Technically Legal - A Legal Technology and Innovation Podcast

Recent Episodes

1. 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.

2. 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.

3. 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.

4. 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.

5. 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.

6. The AI Pilot is Over: Legal's Moment to Move Beyond Experiments and Avoid the Innovator's Dilemma (Sabastian Niles, President & CLO Salesforce)

   Apr 30, 2026

   Sebastian Niles, President and Chief Legal Officer of Salesforce, discusses his open letter to the legal community arguing that the era of AI pilots is over and law firms must move beyond experimentation to adopt agentic AI or risk obsolescence. He outlines four systems—engagement, agency, work, and context—that legal departments and law firms should implement to avoid the innovator's dilemma, while sharing real-world examples of AI agents Salesforce has deployed internally for billing compliance, intake triage, and contracting at scale.

7. Ayana Dow on Updating Crypto Regulation and Preserving the Freedom to Build (Senior Counsel, Defi Education Fund)

   Apr 16, 2026

   Ayana Dow, Senior Counsel at the DeFi Education Fund, discusses her career trajectory from government affairs and regulatory law to policy advocacy in decentralized finance. The episode covers her work on crypto regulation, the distinction between DeFi developers and centralized crypto entities, recent SEC and CFTC guidance on digital assets, and pending legislation like the Market Structure Bill that would expand CFTC authority over crypto commodities.

8. Descrybe's Quest to Democratize Legal Research (Kara Peterson & Richard DiBona)

   Apr 2, 2026

   Kara Peterson and Richard DiBona, husband-and-wife co-founders of Descrybe, discuss their mission to democratize legal research through an AI-native platform. Starting from a personal employment law issue during the pandemic, they built a free case law search tool and evolved it into a chat-based legal research assistant that challenges the high-cost legacy players like Westlaw and LexisNexis by offering comparable functionality at $75/month. The episode covers their unfunded two-person operation, their massive data curation effort (100+ billion tokens spent on cleaning and structuring primary law), and their benchmarking research showing purpose-built legal AI tools significantly outperform general-purpose models on legal reasoning tasks.

9. The Uberization of UPL? How AI Is Outpacing the Unauthorized Practice of Law (Ken Crutchfield, Bill Henderson, Jim Doppke)

   Mar 19, 2026

   Chad Mayne hosts a panel discussion on how AI and large language models are disrupting unauthorized practice of law (UPL) regulations. Strategic advisor Ken Crutchfield, Indiana University Law Professor Bill Henderson, and ethics attorney Jim Doppke examine the intersection of AI technology and legal regulation, exploring how LLMs enable consumers and non-lawyers to access legal services traditionally monopolized by licensed attorneys, and what regulatory frameworks might emerge as technology outpaces century-old UPL rules.

10. From Water Pistols to Tanks: Why Data Science is the Gold Standard to Counter Class Action Fraud (Donald Beshada, CEO, Covalynt)

    Mar 5, 2026

    Donald Beshada, CEO of Covalent, discusses how data science is being used to combat fraud in class action litigation. Beshada traces his career from big law defense attorney to plaintiff-side litigator to entrepreneur, explaining how he identified and began solving the problem of fraudulent class action claims that spike when claim rates jumped from 1-2% to 80-90% or higher. He details Covalent's evolution from Claims Score to a complex litigation data intelligence platform that uses data science to validate claimants, identify fraud patterns, and support both plaintiffs and defendants in class actions.