Zach Abramowitz is Legally Disrupted

Alex Su is one of those people I need to catch up with every now and then just to see what he's thinking. Since we recorded this, Alex was named President of Latitude Legal. He understands both the people selling lawyers on change and the lawyers they're trying to convince, and those two groups don't always see the same world. We get into Harvey, Legora and Claude, the billable hour, junior associates, where human judgment still matters, why trust may be part of Harvey's moat, and how both of us are using AI differently now than we were in 2023. 0:00 Zach's Hot Disruptive Legal Take 3:22 Harvey vs. Legora vs. Claude 5:58 Can Claude Gobble Up Harvey? 8:00 Why Haven't Junior Associates Been Replaced? 10:30 In-House Is Outpacing Law Firms on AI 12:49 Why Hasn't AI Killed the Billable Hour? 17:49 Why Hourly Rates Could Go Up 20:04 Is Anyone Less Busy Because of AI? 22:39 Where AI-Native Law Firms Could Win 24:28 If NDAs Are Never Litigated, Why Sign Them? 28:06 AI Made My Content More Human 31:11 How We Actually Use AI for Writing 38:28 How Many Lawyers Do You Need With AI? 40:22 When AI Gets Better, Trust Matters More 44:50 Has Harvey Built a Moat? 46:54 How Do You Compete With Harvey? 49:06 Is CLM Dead in the Water? Subscribe to Zach’s newsletter: https://www.legallydisrupted.com/ Follow Zach on X: https://x.com/ZachAbramowitz?lang=en Follow Alex: https://www.linkedin.com/in/alexander-su Engage Killer Whale Strategies: https://www.killerwhalestrategies.com

Legora just acquired Wexler, and I think it's the clearest signal yet that AI in law is moving from transactional work to litigation. Gregory Mostyn, co-founder and CEO of Wexler, built the company just to the right of discovery. Not doc review, what happens when the documents actually hit the lawyers. He explains why he bet on facts instead of documents, why he stayed a scalpel while Harvey and Legora built Swiss Army knives, and why a company that wasn't for sale sold anyway. I also pushed him on the two questions I get from lawyers every week. Are we in a bubble? And if the models are this good, why buy anything at all instead of building it yourself? His answer to the second one is the part I'd replay. And yes, the company is named after Kim Wexler. In this episode: 00:00 - Zach’s Hot Disruptive Legal Take 07:33 - Already Seeing the Benefits of Joining Legora 08:26 - Wexler Is Just to the Right of eDiscovery 10:44 - The Atomic Unit of Analysis Is Facts 13:12 - Building a “Case Brain” 15:02 - Scalpel vs. Swiss Army Knife 17:21 - AI for Litigators 21:08 - Are We in an AI Bubble? 24:24 - Product Advice from an Old-School Judge 26:53 - Why Security and Accuracy Are More Important than Speed 28:59 - The Main User of Wexler Is the Wexler Agent 30:55 - Can You Run AI Live in a Deposition? 33:57 - Can Lawyers Build This Themselves? 38:46 - Story behind Legora’s Acquisition 43:50 - Getting in the Room Is the Hard Part 46:01 - Will AI Kill Relativity? 46:58 - Inspired by Kim Wexler from Better Call Saul Subscribe to Zach’s newsletter https://www.legallydisrupted.com/ Follow Zach on X https://x.com/ZachAbramowitz?lang=en Follow Gregory https://uk.linkedin.com/in/gregory-mostyn-9b3a89b8 Engage Killer Whale Strategies https://www.killerwhalestrategies.com

