Zach Abramowitz is Legally Disrupted

Hosted by Zach Abramowitz

Technology

Website RSS feed

Episodes

Latest episode

Sep 2026

Language

About the show

This is a podcast for the people who want to understand and shape the future of the law. Hey there, I'm Zach Abramowitz and I am Legally Disrupted! 15 years ago, my legal career was disrupted by tech. Today, I'm advising the some of the most influential legal service providers in the world on their AI strategy and investing in some of the promising #legalAI startups. Every week, I talk to the builders, founders, operators, and decision-makers driving change in a legal ecosystem being reshaped by AI. We don't just revel in the gloriousness of AI -- we do that too! But, we also break down complex ideas and separate signal from noise. Our content focuses on what’s real, what matters, and what everyone else is missing. So what are you waiting for? Let's get disrupted!

Listen to episodes

60 recent

September 28, 2026Episode 6546 min

E61 - How To Get a Job at Harvey, Katie Burke, COO, Harvey

Lawyers have been reaching out to me about breaking into legal tech for years. Now engineers at some of the biggest tech companies in the world are looking at Harvey too, and I think that's the clearest signal yet that professional services became a hot space to be in, and that just wasn't true a few years ago. Katie Burke spent nearly twelve years at HubSpot before betting on Winston, Gabe and Harvey. She explains why Harvey doesn't want lawyers running from Big Law, what makes someone stand out in an interview, and why top engineers suddenly want to work in legal. And yes, someone still tweets that Harvey is going to zero every six months. In this episode: 0:00 Zach’s Hot Disruptive Legal Take 4:22 Why Katie Burke Left HubSpot for Harvey 8:48 Betting on Winston and Gabe in Their 20s 11:39 The “Harvey Is Going to Zero” Tweet Cycle 12:54 Is There Actually a Moat in Legal AI? 15:23 Is Harvey Only for Big Law Juniors? 18:01 Can Harvey Compete With the Frontier Models? 20:55 Harvey’s Killer Feature May Be Its SLAs 22:37 Why Top Engineers Suddenly Want to Work in Legal 25:40 How Many Harvey Employees Are Lawyers? 27:34 Who Works Harder: Big Law or Harvey? 30:18 Does Working at Harvey Burn People Out? 32:30 The #1 Way to Stand Out in a Harvey Interview 36:18 Where Harvey Is Hiring Right Now 38:00 The HubSpot Playbook at Harvey 39:50 Should You Even Make a Three-Year Plan? 41:18 Dharmesh Shaw Called It in 2023 42:30 You Don’t Need to Write Code to Use AI 45:08 Where to Find Open Roles at Harvey Subscribe to Zach’s newsletter: https://www.legallydisrupted.com/ Follow Zach on LinkedIn: linkedin.com/in/zachabramowitz Follow Zach on X: https://x.com/ZachAbramowitz?s=20 Follow Katie: https://www.linkedin.com/in/katie-burke-965767a/ Engage Killer Whale Strategies: https://www.killerwhalestrategies.com

September 9, 2026Episode 6451 min

E60 - Alex Su, President, Latitude Legal

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

August 30, 2026Episode 6348 min

E59 - Legora and Legal AI are Moving into Litigation: Greg Mostyn, CEO Wexler.ai

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

August 19, 2026Episode 6255 min

E58 - Zach and Richard’s Excellent Legal AI Adventure: Will Legal AI Cause Legal to Actually Change?

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

August 16, 2026Episode 6148 min

E57 - We are a Judgement-First Law Firm, Brian Belt, Founding Partner, Acevedo Belt

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

August 12, 2026Episode 6059 min

E56 - AI-Pilled, Not AI-First: Arlo Devlin-Brown, Founding Principal, TDB Law

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

July 29, 2026Episode 5943 min

E55 - Lawyers Leaving Trad Law for AI-First Firms? Norm Law Partner Batya Nadler

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

July 17, 2026Episode 581 hr 6 min

E54 - Who Will Win AI for In-House Counsel? Ross McNairn, CEO Wordsmith.ai

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

June 23, 2026Episode 5737 min

E53 - The AI First Firm Valued at Close to $1 Billion, Manifest OS CEO Dan Mishin

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

June 16, 2026Episode 5656 min

E52 - Is Legal AI a Trillion-Dollar Opportunity? Legora CEO, Max Junestrand

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