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Scaling Laws
Why the Online Advertising Market is Broken
In December 2020, ten state attorneys general sued Google, alleging that the tech giant had created an illegal monopoly over online advertising. The lawsuit is ongoing, and just this January, new allegations in the states’ complaint were freshly unsealed: the states have accused Google of tinkering with its ad auctions to mislead publishers and advertisers and expand its own power in the marketplace. (Google told the Wall Street Journal that the complaint was “full of inaccuracies and lacks legal merit.”)
The complaint touches on a crucial debate about the online advertising industry: does it, well, work? This week on Arbiters of Truth, our series on the online information ecosystem, Evelyn Douek and Quinta Jurecic spoke with Tim Hwang, Substack’s general counsel and the author of the book “Subprime Attention Crisis: Advertising and the Time Bomb at the Heart of the Internet.” Tim argues that online advertising, which underpins the structure of the internet as we know it today, is a house of cards—that advertisers aren’t nearly as good as they claim at monetizing our attention, even as they keep marketing it anyway. So how worried should we be about this structure collapsing? If ads can’t convince us to buy things, what does that mean about our understanding of the internet? And what other possibilities are there for designing a better online space?
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Release Schedules and Iterative Deployment with Open AI's Ziad Reslan
51:08|Ziad Reslan, a member of OpenAI’s Product Policy Staff and a Senior Fellow with the Schmidt Program on Artificial Intelligence, Emerging Technologies, and National Power at Yale University, joins Kevin Frazier, AI Innovation and Law Fellow at the University of Texas School of Law and a Senior Editor at Lawfare, to talk about iterative deployment--the lab’s approach to testing and deploying its models. It’s a complex and, at times, controversial approach. Ziad provides the rationale behind iterative deployment and tackles some questions about whether the strategy has always worked as intended.
A Year That Felt Like a Decade: 2025 Recap with Sen. Maroney & Neil Chilson
53:48|Connecticut State Senator James Maroney and Neil Chilson, Head of AI Policy at the Abundance Institute, join Kevin Frazier, the AI Innovation and Law Fellow at the University of Texas School of Law and a Senior Editor at Lawfare, and Alan Rozenshtein, Associate Professor at Minnesota Law and Research Director at Lawfare, for a look back at a wild year in AI policy.Neil provides his expert analysis of all that did (and did not) happen at the federal level. Senator Maroney then examines what transpired across the states. The four then offer their predictions for what seems likely to be an even busier 2026.
Cass Sunstein on What AI Can and Cannot Do
43:03|Alan Z. Rozenshtein, Lawfare senior editor and associate professor of law the University of Minnesota, speaks with Cass Sunstein, the Robert Walmsley University Professor at Harvard University, about his new book, Imperfect Oracle: What AI Can and Cannot Do. They discuss when we should trust algorithms over our own judgment, why AI can eliminate the noise and bias that plague human decision-making but can't predict revolutions, cultural hits, or even a coin flip—and, perhaps most importantly, when it makes sense to delegate our choices to AI and when we should insist on deciding for ourselves.
AI Chatbots and the Future of Free Expression with Jacob Mchangama and Jacob Shapiro
53:51|Renée DiResta, Lawfare contributing editor and associate research professor at Georgetown's McCourt School of Public Policy, and Alan Z. Rozenshtein, Lawfare senior editor and associate professor of law the University of Minnesota, spoke with Jacob Mchangama, research professor of political science at Vanderbilt University and founder of The Future of Free Speech, and Jacob Shapiro, the John Foster Dulles Professor of International Affairs at Princeton University. The conversation covered the findings of a new report examining how AI models handle contested speech; comparative free speech regulations across six jurisdictions; empirical testing of how major chatbots respond to politically sensitive prompts; and the tension between free expression principles and concerns about manipulation in AI systems.
Rapid Response on the AI Preemption Executive Order
56:12|In this rapid response episode, Lawfare senior editors Alan Rozenshtein and Kevin Frazier and Lawfare Tarbell fellow Jakub Kraus discuss President Trump's new executive order on federal preemption of state AI laws, the politics of AI regulation and the split between Silicon Valley Republicans and MAGA populists, and the administration's decision to allow Nvidia to export H200 chips to China. Mentioned in this episode:Executive Order: Ensuring a National Policy Framework for Artificial IntelligenceCharlie Bullock, "Legal Issues Raised by the Proposed Executive Order on AI Preemption," Institute for Law & AI
Graham Dufault on small businesses and navigating EU AI laws
45:17|Graham Dufault, General Counsel at ACT | The App Association, joins Kevin Frazier, AI Innovation and Law Fellow at the University of Texas School of Law and a Senior Editor at Lawfare, to explore how small- and medium-sized enterprises (SMEs) are navigating the EU's AI regulatory framework. The duo breakdown the Association's recent survey of SMEs, which included the views of more than 1,000 enterprises and assessed their views on regulation and adoption of AI. Follow Graham: @GDufault and ACT | The App Association: @actonline
Caleb Withers on the Cybersecurity Frontier in the Age of AI
48:17|Caleb Withers, a researcher at the Center for a New American Security, joins Kevin Frazier, the AI Innovation and Law Fellow at the University of Texas School of Law and a Senior Editor at Lawfare, to discuss how frontier models shift the balance in favor of attackers in cyberspace. The two discuss how labs and governments can take steps to address these asymmetries favoring attackers, and the future of cyber warfare driven by AI agents.Jack Mitchell, a student fellow in the AI Innovation and Law Program at the University of Texas School of Law, provided excellent research assistance on this episode.Check out Caleb’s recent research here.
A Startup's Perspective on AI Policy
51:48|Andrew Prystai, CEO and co-founder of Vesta, and Thomas Bueler-Faudree, co-founder of August Law, join Kevin Frazier, AI Innovation and Law Fellow at the University of Texas School of Law and a Senior Editor at Lawfare, to think through AI policy from the startup perspective. Andrew and Thomas are the sorts of entrepreneurs that politicians on both sides of the aisle talk about at town halls and press releases. They’re creating jobs and pushing the technological frontier. So what do they want AI policy leaders to know as lawmakers across the country weigh regulatory proposals? That’s the core question of the episode. Giddy up for a great chat! Learn more about the guests and their companies here:Andrew's Linkedin, Vesta's LinkedinThomas’s LinkedIn, August’s LinkedIn
Anthropic's General Counsel, Jeff Bleich, Explores the Intersection of Law, Business, and Emerging Technology
36:51|Jeff Bleich, General Counsel at Anthropic, former Chief Legal Officer at Cruise, and former Ambassador to Australia during the Obama administration, joins Kevin Frazier, AI Innovation and Law Fellow at the University of Texas School of Law and a Senior Editor at Lawfare, to get a sense of how the practice of law looks at the edge of the AI frontier.The two also review how Jeff’s prior work in the autonomous vehicle space prepared him for the challenges and opportunities posed by navigating legal uncertainties in AI governance.