Law://WhatsNext

Tom Rice and Alex Herrity

How are leading practitioners leveraging emerging technologies and ways of working to pursue their passion and objectives, and as a by product what are the implications for the future of legal practice? Let’s explore this together. What to expect:

- Focused conversations with leading practitioners; technologists and educators
- Deep dives into the intersection of law, technology, and organisational behaviour
- Practical analysis and visualisation of how AI is augmenting our potential
- Insights from adjacent industries that might inform our own

Play

Open in

20 episodes
Avg 38 min
English

Episodes 20

Newest Oldest Longest

All20 Unplayed20 In progress0 Played0

S2 · E19
July 8 · 35 min
Legal Tech Trends with Peter Duffy (Q2 2026)
🎙️ Peter Duffy is back for our quarterly deep dive into the biggest stories from his ever-popular Legal Tech Trends newsletter. It's been quite the quarter: a $500 million headline from Kirkland, frontier model companies falling over each other to claim legal, and the US government switching off a frontier model for the entire world. As Peter puts it: "What a bizarre world that we live in." --- What we dive into: Kirkland's $500m statement of intent — The announcement that rocked the market, and the nuance beneath it: Palantir (not an internal team) is helping building a platform, third-party procurement continues, and what counts as "investment" when partner hours bill at thousands of dollars? Either way, the proprietary layer marks that fascinating shift from service provider to potential product provider. The frontier land grab for legal — Ex-Ironclad CEO Jason Boehmig joins OpenAI to lead its legal vertical, Freshfields signs a multi-year deal with Anthropic, and Perplexity launches Computer for Counsel. Peter shares his three-lens test for reading these partnerships — and why the real battle might be for the interface lawyers work through every day. The fortnight the US switched off Fable — AI's first true geopolitical moment. A jailbreak, an export-control order, and the awkward detail that other models could reportedly do the same thing. We nerd out on the eerily prescient Europe 2031 scenario published the day before, and what it all means for sovereignty and model dependency. Revolut Partners and the AI-audited panel — Out goes the static law firm panel; in comes a performance-based roster with quarterly reviews and internal AI tools to run RFPs and scrutinise advice and invoices. --- Listen if: You want a hype-free tour of the quarter that was. Rate, subscribe, comment, and share if you enjoyed this chat with Peter! --- For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/. --- Show notes / links: Peter's Legal Tech Trends newsletter: https://legaltechtrends.substack.com/ Europe 2031: https://europe2031.ai/ Legal Hops Amsterdam — Peter's quarterly meet-up (boat party included): https://www.linkedin.com/groups/12922521/
S2 · E18
July 1 · 30 min
Governing AI Agents Like a Legal System with Will Lilley
🎙️ This week we sit down with Will Lilley who has built something genuinely strange and uniquely clever: the Vibe Justice System, a working governance layer for AI-assisted work, complete with courts, a constitution, a Gazette, and 150+ recorded judgments that cite one another like real case law. It began with a familiar frustration. AI agents make endless micro-decisions as they work, then forget them the moment a session ends. Will calls this "drift," and his answer was to give the agent a "definition of correct" that is explicit, durable and self-enforcing. The crucial distinction, as he explains, is that this isn't a bigger or better CLAUDE.md. A rules file tells an agent what to do, but the agent forgets to read it, and you could never write down every rule your workflow needs in the first place. --- Will's system is principle-based, like common law: instead of front-loading every instruction, it lets the agent reason against principles and generatively build its own rule system — recording decisions as judgments, citing precedent, and aligning over time around what "correct" means for the project. For our audience, Will frames the potential utility of the system as being capable of applying across three buckets of work: project work (any repo or directory: code, contracts, a litigation timeline, a due-diligence checklist), linear workflows that move through deterministic steps, and non-linear work, with litigation as the apex case where you only know the next move from the current one. --- Connect with Will Lilley — Product Operations at Clara | LinkedIn Vibe Justice System — the full repo, including the Gazette, Acts and judgments: github.com/wlilley93/vibe-justice-system --- If you enjoyed this conversation, please share it with someone who'd get something out of it — and if you have a moment, tell us what resonated, what didn't, and rate the show (it genuinely helps us reach more listeners and land great guests). --- For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠⁠⁠⁠.
