Legally Disrupted
How AI is rewriting the rules for lawyers, in-house teams, and legal operations. Hosted by Zach Abramowitz.
37 episodes curated
Episodes
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 Kyle shares how early frustrations with outdated legal workflows pushed him to build internal tools, why generative AI changed everything, and what it really takes to break into the legal AI space today.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
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
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 t
E42 - Is Legal AI in Trouble or Just Getting Started? Cosmonauts Founder, Timo Karakashev
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 ex
E41 - The Future of AI is People: Legal Quants Founders Jamie Tso & Raymond Sun
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 fr
E40 - Lawyer Value in an AI World: Litigator, Coder & AI Evangelist Damien Riehl
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 ampl
E39 - AI vs Legacy SaaS in Legal: Min-Kyu Jung, CEO Ivo
Zach sits down with Min-Kyu Jung, founder of Ivo, to unpack one of the most honest AI startup stories in legal tech. This episode explores what it really takes to pivot in an AI revolution, why CLM may be in trouble, and how in-house legal teams are rethinking ROI in the age of AI. In this episode: Why Ivo scrapped its original product to go all-in on LLMs The “innovator’s dilemma” facing legacy CLM vendors Why in-house legal and law firms are fundamentally different AI markets How AI playbooks and redlining actually create ROI The shift from “adoption” to measurable business impact Why speed
E38 - How Will SaaSpocalypse Affect AI For Legal: Spellbook CEO Scott Stevenson
Zach checks in with second-time guest, Spellbook CEO, Scott Stevenson for a wide ranging conversation on some of the hottest topics of the day: Why positioning AI for Legal as a two horse race is deeply flawed The benefits of selling direct to lawyers as opposed to Chief Innovation Officers In-house legal buyers versus law firms BigLaw versus small and medium size law firms How AI Startups will need to contend with the SaaSpocalypse Learn More: Scott - https://www.spellbook.legal/ Zach - https://www.legallydisrupted.com/ Follow Along: Scott - https://x.com/scottastevenson?s=20 Zach - linkedin.
E37 - Zach and Richard’s Excellent Legal AI Adventure: Claude and the Legaltech Apocalypse
Zach reunites with Richard Tromans of Artificial Lawyer for another wide-ranging Legal AI Adventure, breaking down what it really means now that major AI players like Anthropic are officially entering the legal market. From the impact on commoditized legal AI tools to the rise of vibe coding, agentic workflows, and the looming decline of legacy legal tech implementations, Zach and Richard explore where legal AI is heading, and where lawyers should (and shouldn’t) be placing their bets as the industry moves toward an AI 2.0 era. In this episode: Will LLMs Kill LegalAI or Legacy SaaS Vibe coding
E36 - Too Much FOMO: Why I'm Back on the Legal AI Startup Investor Train with Sandstone CEO Nick Fleisher
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 lega
E35 - Are Legal AI Assistants Moving In-House? GC AI Founder Cecilia Ziniti
Zach speaks with Cecilia Ziniti, founder and CEO of GC AI, about why in-house legal teams are often ahead of law firms when it comes to adopting AI - and what that signals for the future of the profession. Drawing on her experience as a former general counsel and AI leader, Cecilia explains why legal AI must be purpose-built for real workflows, how trust and precision shape adoption, and why lawyers who learn to work with AI will gain a lasting edge. In this episode: Why in-house legal teams are leading AI adoption The limits of generic AI tools for legal work What lawyers actually need from A
E34 - How Will AI Work with Document Management? NetDocuments CPO Dan Hauck
Zach sits down with NetDocuments Chief Product Officer Dan Hauck to unpack how AI is truly being used inside law firms and in-house legal teams today - from large-scale document profiling to agentic assistants that search, summarize, and edit directly within the DMS. Recorded live at ND Inspire conference, Dan explains why lightweight models are unlocking new automation, how in-house teams are often leading on adoption, and why the real ROI of legal AI goes beyond efficiency to include better onboarding, less isolation, and more confident decision-making for lawyers at every level. In This Epi
E33 - Building the AI-First Law Firm: Jen Berrent on Covenant and the Next Era of Legal Services
Zach talks with Jen Berrent, former WeWork executive and founder of Covenant, an AI-first law firm reimagining how deals get done. They dive deep into what it means to build a law firm from the ground up around artificial intelligence — not as a tool, but as the foundation. Jen shares her perspective on why too much work still runs through Big Law, how AI is transforming the middle tier of legal work, and what it takes to balance human expertise with machine efficiency. In this episode: What an “AI-first” law firm actually looks like How Covenant is redesigning legal workflows from scratch The
E32 - Harvey Co-Founder Gabe Pereyra on Building the Fastest-Growing Legal AI Company in History
Zach sits down with Harvey cofounder Gabe Pereyra to talk about what changed after “Attention Is All You Need,” why partners - not juniors - are driving Harvey’s adoption, and how AI is teaching law firms to learn faster than ever. In this episode: The origin story of Harvey and how it became the “Dallas Cowboys of Legal Tech” Lessons from the early days of AI at Google Brain and DeepMind Why the real opportunity isn’t automation — it’s amplification How top law firms are already using AI for high-level strategic work The emerging hybrid model of AI + human legal reasoning Why firm size and st
E31 - Zach and Richard's Excellent Legal AI Adventure: Robin AI's Struggles and the Future of LegalTech
Zach and Richard delve into the recent challenges faced by Robin AI, a pioneering legal tech company that has laid off staff and is seeking a buyer due to disappointing growth. They explore the significance of this news within the broader AI and legal tech industry, discussing whether Robin AI's struggles signal larger issues in the AI market. In this episode: Robin AI's Struggles Personal Connections and Reflections Speculations and Broader Implications Comparing AI Legal Tech Companies Legal Experts in Tech Companies Investment in AI-Driven Legal Services The Importance of Expertise with AI