This week Matt and David talk with pricing expert Lindsay Owens about Google's plan to turn its Gemini AI into your personal shopping assistant. It sounds convenient until you realize it's actually a massive surveillance pricing operation. Google just announced partnerships with Walmart, Visa, MasterCard, and others to use everything they know about you (emails, photos, calendar, searches) to help retailers personalize prices and steer you toward higher-priced products. Lindsay, who went viral calling this out on Twitter, explains how Google's own reply basically admitted they "restrain price", a pretty wild admission for a company facing antitrust lawsuits. It's a sobering conversation about how AI shopping could turbocharge price discrimination, why major retailers are handing over their pricing power to Google, and whether we can stop this before it's too late.

In the twilight of the Biden Administration, FTC Chair Lina Khan filed a price-fixing case against Pepsi, using the powerful but little-enforced Robinson-Patman Act. A few months into Trump’s 2025 term, that lawsuit was dead and buried by the new regime, leaving only a bunch of redacted documents and a lot of questions for the public to pore over.

Our guest today is Stacy Mitchell, the co-executive director of the Institute for Local Self-Reliance, who recently convinced a judge to release those files. Together, Matt and David break down how Pepsi and Walmart worked together to set “price gaps,” and how similar techniques are used throughout the economy, driving up prices for everyone, even as Walmart gets to take credit for having the lowest prices around.

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As a holiday treat, we bring you a new conversation with author and Organized Money alum Cory Doctorow about his new book Enshittification: Why Everything Suddenly Got Worse and What to Do About It. Recorded earlier this year at a live book event, David asks Cory to expand on the thesis of the book: that digital platforms are now locked in a cycle of decay, seeing our technology become less intuitive, less useful, and less private. For Cory, this cycle is a choice, driven by government policy favoring lax antitrust enforcement, strong digital rights management, and wholesale regulatory capture.

In this wide ranging conversation they discuss how market consolidation and DRM has shifted the balance of power away from workers, who are no longer able to defend themselves with the technology they are forced to use. They also get into the history of digital rights management, why Cory isn't on Audible, algorithmic pricing, and how coalition building and policy change might just be the way out of the enshitification cycle.

Organized Money will be back in the new year. Thanks for listening!