As the last decade’s big social media platforms crumble, Paul and Rich reflect on the (false) promise of the “global town square,” and the suggestion that putting millions of people in a giant room together could be productive in any way. If the era of building software to facilitate networked connections is truly on the way out, does AI promise a return to an earlier, utility-based era of technology?

When Paul suggests recording a podcast about public figures they admire, Rich has a counter-offer—why not talk about people they hate instead? But this particular exercise has a catch: They can only discuss things they admire or feel they can learn from said figures, a very tricky exercise with certain politicians! A countdown of five business and political leaders that some large number of people hate—plus listen to the very end to hear exactly how Paul compares himself to Taylor Swift.

When Paul injures himself and is advised by his wife, Rich, and ChatGPT (seriously) to seek emergency medical attention, he goes to the urgent care and marvels at their utterly Byzantine technological set-up, from parallel, disconnected patient portals to being handed a literal CD-ROM with his X-rays. What can we learn from systems built for the captive user—and how does that apply to enterprise software more broadly?

What makes a person pay $120 for a tote bag—or fall in love with your software? Paul and Rich use a recent article about a TikTok influencer’s pricey (and popular!) tote bag to discuss our relationships with the things we buy, from unboxing videos (“commerce translated into emotional satisfaction”) to technologists’ largely incorrect assumption that adding one more feature will fundamentally change the way users feel about their product.

Paul tries to talk about his current obsession—synthesizers—on a hardware and software level, but Rich turns the tables to talk about Paul’s obsession itself. After Rich repeatedly asks Paul, “What are you doing?” they discuss the appeal of minimally online hobbies (and, by extension, software) in an extremely online world.

Men will literally record a podcast about their anxiety rather than go to therapy. How do you run a business when the world is on fire in so many ways? Paul and Rich talk about the state of things—including whether their perceptions of said things are even accurate—and how they should work, what to consider as they grow their company, and when to turn off. Gotta keep going.

Our friends find themselves in a new, corporate co-working space, determining that this, finally, is the thing that will push their digital product over the edge. Then, in a typically wide-reaching (cough) conversation, Rich and Paul discuss the current status of free speech discourse, in the context of the drama around Substack, and—well, as Rich puts it—“Who the hell asked technologists to be the arbiters of free speech?” Paul confesses that he dislikes mess, which would deeply shock anyone who saw his office desk.

Rich and Paul ring in 2024 assessing the biggest technological development of last year, this year, and possibly many future years to come: Generative AI. Why did AI truly find a mainstream foothold in 2023—and how is the space going to evolve in the coming months? Plus: They engage in some (corporate) roleplay, and get really into character.

Rich and Paul talk about their willingness to be humiliated in a corporate context. It sounds just a little like they crave it. Especially Paul. Which is weird but whatever. Then they talk about how you can't automate relationships—how you can't remove interaction from the loop. They discuss what they learned this year, and what they hope to learn next year.

Our friend Jim Nielsen cataloged all the podcasts we didn't record, so Paul and Rich doubled down and recorded five new podcasts in a hurry. The end result is exactly what you would expect. YouTube edition features extra-ridiculous stock imagery.