Zach Abramowitz is Legally Disrupted

Hosted by Zach Abramowitz

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May 2026

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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!

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52 recent

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

May 31, 2026Episode 5548 min

E51 - Can Open Source Compete with Harvey and Legora? Mike OSS Founder William Chen

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

May 17, 2026Episode 541 hr 15 min

E50 - Inside Harvey with Winston Weinberg, Founder & CEO of Harvey

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

May 11, 2026Episode 5346 min

E49 - Harvey and Legora vs AI First Firms, Logan Brown, Soxton

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

April 30, 2026Episode 5245 min

E48 - What Top VCs Actually Think About Legal AI with Keith Rabois, Khosla Ventures

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

April 28, 2026Episode 5150 min

E47 - Zach and Richard’s Excellent Legal AI Adventure: Harvey and Legora vs Claude?

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

April 19, 2026Episode 5050 min

E46 - AI for Judges? AAA CEO Bridget McCormack and Learned Hand CEO Shlomo Klapper

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

April 3, 2026Episode 4945 min

E45 - How to Get a Job at Legora, Harvey and Other Legal AI Startups, Kyle Poe, VP of Legal Innovation at Legora

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

March 26, 2026Episode 4831 min

E44 - Building a Law Firm and a Product: LawPro.ai Co-Founder and Zirkin Schmerling Partner, Josh Schmerling

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

March 19, 2026Episode 4739 min

E43 - AI and the Future of In-House Legal, Sandstone Co-Founder Jarryd Strydom

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