Richard Tromans of Artificial Lawyer is back with Zach and on the attack as they square up over whether massive Legal AI funding, truly signals systemic transformation. They then discuss whether these massive sums of money are hitting a tipping point and what could happen if the levee breaks. Maybe the legal industry is simply running in place. In this Episode: 00:00 Zach’s Hot Disruptive Legal Take 00:42 Could Harvey be Valued at $16B? 01:50 Legal AI Fatigue 03:20 Harvey, Legora and The Big Short? 08:46 Legal AI a Luxury Handbag Market? 10:31 AI Wizards and Muggles in Big Law 13:35 The Seeds of Systemic AI Impact 21:36 Valuations Signal Technology is Essential In Legal Service Delivery 23:02 Jevons Paradox and the Volume of Modern Contracts 30:08 AI Still Needs Daycare 36:48 “New Mod” and “AI First” Firms are Pressuring Big Law 44:18 Is the Market Wrong on TR/Lexis 49:48 Are Chief AI Officers CINOs Differently Packaged? Subscribe to Zach’s newsletter https://www.legallydisrupted.com/ Follow Zach on X https://x.com/ZachAbramowitz?lang=en Engage Killer Whale Strategies https://www.killerwhalestrategies.com Learn more about Richard - tromansconsulting.com , artificiallawyer.com Follow Richard - linkedin.com/in/artificiallawyer , https://x.com/ArtificialLawya

A 35-Year Big Law Veteran Is Doing the Best Work of His Career With AI But He Doesn’t Call His Firm AI-First. Brian Belt explains why Acevedo Belt is “judgment-first,” why he thinks legal AI is a bargain, and how AI is changing everything from junior-lawyer training to the kinds of matters a small firm can take on. In this episode: 0:00 Zach's Hot Disruptive Legal Take 4:25 The Big Law Veteran Who Loves AI 6:21 "Harvey Writes Better Than I Do" 7:39 Why "ROI" Is the Wrong Metric 11:13 Clients Notice the Difference 13:47 You Can Finally Train Junior Associates 16:07 New Way to Train Associates 21:17 Scaling Up and Scaling Down 24:24 Why Harvey Is Better for Small Firms 28:46 Legal AI is a Bargain! 34:46 Process Mapping & the Best Use Cases 36:59 Why Not Just Use the Base Models? 37:54 Do Your Old Big Law Colleagues Get It? 40:32 What Is a "Judgment-First" Law Firm? 43:21 Do the Best Lawyers Run on No Sleep? Subscribe to Zach’s newsletter: https://www.legallydisrupted.com/ Follow Zach on X: https://x.com/ZachAbramowitz?lang=en Follow Brian on LinkedIn: https://www.linkedin.com/in/brianbelt Engage Killer Whale Strategies: https://www.killerwhalestrategies.com

What happens when a veteran litigator starts treating AI less like a chatbot and more like an operating system for his cases? In this episode, Zach speaks with Arlo Devlin-Brown, founder of TDB Law, about how AI is changing the way he actually practices law. They discuss why AI may be particularly powerful for litigators, how Arlo has built an AI-powered system that continuously tracks his cases, and why the technology is more useful for exploring arguments and strategy than simply generating finished work. The conversation also explores the future of junior lawyers, why big law’s leverage model may be under pressure, and why Arlo rejects the idea that firms should sell themselves as “AI-native” rather than simply being excellent lawyers who use AI well. In this episode: Why AI may be more transformative for litigation than transactional law How Arlo uses AI as an operating system and shared memory for his cases Why AI can make junior lawyers more valuable, not obsolete How AI could fundamentally reshape the Big Law leverage model Why “AI-native” law firms may be missing the point Subscribe to Zach’s newsletter https://www.legallydisrupted.com/ Follow Zach on X https://x.com/ZachAbramowitz?lang=en Follow Along on LinkedIn: Arlo - https://www.linkedin.com/in/arlodb Zach - www.linkedin.com/in/zachabramowitz Engage Killer Whale Strategies https://www.killerwhalestrategies.com

What happens when a veteran Big Law attorney leaves a traditional partnership to help build a law firm from scratch? In this episode, Zach speaks with Batya Nadler, Partner at Norm Law, about her decision to join one of the legal industry's most ambitious AI-native firms. They discuss how Norm combines experienced lawyers with legal engineers and AI agents, why repeatable legal workflows are the ideal starting point for automation, and how AI is changing, not replacing, the role of senior attorneys. The conversation also explores why client relationships remain the foundation of legal practice, what skills lawyers need to thrive in an AI-first world, and why Batya believes the future belongs to firms built around AI from day one. In this episode: Why Batya left Big Law to help build an AI-native law firm from the ground up How legal engineers and AI agents are transforming repeatable legal workflows Why senior lawyers remain essential, even as AI automates more legal work How Norm is rethinking the traditional law firm model around AI-native infrastructure What lawyers can do today to become AI-fluent and prepare for the future of legal practice Subscribe to Zach’s newsletter https://www.legallydisrupted.com/ Follow Zach on X Zach https://x.com/ZachAbramowitz?lang=en Follow Batya https://www.linkedin.com/in/batya-nadler-1ba85410 Engage Killer Whale Strategies https://www.killerwhalestrategies.com

