Every staff writer Katie Parrott traces her path from using ChatGPT as a low-cost career coach to building Compound Writing, a plugin that turns editorial feedback into reusable AI workflows. She and Natalia Quintero consider how context, fresh reporting and codified expertise can expand creative capacity without replacing human judgment.

Portola’s founders trace how an embodied AI companion became a storytelling experiment, with users and models co-writing relationships, memories and alien-world lore. The conversation considers AI less as a replacement for writers than as a new medium shaped by improvisation, responsiveness and human taste.

A Platformer writer builds an AI facsimile of Casey Newton, training it on years of columns, edits and Discord messages to write, edit and weigh in like his boss. The experiment finds sharper analysis and useful feedback alongside factual mistakes, failed jokes and the stubborn value of human collaboration.

Kevin Kelly ranges from Annie Dillard’s ecstatic prose to the long arc of technological change, reflecting on why some futures arrive late, sideways, or not at all. The conversation turns on AI’s uncanny usefulness, the difficulty of defining intelligence, and the pleasures of creating for an audience of one.

A writer and technologist describes using AI as both intoxicant and tool, building bespoke software while guarding his mornings and attention so the work that matters does not get flattened into productivity theater. The conversation moves from vibe coding and the collapse of old SaaS moats to the stubborn value of weird books, deep focus and human particularity in an epochal technological shift.

Gary Shteyngart revisits the eerie prescience of Super Sad True Love Story and traces how a culture of ranking, optimization, and screen-mediated life has hollowed out intimacy and pleasure. The conversation turns toward beauty, craft, and conviviality as stubborn forms of resistance to a joyless, hyper-efficient age.

Claire Ho tries to turn herself into an AI-generated on-screen character using Google Flow and Gemini’s video tools, building a glossy podcast hype reel while narrating every glitch, typo, and uncanny surprise. The experiment doubles as a case study in how multimodal AI can act less like a coding assistant than a rough-cut creative producer.

Mark Rober talks with Molly Graham about resisting the churn of the creator economy by treating YouTube less like a slot machine than a long game. The former NASA engineer traces his success to calculated risk, obsessive quality control, and a stubborn commitment to building work, money, and ambition at a pace he can actually sustain.

Molly Graham talks with Manoush Zomorodi about building a career in media while every platform, business model and job description keeps changing underfoot. Their conversation turns disruption into a working philosophy: hold fast to the craft, experiment relentlessly and remember that the body, not just the mind, pays for life on screens.

Ira Glass makes a funny, unexpectedly candid case against commencement speeches as a doomed genre, then explains why family history, old loyalties and one memorable Goucher dorm room changed his mind. The conversation sets up a 2012 graduation address shaped by skepticism, sentiment and a story about his grandmother meeting Adolf Hitler.