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 Kyle shares how early frustrations with outdated legal workflows pushed him to build internal tools, why generative AI changed everything, and what it really takes to break into the legal AI space today.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

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

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

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 often matters more than accuracy in AI UX How contract intelligence is becoming CLM 2.0 Learn More: Min-Kyu - https://www.auckland.ac.nz/en/alumni/our-alumni/40-under-40/a-z-list-of-profiles/min-kyu-jung.html Zach - https://www.legallydisrupted.com/ Follow Along: Min-Kyu - https://www.linkedin.com/in/min-kyu-jung Zach - linkedin.com/in/zachabramowitz

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.com/in/zachabramowitz

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 vs enterprise software Generic AI versus Legal Applications Implementations are a grift The limits of automation What will AI 2.0 mean for lawyers? 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

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

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 AI systems Trust, accuracy, and citations in legal AI How AI is reshaping legal workflows and roles What it means to be an “AI-native” lawyer Learn More: Zach - legallydisrupted.com Cecilia - https://gc.ai/company/about Follow Along: Zach - linkedin.com/in/zachabramowitz Cecilia - https://www.linkedin.com/in/ceciliaziniti

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 Episode The biggest changes Dan has witnessed after 8 years of the Inspire conference How firms are using AI at scale — not just on pilot use cases Why automated document profiling is now possible across millions of docs Understanding small models vs. large models in legal workflows How AI pipelines classify, extract, and enrich metadata instantly New use cases emerging inside the DMS (repapering, diligence, discovery, onboarding) Why in-house teams are often ahead of firms in AI adoption How agentic AI assistants reduce loneliness and cognitive overload The ROI debate: real numbers vs. intangible benefits What lawyers gain: better focus, faster context loading, and stronger client service Why this moment feels like a once-in-a-generation shift in legal technology Learn More: Zach - legallydisrupted.com Dan - https://www.netdocuments.com/company/our-people/dan-hauck/ Follow Along: Zach - linkedin.com/in/zachabramowitz Dan - https://www.linkedin.com/in/danhauck

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 problem with Big Law’s “too much work, too few alternatives” model Why reading comprehension is AI’s legal superpower Building client trust in the age of automation How AI can accelerate deals — without sacrificing rigor The difference between a “relationship ramp” and a “SaaS snowball” The challenges (and advantages) of raising funding in legal AI Lessons from Robin AI’s struggles — and why clarity of business model matters Why this is a once-in-a-generation moment for lawyers who want to innovate Learn More: Zach – legallydisrupted.com Jen – https://covenant.co/about Follow Along: Zach – linkedin.com/in/zachabramowitz Jen – https://www.linkedin.com/in/jenniferberrent

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 structure could shift dramatically in the next decade Rethinking ROI: morale, retention, and client trust as key performance drivers How Harvey is helping firms pitch, collaborate, and win new business The future of AI-first law firms — from pricing models to client partnerships Learn More: Zach - https://www.legallydisrupted.com/ Gabe - https://www.harvey.ai/blog/author/gabe-pereyra Follow Along: Zach - linkedin.com/in/zachabramowitz Gabe - https://www.linkedin.com/in/gabepereyra