Why are some general counsel suddenly becoming the most influential executives in the C-suite? In this episode, Zach speaks with Ross McNairn, founder and CEO of Wordsmith, about why AI is fundamentally changing the role of in-house legal teams. They discuss how legal departments are evolving from cost centers into strategic operators, why generic AI chatbots aren't enough for enterprise legal work, and how the next generation of legal technology will help GCs measure ROI, manage legal operations, and reduce reliance on outside counsel. The conversation also explores why traditional CLM systems have fallen short, the emergence of legal engineering, and what the future of corporate legal teams looks like in an AI-native world. In this episode: •⁠ ⁠Why AI is turning general counsel into technology leaders inside their organizations •⁠ ⁠Why enterprise legal teams need more than ChatGPT to transform their workflows •⁠ ⁠How legal departments can finally measure ROI and demonstrate business value •⁠ ⁠Why traditional CLM systems failed and what comes next •⁠ ⁠How legal engineering is becoming one of the most important new roles in corporate legal Follow Along: Ross - https://x.com/rossmcnairn?lang=en , https://www.linkedin.com/in/rossmcnairn Zach - https://x.com/ZachAbramowitz?lang=en , www.linkedin.com/in/zachabramowitz Subscribe to Zach’s newsletter https://www.legallydisrupted.com/ Engage Killer Whale Strategies https://www.killerwhalestrategies.com

Why would top venture capital firms invest $60 million into an immigration law startup at a $750 million valuation? In this episode, Zach speaks with Dan Mishin, founder and CEO of Manifest, about his vision for transforming one of the most complex and underserved areas of legal practice. They discuss why immigration law became the company's first focus, how AI is helping lawyers process cases faster and more accurately, and why Manifest is building far more than a traditional law firm. The conversation explores the challenges facing both lawyers and clients in the immigration system, the opportunity to create AI-native legal infrastructure, and what happens when software, operations, and legal expertise are combined into a single platform. In this episode: Why investors valued Manifest at $750 million after its first major funding round How AI is transforming immigration law through speed, accuracy, and automation Why Manifest is building legal infrastructure, not just another law firm The hidden operational problems holding back many legal practices How AI-native platforms could help lawyers serve more clients at lower cost Learn More: https://www.legallydisrupted.com/ Follow Along: Dan - https://x.com/mishindan1 , https://www.linkedin.com/in/danielmishin Zach - https://x.com/ZachAbramowitz?lang=en , www.linkedin.com/in/zachabramowitz Subscribe to Zach’s newsletter https://www.legallydisrupted.com/ Engage Killer Whale Strategies https://www.killerwhalestrategies.com

As AI capabilities accelerate, how should law firms and legal departments prepare for a future where agents can perform increasingly complex legal work? In this episode, Zach speaks with Max Junestrand, CEO and co-founder of Legora, about the rapid evolution of legal AI and what it means for the future of legal services. They discuss the recent wave of law firms building their own AI initiatives, why legal teams are adopting AI faster than many realize, and how firms can rethink their business models in an agent-driven world. The conversation also explores the role of legal-specific AI products, the growing importance of transformation partners, and why Max believes legal AI represents a trillion-dollar opportunity. In this episode: Why law firms are investing heavily in AI How legal teams can prepare for a future where AI agents perform increasingly complex work Why legal-specific AI products still matter in a world of Claude, GPT, and other frontier models How AI is changing the economics of legal services and creating new opportunities for firms Why Max believes legal AI could become a trillion-dollar market opportunity Subscribe to Zach’s newsletter https://www.legallydisrupted.com/ Follow Zach on X https://x.com/ZachAbramowitz?lang=en Follow Max on X https://x.com/MaxJunestrand Engage Killer Whale Strategies https://www.killerwhalestrategies.com

