Zach Abramowitz is Legally Disrupted

Zach Abramowitz
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My name is Zach Abramowitz and I am Legally Disrupted. This podcast covers the trends disrupting the legal profession. Once a mild mannered practicing attorney, I now am an entrepreneur and investor in disruptive legal startups. My company, Killer Whale Strategies, helps law firms, legal departments, and anyone else capitalize on the wave of disruption sweeping over the legal industry. Join me as I spotlight key players, significant trends, and innovative companies who are shaking up an age old profession.

  1. 2H AGO

    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 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

    52 min

  2. FEB 12

    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.com/in/zachabramowitz

    1 hr

  3. FEB 5

    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 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

    42 min

  4. JAN 14

    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 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

    51 min

  5. JAN 13

    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 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

    33 min

  6. 12/04/2025

    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 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

    34 min

  7. 11/13/2025

    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 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

    51 min

  8. 11/04/2025

    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 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

    45 min
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Ratings & Reviews

5
out of 5
3 Ratings

About

My name is Zach Abramowitz and I am Legally Disrupted. This podcast covers the trends disrupting the legal profession. Once a mild mannered practicing attorney, I now am an entrepreneur and investor in disruptive legal startups. My company, Killer Whale Strategies, helps law firms, legal departments, and anyone else capitalize on the wave of disruption sweeping over the legal industry. Join me as I spotlight key players, significant trends, and innovative companies who are shaking up an age old profession.

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