Zach Abramowitz is Legally Disrupted

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 Kyle shares how early frustrations with outdated legal workflows pushed him to build internal tools, why generative AI changed everything, and what it really takes to break into the legal AI space today.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

Timo Karakashev, founder of Cosmonauts and legal tech organizer, guides a tour of the legal AI landscape. He contrasts premium legal AI with generic enterprise tools. He explores why precision and UX matter for law, how demand for intelligence outstrips human supply, regional adoption differences, and why niche IP and practitioner-focused innovations are gaining momentum.

Raymond Sun, corporate lawyer and legal engineer who builds frontier AI for legal workflows. Jamie Tso, corporate lawyer who popularized vibe coding and crafts developer-focused AI workflows. They discuss how AI shifts value from products to people. They focus on lawyers building custom models, the rise of bespoke legal tools, and why community and skills will outlast packaged apps.

What does it mean to be a valuable lawyer in the age of AI? In this episode, Zach sits down with litigator, technologist, and AI evangelist Damien Riehl to explore how legal expertise evolves, not disappears, in a world of generative models and automation. From his unique path as both a practicing attorney and self-taught coder to his widely discussed “All the Music” project, Damien argues that the future belongs to lawyers who understand systems, leverage technology, and rethink what clients actually pay for. This is a conversation about professional reinvention, leverage, and why AI may amplify - rather than replace - the best lawyers.   In this episode: Why AI changes how lawyers deliver value, but not why they matter The advantage of lawyers who can code (or at least think like engineers) Damien’s “All the Music” project and what it reveals about IP systems The difference between automation and augmentation in legal work How litigators should think about AI tools today Why understanding technology is becoming table stakes for legal credibility What the next generation of high-value lawyers will look like Learn More: Damien - https://www.ted.com/speakers/damien_riehl Zach - https://www.legallydisrupted.com/   Follow Along: Damien -  https://www.linkedin.com/in/damienriehl Zach - linkedin.com/in/zachabramowitz  

Min-Kyu Jung, founder and CEO of Ivo and former corporate lawyer turned self-taught coder, recounts pivoting his startup to LLM-first contract intelligence. He discusses scrapping the old product, building redlining prototypes, why CLM vendors face an innovator’s dilemma, and how in-house legal teams rethink ROI and speed over pure accuracy in AI workflows.

Scott Stevenson, CEO and co-founder of Spellbook, a legal AI startup that builds contract review and drafting tools. He discusses why legal AI is not a two-horse race. He explains selling straight to lawyers, differences between in-house, BigLaw and small firms, and why rapid product iteration and agents matter. He also covers market shakeups from the SaaSpocalypse and why purpose-built UIs beat generic chat plugins.

Richard Tromans, founder of ArtificialLawyer and legal tech reporter, joins to map the future of legal AI. They unpack Anthropic’s move into legal, vibe coding and agentic workflows. They debate which tools face disruption, why many implementations overpromise, and what AI 2.0 could mean for lawyers.

Zach announces that, for the first time since ChatGPT launched, he's investing in a legal AI startup. In this episode, he's joined by Nick Fleisher, CEO of Sandstone, to unpack why in-house legal teams, not law firms, may be the biggest winners of the AI era. Drawing on Nick's background at McKinsey where he advised law firms on AI, the conversation explores why legacy tools are failing lawyers and how AI can solve a problem that plagues in-house teams: working seamlessly with their business without slowing them down and being a bottleneck. In this episode: Why Zach decided to invest in a legal AI startup now What in-house legal teams actually need from AI Why CLM tools struggle with adoption and ROI How AI changes legal’s relationship with the business Measuring success beyond “time to contract” Why vertical legal software beats generic AI tools What makes Sandstone different from Harvey, Legora, and CLMs References: $10M Seed Round Announcement Learn More: Zach - legallydisrupted.com Nick - sandstone.com Follow Along: Zach - linkedin.com/in/zachabramowitz Nick - https://www.linkedin.com/in/nicholas-fleisher