Sure, you can build “stuff” with AI, but is anyone paying attention to product these days? On this week’s episode, Paul and Rich sit down with someone who is: Hilary Mason, CEO of the immersive online roleplaying game company Hidden Door. After discussing Hilary’s background in data science and machine learning, Paul takes a spin through a game scenario (Brooklyn vampires in a fantasy tavern!) while Hilary outlines the product decisions around Hidden Door’s game mechanics, AI-related or otherwise. Plus: Rich outlines his own attempts to make a game with AI for a family gathering, which, in his words, “led to children crying.”

AI is blurring—and even destroying—the distinctions between disciplines. Do we need a new way to talk about work? On this week’s episode, Paul tests out a few of his AI-era neologisms on a skeptical Rich: Perhaps you are a “custolient,” looking to purchase the services of a “praygency” for your next project? (Yes, Paul insists the “y” in “praygency” is vital.) Are these new blended terms helpful, or just a way of talking around a very uncertain landscape?

Is the future of work sitting back and watching your company of bots plan their offsite? On this week’s episode, Paul is joined in the studio by journalist Evan Ratliff, the host and creator of the wildly popular Shell Game podcast, which is about, per the show’s description, “how Evan tried to build a real startup, run by fake people.” Evan’s AI agents were an exercise in immersive journalism (and yes, they did in fact go wild planning their offsite), but would he ever consider running a company of bots for real?

With AI drastically cutting delivery times in tech and beyond, how should practitioners price their time? On this week’s podcast, Paul tells Rich about a recent experience with a potential client, where he skipped steps and rapidly vibe-coded through the prototyping process and they….didn’t really know what to make of the result. If things that used to take months can now be done in hours, what are clients actually paying for?

Can AI help heal our broken healthcare system? On this week’s podcast, Paul and Rich are joined in the studio by Erynn Petersen, a longtime technologist and the current CEO of Emme, a healthtech startup that works to lower medical costs for both providers and patients. First, she lays out some of the systemic problems that saddle Americans with huge bills (or lead them to avoid seeking care entirely). Then, she discusses how AI tools might revolutionize the industry—as well as the ways the technology could make an unequal system even worse.

People are constantly talking about how AI is transforming engineers’ work, but where does that leave the product manager? On this week’s podcast, Paul (who has hired many PMs) and Rich (who is also a PM himself) tilt the AI-and-code lens away from the engineers and onto the role they describe as the diplomat of software creation, liaising between business, design, and engineering needs. Should PMs feel threatened by LLMs, or empowered by them? How can they use these tools to add value to the org and their role within it?

Public opinion on LLMs like Claude varies widely—but how do the people who actually work at Anthropic think about it? On this week’s podcast, Paul and Rich are joined in the studio by New Yorker staff writer Gideon Lewis-Kraus to discuss his recent feature, which he reported from within Anthropic HQ. They discuss the piece, and then they hash out the real questions: What’s the correct literary metaphor for an LLM? Does an AI company really need psychologists for its chatbots? And, perhaps most importantly, should you be polite to Claude?

Anthropic founder Dario Amodei wants AI to be regulated. Will anyone listen? On this week’s podcast, Paul and Rich dive into Amodei’s recent (lengthy) essay, “The Adolescence of Technology,” which argues for social responsibility both from within and around the AI industry. Amodei might have the best intentions, but with less mindful competitors in the space, are his ideas nothing more than wishful thinking?