What Claude Means for Legal AI with Winston Weinberg

Winston Weinberg Anthropic dropped a legal plugin for Claude Cowork and $285 billion in market value evaporated in 48 hours. Thomson Reuters fell 16%. RELX plunged 14%. Bloomberg is calling it the “SaaSpocalypse.” But is the panic justified? For the first time, a foundation model company is packaging legal workflow tools directly into its platform…

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Will AI Create Better Lawyers or Fewer Lawyers with Antti Innanen & Lev Loukhton

Ted sits down with Antti Innanen, Founder & CEO of Dot. Legal Design, and Lev Loukhton, Founder of GrayHair Venture Partners, for a candid debate on the future of legal work in the age of AI, exploring automation, strategic versus routine legal tasks, cultural resistance within law firms, and what lawyers must do now to remain relevant in a rapidly transforming profession.

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AI, Valuations, and the LegalTech Reckoning with Rudy DeFelice

Ted sits down with Rudy DeFelice, Global Head at Harbor Labs, to explore how AI is reshaping the legal technology landscape, from shifting market valuations and investor reactions to the broader democratization of legal services. They discuss what history can teach us about technological disruption, the rise of the “wisdom economy,” and why human judgment, collaboration, and emotional intelligence will matter more than ever in the future of law, and more.

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