S2 · E17
June 24 · 39 min
Pop the Hood: Antti Innanen on Building Legal AI in the Open
67 agents, 155,000 lines of code, and not really a product — why one of the most insightful legal AI experiences right now is one you can see inside. --- 🎙️ This week we sit down with Antti Innanen — Finnish lawyer, law firm founder, legal designer and professor of practice — the mind behind Lavern, and one of the most prolific builders in legal tech, shipping open-source experiments at rap-album pace. Lavern is the headline act — 67 specialist legal agents that debate, verify, and escalate, released free under Apache 2.0 not as a product but as an artifact you're invited to pull apart. As Antti puts it, it's the first agentic legal tool where you can actually pop the hood and look inside. --- This is a conversation about building in the open. Antti walks us through Lavern live — the intake modes, the 67-agent roster (Easter eggs included), the verification loops — and uses it as a way into bigger questions: why context is the whole game in legal AI, what it costs to run agents at the frontier, why he's closing a beloved legal-design business even as its ideas finally become scalable, and why "f***ing around" with AI might be the most responsible thing a lawyer can do right now. --- Connect with Antti Innanen — Lawyer, legal designer & builder | Lavern (GitHub repo, 100% open) | Find him on LinkedIn --- If you enjoyed this conversation, please share it with someone who'd get something out of it — and if you have a moment, tell us what resonated, what didn't, and rate the show (it genuinely helps us reach more listeners and land great guests). One thing we'd love to hear: if you've forked or remixed Lavern — or taken it somewhere Antti didn't expect (access to justice, strategy, anything) tell us. We'd love to see it! ---
S2 · E16
June 10 · 37 min
Return on Token: Shawn Curran on Lawyer-Builders, Open Source, and the Real Cost of AI
🎙️ This week we sit down with Shawn Curran, CEO of Jylo — for a conversation that starts where a lot of legal teams and law firms are quietly stuck: Now that almost anyone can build software, should they? Shawn is unusually well placed to answer. He spent the best part of two decades as a technologist inside private practice — McGrigors, Latham & Watkins, Freshfields, then head of legal tech and later director at Travers Smith, before spinning Jylo out of the firm two and a half years ago. --- He's watched the industry crawl from paper files 📄 to systems of record 🗄️ to systems of productivity ⚙️ and now to what he calls "systems of intelligence" 🧠. So when he says the barrier to building software is "literally on the floor" 📉, it lands with some authority. And he's thrilled about it. The open-source wave of lawyer builders democratising access to their products — Will's MikeOSS, Antti Innanen's Lavern — is, to Shawn, a long-overdue correction. Now the person who actually understands the work describes it in plain English and watches it take shape. --- This discussion plays out against a legal technology market that refuses to sit still. One week it's a new open-source release; the next, Kirkland & Ellis commits half a billion dollars to its own platform; the week after, a frontier lab ships a legal plugin. Shawn admits he loses a faintly ridiculous amount of time to "is this Jylo for free?" emails. Which brings us to Shawn’s stand out observation from our conversation - we talk endlessly about ROI; Shawn would rather we talked about ROT (return on token). If a firm spends thirty grand vibe-coding something nobody ever opens, it hardly matters that it would have cost two hundred grand in engineers; it's still money set on fire. "Return on token. What's the return on token? 'Rot.' … There's a lot of rot out there." Shawn warns that as token prices climb rather than fall, the honeymoon phase of trying everything is going to give way to harder questions about what's actually worth the spend. --- Connect with Shawn Curran — CEO of Jylo --- If you enjoyed this conversation, please do share it with a colleague or community wrestling with the same questions — and if you have a moment, tell us what resonated, what didn't, and rate the show. It genuinely helps us grow the audience and land great guests. --- For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠⁠⁠.
S2 · E15
June 2 · 30 min
AI-Native Hiring and Organisational Alignment with Stephanie Dominy
🎙️ This week we sit down with Stephanie Dominy — General Counsel and Head of Ops at Tessl. Stephanie has practised law for nearly three decades, but at Tessl she hires across the whole organisation, including against one of its operating principles: "Be AI Native." What begins as "how do you spot an AI-native engineer?" becomes "how do you hire an AI-native lawyer?" — and then a deeper question still: if AI can already draft, research and build, what is the irreducibly human part of legal work? Stephanie's answer is taste and judgment. She explains why Tessl keeps iterating on how it hires, most recently reverse-engineering its interviews (inspired by Sierra's AI-native interview framework). From there we touch on cognitive surrender, the commoditisation of knowledge, legal training pathways, and her observation that those with humanities backgrounds are often better equipped to interrogate AI than purely data-driven minds. --- Tom is equally sceptical of organisational efforts to adopt this technology. He points to Claude's Constitution — the document Anthropic uses to steer a probabilistic model through competing demands via a clear order of precedence — and argues it isn't so different from a legal constitution, and is a surprisingly useful mirror for any company trying to go AI-native. (It's also humbling, he suggests, to work out where you sit in the "model stack.") His argument: every organisation is made up of teams with competing priorities, so be deliberate about where to go all-in. His example — the overzealous sales team optimising for deals while legal supercharges risk prevention. Today those incentives collide only occasionally, and human leaders resolve them. But as each team is amplified by AI, the collisions get faster, and their resolution is quietly outsourced to the model — piling on competing instructions that degrade its performance. --- Tom and Stephanie are taking this one to the stage — Wednesday 3 June 2026, at Crafty Fest, Regent's University London. Crafty Fest is Europe's largest festival for the in-house legal community, and their session picks up exactly where this episode leaves off. --- Connect with Stephanie Dominy, General Counsel & Head of Ops at Tessl. And the open question Stephanie left us with: if you've built something that actually works for testing taste and judgment — an interview question, a practical test, anything — we want to hear it. Bring it to Crafty Fest, or drop it in the comments 👇 --- For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠⁠.
