🎙️ 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."

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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.

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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!

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For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/.

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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/

🎙️ 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.

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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. 

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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

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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).

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For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠⁠⁠⁠.

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.

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🎙️ 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.

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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.

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Connect with Antti Innanen — Lawyer, legal designer & builder | Lavern (GitHub repo, 100% open) | Find him on LinkedIn

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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!

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🎙️ 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. 

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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.

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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. 

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Connect with Shawn Curran — CEO of Jylo 

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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.

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For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠⁠⁠.

🎙️ 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.

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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. 

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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.

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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 👇

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For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠⁠.

🎙️ 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.

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For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠.

🎙️ 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. 

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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.  

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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. 

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Connect with Mary O'Carroll — through Legal Eng Consulting Group (LECG) | on Substack | or LinkedIn

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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.

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For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠.

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.

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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.

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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.

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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.

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For more conversations at the intersection of law and technology, head to⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠.

🎤 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.

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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.

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Connect with Bilva Chandra — on LinkedIn | Or by subscribing to Role Model, her new newsletter on AI and society.

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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.

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For more conversations at the intersection of law and technology, head to⁠⁠ https://lawwhatsnext.substack.com/⁠⁠.

🎤 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.

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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.

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"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.

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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 

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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.

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For more conversations at the intersection of law and technology, head to⁠ https://lawwhatsnext.substack.com/⁠.