Practical, no-hype conversations with lawyers, founders, and practitioners on the frontlines of AI in law. Every week, on YouTube and Spotify.
Law firms are asking how AI can make work more efficient. Jan Roggen argues that efficiency is only the first step. We discuss how firms can make better AI decisions, build lasting adoption, and reinvest the time they save into innovation and new ways of working.
with Andrew Haling
What happens when a personal injury firm choses Claude over a specialized legal AI? Andrew Haling shares how he built a Claude skill ecosystem around his own way of practicing, and why judgment, supervision and firm knowledge matter more than any prompt.
with Lauren E. Diaz
AI is changing how lawyers learn, work and develop, but the fundamentals still matter. We discuss what good AI training looks like, how firms can build real capability, and why technology works best when it strengthens rather than replaces legal judgment.
with Mike Bittner
What does it look like when a lawyer runs his practice on an legal AI operating system? Mike Bittner shares how he uses Claude, AI skills and agentic workflows to run a solo practice, from contract review and matter setup to timekeeping, billing and institutional knowledge.
with Nitesh Daryanani
How should lawyers use Claude for litigation and legal research? Nitesh Daryanani walks through a live legal research workflow with Claude using Midpage for finding and verifying cases. We also discuss hallucinations, legal judgment, MCP connectors and the future of general and specialized legal AI tools.
with Veronica Lopez
More AI tools is not what lawyers need to hear. They need to learn how to use one well. I sit down with Veronica Lopez to talk about moving beyond prompting, building Skills and workflows, learning under firm constraints, and why deeper AI knowledge makes you a smarter buyer and practitioner.
with Wendy Jephson
The value was never in the work product. It was in the thinking that went into it. So how do you get that thinking out of a lawyer's head and into an AI playbook? Legal AI, know-how, judgment, cognitive offloading, and what's really left as a law firm's moat.
with Aleksandra Czubek
How a lawyer at a big international firm uses AI without Harvey or Legora: breaking legal work into steps, building a Claude skill for NIS2 assessments, contract review workflows, and a sensible take on client data confidentiality under GDPR. Practical legal AI for lawyers who feel behind.
with Casey O'Grady
Can a law firm still compete in ten years without restructuring around AI? Inside Blueshoe, an AI-native plaintiff law firm: rebuilding legal intake with agents, hiring lawyers who use AI well, case valuation with data, and where partners should start with AI.
with Kim Mason
Only 4.5% of people paying for Microsoft Copilot actually use it. So where does AI adoption fit when everyone is already overworked? Kim Mason on training drips per role, why the first months slow you down before any ROI, and whether your IT partner can take you further.
with Sarah Eldon Cullen
Clients are showing up with the draft already written. So where does a lawyer's value sit now? Sarah Eldon Cullen on the 80/20 split, why knowledge management is the real moat, and what vendor lock-in costs boutique law firms. Legal AI, AI strategy, and the Nordic view.
with Horatiu Druma Strugariu
When should a law firm buy a point solution instead of just using Claude? Horatiu Druma-Strugariu on where legal AI is heading, why litigation resists automation, why knowledge management shouldn't be treated as a supporting function, and why firms may end up looking a lot like banks.
with Dillon Harindiran
Who do you trust to hold your law firm's institutional knowledge, and what happens when your vendor becomes your competitor? Dillon Harindiran on why knowledge management has been stuck for decades, why your DMS matters less than you think, the shift to usage-based pricing in legal AI, and how every matter is really a story.
with Denisa Kopandi
How a senior associate uses AI to reviews contracts, runs due diligence, and does legal research without getting burned by hallucinations. Prompting tricks, a verification ritual, why playbooks break in civil law jurisdictions, and how to actually evaluate legal AI vendors.
with Goerge Hannah
Will AI automate the junior lawyer out of existence and who wins legal AI, the tools or the model makers? George Hannah on the junior lawyer paradox, foundation models pushing into legal, Harvey vs Legora vs open source, whether data is still the moat, and where a lawyer who's fallen behind should start.
