Technically Legal - A Legal Technology and Innovation Podcast

Hosted by Percipient - Chad Main

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Episodes

100

Latest episode

Aug 2026

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About the show

Technically Legal is a legal tech podcast exploring how technology is transforming the legal landscape. Each episode features insightful interviews with legal innovators, tech pioneers, and forward-thinking educators who are leading this change. Our guests share their experiences and insights on how technology is reshaping legal operations, revolutionizing law firm practice, and driving the growth of innovative legal tech companies. We also explore the broader implication of technology on everyone involved in the legal system, from practitioners to clients. The podcast is hosted by Chad Main, an attorney and founder of Percipient, a tech-enabled legal services provider. Chad launched Percipient on the belief that when technology is leveraged correctly, it makes legal teams more effective. Technically Legal Podcast is an ABA Web 100 Best Law Podcasts Honoree.

Listen to episodes

60 recent

August 6, 202631 min

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

In this episode April Miller Boise, with stints as Chief Legal Officer at Intel and managing partner at Thompson Hine, shares insights from her career. The conversation explores the shifting dynamics between corporate legal departments and outside counsel and the necessity of embracing legal technology. April also provides advice for junior lawyers on developing long-term expertise and trusted relationships in an AI-driven environment. Things we Talk About in this Episode Career progression: From Wall Street M&A partner and law firm managing partner to Chief Legal Officer. The fundamental differences between driving P&L at a law firm versus serving on an executive leadership team in-house. Addressing the widening gap between corporate expectations and traditional law firm service delivery models. Experience navigating global manufacturing, innovation, and supply chain transformations at Eaton and Intel. Practical approaches to generative and agentic AI adoption in legal departments and outside counsel. Key attributes for modern legal talent: Intellectual curiosity, agility, and comfort with calculated risks. Career advice for young lawyers: Balancing AI efficiency tools with the 10,000-hour principle of skill-building. Why historical legal tech struggled to scale and how current enterprise AI investments are fundamentally altering the legal landscape.

July 23, 202650 min

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

In this episode, theoretical neuroscientist Vivienne Ming discusses her new book, Robot Proof - When Machines Have All the Answers, Build Better People . The conversation examines the intersection of artificial intelligence and knowledge work, exploring how professionals can adapt to an increasingly automated economy. The discussion contrasts the limitations of basic AI task automation with the advantages of human-AI collaboration—the "cyborg" model—for solving complex, ill-posed problems. Ming highlights her research on forecasting market outcomes, the critical role of endogenous motivation, and how the legal industry and other elite professions must rethink entry-level training. Key Topics Discussed Theoretical Neuroscience and Early AI: Ming's background and the evolution of machine learning models from early academic research to modern agentic AI. The Polymarket Experiment: An analysis comparing the forecasting accuracy of standalone AI, unassisted humans, and human-AI collaborators, revealing the superiority of deep human-machine integration. Automation vs. Augmentation: The pitfalls of the traditional "human-in-the-loop" model and why replacing menial tasks often neglects essential human problem-solving skills. Well-Posed vs. Ill-Posed Problems: Identifying the specific areas where AI excels (algorithmic, factual answers) and where human intelligence remains superior (navigating uncertainty and undefined parameters). Labor Disruption and Economic Shifts: Examining historical technological revolutions, the Jevons paradox, and the future demand for specific, highly adaptable human skill sets. Endogenous Motivation: How internal drivers like curiosity, resilience, and perspective-taking predict professional success more accurately than standard extrinsic incentives. Practical AI Strategies: Actionable methods for professionals to refine their skills, including using AI as a critical "nemesis" to challenge assumptions and encourage deep, effortful processing. The Future of Elite Professions: The macro-level challenges facing organizations in developing junior talent—such as associate attorneys—when the entry-level tasks traditionally used for training are automated. Things We Talk About in this Episode Socos: Vivienne Ming's philanthropy and research newsletter ( socos.org ). Thinking, Fast and Slow: Authored by Daniel Kahneman . Anthropic Research: A study published in Science detailing the productivity of AI-assisted programmers . BCG AI Study: Research analyzing AI integration and performance among management consultants. Raj Chetty: Economic research regarding peer role modeling, education, and socioeconomic mobility.

July 9, 202630 min

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

This episode features a discussion between host Chad Main and Rebecca Anderson, Head of Legal EMEA, Associate General Counsel at Microsoft , regarding the integration of artificial intelligence in corporate legal departments. The conversation covers Rebecca's career progression from a law firm associate to an international in-house counsel role. The core of the discussion examines Microsoft's internal AI deployment strategies, including the shift from personal productivity to intent engineering. Additionally, the episode addresses changing expectations for outside counsel regarding AI adoption and outlines the necessary skills for future legal professionals. Episode Highlights AI Deployment Phases: AI integration in legal departments progresses through three stages: personal productivity (prompt engineering), context engineering (curating institutional knowledge), and intent engineering (autonomous agents operating with human guardrails). Scaling Legal Support: Corporate legal teams can manage high volumes of client requests by utilizing AI-driven triage systems overseen by paralegals, which allows senior lawyers to focus on complex, high-value legal work. Expectations for Outside Counsel: Corporate clients expect law firms to implement AI strategies to improve efficiency, which will likely shift the industry's economic focus from billable hours to value-based billing. Future Legal Skills: While AI literacy and data curation are critical, foundational skills such as human judgment, emotional intelligence, and strategic business context remain essential for legal professionals. Things we talk about: Copilot for Legal