S2 · E14
May 19 · 34 min
The Defensibility Question: Helen Fan on What Survives When Frontier Models Climb the Stack
🎙️ This week we sit down with Helen Fan — California lawyer, Chief AI Officer at a Silicon Valley boutique firm, and one of the most original voices currently writing and building in legal AI. What makes Helen unusual is the combination. She is a practising cross-border lawyer who is also genuinely technically literate — building, testing and writing about agentic systems at a level most lawyers (and a fair few engineers) do not reach. And she sits squarely on the bridge between the US and China technology frontiers (building legal tech communities in each). "My role is really about being a bridge — between tech people and legal professionals, and between the US and Asia." It is a rare vantage point — and one that has produced one of the more original frameworks we have come across in the legal AI conversation this year. Our conversation is in two halves. First, we ground the conversation in the Legal AI Value Stack — Helen's five-level framework for thinking about defensibility in a world where frontier models keep climbing the stack. Then we get into the fun part: OpenClaw LLP, her public experiment to actually walk the roadmap herself. We get into the design choices behind her two AI associates, the four-layer security framework she has built, the Argument Report skill, her custom debrief skill which has her agents look back over recent work and recommend tweaks, why she ended up on Discord, and her honest reflections after the first 60 days. Key References Connect with Helen Fan — California lawyer & Chief AI Officer | LinkedIn | Substack | Personal site The Legal AI Value Stack — Five Levels of Defensibility — Helen's now widely-shared framework. Start here if you have not read it yet. The OpenClaw LLP AI-Native Law Firm Experiment — Helen's public 100-day project, documented on LinkedIn and her site. Helen's Stanford Presentation — A quick video run-through of the talk Helen gave at Stanford a few weeks before this recording. If you enjoyed this conversation, please share it with someone or a community who you think would find it valuable . And if you have a moment, rate the show and tell us what landed — it helps us reach more people and keep getting brilliant guests like Helen. --- For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠.
S2 · E13
May 6 · 35 min
Legal Engineering's Moment - Mary O'Carroll on her new CEO Role and the skill set that is becoming highly prized
🎙️ This week we sit down with Mary O'Carroll - the newly announced CEO of Legal Eng Consulting Group (LECG), and one of the most influential figures in the legal operations and legal technology industry. Mary's career arc is, by her own admission, a “portfolio” one. She built and led legal operations at Google. She founded and grew the CLOC community into the global home of legal ops. She moved into big law as Chief Operating Officer at Goodwin. She has sold legal technology (Ironclad), advises investors (she is an Executive in Residence at Signal Fire), technology companies (Sandstone), hosts her own podcast Pearls On Gloves Off, authors her own Newsletter, and — as of yesterday is now the full-time CEO of LECG, a boutique legal operations consulting and services firm focused on what she calls legal engineering. --- Alex and I are big fans and friends of Mary - few people in the legal industry benefit from her wide ranging experience and perspective. Even fewer can so succinctly distill the objectives, incentives, opportunities and competing priorities of the firms, teams, tech companies and individuals that make up our unique legal ecosystem, and none with the energy, candour and piercing intellect Mary brings to every conversation. --- In the short time we spend together we get into: The CEO Announcement — Mary uses the episode to confirm she is joining LECG as full-time CEO. She explains why! What a Legal Engineer actually is? Mary defines the legal engineer as someone who can understand legal processes, re-engineer them, and then leverage technology to automate, accelerate, optimise and maintain them. The Billable Hour is the Operating System — Drawing on her recent Substack piece, Mary explains why everyone has been focused on the wrong half of the billable hour problem. Pricing on a fixed fee is the easy bit. The harder bit is the underlying incentive structure of a law firm. If you give an associate a tool that turns eight hours into one and tell them they still need to hit hours, you have created a structure that is at odds with the technology itself. It is, she says, "a hundred percent the innovator's dilemma." The View from the VC Side — As an Executive in Residence at Signal Fire, Mary has watched venture capital wake up to legal in a serious way. --- Connect with Mary O'Carroll — through Legal Eng Consulting Group (LECG) | on Substack | or LinkedIn --- If you enjoyed this conversation, please share it with someone or a community who you think would find it valuable . And if you have a moment, rate the show and tell us what landed — it helps us reach more people and keep getting brilliant guests like Mary. --- For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠.
S2 · E12
April 28 · 40 min
The Quantum Paradox: Rebecca Keating and Laura Wright on the Race to Get Encryption-Ready
Google says it will be able to break RSA encryption by 2029. Third-party actors are already collecting encrypted data on the assumption they'll be able to read it later. The UK has just committed £2 billion to a quantum strategy. 🎙️This week we sit down with Rebecca Keating and Laura Wright — barristers at 4 Pump Court and the co-authors of A Practical Guide to Quantum Computing and the Law. Both are a rare breed of Barrister with technical credentials to complement their deep legal expertise. Rebecca worked in-house at Dropbox before being called to the Bar in 2017, sits on the ICO's Technology Advisory Panel, and has acted in one of the only quantum-related cases to pass through the UK courts. Laura took an MSc in Computing Science at Imperial mid-career — her final project was a new coding language for legal contracts — and now writes and speaks regularly on smart contracts, AI liability, and quantum risk. --- What You'll Learn What is Quantum Computing — Alex surprises us all with his own definition and a sneak preview into how he likes to prepare for our podcast conversations! 👀 The Quantum Paradox — Rebecca's framing for the central tension of the technology - the ability of quantum computers to upend the security systems that are the basis upon which we keep information safe, but there's also the capability to have even more secure systems than we have ever had. Harvest Now, Decrypt Later — This is not a future threat. Third-party actors are already collecting RSA-encrypted data they can't read today on the assumption they'll be able to decrypt it within a few years. NIST's quantum-readiness window of 2030–2035 is, in Rebecca's view, too late to start the conversation — particularly for anyone holding sensitive medical, political, or nationally significant data. Contracting for Quantum Computing as a Service — Customers won't own quantum computers — they'll access them remotely on a pay-as-you-go basis. Laura walks through what features are likely to make "QCaaS" contracts genuinely different from SaaS. --- Connect with Rebecca Keating — Barrister at 4 Pump Court | Member, ICO Technology Advisory Panel Connect with Laura Wright — Barrister at 4 Pump Court | Co-host, 4 Pump Court podcast Their book — A Practical Guide to Quantum Computing and the Law (Law Brief Publishing, December 2024). The Law of AI (2nd edition, Sweet & Maxwell) — Rebecca and Laura author the chapter on AI and Professional Liability. Society for Computers and Law (SCL) — Rebecca and Laura's recent SCL webinar on quantum legal issues was the catalyst for this episode. Both (+ Tom) are members of the SCL - a leading educational charity for the tech law community in the UK. --- If you enjoyed this conversation, please share it with someone or a community who you think would find it valuable . And if you have a moment, rate the show and tell us what landed — it helps us reach more people and keep getting brilliant guests like Rebecca and Laura. --- For more conversations at the intersection of law and technology, head to⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠.
