Zach Abramowitz is Legally Disrupted

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

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 Legal Innovators London Event Preview The Future of AI in Law Firms   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

In Episode 30 of 'Legally Disrupted,' Zach engages in a thought-provoking discussion with Catherine Kemnitz, Axiom's Chief Strategy Officer. They address a LinkedIn debate on how AI will disrupt both Contract Lifecycle Management (CLM) and Alternative Legal Service Providers (ALSPs). Katherine offers insights from her extensive legal industry experience, including her tenure at Axiom and Thomson Reuters, highlighting major transactions and strategic pivots influenced by technological advancements.    In this episode: Catherine Kemnitz's Career Journey  Axiom's Strategic Moves and Innovations  The Impact of AI on Legal Services  Generative AI and Legal Tech Evolution AI Adoption in Legal Departments vs. Law Firms  Axiom's Approach to AI and Future Outlook  Learn More: Zach - https://www.legallydisrupted.com/ Catherine - https://www.axiomlaw.com/about-us/our-team   Follow Along: Zach - linkedin.com/in/zachabramowitz Catherine - https://www.linkedin.com/in/catherinekemnitz

Zach sits down with Centari founder Kevin Walker to unpack the opportunities and obstacles of selling AI to law firms when it isn’t a generalized assistant like ChatGPT or Harvey. Kevin makes the case for why tackling highly specialized problems, such as Deal Intelligence, delivers unique, lasting value to firms.   In this episode: Understanding Centari's Vision  Unique Market Insights and Adoption Challenges and Opportunities in Legal Tech  Building Trust with Law Firms  Future of Legal Practices Fried Frank Partnership  Navigating Market Noise First Principles and Differentiation AI Adoption in Law Firms Reddit Thread Controversy  Building a Strong Company Culture   Learn More: Zach - https://www.legallydisrupted.com/ Kevin - https://www.centari.com/about-us   Follow Along: Zach - linkedin.com/in/zachabramowitz Kevn - https://www.linkedin.com/in/kpwalker1, https://x.com/_kevinwalker?lang=en

Richard Tromans, founder of Artificial Lawyer and expert in legal tech, joins Zach to explore the revolutionary landscape of AI in legal services. They dive into the implications of non-lawyer ownership, the potential of AI in transactional work, and the evolving business models of AI-first firms. Richard elaborates on how these new entities might disrupt traditional firms and the regulatory challenges surrounding them. The discussion also touches on the practical ROI of legal tech and what this shift means for future market dynamics.

In this episode of 'Legally Disrupted,' host Zach Abramowitz introduces a new recurring segment called 'Zach and Richard's Legal AI Adventure' with Richard Tromans from Artificial Lawyer. They discuss the rapid evolution in the legal tech sphere, particularly focusing on big deals and announcements from legal AI companies like Harvey and Legora. The duo debates the impact of generative AI productivity platforms on the legal market, the notion of a 'land grab' as firms race to adopt AI, and the potential for AI to become universally adopted in legal workflows. They also touch on the pricing dynamics of legal tech and the challenges faced by legacy companies in incorporating AI.   In this episode: Summer Surge in Legal AI Deals  Generative AI Platforms for Lawyers Market Share and Productivity Tools Global Legal Market and Pricing Strategies Emerging Competitors and Market Dynamics  The Battle for Legal AI Dominance The Future of Legal Tech Giants: Mergers and Acquisitions  The Role of Investors in Legal Tech  The Importance of Specialization in Legal Tech  The Future of AI in Legal Tech: Assistants vs. Automators 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