What happens when a former lawyer looks at the biggest names in legal AI and decides he can build a competing product in two weeks? In this episode, Zach speaks with Will Chen, founder of Mike, an open-source legal AI platform that has quickly gained attention for challenging conventional wisdom in legal tech. They discuss why some lawyers are frustrated with existing legal AI products, the rise of vibe coding, and how AI is making software development more accessible than ever. The conversation also explores open-source legal AI, the growing movement toward law firms building their own tools, and why some believe the future of legal technology may be far more decentralized than today's market leaders expect. In this episode: Why Will believes many legal AI products are little more than thin wrappers around frontier models How vibe coding is enabling lawyers to build software without traditional engineering backgrounds The case for open-source legal AI and local-first deployment in law firms Why more firms are exploring building their own AI tools instead of buying them How AI could lower the barriers to starting a law firm or legal tech company Learn More: https://www.legallydisrupted.com/ Follow Along: Will - https://x.com/willchen500 , https://hk.linkedin.com/in/will-chen-0bb0a477 Zach - https://x.com/ZachAbramowitz?lang=en , https://www.linkedin.com/in/zachabramowitz

How did Harvey become the defining company in legal AI and where does the industry go from here? In this episode, Zach speaks with Winston Weinberg, founder and CEO of Harvey, about the company’s rapid rise at the center of the legal AI boom. They discuss how law firms are actually adopting AI, why legal workflows are uniquely suited for large language models, and what it takes to build products trusted by the world’s top legal organizations. The conversation also explores the evolving relationship between lawyers and AI, the challenges of scaling legal technology, and why the next generation of legal professionals may work very differently than the last. In this episode: How Harvey became one of the most influential companies in legal AI What law firms are actually looking for when adopting AI tools Why legal work is especially well-suited for large language models The biggest challenges in building trusted AI products for lawyers How AI could fundamentally reshape the future of legal practice and legal careers Learn More: Winston - https://www.harvey.ai/blog/author/winston-weinberg Zach - https://www.legallydisrupted.com/ Follow Along: Winston - https://www.linkedin.com/in/winston-weinberg Zach - linkedin.com/in/zachabramowitz

What happens when you rebuild a law firm from scratch in the age of AI? In this episode, Zach speaks with Logan Brown, founder of Soxton, an AI-first law firm serving startups as an on-demand, AI-powered general counsel. They discuss how Soxton is rethinking legal services from the ground up, why fixed pricing and automation are expanding access to legal help, and where traditional law firms still have the edge. The conversation also dives into the explosion of new startups, the rise of AI-driven litigation, and whether Big Law is facing a slow but inevitable transformation. In this episode: How AI-first law firms are redesigning legal services and pricing models Why startups are delaying hiring in-house counsel with AI-powered alternatives Where traditional law firms still win—and where they’re most vulnerable Why AI could drive both more startups and more litigation How legal careers and firm structures may fundamentally change in the next decade Learn More: Logan - https://fortune.com/2026/04/05/logan-brown-soxton-founder-2-5-million-ai-powered-law-firm-started-da-office-12-years-old/ Zach - https://www.legallydisrupted.com/ Follow Along: Logan - https://www.linkedin.com/in/logan-brown-03765552 Zach - linkedin.com/in/zachabramowitz

Money is pouring into legal AI, but how do top-tier investors actually evaluate the space? In this episode, Zach speaks with Keith Rabois, Managing Director at Khosla Ventures and one of the most successful investors of the past two decades, about how he thinks about legal tech in the age of AI. They discuss why elite founders are suddenly flocking to legal, the risks facing application-layer startups, and what separates real opportunities from hype. The conversation also explores why Rabois invested in Spellbook, why he’s skeptical of some of the biggest names in legal AI, and how changing incentives across law firms and in-house teams are reshaping the market. In this episode: Why top VCs are following talent, not verticals, into legal AI The biggest risk facing legal AI startups: speed of replication and weak moats Why in-house legal teams may be a better market than Big Law What makes Spellbook compelling, and why contracts are the real opportunity How AI is challenging traditional software economics and long-term value Learn More: Keith - https://www.khoslaventures.com/team/keith-rabois Zach - https://www.legallydisrupted.com/ Follow Along: Keith - https://www.linkedin.com/in/keith Zach - linkedin.com/in/zachabramowitz