with Oscar Octavio Hinojosa Guerra
Inside an AI-native boutique law firm: 19 Claude agents, no code, 21 years of legal judgment. Oscar Octavio Hinojosa Guerra explains the 10x lawyer, his adversarial agent Hans, and why a four-lawyer firm in Mexico beats Big Law with faster, better, and cheaper service. And why he's still the final gate on every document.
with Kaichen Xu
AI is about to break the billable hour and Kaichen Xu has modeled exactly when. Kaichen (founder of AI Lawyer Lab, ex-BigLaw partner and unicorn GC) breaks down the 30-50% automation threshold where a fixed fee beats the billable hour, why redesigning whole workflows beats automating tasks one by one, and what running a pilot practice, not a pilot project, actually looks like.
with Pranav Anand & Elgar Weijtmans
Inside the AI labs two law firm insiders run to test bleeding edge AI before any tool reaches client work. We discuss agentic AI in law firms, the sandbox strategy that kills shadow IT, how experimentation saves firms from bad legal AI decisions, and knowledge management with AI.
with Will Chen
Will Chen built Mike OSS, an open source legal AI alternative to Harvey and Legora, in 2 weeks. Now GitHub's fastest growing legal AI project. We discuss legal AI pricing, Harvey vs Legora, open source for law firms, and data sovereignty in legal tech.
with Melina Efstathiou
Legal AI is dead. But is it? Melina Efstathiou thinks differently. In this episode, we explore the three pillars of AI readiness for law firms - infrastructure, knowledge, and the human side. We talk about where a partner should start, her RAC framework for AI governance, and her take on the recent marketing narrative of legal AI vendor.
with Horace Wu
Horace Wu spent 8 years building Syntheia after practicing at Shearman & Sterling, DLA Piper, and King & Wood Mallesons. We talk the state of legal data, why Microsoft doesn't need Copilot to be good, why we are trying to measure AI ROI in a wrong way, and what he'd tell himself 8 years ago.
with Helen Fan
Helen Fan on building an AI-native law firm: OpenClaw LLP, the Legal AI Value Stack, and the 5-step transformation roadmap for boutique law firms. We cover AI agents in legal practice, building skills, AI transparency, and why boutiques are best positioned to win with AI.
with Jiyun Hyo
Lawyers spend roughly 2/3 of their day on work that doesn't need a JD. Jiyun Hyo, founder and CEO of Givance is betting an MSO can take all of that off their plate, backed by angels from Meta AI, Google, and NVIDIA. We get into the AI-native test, agents vs workflows, and where vibe coding hits walls.
with Damien Charlotin
Cambridge-trained international arbitration lawyer, Senior Research Fellow at HEC Paris, and builder of the most referenced AI hallucination database in legal, Damien Charlotin, on why specialized legal AI tools might actually lead to more hallucinations, the data problem blocking AI adoption, and a fresh take on where legal AI competition is coming from.
with Kyle Bahr
23 years in legal, now AI Innovation Manager at Cleary Gottlieb: Kyle Bahr on why enhancement beats efficiency as the mindset for legal AI, what 1,000+ hallucination cases actually tell us about the profession (it’s not what you think), and the cognitive load of managing AI agents that nobody is talking about yet.
with Anastasia Boyko
Anastasia Boyko has seen legal from every angle - big law, Axiom, Yale Law School, university CIO, legal AI at Filevine. We talked about why firms that get clear on their purpose make better AI decisions, why curiosity fades after law school, and why the AI champion keeps burning out.
with Paul Crafer
You're one prompt injection away from leaking client data and most law firms don't have governance in place. Paul Crafer, VP EMEA of Assessed Intelligence breaks down how to actually operationalize AI governance before something goes wrong.
with Ben Chiriboga
Lawyers worry AI will wipe out their careers. Ben Chiriboga, founder of the talent platform Reframe.lawyer spent a decade in legal tech and rejects that framing entirely, because the historical record of technology and upskilling says something different.
with Anna Guo
AI is moving from chatbots to autonomous systems. Anna Guo, founder of Legal Benchmarks and a former legal counsel in Google and Ant Group on how legal AI benchmarking is evolving, why agentic tools change the evaluation problem, and how law firms should think about build vs buy decisions, guardrails, and responsible AI adoption.
with J.P. Mohler
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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