June 25, 202629 min

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

In this episode of Technically Legal, veteran patent lawyer Laurence Brown and Partner at the UK-based intellectual property firm EIP discusses the evolving concept of the "AI-native" law firm and how EIP is actively navigating this transition through their hybrid intelligence service, Visser AI. Laurence shares insights from his 25-year career, discussing how EIP uniquely integrates litigators and patent attorneys to provide comprehensive IP services. The core of the conversation centers on Visser AI , named after the renowned European patent attorney Derk Visser, which leverages specialist AI tools to accelerate patent drafting and prosecution. The discussion covers the shifting economics of legal billing, the transition from billable hours to fixed fees, and how AI is actively redesigning traditional, linear patent workflows. Laurence also believes AI not only delivers faster, more cost-effective results for clients without compromising quality, but also makes the day-to-day work of attorneys more engaging. Things We Talk About in this Episode Defining AI-Native: A true AI-native firm goes beyond simply prompting a frontier model; it involves fundamentally redesigning workflows to fully leverage AI technology. The Economics of AI: The efficiency gained through AI allows firms to offer competitive fixed fees, providing cost reductions for clients while maintaining law firm profitability. Redesigning Workflows: AI tools enable parallel workflows in patent drafting, such as senior attorneys structuring claims while juniors draft the description, breaking the traditional linear process. Specialist vs. Generalist AI: When it comes to complex patent law, purpose-built platforms like Patently significantly outperform general-purpose LLMs in quality and contextual understanding. European AI Regulation: The European patent industry's conservative nature has led to risk-centered AI guidelines, but the conversation is shifting toward the potential disservice of not utilizing these tools to assist clients.

June 11, 202631 min

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

Tyler Foreman, the Vice President of AI at Rocket Lawyer , joins the show to discuss the intersection of artificial intelligence and the legal industry. Foreman shares his untraditional legal tech career path, spanning engineering at Intel, drone data analytics, and ultimately making the move to legal via contract lifecycle management (CLM) at DocuSign, before diving into his current work at Rocket Lawyer helping to provide legal resources for small-to-medium businesses and individuals. The conversation focuses on how modern generative AI and Large Language Models (LLMs) act as a legal operating system to simplify contract reviews, document drafting, and client intake, while maintaining essential connections to human attorneys.

May 28, 202651 min

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

We catch up with legal tech entrepreneur Nathan Wenzel to discuss his journey from founding and exiting SimpleLegal to launching his newest venture, LegalOperator.ai (formerly Lexiomatic). Nathan shares insights on the evolution of private equity (PE) structures, the shifting economics of the enterprise software market, and how artificial intelligence is disrupting traditional software development and corporate legal operations. Key Takeaways The Reality of Private Equity: Nathan breaks down the differences between growth PE, transition PE, and dividend-focused PE, highlighting his experience with operational scaling post-acquisition. The Death of Overpriced SaaS: With AI lowering the barrier to entry for building software, traditional $100,000+ enterprise software pricing models are facing immense pressure to become lean, affordable, and transparent. The "Vibe Coding" Phenomenon: While "vibe coding" (loosely describing an app to an AI) works for quick prototypes, building enterprise-grade software still requires meticulous specifications, security infrastructure (like SOC 2 compliance), and robust edge-case testing.

May 14, 202634 min

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

Jamie Tso and Ray Sun, the founders of LegalQuants , discuss a fundamental shift in the legal profession: the transition from legal engineering to "legal quant" work. The conversation explores how technically fluent lawyers are using vibe coding, frontier AI models, and first-principles thinking to move beyond mere efficiency and toward the complete redesign of legal services. Jamie and Ray share their backgrounds in Big Law and their journeys into building custom legal tech tools. They delve into the origins of the LegalQuants community—an exclusive, invitation-only network of "builders"—and discuss the future of the billable hour in an era where AI can automate routine intellectual labor. Episode Highlights Jamie and Ray's origin stories: From annotating mutual fund prospectuses to early experiments with machine learning and TensorFlow. Ray's background as one of the world's first Legal Engineers and the creation of his Global AI Regulation Tracker. Defining the Legal Quant: How they differ from traditional Legal Engineers by seeking "alpha" and redesigning legal workflows from first principles. The growth of the LegalQuants community: From a small WhatsApp group to a global network of elite lawyer-builders. The "Unicorn Talent" gap: Why the next generation of elite legal work is defined by the operator, not the tool. The death of the friction-based pricing model and the future of value-based billing. Stress-testing Claude and Anthropic's Legal Plugin: Why the "ceiling" of AI utility is set by the lawyer's ability to design custom skills. Things We Talk About in this Episode LegalQuants Substack: legalquants.substack.com – Weekly digests and deep dives into legal AI strategy. Global AI Regulation Tracker: techieray.com – Ray Sun's interactive map of worldwide AI laws and policies.

