Zach Abramowitz is Legally Disrupted
This is a podcast for the people who want to understand and shape the future of the law.
Hey there, I'm Zach Abramowitz and I am Legally Disrupted! 15 years ago, my legal career was disrupted by tech.
Today, I'm advising the some of the most influential legal service providers in the world on their AI strategy and investing in some of the promising #legalAI startups. Every week, I talk to the builders, founders, operators, and decision-makers driving change in a legal ecosystem being reshaped by AI. We don't just revel in the gloriousness of AI -- we do that too! But, we also break down complex ideas and separate signal from noise. Our content focuses on what’s real, what matters, and what everyone else is missing. So what are you waiting for? Let's get disrupted!
Listen on:
Episodes
Wednesday Feb 25, 2026
Wednesday Feb 25, 2026
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
Thursday Feb 19, 2026
Thursday Feb 19, 2026
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
Thursday Feb 12, 2026
Thursday Feb 12, 2026
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
Thursday Feb 05, 2026
Thursday Feb 05, 2026
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
Wednesday Jan 14, 2026
Wednesday Jan 14, 2026
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.comNick - sandstone.com
Follow Along:Zach - linkedin.com/in/zachabramowitzNick - https://www.linkedin.com/in/nicholas-fleisher
Tuesday Jan 13, 2026
Tuesday Jan 13, 2026
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.comCecilia - https://gc.ai/company/about
Follow Along:Zach - linkedin.com/in/zachabramowitzCecilia - https://www.linkedin.com/in/ceciliaziniti
Thursday Dec 04, 2025
Thursday Dec 04, 2025
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.comDan - https://www.netdocuments.com/company/our-people/dan-hauck/
Follow Along:Zach - linkedin.com/in/zachabramowitzDan - https://www.linkedin.com/in/danhauck
Thursday Nov 13, 2025
Thursday Nov 13, 2025
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.comJen – https://covenant.co/about
Follow Along:Zach – linkedin.com/in/zachabramowitzJen – https://www.linkedin.com/in/jenniferberrent
Tuesday Nov 04, 2025
Tuesday Nov 04, 2025
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
Thursday Oct 30, 2025
Thursday Oct 30, 2025
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