S2 · E11
April 13 · 43 min
Inside the Machine: Bilva Chandra on Trust, Truth, and the Future of Knowledge in an AI World
🎤 This week we sit down with Bilva Chandra — who has spent the bulk of her career working on AI safety, ethics, and governance at the places where it matters most. Her CV reads like a guided tour of the AI governance landscape: she's worked at OpenAI, RAND, the US AI Safety Institute (now CAISI), and most recently Google DeepMind. She's been inside the frontier labs building the technology and inside the institutions trying to govern or influence its development — often thinking about the same problems from both sides of the table. --- One of the catalysts for our conversation emanated from her recent contribution to a Google DeepMind paper — Architecting Trust in Artificial Epistemic Agents — exploring what happens when AI systems become active participants in how knowledge is created and shared. But it's Bilva's broader career at the intersection of AI and society that makes this conversation so compelling: she's someone who genuinely cares about getting this right, and isn't afraid to say when she's worried. We cover a lot of ground — from the practical challenge of making AI systems reliable enough for enterprise adoption, to the deeper worry about what happens to human judgment when cognitive work is increasingly offloaded to machines. What emerges is a picture of someone who is both genuinely optimistic about what AI can unlock and deeply clear-eyed about the societal fault lines it's accelerating. Bilva doesn't treat AI risk as a theoretical exercise. She frames it as a human problem — one tangled up with polarisation, declining trust in institutions, and an information environment that was already broken before the first LLM shipped. --- Connect with Bilva Chandra — on LinkedIn | Or by subscribing to Role Model, her new newsletter on AI and society. --- If you enjoyed this conversation, please share it with someone who you think would find it valuable — especially anyone grappling with how to govern AI responsibly in their organisation. And if you have a moment, rate the show and tell us what landed — it helps us reach more people and keep getting brilliant guests like Bilva. --- For more conversations at the intersection of law and technology, head to⁠⁠ https://lawwhatsnext.substack.com/⁠⁠.
S2 · E10
April 8 · 44 min
The AI Dividend: David Bushby on Corporate Teams Going It Alone
🎤 This week we sit down with David Bushby — Head of Legal Operations at Canva and the voice behind In Counsel Weekly — for a conversation that's part provocation, part practical playbook, and part three mates who love this stuff catching up over a good topic. David follows Sam Lewis as the second member of the brilliant Canva legal team to join us for a chat, and from our vantage it's easy to discern the talent, curiosity and sense of fun they must have coursing through their team. --- David has spent the last couple of years at the forefront of AI adoption in legal — not as a commentator, but as a practitioner. Custom GPTs, Claude skills in Cowork, vibe-coded legal research tools, Chrome extensions that make SaaS platforms do things they were never designed to do. He's materially contributing to the building of an AI-native legal function in real time. --- "I just started to feel, by the end of last year — we just really need to go it alone. We can control what tools we use... maybe the AI dividend is just up to us on the in-house side." Here's a big question David has been grappling with (and we get into it straight away during our catch up): are law firms passing on their AI productivity savings to clients? The invoice data says no. The rate increases — 12–16% in the US and UK, with individual partner hikes of 25–35% — say definitely not. And at the line-item level? Nothing. So what does a smart in-house legal ops team do? They begin to contemplate going it alone. David walks through Canva's owners mindset approach to outsourcing, the vibe-coded tools his team is building in Claude Code, and why the AI dividend might just be something in-house teams have to take for themselves. --- Connect with David Bushby — by subscribing to In Counsel Weekly — David's popular bite-sized weekly newsletter for in-house counsel | Or find him on LinkedIn --- If you enjoyed our conversation, please do share it with someone who you think would be interested in listening (or is equally passionate or enraged by law firm productivity). And if you've got a spare minute, please rate the show and tell us what landed 🙏 It helps us grow our audience and continue to attract great guests like David. --- For more conversations at the intersection of law and technology, head to⁠ https://lawwhatsnext.substack.com/⁠.
