Return on Token: Shawn Curran on Lawyer-Builders, Open Source, and the Real Cost of AI

Return on Token: Shawn Curran on Lawyer-Builders, Open Source, and the Real Cost of AI

🎙️ This week we sit down with Shawn Curran [https://www.linkedin.com/in/shawn-curran-b5b5858/], CEO of Jylo [https://jylo.ai/] — 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 [https://mikeoss.com/], Antti Innanen's Lavern [https://lavern.ai/] — 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 [https://www.linkedin.com/in/shawn-curran-b5b5858/] — 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/⁠⁠⁠⁠⁠⁠⁠ [https://lawwhatsnext.substack.com/].

AI-Native Hiring and Organisational Alignment with Stephanie Dominy

🎙️ This week we sit down with Stephanie Dominy [https://www.linkedin.com/in/stephaniedominy/] — General Counsel and Head of Ops at Tessl [https://tessl.io/].  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 [https://sierra.ai/blog/the-ai-native-interview]). 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 [https://www.anthropic.com/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 [https://crafty-counsel.com/events/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 [https://www.linkedin.com/in/stephaniedominy/], 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/⁠⁠⁠⁠⁠⁠ [https://lawwhatsnext.substack.com/].

The Defensibility Question: Helen Fan on What Survives When Frontier Models Climb the Stack

🎙️ This week we sit down with Helen Fan [https://www.linkedin.com/in/helenfanlegalai/] — 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 [https://www.linkedin.com/in/helenfanlegalai/] | Substack [https://helenfan1.substack.com/] | Personal site [https://helenlab.com/] The Legal AI Value Stack — Five Levels of Defensibility [https://helenfan1.substack.com/p/the-legal-ai-value-stack-five-levels] — Helen's now widely-shared framework. Start here if you have not read it yet. The OpenClaw LLP AI-Native Law Firm Experiment [https://helenlab.com/openclawlaw/] — Helen's public 100-day project, documented on LinkedIn and her site. Helen's Stanford Presentation [https://www.youtube.com/watch?v=ZG1Js1LT86I] — 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/⁠⁠⁠⁠⁠ [https://lawwhatsnext.substack.com/].

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 [https://www.linkedin.com/in/maryshenocarroll/] - the newly announced CEO of Legal Eng Consulting Group (LECG) [https://www.lecg.com/], 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 [https://cloc.org/] into the global home of legal ops. She moved into big law as Chief Operating Officer at Goodwin [https://www.goodwinlaw.com/en]. She has sold legal technology (Ironclad [https://ironcladapp.com/]), advises investors (she is an Executive in Residence at Signal Fire [https://www.signalfire.com/]), technology companies (Sandstone [https://sandstone.com/]), hosts her own podcast Pearls On Gloves Off [https://open.spotify.com/show/0DrT5PPH1gKOJQWkygHPV9], authors her own Newsletter [https://maryocarroll.substack.com/], 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 [https://www.lecg.com/about-us] (LECG) | on Substack [https://substack.com/@maryocarroll] | or LinkedIn [https://www.linkedin.com/in/maryshenocarroll/] --- 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/⁠⁠⁠⁠ [https://lawwhatsnext.substack.com/].

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 [https://www.linkedin.com/in/rebeccakeating/] and Laura Wright [https://www.linkedin.com/in/laura-wright-817a93116/] — barristers at 4 Pump Court [https://www.4pumpcourt.com/] and the co-authors of A Practical Guide to Quantum Computing and the Law [https://www.lawbriefpublishing.com/2024/12/free-chapter-from-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 [https://www.linkedin.com/in/rebeccakeating/] — Barrister at 4 Pump Court [https://www.4pumpcourt.com/our-people/rebecca-keating/] | Member, ICO Technology Advisory Panel Connect with Laura Wright [https://www.linkedin.com/in/laura-wright-817a93116/]— Barrister at 4 Pump Court [https://www.4pumpcourt.com/our-people/laura-wright/] | Co-host, 4 Pump Court podcast Their book — A Practical Guide to Quantum Computing and the Law [https://www.lawbriefpublishing.com/2024/12/free-chapter-from-a-practical-guide-to-quantum-computing-and-the-law/] (Law Brief Publishing, December 2024). The Law of AI (2nd edition, Sweet & Maxwell) [https://www.amazon.com/Law-Artificial-Intelligence-2nd/dp/0414114507]— Rebecca and Laura author the chapter on AI and Professional Liability. Society for Computers and Law (SCL) [https://www.scl.org/about-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/⁠⁠⁠ [https://lawwhatsnext.substack.com/].