Practical, no-hype conversations with lawyers, founders, and practitioners on the frontlines of AI in law. Every week, on YouTube and Spotify.
Episode with J.P. Mohler, Co-Founder of General Legal, a YC-backed AI-native law firm, on rethinking commercial contracts through flat-fee pricing, AI-first workflows, lawyer oversight, and faster turnaround. A practical discussion on legal tech, law firm economics, and client expectations.
with Kaj Rozga
Kaj Rozga (16+ years across government, BigLaw, in-house) on how GenAI changes the value proposition and why trust is easy to lose. We cover pilot strategy, workflow fit, champions, internal capacity, existing tools vs new vendors, and a sober view of how fast the legal market will actually shift.
with Gayk Ayvazyan
Gayk Ayvazyan, corporate lawyer and a mediator discusses how the pace AI creates is generating a new category of conflict, why mediation may be one of the last professional contexts where AI hits a hard wall, and what a decade of working with founders teaches you about the gap between signing up for a tool and actually using it.
with Philip Young
What happens when a litigator also thinks like a builder? Philip Young, CEO & Co-Founder of Garfield AI, explains how they built a regulated AI-driven legal service for small debt recovery. We dive into why legal automation succeeds only when the workflow is structured, bounded, and designed around real court stages and talk about systems engineering vs legal process, why advocacy should stay human, and how a regulated AI law firm thinks about safety and accountability.
with Dr. Dusan Pavlovic
AI governance & regulation by technology with Dr. Dusan Pavlovic (REA Independent Ethics Expert; UNDP AI advisor; data protection specialist). We discuss why enforcement is hard, why standards matter, why autonomy changes accountability, and why transparency is the limiting constraint in legal grade AI.
with Eve Vlemincx
Law firm AI strategy is mostly cosmetics. In this podcast, Eve Vlemincx (Stanford GSB facilitator, HBR Advisory Council, author “The Legal SHIFT”) explains what real strategy looks like: incentives, culture, governance, and why 70% of AI rollouts fail in law. If you’re a managing partner trying to separate AI governance from AI theatre, this is an episode worth watching.
with Luke Pigram
Big Law has ideas. Boutique firms have speed. And Sierra Legal has an unfair advantage: lawyers who can actually build legal software. In this podcast, Luke Pigram breaks down how a remote-first firm built its own control center and added AI only after the operational foundations were in place. This episode covers internal legal ops automation, secure GenAI use, and what real adoption looks like beyond prompt libraries and vendor hype.
with Jean Gan
In this episode, I sit down with Jean Gan, Senior In-House Legal Counsel and founder of Global Legal AI and AIgnite Women, to talk about AI governance from the inside. We cover why legal responsibility can’t be delegated to tools and how in-house teams should think about AI risk before adoption.
with Elgar Weijtmans
Legal AI isn't magic. Elgar Weijtmans, Head of Technology at HVG Law explains how most vendors use the same AI models. We cover what actually matters under the hood, ISO/SOC2 claims, agent risks&pitfalls and how law firms should audit legal tech vendors.
with Neil Jennings
Neil Jennings, founder of GLF Strategic Compliance, breaks down AI governance, privacy risk, and cross-border regulation. We discuss AI not being a silver bullet, California vs EU AI rules, shadow AI, bias, dark patterns, and how firms should define purpose, risk tolerance, and governance before adopting AI.
with Vaishali Gopal
In this conversation, Vaishali Gopal, VP of legal innovation at Counselect, shares a practical approach to legal ops transformation: business alignment, process-first design, data/knowledge foundations, automation vs AI, contract playbooks, change management, and build vs buy for legal tech.
with Lindsay Kim Chung
Legal AI for corporate investigations. Lindsay Kim Chung, CEO and founder of TensorCase on evidence review, investigation workflows beyond chatbots, explainable AI outputs, and secure handling of sensitive compliance data.
with Lev Loukhton
Former BigLaw M&A partner Lev Loukhton explains how AI is reshaping law firms, from adoption pressures to real-world value. Lev left the practice to become a legal tech investor, founder of GrayHair Venture Partners and in this conversation, we cover data foundations, privacy tradeoffs, and what separates winning legal tech from hype.
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