Molly Graham and Ashley Murphy field workplace dilemmas that resist tidy business-book answers, from how to disagree with a CEO without losing integrity to when a company’s culture is simply a reflection of its founder. The conversation also traces the difference between coaches, therapists and advisors, and argues that so-called generalists are really specialists who need sharper language for the problems they solve.

Product leader Noah Weiner explains why many companies asking for AI help really need a return to first principles first, with the technology serving as a tool rather than a strategy. The conversation follows his “free range” consulting practice through small businesses, private equity turnarounds and startup law, while arguing that AI is compressing discovery, prototyping and decision-making into a far faster operating rhythm.

Mustafa Suleiman argues that Microsoft’s evolving partnership with OpenAI has pushed the company toward model self-sufficiency, even as he insists the alliance remains central to its AI strategy. In a wide-ranging conversation, he defends the coming wave of enterprise automation, rejects claims of machine consciousness, and says the technology will have to prove itself by making people healthier, happier, and more capable.

Molly Graham reflects on walking away from the executive roles she was built to excel at and the longer, messier search for work that actually made her feel alive. In conversation with Anne Morris, she treats purpose less as a grand calling than as a practical process of noticing what energizes you, what proves draining, and what kind of impact feels close enough to matter.

Figma’s CMO argues that great marketing in 2026 is less about channel tactics than about creating coherence across product, growth, brand and community. The conversation traces how that mandate changes in an AI-saturated market, why shared goals matter more than siloed metrics, and how companies keep their taste and humanity as they scale.

Nilay Patel and New York Times reporter Ryan Mac sift through SpaceX’s blockbuster IPO filing to ask what Elon Musk’s ownership of X has actually become and why the company’s shrinking social platform may not matter. Their conversation turns into a broader indictment of a market structure that keeps rewarding Musk with more power even as corporate governance, shareholder accountability, and business fundamentals erode.

Chris Lipp argues that real authority at work comes less from title or dominance than from a felt sense of control, internal conviction, and willingness to act. The conversation traces how people build that kind of personal power through responsibility, values, fairness, and even the way they guide a meeting.

Labor economist Catherine Ann Edwards argues that the real danger is not an AI apocalypse but a government safety net too weak to handle ordinary job loss, recessions and worker disempowerment. As chip workers at Samsung win huge bonuses through union pressure, she makes the case for stronger unemployment insurance, labor power and tax policy instead of waiting for a technological crisis.

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.

Alex Kantrowitz and MG Siegler parse an uneasy moment for Big Tech, from Google’s lagging AI product strategy to Apple’s foldable ambitions and Meta’s muddled subscription push. The conversation argues that agents and chatbots are converging into a new interface for the web, one that could reorder who controls computing itself.

Benedict Evans argues that AI is a platform shift on the scale of the internet or mobile: transformative, messy, and still too early for anyone to know where the real value or disruption will settle. He pushes back on jobpocalypse panic, sketching a slower, more uneven reshaping of work in which adoption, distribution, and new kinds of services matter more than apocalyptic forecasts.

A brisk, skeptical tour through the latest AI exuberance weighs soaring token bills against meager signs of productivity, while tracing how enterprise spending, circular financing and chip mania are feeding the boom. The conversation also turns to Anthropic’s leap past OpenAI, Robinhood’s plan to let chatbots trade, and the uneasy feeling that useful tools are being inflated by reckless incentives.

Ezra Klein and Republican strategist Liam Donovan argue over whether Donald Trump is sacrificing winnable races to tighten his grip on the GOP. Their conversation ranges from Ken Paxton and Susan Collins to Tucker Carlson and J.D. Vance, tracing a party whose future may depend less on policy than on loyalty, attention and grievance.

Claire Vo puts Anthropic’s new Opus 4.8 through early coding and strategy tests, finding a model that can nail a one-shot feature build yet falter on bug fixing, edge cases and business analysis. The result is a portrait of impressive raw capability undercut by shaky grounding, uneven ambition and a stubborn inability to finish the last mile.

Caroline Wanga traces a career built less on certainty than on curiosity, describing how a series of self-made maps helped her test roles, recognize her strengths and know when it was time to move on. The conversation widens into a candid philosophy of work, urging people to trade personal branding for personal purpose and to treat failure and doubt as material for growth.

Shake Shack’s digital transformation shows how a hospitality-first brand can add kiosks, mobile ordering, and personalization without turning the customer experience into a machine. The conversation traces how the fast-casual chain scaled by learning from competitors, using data carefully, and treating technology as a support for human judgment rather than a substitute for it.

A spirited debate over whether AI agents will erase jobs or reorganize them argues that automation mostly cheapens yesterday’s expertise, making human judgment, taste and direction more valuable. Drawing on life inside an aggressively AI-native company, the conversation pushes back on layoffs-and-doom narratives and treats adaptation, not retreat, as the real dividing line.

Former Twitter CEO Dick Costolo sizes up a coming wave of AI and space IPOs, arguing that narrative discipline will matter as much as quarterly numbers when SpaceX, OpenAI, and Anthropic face public-market scrutiny. The conversation also turns to Meta’s internal malaise, Twitter’s stubborn durability, and the social backlash building around data centers and AI wealth.

Anthropic’s Boris Cherny argues that AI coding tools are already blurring the boundaries between engineer, manager and designer, even as their labor-market effects remain unsettled. Around that debate, the conversation traces how companies are pushing workers to adopt AI, rewarding token usage unevenly and fumbling toward a broader social response to automation.

Craig Mod joins Paul Ford and Rich Ciotti to talk about building bespoke accounting software for his unusually tangled life as a Japan-based American writer, publisher and membership entrepreneur. What starts with taxes and receipts opens into a wider argument about who gets to make software in the age of AI, and what kinds of human judgment still matter.