S2 · E9
March 27 · 34 min
Legal Tech Trends with Peter Duffy (Q1 2026)
🎙️Peter Duffy is back for our quarterly deep dive into the biggest stories from his ever-popular Legal Tech Trends newsletter (celebrating its recent 50th edition 🎉). This time around, the conversation is dominated by one name: Anthropic. Between a legal plugin that spooked public markets, a viral tweet showcasing a "Claude-native" law firm, and a principled stand-off with the US Defense Department that sent millions of users switching sides — it's been quite the quarter. What we else dive into: Vibe coding hits legal — From weekend hackathons to working prototypes in 30 minutes. Peter explains why it's transforming ideation and prototyping, but flags the considerable leap from "amazing demo" to "enterprise-ready." Plus, Alex reveals his salmon regulation app “Branchly” is storming the charts over at vibecode.law. The privilege and compliance watch-outs — An SRA investigation into a solicitor uploading client docs to ChatGPT, a US ruling that use of consumer Claude waived attorney-client privilege, and judges struggling with where "AI" begins and ends. Shadow IT is alive and well. The LLM numbers blind spot — Peter's public service announcement: LLMs are not designed for numerical calculations and it's one of the easiest ways to trigger hallucinations. The McKinsey security incident — A security researcher accessing 45 million+ internal chatbot messages. Not an AI-specific problem per se, but a timely reminder that vibe-coded tools and internal chatbots need proper security scrutiny — especially when you have client data and a reputation on the line. Harvey, Legora, and the question you shouldn't be asking — "Which one should I buy?" Maybe start with your problems, not the product. Talk to your users, define your requirements, understand the commercial value — then go to market with a structured evaluation. --- Listen if: You want a grounded, hype-free take on the quarter that put legal AI firmly in the mainstream spotlight. --- Rate, subscribe, comment, and share if you enjoyed this chat with Peter! --- For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/.
S2 · E8
March 19 · 1 hr 27 min
The Outsider Inside: Nick West on Rewiring the Law Firm
🎤 This week we sit down (for our first in-person episode) with Nick West — Partner and Chief Strategy Officer at Mishcon de Reya — who has spent two decades working at the intersection of law, technology and business model innovation. Nick’s path is one of the more unusual and instructive in the industry: competition lawyer at Linklaters, strategy consultant at McKinsey, product leader at LexisNexis, Managing Director of Axiom UK, and now the person responsible for technological transformation and R&D at Mishcon. He founded MDR Lab (one of the first legal tech startup incubators) and the MDR Group (collection of specialist consultancy businesses that sit alongside but separate from the core Mischon legal practice), built one of the industry’s first in-house data science teams, and has overseen the firm’s AI adoption journey from early experimentation through to commercial platform deployment. There are few people in the legal industry who’ve thought as deeply — or as practically — about how law firms actually work and how they might need to change. The conversation is wide-ranging — we cover the full arc of Nick’s career, the evolution of innovation culture inside a law firm, how Mishcon adopted AI (and what they got wrong along the way), the productivity question everyone’s asking, what happens when clients start sending genuinely good AI-drafted documents, and the early “signals” for where the business model of law might be heading. --- Connect with Nick West Partner and Chief Strategy Officer at Mishcon de Reya --- If you enjoyed this conversation please do share it with someone or a community who you feel would benefit from listening. If you have any more time do tell us what resonated; what didn't; and, rate the show (it helps us grow the audience and get great guests like Nick)! --- For more conversations at the intersection of law and technology, head to⁠ https://lawwhatsnext.substack.com/⁠.
S2 · E7
March 13 · 14 min
Who Pays for the Truth? The UK's Copyright Battle with Big Tech with Matt Rogerson
🎙️This week Tom sits down with Matt Rogerson — Global Policy Director at the Financial Times and one of the more prominent and forceful voices in the UK press and publishing industry on the question of AI companies using copyrighted content without permission or payment. The timing could hardly be more significant. We recorded this conversation on the day the House of Lords Communications and Digital Committee published what may prove to be the most consequential UK report on AI and creative industries to date: AI, Copyright and the Creative Industries — an 85-page report drawing on testimony from Google, Meta, Microsoft, OpenAI and dozens of creative industry bodies, whose conclusions could not be clearer: the UK's copyright framework is not outdated, the problems stem from widespread unlicensed use, and the government should rule out a commercial text and data mining exception entirely. And just one week earlier, the FT helped launch SPUR — the Standards for Publisher Usage Rights coalition — alongside the BBC, The Guardian, Sky News and The Telegraph: a coalition not just defending the status quo, but getting on the front foot to build shared technical standards and licensing frameworks so AI developers can access quality journalism through rights-cleared channels. What provoked this conversation was a pamphlet published by Public First, a UK policy consultancy, titled "Text & Data Mining and its value to the UK economy" — which called for a broad commercial exception to UK copyright law, extending the argument to cover AI inference as well as training. Matt's reaction on LinkedIn was characteristically direct, and it got us talking. --- During our conversation, Matt dismantles several of the core narratives being advanced by AI lobbyists — the anthropomorphisation of models to normalise unlicensed use; the claim that licensing infrastructure is too hard to build; and the idea that the UK must weaken copyright to remain competitive. He makes a compelling case that the real opportunity lies not in capitulating to US hyperscalers, but in building sovereign AI models with transparent training data and proper licensing — pointing to the Allen Institute, a US model co-funded by the government and Nvidia, as proof that this is already happening. Matt highlights the infrastructure already being built to support fair licensing: Microsoft's Publisher Content Marketplace, the FT's existing commercial API access, and emerging thinking from writers like Florent Daudens on what a post-browser, agentic news economy could look like. The claim that it's "too hard" for AI companies to pay for content is not just wrong — it's being actively disproved by the market. And we close on what may be the most consequential long-term argument of all: the slop spiral. If there is no economic incentive to produce high-quality journalism — because AI companies can take it for free — the supply of reliable information degrades. AI models trained on and retrieving from an increasingly polluted information environment produce worse outputs. Trust erodes. And we drift into a world where the information we consume is dependent wholly on the alignment of a particular model and the commercial interests of those administering it. Matt makes the case that secure news and information supply chains could become a national security issue if this dynamic starts to accelerate. --- If you enjoyed this conversation please do share it with someone or a community who you feel would benefit from listening. If you have any more time do tell us what resonated; what didn't; and, rate the show (it helps us grow the audience and get great guests like Matt)! --- For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/.