Is the legal AI race still a two-horse battle, or has a new contender changed everything? In this episode, Zach speaks with Richard Tromans, founder of Artificial Lawyer, about the rapid rise of Claude and what it means for the broader legal tech ecosystem. They unpack how frontier model providers are reshaping the market, why law firms are experimenting with multiple AI tools at once, and whether general-purpose AI could start replacing legal-specific platforms. The conversation also explores shifting buying behavior in law firms and in-house teams, the real “moats” in legal AI, and why recent hallucination controversies may say more about legal workflows than the technology itself. In this episode: Why Claude is suddenly at the center of the legal AI conversation How general-purpose AI tools could disrupt legal tech spending The real competitive moat in legal AI: brand, trust, and distribution Why law firms are adopting multiple AI models instead of picking one What AI hallucination cases reveal about legal workflows - not just the tech Learn More: Zach - https://www.legallydisrupted.com/ Richard - tromansconsulting.com , artificiallawyer.com Follow Along: Zach - linkedin.com/in/zachabramowitz Richard - linkedin.com/in/artificiallawyer , https://x.com/ArtificialLawya

Recording at LegalWeek in New York, Zach sits down with Shlomo Klapper (founder of Learned Hand) and Bridget McCormack, former Chief Justice of the Michigan Supreme Court and now CEO of the American Arbitration Association, to challenge one of the biggest double standards in legal AI: “AI for me, but not for thee.” Lawyers are now widely using AI, but the moment it touches judges or arbitrators, support drops off. That hesitation comes as courts are under real strain, with judges handling thousands of cases a year and only minutes to decide each one, and no realistic way to keep up. Shlomo describes Learned Hand’s “AI law clerk,” built to support judicial research, analysis, and drafting, while Bridget brings the perspective of someone who has both made decisions on the bench and now leads a major dispute resolution institution. The conversation moves beyond AI as an assistant and into a harder shift: AI as part of decision-making itself, and whether the system can continue to function without it. Learn More: Bridget - http://www.aaaicdrfoundation.org/director/bridget-m-mccormack Shlomo - https://www.learned-hand.ai/ Zach - https://www.legallydisrupted.com/ Follow Along: Bridget - https://www.linkedin.com/in/bridget-mary-mccormack-26700b30 Shlomo - https://www.linkedin.com/in/sklapper Zach - linkedin.com/in/zachabramowitz

What does it actually look like to go from practicing law to building the future of legal AI? In this episode, Zach speaks with Kyle Poe, former Big Law partner and now a leader at Legora, about his unconventional path from litigation to legal tech. Kyle shares how early frustrations with outdated legal workflows pushed him to build internal tools, why generative AI changed everything, and what it really takes to break into the legal AI space today. They also dive into how billing models are evolving, the emergence of the “legal engineer,” and why relationships and adaptability may matter more than ever in an AI-driven legal industry. In this episode: How Kyle transitioned from Big Law to a leading role in legal AI Why generative AI is a true inflection point for legal practice The emergence of the “legal engineer” and new career paths for lawyers What lawyers get wrong about breaking into legal tech—and how to do it right How AI is shifting legal careers toward relationships, adaptability, and high-agency work Learn More: Kyle - https://legora.com/blog/a-window-of-opportunity-the-lawyer-rewiring-legal-practice-for-the-ai-age Zach - https://www.legallydisrupted.com/ Follow Along: Kyle - https://www.linkedin.com/in/jkylepoe Zach - linkedin.com/in/zachabramowitz