April 30, 202640 min

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

We welcome back Sabastian Niles, President and Chief Legal Officer at Salesforce , to discuss his recent " Open Letter to Law Firms ." As the legal industry hits a critical inflection point, Sabastian argues that the era of "AI theater" and small-scale pilots is over. The conversation dives deep into the Innovator's Dilemma facing law firms, the shift toward agentic AI, and how firms must reimagine their business models to remain competitive. Sabastian highlights that legal professionals are uniquely positioned to lead the charge in trusted AI transformation, provided they embrace transparency, data integration, and shared efficiency gains with their clients. Specifically, he offers four systems law firms and other service providers must establish if they want to succeed in the AI era: System of Engagement: A unified digital interface that replaces fragmented tools with seamless, real-time collaboration between firms and clients. System of Agency: An ethically governed AI framework that scales firm capacity and reimagines service delivery while maintaining strict human oversight and compliance. System of Work: A trusted, enterprise-grade platform that integrates daily professional applications into a cohesive, high-performance workflow. System of Context: A secure "single source of truth" for client data that ensures strategic counsel is grounded in history while protecting attorney-client privilege. Other Things We Talk About in this Episode The End of the Pilot Era: Moving beyond experimentation to integrated, unified AI platforms is no longer optional—it is a prerequisite for competitiveness. The Relationship Challenge: AI should be used to break down internal silos, allowing firms to bring their "tribal knowledge" and collective intelligence to every client engagement. System of Agency: A shift from manual workflows to "agentic" systems where AI agents handle triage, research, and routine queries (e.g., Salesforce's Outside Counsel Support Agent). Value-Based Evolution: Law firms must navigate the friction between the billable hour and AI-driven efficiency by focusing on superior outcomes and shared savings. Trust as Propulsion: In legal services, trust isn't just a guardrail; it's a growth lever. Mastering "Trusted Agentics" ensures human-aligned AI that respects privilege and confidentiality.

April 16, 202636 min

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

Ayana Dow, Senior Counsel at the DeFi Education Fund (DEF) shares her unique career trajectory from Big Law and Capitol Hill to the forefront of decentralized finance policy. The discussion centers on the critical need for regulatory clarity in crypto, the distinction between decentralized protocols and centralized entities, and the ongoing efforts to educate lawmakers on blockchain technology. Key takeaways include an analysis of how current market structure bills might shift oversight to the CFTC and the importance of protecting software developers to ensure the continued innovation of DeFi systems. Episode Highlights From Big Law to D.C. Policy: Dow discusses her transition from traditional M&A and regulatory work to policy-focused roles. Experience on the Hill: Insights from Dow's time as a policy fellow for Congressman Jim Clyburn and her internship at the CFTC. The Tennis Connection: How the real-time problem-solving skills learned as a collegiate tennis player apply to navigating shifting SEC guidance. The Crypto "Genesis Block": Why the potential for financial inclusion and "debanking" issues drew Dow to the crypto industry. Mission of the DeFi Education Fund: An overview of DEF's role as a nonpartisan advocacy group focused on sound policy and judicial education. Law Firm vs. In-House Policy: The structural challenges of conducting long-term policy work within the billable hour model of a traditional law firm. Why Focus on Developers?: Understanding why the DeFi Education Fund prioritizes the protection of software developers over specific tokens or protocols. Market Structure & Regulatory Harmonization: A breakdown of recent SEC and CFTC guidance and the future of congressional legislation. The Impact of Chevron Deference: Discussion on how the removal of Chevron deference changes how agencies and judges interpret financial laws. Resources Mentioned DEF's Myth v. Fact Sheet on the BRCA ( Link ) A DEF blog post on the Promoting Innovation in Blockchain Development Act of 2026 A DEF Letter to the SEC in response to Citadel Securities

April 2, 202638 min

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

Kara Peterson and Richard DiBona, the husband-and-wife co-founding team behind Descrybe, discuss the legal research platform they built designed to "democratize access to the law." The discussion explores the unique dynamics of married cofounders and how they are leveraging Generative AI to disrupt a landscape long dominated by high-cost legacy providers. Richard, a software engineer, and Kara, a marketing expert, share their journey from a personal legal issue to building a platform that processes over 100 billion tokens of legal data. They explain why they chose to build an AI-native system from the ground up rather than simply layering a "wrapper" over existing models—a decision that allows them to offer professional-grade tools at a fraction of the traditional cost. In this episode, they discuss: 🔷 Why legacy legal research platforms have maintained such strong moats—and how AI changes that 🔷 The difference between "wrapper" AI tools and building a system from the ground up 🔷 How their structured, multi-step reasoning process improves accuracy and reduces hallucinations 🔷 What benchmarking against the Bar Exam reveals about legal AI performance 🔷 Where Descrybe is headed as they expand their toolkit

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