S2 · E6
March 6 · 38 min
AI Security, Agentic Risk & What lawyers need to understand with Rok Popov Ledinski
We sit down with Rok Popov Ledinski — an independent legal AI and data consultant whose background spans high-security enterprise engineering through to advising law firms on their AI and security strategy. Our initial interest in Rok's work was sparked by his YouTube channel, where he's been producing sharp, accessible breakdowns of the real risks underpinning today's AI tools. Within minutes, we're into a forensic dissection of Anthropic's Claude Cowork — the agentic tool pitched at non-developers that launched earlier this year. Rok walks us through the contradictions in Anthropic's own technical documentation: a tool demonstrated by its creators as a way to organise your desktop, while the same support pages advise against granting it access to sensitive local files. A tool marketed for running tasks autonomously in the background — while its activity isn't captured by audit logs. A tool whose safety guidance asks users to watch for "suspicious actions that may indicate prompt injections" — aimed at an audience that, as Rok points out, has largely never heard of prompt injections. Rok explains, in terms accessible to non-technical listeners, how hidden instructions embedded in an innocuous document can hijack an AI agent into exfiltrating sensitive client data. His hypothetical attack vector for law firms is disarmingly simple: find lawyers on LinkedIn who are openly using Cowork, send a document to their publicly available email address containing concealed instructions, and let the agent do the rest. But this isn't an anti-AI conversation. Rok is emphatic that these tools should be used — just not naively. Drawing on enterprise security frameworks from companies like Cisco, he advocates for a practical middle ground: map what your AI has access to, create sanitised copies of sensitive folders, scope permissions tightly, vet your MCP servers and plugins, and understand (physically, not just contractually) how data flows through your systems. Key Takeaways The Cowork Paradox: Anthropic's own documentation reveals a tension between how Cowork is marketed (autonomous, background task execution) and how it should be used (limited permissions, no sensitive files, manual monitoring for prompt injections). Security attacks are now a "When," Not an "If": Unlike traditional cybersecurity breaches, prompt injection attacks exploit a fundamental limitation of large language models — they can't distinguish instructions from data. Research shows success rates as high as 90% for some proprietary LLMs. Claude is among the more resistant, but not immune. Practical Security for Legal Teams: Rok's actionable advice for in-house teams and law firms includes: creating clean data environments separate from originals; using self-hostable workflow tools like n8n; scoping AI permissions to the minimum necessary; and conducting genuine due diligence on every plugin and MCP server before connecting it to your systems. Key References Rok's YouTube Channel: where our interest in Rok's work began, and a recommended follow for anyone wanting to stay across the security dimensions of legal AI adoption Rok's LinkedIn — he hosts weekly live sessions every Saturday with a security expert specialising in air-gapped, offline AI deployments in regulated industries The Art of Modern Legal Warfare — Rok co authors with a former guest and friend of the show Anna Guo and Sakshi Udeshi a series of vulnerability types specific to legal AI use cases. If you enjoyed this conversation please do share it with someone or a community who you feel would benefit from listening. If you have any more time do tell us what resonated; what didn't; and, rate the show (it helps us grow the audience and get great guests like Rok)!
S2 · E5
February 25 · 45 min
AI Governance: Ethics, Agents & the Human Question with Catie Sheret, Oliver Patel & Peter Lee
🎙️Alex and Tom step aside for this one — handing the mic to their friend Catie Sheret (General Counsel at Cambridge University Press & Assessment), who hosts a rich three-way conversation with Oliver Patel (Head of Enterprise AI Governance at AstraZeneca) and Peter Lee (Partner at Simmons & Simmons). Three very different vantage points — converging on the same question: how do you actually make AI governance work in practice? What begins with a definitional exercise (what is AI governance, anyway?) quickly evolves. Oliver draws a sharp line between AI ethics, responsible AI, AI governance and AI safety as related but distinct disciplines — and makes a passionate case that governance is fundamentally change management, not compliance theatre. Peter describes the "golden thread" he sees in the best organisations: corporate philosophy flowing from the boardroom right down into the tools people use every day. Catie grounds everything in context — arguing that your principles only stick when they're anchored to what your organisation actually does: content IP at Cambridge, medical ethics at AstraZeneca etc. The conversation builds through the practical mechanics — use case assessment, vendor oversight, committee structures, crisis preparation — before arriving at the question everyone's wrestling with: agentic AI. Peter frames it as a mindset shift from "can we trust the output?" to "what actions can this system initiate?" Oliver goes further: the fundamental logic of agentic AI, he argues, is to take the human out of the loop — and organisations need to confront that honestly rather than pretending otherwise. There's a wonderful thread on human flourishing running throughout — Peter's insistence that philosophers have never been more important, Oliver's pride in AstraZeneca's "Thriving in the Age of AI" literacy programme, and a closing round of book recommendations that ranges from Richard Susskind's How to Think About AI to Jenny O'Dell's How to Do Nothing (Oliver's brilliantly contrarian pick about the importance of stepping away from screens entirely) to Governing the Machine by Ray Eitel-Porter, Paul Dongha, Miriam Vogel. It's a masterclass in how to think about governance as something that enables rather than constrains — hosted with warmth and real expertise by Catie. If you enjoyed this episode, please do share it with another friend, team or community who might also enjoy it! Please do let us know what resonated (by comment) and rate the show (if you haven't already)! We appreciate your time, attention and support! For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/ for: (i) insights from leading practitioners, technologists, and educators; (ii) deep dives into the intersection of law, technology, and organisational behaviour; and (iii) practical analysis and visualisation of how AI is augmenting our potential.
