Legal Innovation Spotlight

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Oct 22, 2025 • 47min

The Limits of AI Modeling: Human Complexity, Culture, and Moral Judgment with Kevin Lee

Ted sits down with Kevin P. Lee, Law Professor at NCCU School of Law, to discuss the ethics of AI and its implications for law and democracy. From the philosophy of science to the role of human judgment in computational law, Kevin shares his expertise in jurisprudence, ethics, and technology. With insights on privacy, professional identity, and access to justice, this conversation challenges law professionals to consider how innovation can align with responsibility.
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Oct 15, 2025 • 50min

AI Is the Leverage: How Automation Is Rewriting the Economics of Law with Richard Tromans

Ted sits down with Richard Tromans, Founder of Artificial Lawyer, to discuss how AI and automation are driving the next industrial revolution in law. From the cultural barriers holding firms back to the data strategies powering real transformation, Richard shares his expertise in legal innovation, process improvement, and business model evolution. With insights on why AI is becoming the new means of production in legal services, this conversation helps law professionals rethink how they deliver value in an increasingly automated world.
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Oct 8, 2025 • 48min

89 - Legal Innovation Lessons: What Works, What Doesn't, and Why with Rob Saccone

Rob Saccone, CTO at Lega and a legal tech veteran with over 25 years of experience, shares invaluable insights on the lessons learned from failed innovations like Clearspire and Atrium. He emphasizes the importance of adapting law firm business models to client needs and the pressures AI places on traditional billing. Discussing the challenges of alternative fee arrangements, he warns of the risks of not investing in innovation. Rob also explores the potential of practical Gen AI deployments and the need for a shift in partnership mindsets to foster growth.
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Oct 1, 2025 • 47min

Protecting Reputation While Embracing Risk: How Law Firms Can Adopt Technology Wisely with David McCarville

Ted sits down with David McCarville, Director at Fennemore Craig, P.C., to discuss how AI, R&D, and alternative business models are reshaping the legal industry. From implementing alternative fee arrangements to creating playbooks that train the next generation of attorneys, David shares his expertise in innovation, governance, and client-focused solutions. With insights on balancing work-life culture while driving technological change, this conversation offers law professionals a practical look at the future of legal services.
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Sep 24, 2025 • 46min

The Gig Is Up: Why Law Firm Resistance to Technology Won’t Work Anymore with Lev Loukhton

Lev Loukhton, a legal tech investor and former M&A partner with over 20 years of experience, discusses the transformative impact of AI on the legal profession. He highlights how AI can enhance due diligence and streamline transactional work, enabling firms to meet client demands effectively. Lev also addresses cultural resistance within law firms, the importance of experimenting with risk, and the growing trend of clients utilizing AI to bypass delays. He emphasizes the need for firms to adapt their pricing models and embrace administrative automation for better client service.
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Sep 17, 2025 • 47min

Why Storytelling and Data Together Will Define the Next Era of Legal Innovation with Ben Chiriboga

Ted sits down with Ben Chiriboga, Chief Growth Officer at Nexl, to discuss how storytelling, business thinking, and technology are reshaping the legal profession. From his journey from practicing law to leading in legal tech, to the rise of AI and agentic workflows, Ben shares his expertise in growth strategy, innovation, and career development. With insights on why law is in a “time between worlds,” this conversation challenges legal professionals to rethink how they adapt, lead, and grow in the future of law.
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8 snips
Sep 10, 2025 • 45min

KM&I and Legal Tech Connect: Bridging Builders, Buyers, and Funders with Patrick DiDomenico and Kevin Klein

Patrick DiDomenico and Kevin Klein, co-founders of Legal Tech Connect, share their extensive backgrounds in legal tech and innovation. They dive into the evolution of legal technology and discuss their upcoming Innovators and Investors event. The conversation highlights AI's transformative impact on law firms, emphasizing the necessity for traditional practices to adapt. Insights on the challenges faced by legal tech startups and the vibrant upcoming KM&I and Legal Tech Connect events in New York City showcase the exciting future of legal innovation.
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Sep 3, 2025 • 47min

84 - The Collapse of Information Arbitrage: How AI Is Reshaping Consulting and Law with Usman Sheikh

Usman Sheikh, Managing Director at High Output Ventures, dives into how technology and AI are transforming consulting and legal services. He discusses the collapse of information arbitrage and the limitations of traditional partnership models. Usman highlights the shift toward innovative business strategies and the future of work in law. With insights on the need for adaptability and new fee structures in consulting amid budget constraints, he paints a picture of the challenges and opportunities that lie ahead in these industries.
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Aug 27, 2025 • 48min

83 - The U.S. AI Action Plan: Export Controls, National Security, and Industry Impact with Ray Sun

Ted sits down with Ray Sun, Tech Lawyer at Herbert Smith Freehills Kramer, to discuss the global landscape of AI regulation and its impact on the future of law. From building the Global AI Regulation Tracker to unpacking the contrasting AI policies of China and the U.S., Ray shares his expertise in technology law and policy. With insights on how AI regulation is becoming a geopolitical battleground, this conversation helps law professionals understand the opportunities and risks shaping legal practice in an AI-driven world.
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Aug 20, 2025 • 52min

82 - The Overlooked Role of Subject Matter Experts in Legal AI Success with Sarah Thompson

Ted talks with Sarah Thompson, Chief Product Officer at BlueStar and a legal tech veteran with over 20 years of experience. They dive into how AI and Microsoft 365 are revolutionizing legal investigations and eDiscovery. Sarah explains the importance of custom AI solutions and human oversight in legal practices. The conversation also touches on evolving cloud integration and the challenges of managing legal data. Finally, they discuss how technological advancements are reshaping professions, highlighting the need for adaptability in a fast-changing legal landscape.

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