222: The Philosopher Teaching AI to Be Good

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.

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. 

What does 21st century authoritarianism look like in the United States? Author and Atlantic staff writer George Packer joins Offline to talk about America’s zombie democracy, who could be the most dangerous MAGA heir, and how Democrats should be fighting for the country. For our last episode of 2025, George and Jon connect the dots between Trump, polarization, oligarchs, AI, social media, Charlie Kirk and more. 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. 

Julie Scelfo, founder of Mothers Against Media Addiction, sits down with Jon to talk about the impacts AI and social media are having on our kids…and what we can do to stop it. Julie breaks down what change parents can effect vs. policy makers, the horrors kids are normalizing on social media, and the corruption at the highest echelons of government that are preventing safety features from being mandated.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.

Economist and techno-optimist Noah Smith, author of the Noahpinion Substack, joins Offline to debate the promise of artificial intelligence, the benefits of online fragmentation (could it be good for our society?) and whether liberal nationalism is feasible—and a good thing. Though Noah and Jon differ on a lot of “Offline” themes, they find common ground on the dangers of social media, leftist scolds, and a country with an identity crisis.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. 

What happens when the AI bubble bursts, how did Meta get away with it yet again, and…is Elon “Bubba”? Max Fisher pays Offline a visit to take stock of the year in memes, conspiracy theories, and information siloes. He and Jon meet the ghosts of twitter fights past and future, compare notes on staying off their phones, and chat about what they’re watching right now…besides Zohran and Trump flirting.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.