S2 · E4
February 11 · 40 min
When will Legal vibe like code with Chris Bridges & Matt Pollins
The vibe coding conversation in legal has gone full culture war: one side says they've built a billion-dollar startup in 10 minutes, the other says don't bother. The truth — as usual — is far more interesting than either extreme. 🎙️This week we sit down with Chris Bridges (Co-Founder & COO, Tacit Legal) and Matt Pollins (Co-Founder & CPO, Lupl) — two legal technologists who live in the same small town in West Sussex and who've channelled that proximity into building vibecode.law, an open-source platform where the legal community can share, discover and upvote vibe-coded legal tech projects. The platform launched just over a week before we recorded and already had 18 projects — from a SaaS inflation calculator for contract lawyers to a Harvey for Mongolian law to a tool that unlocks track changes when a passive-aggressive opposing lawyer has locked them down. During our chat, we explore: Why vibe coding's real value is compressing the feedback loop between idea and prototype — not replacing developers The structural gap: how 25 years of developer tooling (linting, testing, documentation, standards) gives engineering focussed AI tools a head start that legal tech can't shortcut Why the adversarial nature of law makes standardisation fundamentally harder than in software vibecode.law: what it is, the projects landing on it, and the product thinking behind building a two-sided community Responsible vibe coding and why we're probably 6–12 months from a data exposure incident The T-shaped lawyer: curiosity as the defining skill for the next generation Connect with our guests: Chris Bridges — tacit.legal | author of When will legal vibe like code Matt Pollins — agents.law | lupl.com Check out vibecode.law to explore or submit your own projects. --- If you enjoyed this episode, please like, subscribe, comment, and share! For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/
S2 · E3
January 28 · 31 min
Vibe Lawyering with Artur Serov
🎙️ This week we sit down with Artur Serov — a Senior Commercial Counsel working in-house across corporate, commercial, and AI compliance — who has been quietly vibe coding legal tech solutions that rival features in commercial platforms. This is a practical, how-I-did-it episode. Artur walks us through his journey from first principles — the failed early experiments, the tools that unlocked progress, and the specific steps any curious lawyer could follow to start building. Artur shares his screen during our conversation to demo a Word add-in with features he couldn't find in commercial legal tech (party-aware context, risk appetite dials, AI-powered negotiation prep), and previews a more ambitious workspace prototype where AI retains memory across an entire transaction lifecycle. Since publishing this prototype has evolved, and you can read more about that here. Artur is candid about what's now possible: with Claude Opus 4.5 and Gemini 3, self-built solutions can get remarkably close to enterprise-grade. But he's equally honest about the remaining hurdles — deployment, maintenance, security — and his belief that a growing community of "vibe lawyers" will help solve them together. --- What you might take from this conversation: The First Principles Path to Technical Fluency — How Artur went from zero coding experience to working prototypes, using Claude as a teacher and Google Antigravity as his development environment What's Missing from Commercial Legal Tech — Why context is the killer feature, and how Artur built deal-aware AI that knows who you represent, what you're negotiating, and what risks you're willing to take The Workspace Vision — A prototype where AI memory persists across NDAs, partnership agreements, and every document in a transaction — with your playbooks and policies embedded as reference materials Why Building Makes You Better at Everything Else — From vendor negotiations to IT collaboration, how technical fluency transforms your effectiveness as in-house counsel How to Get Started — Artur's practical advice: a Claude subscription, Google Antigravity, and the willingness to ask "how do I do this?" --- Connect with Artur: LinkedIn | Github --- If you found this episode interesting, please tell us and do share it with a friend, colleague or community who might take something from it! For more, head to⁠ lawwhatsnext.substack.com⁠ for: (i) Focused conversations with leading practitioners, technologists, and educators; (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis of how AI is augmenting our potential.
