James Grimmelmann on the copyright threat to AI companies
James Grimmelmann is a professor of law at Cornell University and a leading expert on copyright law. Grimmelmann walks through the complex process courts use to determine whether training AI models on copyrighted materials—like OpenAI using New York Times articles—is infringement or fair use. He highlights key precedents like the Google Books case, emphasizing how courts weigh transformative uses against potential market harms.The discussion addresses the nuances of generative AI, notably cases where models inadvertently reproduce large excerpts from training materials. Grimmelmann argues that while the industry has largely addressed explicit "regurgitation," ambiguity remains around subtler forms of copying, particularly with image-generating models, which could substantially impact copyright holders like Getty Images.Grimmelmann and the hosts delve into potential legal outcomes, including moderate rulings that force licensing agreements, or harsher ones that could significantly restrict the availability of open-source AI models. The interview also touches on Congress's historical reluctance to intervene in contentious digital copyright issues, leaving critical decisions to be gradually shaped by court rulings.Dean and Tim conclude that while an outright shutdown of generative AI by courts is improbable, the forthcoming legal decisions will likely reshape the industry's structure, potentially favoring larger companies capable of negotiating extensive licensing deals. Grimmelmann anticipates initial district court rulings within the year and appellate decisions by 2026, setting the stage for a pivotal shift in how AI companies use copyrighted works. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.aisummer.org
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Andrew Lee on running an AI email startup
Andrew Lee is the co-founder of Shortwave, an AI-powered email app. He’s also Tim’s brother.Andrew shares how Shortwave evolved from a conventional email app into a multi-LLM system that automates inbox organization, drafts messages, and performs advanced search via agentic reasoning. He explains how recent improvements in model performance have dramatically changed what is possible for an app like Shortwave. He discusses which models Shortwave uses, the tradeoffs between open and closed models, and where AI-powered email is going next. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.aisummer.org
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Dean and Tim on Deep Research and the Paris Summit
In this episode, Dean and Tim discuss Dean’s trip to Paris for the AI Action Summit, including Vice President Vance’s speech on AI. They talk through the European outlook on AI regulation, European resentment toward America, and the stark shift in policymaker attitudes toward AI safety. Then they turn to OpenAI’s new Deep Research agent, chatting about their experience with the product and reflecting on what it means for the future of policy research. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.aisummer.org
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Kashmir Hill on falling love with ChatGPT
Kashmir Hill is a reporter at the New York Times who focuses on the social impacts of new technology. In this episode, she describes how users are customizing chatbots like ChatGPT to fulfill emotional and even erotic needs, often bypassing built-in safeguards. These fantasy conversations are usually harmless, but there are potential pitfalls—especially where children are involved. Kashmir also discusses about how policymakers should deal with the emergence of uncannily accurate facial recognition technology."She Is in Love With ChatGPT" by Kashmir Hill in the New York Times, 2025.Your Face Belongs to Us. Book by Kashmir Hill published in 2023."The Secretive Company That Might End Privacy as We Know It" by Kashmir Hill in the New York Times, 2020. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.aisummer.org
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Sophia Tung on riding a self-driving taxi in China
Tim and Dean chat with Sophia Tung, an entrepreneur, engineer, and now YouTuber, about her recent experience in a Chinese self-driving taxi from Apollo Go, a subsidiary of Baidu. Apollo Go is a bit like China’s Waymo, but Sophia found the experience of riding in an Apollo Go taxi to be far worse than riding in a Waymo. We talk about her experience in China as well as the broader implications: is China just a few years behind American AV companies, or is there a deeper problem? This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.aisummer.org
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