The Enshitification of Big Tech: A Conversation with Cory Doctorow

Since taking office in January, Trump has issued several executive orders targeting major Democratic-aligned law firms, revoking their security clearances and threatening the government contracts of their clients. These law firms are among the "big law" firms that not only wield a great deal of money and power in Washington but also play a significant role in the political establishments of both parties. In this episode, Matt and David deconstruct how big law works with Jonathan Kanter, former head of the Antitrust Division of the Justice Department and a former partner at a big law firm. They discuss how these firms make their money, how they became so deeply enmeshed in our politics, and the consequences of Trump's actions, including the chilling effect they are having and the potential for a new way of organizing the Democratic Party. This is part 1 of a 2 part episode with Jonathan Kanter, next week we discuss his work at the Antitrust Division, and the future of anti-monopoly policy. 

Why is it that Walmart can sell bananas for less than what an independent grocer pays for it wholesale? In this episode, David and Matt expose how major retailers like Walmart and Dollar Stores use their sheer size to strong-arm suppliers into giving them special deals—while smaller, independent grocers are stuck paying higher prices. They talk to Randy Arceneaux, CEO of Affiliated Foods, and antitrust lawyer Chris Jones about how this system is not only unfair but likely illegal under the long-ignored Robinson-Patman Act, which bans price discrimination. From grocery wholesalers forced to “subsidize” Walmart, to toilet paper and pet food shortages that only seem to affect smaller stores, to how credit card fees hit independents much harder, this episode unpacks how monopolistic practices are reshaping the grocery business—and why the fight to fix it is heating up.

On March 18th, the White House sent a letter to the two democratic commissioners at the FTC that they had been fired. Clear Supreme Court precedent reinforces that FTC commissioners cannot be fired at-will by the executive. So what happens next? Today on the show Matt and David talk to one of those commissioners, Alvaro Bedoya, about his attempted firing. They discuss the context, consequences, and legal precedent of what's happening at the FTC, along with Trump's potential goals, the importance of the commission's work, and the uncertain future of an agency in crisis.

How did Silicon Valley's ideology go from utopian dreams to self serving power grabs? David and Matt dive into the power dynamics of Big Tech with author, activist, and anti-monopoly advocate Cory Doctorow. They explore how Silicon Valley’s early ideals of openness and innovation gave way to corporate dominance, leading to what Doctorow calls “enshitification”—the systematic decay of platforms as they prioritize profits over users. The conversation unpacks the monopolistic strategies of giants like Amazon and Google, the erosion of competition through regulatory capture, and the role of interoperability in breaking Big Tech’s grip. Check out more of Cory's writing and his new book Picks and Shovels, on his website.

Are Elon Musk's efficiency strategies brilliant or reckless? David and Matt explore this question with procurement expert Rich Ham, CEO of FineTune, who reveals what efficiency really means in large organizations. They discuss how companies often waste money through  inefficient buying of complex services, Rich explains how slashing budgets isn't always the smartest way to save. Using comparisons to the movie "Office Space," they examine how  how procurement teams are stretched thin, and how suppliers take advantage of the lack of oversight. They then turn their attention to Musk's strategies at DOGE, questioning whether drastic cuts are the best path to savings or if they might lead to unintended and costly consequences.

What does it look like when government actually works for the people? Matt and David explore this question with Lina Khan, whose groundbreaking tenure as FTC Chair rewrote the playbook for federal agencies. Khan details how she transformed an understaffed agency into the spearhead of a governance revolution - confronting corporate giants, championing consumer rights, and proving that government can be a powerful force for positive change. Their conversation offers a window into a transformative moment in American governance, where old assumptions about corporate power are being challenged and new possibilities are emerging.

When it comes to utilities - why are we paying so much for service that can be so unreliable? In this episode, Matt and David expose how a small group of economists and some untrustworthy models have allowed utility companies to inflate rates and spend on dubious projects. Former utility executive Mark Ellis helps explain the "scam" that has misled regulators and advocates, leading to excessive profits for investor-owned utilities at our expense. They break down utility regulation, how rates are set, and the surprising difference in rate increases between investor-owned and public utilities. Prepare to demand some serious reform!Read Mark's report: Rate of Return Equals Cost of Capital: A Simple, Fair Formula to Stop Investor-Owned Utilities from Overcharging the Public

Former DOJ Antitrust Division head Doha Mekki takes us behind the scenes of some of the most consequential monopoly cases in recent history, including the landmark Google search case. Drawing from her unique experience serving in both the Trump and Biden administrations, Mekki reveals how antitrust enforcement is essentially "policing for white collar crime" - albeit with a budget smaller than Apple's legal department. She shares surprising insights about building cases against tech giants, including how behavioral economists helped win against Google by explaining the "human element" of default search settings, and offers a fresh perspective on the generational shift happening in antitrust enforcement. 

The recent egg shortages and avian flu outbreaks aren't just hurting our pocketbooks, they reveal how the consolidation of American agriculture has created dangerous vulnerabilities in our food system. David and Matt dive deep into the precarious state of American farming with Jeff Bender, a North Carolina farmer with 40 years of experience. Bender explains how farming has transformed from the diverse "Old MacDonald" model of small family farms to a rigid, industrial system dominated by monocultures and massive operations, where a single disease outbreak could devastate entire sectors of food production. 

When Congress moved to force TikTok's sale from its Chinese parent company ByteDance, it sparked a complex battle over national security, free speech, and the future of tech regulation. Matt and David bring together unlikely allies Zephyr Teachout, a progressive law professor, and Joel Thayer, a conservative tech policy expert, who co-authored a Supreme Court brief supporting the law. They reveal how TikTok's case could reshape how we regulate Big Tech, exploring thorny questions about algorithmic control, foreign ownership of communications infrastructure, and whether Americans should trust Silicon Valley any more than Beijing. The episode offers a surprisingly hopeful take on a watershed moment in the ongoing struggle to govern digital platforms, suggesting that meaningful tech regulation might finally be possible – if we're willing to try.