnesota exposes Americans’ algorithm silos. Then, he and Jon explore the rise of a 23-year-old YouTuber who ignited the right’s fascination with fraud in Minnesota, and break down five media trends that will reshape the industry in 2026 and beyond.

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.