Technically Legal - A Legal Technology and Innovation Podcast

Recent Episodes

1. On AI Evals, TAR vs. LLMs and What Will be Different Next Year - Aron Ahmadia (VP Applied Science, Relativity)

   Sep 17, 2026

   Aron Ahmadia, VP of Applied Science at Relativity, discusses AI evaluation methodologies and the transition from Technology Assisted Review (TAR) to generative AI in legal document review. The conversation covers the Redgrave study comparing TAR, human review, and Relativity's aiR for Review tool, with findings showing aiR for Review achieved 88% recall versus 64% for human reviewers. Ahmadia emphasizes the importance of building evaluations as durable products and explains how generative AI differs fundamentally from traditional machine learning approaches in legal document classification.

2. Moving Beyond the Billable Hour: Pricing Legal Work in the AI Age (Emily Logan Stedman - Husch Blackwell)

   Sep 3, 2026

   Emily Logan Stedman, a commercial litigator at Husch Blackwell in Milwaukee, discusses her year-long effort to implement Alternative Fee Arrangements (AFAs) for litigation work, moving beyond the traditional billable hour model. She details her methodical approach using AI to analyze historical billing data and structure phased flat fees, strategic counsel subscriptions, and predictable contract review pricing. The conversation covers both the practical mechanics of pricing litigation work and the wellness benefits of reframing how legal services are billed and delivered to clients.

3. AI Regulation: Where it is and Where it Might (or Should) Go (Justin Wales CLO @ Crypto.com & Author of AI Legal Handbook)

   Aug 20, 2026

   Justin Wales, Chief Legal Officer of Crypto.com and author of The AI Legal Handbook, discusses the emerging regulatory landscape for artificial intelligence, liability frameworks, and practical applications of AI in legal practice. He outlines seven foundational principles for AI regulation, emphasizing proportional oversight, human-centered accountability, and transparency over prohibition, while addressing the black box problem, copyright issues in machine learning, and the governance challenges of artificial general intelligence (AGI).

4. From Managing Partner to Intel CLO: Career Lessons and Thoughts on Modern Legal Practice (April Miller Boise)

   Aug 6, 2026

   April Miller Boise, former Managing Partner at Thompson Hine and Chief Legal Officer at Intel, discusses her career trajectory from Wall Street M&A practice to in-house leadership roles. She explores the widening gap between corporate legal departments' expectations and traditional law firm service delivery models, addresses the impact of AI adoption on legal practice, and offers mentorship advice for junior lawyers navigating an industry in transformation.

5. When Machines Have the Answers, Build Better Humans With AI Augmentation Not Automation (Vivienne Ming, Scientist, Professor, Author)

   Jul 23, 2026

   Vivienne Ming, a theoretical neuroscientist, professor, and author, discusses her book 'Robot Proof: When Machines Have All the Answers, Build Better People.' She explains her research on human-AI collaboration, where she found that the best outcomes occur not through automation or passive AI adoption, but through 'cyborg' interactions where humans and AI co-create solutions by challenging each other's assumptions. Ming argues that to remain relevant in an AI-driven world, humans must develop deeply human traits like curiosity, resilience, endogenous motivation, and intellectual humility—skills that cannot be automated and are increasingly valuable as AI handles well-posed problems.

6. Inside Microsoft Legal: A Look at AI Use Built for Scale (Rebecca Anderson - Head of Legal EMEA Microsoft)

   Jul 9, 2026

   Rebecca Anderson, Head of Legal for EMEA and Associate General Counsel at Microsoft, discusses Microsoft's approach to deploying AI across a massive legal department serving 63 countries and over 10,000 business clients. She outlines a three-phase framework for AI adoption in legal—personal productivity, context engineering, and intent engineering—and explores how in-house counsel is partnering with law firms in new ways as AI reshapes legal work. Anderson emphasizes that the future of legal is not about jobs lost to AI, but about the legal professionals lawyers will become with the technology.

7. Cost, Speed and Quality - One Law Firm's Quest to Deliver All Three (Laurence Brown, Partner EIP and Head of Visser AI)

   Jun 25, 2026

   Laurence Brown, a partner at UK-based patent firm EIP and head of Visser AI, discusses how his firm is breaking the traditional trade-off between cost, speed, and quality in legal services through AI integration. Brown explains the concept of an 'AI native law firm,' details how EIP has launched Visser AI as a hybrid intelligence division that redesigns patent workflows using specialized AI tools, and shares how the firm has achieved approximately 30% cost reductions while maintaining quality and improving turnaround times. The conversation covers fixed-fee billing models, regulatory challenges in Europe, and how AI augments rather than replaces attorney expertise in patent drafting.

8. Affordable & Accessible: The Democratization of Legal Tech (Tyler Foreman VP of AI - Rocket Lawyer)

   Jun 11, 2026

   Tyler Foreman, VP of AI at Rocket Lawyer, discusses the democratization of legal technology through conversational AI. He explains how Rocket Lawyer's new agentic AI legal operating system, Rocket Copilot, makes legal services accessible to small businesses and individuals by combining document automation, contract review, and human legal expert access. The conversation covers Tyler's nonlinear career path from Intel and geospatial analytics to DocuSign's contract lifecycle management and his current mission to level the playing field in legal tech.

9. Building Software for Less: The Death of Expensive SaaS in the AI Era? (Nathan Wenzel - LegalOperatorAI)

   May 28, 2026

   Nathan Wenzel, founder of Simple Legal (acquired 2019) and now founder of Legal Operators AI, discusses building lean, sustainable startups in the AI era. He explains how his new product—an AI-powered legal helpdesk integrated into Slack and Teams—enables non-legal employees to get instant answers to common legal questions while protecting legal teams from constant interruptions. Wenzel argues that AI fundamentally changes software economics, enabling lower pricing, smaller teams, and transparent pricing models, contrasting sharply with the VC-backed growth-at-all-costs approach of the 2010s.

10. The Rise of the Legal Quants (Jamie Tso & Raymond Sun)

    May 14, 2026

    Jamie Tso and Raymond Sun, co-leaders of the Legal Quants movement, discuss the rise of AI-fluent lawyers building their own tools rather than relying solely on purpose-built legal tech platforms. Both former big law associates with coding backgrounds, they explain how Legal Quants differs from legal engineers—focusing on reimagining legal work from first principles using frontier AI models rather than optimizing existing workflows. The episode covers their vision for a more liquid legal services market, the future of legal pricing beyond billable hours, and their stress testing of Anthropic's Claude for Legal.