Zach Abramowitz sits down with Josh Schmerling, partner at Zirkin & Schmerling and co-founder of LawPro.ai, to explore how building technology inside a law firm is reshaping personal injury practice. Josh shares how an internal tool for processing medical records evolved into a broader litigation platform, and what it means to commercialize a product while still running a high-volume plaintiff’s firm. The conversation dives into product-market fit, adoption dynamics, and how tech, combined with private equity, could fundamentally change the competitive landscape of PI law. In this episode: How an internal tool became a market-facing legal tech product The advantages (and tensions) of building software inside a law firm What drives real product-market fit in legal tech Adoption trends across personal injury firms The role of private equity in reshaping the PI ecosystem Learn More: Josh - https://www.lawpro.ai/team/josh-schmerling Zach - https://www.legallydisrupted.com/ Follow Along: Josh - https://www.linkedin.com/in/josh-schmerling-287489ab Zach - linkedin.com/in/zachabramowitz

What are in-house lawyers actually doing with AI right now? In this episode, Zach speaks with Jarryd Strydom, co-founder of Sandstone, about what he learned from a cross-country road trip meeting with corporate legal teams across the United States. They discuss how legal departments are experimenting with AI tools, the growing “build vs. buy” debate as lawyers explore vibe-coding their own workflows, and why legacy legal tech infrastructure may struggle in an AI-native world. In this episode: What in-house lawyers across the U.S. are actually doing with AI today The rise of “vibe coding” and the new build vs. buy debate for legal teams Why traditional CLM systems often fail to capture real business context How AI could finally unlock institutional legal knowledge inside companies Why legal teams are being pushed to adopt AI as other departments move faster How AI might reshape the structure of in-house legal teams What junior lawyers should be thinking about in an AI-driven legal market Learn More: Jarryd - https://www.event.law.com/corpcounsel-gcc-east/speaker/2017419/jarryd-strydom Zach - https://www.legallydisrupted.com/ Follow Along: Jarryd - https://www.linkedin.com/in/jarrydstrydom Zach - linkedin.com/in/zachabramowitz

Just in time for Legal Week, Zach sits down Cosmonauts founder and legal tech insider Timo Karakashev for a wide-ranging conversation about where the legal AI market really stands. Timo shares what he’s seeing on the ground: growing demand for “premium” legal AI tools, dissatisfaction with generic enterprise AI solutions, and a market that’s still in the very early innings of adoption. In this episode: Why legal AI tools like Harvey and Legora feel “premium” compared to generic AI The growing dissatisfaction with enterprise AI tools like Copilot Why demand for intelligence in legal work far exceeds human supply How legal AI adoption differs across regions, including Australia The debate over whether AI will disrupt or strengthen the SaaS model Why IP law has historically lagged in tech adoption and why that’s changing How legal tech conferences are evolving to focus more on practitioners and operators ⁠Why innovation at the top of the market could eventually improve access to justice Learn More: Timo - https://www.crunchbase.com/person/timo-karakashev Zach - https://www.legallydisrupted.com/ Follow Along: Timo - https://uk.linkedin.com/in/timo-from-cosmonauts Zach - linkedin.com/in/zachabramowitz

What if AI doesn’t just replace software, but shifts the value of a tech company from the product to the people? That’s the real shift hiding in plain sight. As the models get better and cheaper, the product layer starts to collapse. And when that happens, the leverage doesn’t sit with whoever licensed the right platform. It sits with the lawyers who understand what’s happening underneath, the ones building their own workflows, configuring the models directly, and rethinking how legal work is produced in the first place. This isn’t about another AI tool. It’s about agency. It’s about moving from billing time to designing systems. And the gap forming right now between lawyers who experiment and lawyers who hesitate is going to matter a lot more than the next headline valuation. In this episode: We’re probably focused on the wrong layer As the models improve, the product matters less Leverage is shifting toward lawyers willing to build This isn’t about adopting AI - it’s about agency The gap forming right now is going to compound References: Legal Quants - https://www.legalquants.com/ Learn More: Zach - https://www.legallydisrupted.com/ Follow Along: Jamie - https://hk.linkedin.com/in/jttso Raymond - https://au.linkedin.com/in/raymond-sun-64576a122 Zach - linkedin.com/in/zachabramowitz