S2 · E2
January 21 · 59 min
Evals & Benchmarking Legal AI with Anna Guo
We sit down with Anna Guo — a Singapore-based lawyer, startup advisor, and founder of LegalBenchmarks.ai — who has quietly built one of the most rigorous practitioner-driven evaluation frameworks for legal AI tools in the industry. Her community now spans close to 900 legal and AI professionals. Her research has produced findings that challenge industry assumptions: that legal-specific AI tools don't always outperform general-purpose models, that accuracy isn't actually the top driver of lawyer adoption, and that in some drafting tasks, AI is already matching or exceeding human reliability. This is a watch-don't-only-listen episode. Anna shares her screen throughout — running us through a live, double-blind benchmarking exercise where we rank outputs from legal AI, general-purpose AI, and human lawyers without knowing which is which. She also demonstrates how prompt injection attacks can bypass AI guardrails using techniques as simple as low-resource languages (Vietnamese or ASCII code?), surfacing security risks that become particularly acute as we move closer toward widespread agentic AI adoption. What You'll Learn: The Three Dimensions of Tool Evaluation — Why measuring accuracy alone misses the point, and how Anna assesses output reliability, output usefulness, and platform workflow support as distinct layers What Actually Drives Adoption — Survey data revealing that lawyers prioritise context management and verification over raw accuracy when choosing AI tools Where Humans Still Win — High-judgment, context-sparse tasks requiring commercial reasoning remain firmly in human territory; routine, context-complete work is where AI excels Prompt Injection in Practice — Live demonstrations of how attackers can trick AI models into revealing harmful information using low-resource languages and clever framing --- Connect with Anna: LinkedIn | LegalBenchmarks.ai --- If you found this episode interesting, please tell us and do share it with a friend, colleague or community who might take something from it! For more, head to lawwhatsnext.substack.com for: (i) Focused conversations with leading practitioners, technologists, and educators; (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis of how AI is augmenting our potential.
S2 · E1
January 7 · 29 min
Vibe Coding a Doc Review Assistant with Anson Lai
Season 2 is here. In our opener, we sit down with Anson Lai — commercial counsel by day, relentless tinkerer by night — who walks us through how he built and published a document review tool as a Microsoft Word add-in that rivals offerings from legal AI startups raising hundreds of millions. The kicker? He did it in weeks. And he's giving it away. This isn't theoretical. Anson shares his screen, shows us the tool live, and opens the hood on what makes it work. No mystique. No black box. Just a lawyer who got tired of copy-pasting contracts into ChatGPT tabs and decided to do something about it. What You'll Learn: "Vibe Coding" — How conversing with AI tools (not just instructing them) shaped better technical decisions "Bring Your Own Key" Architecture — Why your documents going straight to Google's API (with no middleman) actually matters Where the Real Moat Lives — If building software now takes hours not months, differentiation lies in the refinements — the nested lists, tables, and edge cases where most AI tools quietly fall apart Connect with Anson: LinkedIn | GitHub (Open Source Project) If you found this episode interesting, please like, subscribe, comment, and share! For more, head to lawwhatsnext.substack.com for: Focused conversations with leading practitioners, technologists, and educators Deep dives into the intersection of law, technology, and organisational behaviour Practical analysis of how AI is augmenting our potential
S1 · E29
Dec 30, 2025 · 19 min
Our First Year in Review 2025
Welcome to Law://WhatsNext - the show where we catch up with leading practitioners (lawyers; technologists; educators and more) who are leveraging emerging technologies to pursue their passion and objectives, and as a by product we get nerdy trying to understand the implications for the future of legal practice (and more broadly, knowledge work). To keep up with the pace of change and developments subscribe to this channel or to our newsletter at: https://lawwhatsnext.substack.com/ ---- In this episode, we've distilled a year of extraordinary dialogue into one 20-minute highlights reel. We've spent 2025 in conversation with legal industry pioneers — the general counsels, technologists, and educators redefining how law is practised, learned, and delivered. These are some of our standout moments from a series of compelling global conversations. What made the reel (this could honestly be a multi-part series): Part 1: Hype vs. Reality — Is AI progress real? Kevin Cohn (the soon to be CEO of Brightflag) provokes that the trough of disillusionment is coming but that shouldn't blight the reality that the value in the skills and expertise we used to highly prize are dramatically eroding Part 2: Agency, authenticity & trust Dana Rao (the former GC & Chief Trust Officer at Adobe) demonstrates that we can be the agents (rather than mere subjects) of positive change, and we loved learning more about the work he and his team at Adobe invested to build the Content Authenticity Initiative (to counter the ever increasing proliferation of deepfakes) Part 3: Leading in disruptive times Jessica Block (EVP at Factor) used a recent read (Notes on Complexity by Neil Theise) as the lens through which she explained the importance of cultivating the right environment (over systems) for the emergent properties of transformational change to "bubble" up. Part 4: Evaluating what's actually working Sigge Labor (President at Legora) explained for us the work that Legora performs to understand frontier model performance and how they react to new developments and assess leaps in capabilities. We anticipate that in 2026 more and more legal teams and firms will invest in their evaluation capabilities, and this conversation (that accompanied the release of GPT5 in the summer) is one to check out if you haven't already. Part 5: The skills we might lose Dan Hunter (Executive Dean, The Dickson Poon School of Law, King's College London) talked of the "terrifying bind" we encounter as we offload more and more cognitive work to compute - the work may get easier and more efficient but our cognitive development doesn't replicate (in terms of resilience) the old training training pathway. He has immediate concerns in the classroom and anticipates a coming gap in law firm talent pipelines. These are just glimpses. Check out our Spotify, Apple Podcasts, or Substack pages for the full conversations. Thank you for listening, supporting, and championing the show. We wish you a happy new year — Series 2 is coming soon 👀

Showing 1–20 of 20 episodes