Zach Abramowitz is Legally Disrupted

Recording at LegalWeek in New York, Zach sits down with Shlomo Klapper (founder of Learned Hand) and Bridget McCormack, former Chief Justice of the Michigan Supreme Court and now CEO of the American Arbitration Association, to challenge one of the biggest double standards in legal AI: “AI for me, but not for thee.” Lawyers are now widely using AI, but the moment it touches judges or arbitrators, support drops off.
That hesitation comes as courts are under real strain, with judges handling thousands of cases a year and only minutes to decide each one, and no realistic way to keep up. Shlomo describes Learned Hand’s “AI law clerk,” built to support judicial research, analysis, and drafting, while Bridget brings the perspective of someone who has both made decisions on the bench and now leads a major dispute resolution institution. The conversation moves beyond AI as an assistant and into a harder shift: AI as part of decision-making itself, and whether the system can continue to function without it.
Learn More:
Bridget - http://www.aaaicdrfoundation.org/director/bridget-m-mccormack
Shlomo - https://www.learned-hand.ai/
Zach - https://www.legallydisrupted.com/
 
Follow Along:
Bridget - https://www.linkedin.com/in/bridget-mary-mccormack-26700b30
Shlomo - https://www.linkedin.com/in/sklapper
Zach - linkedin.com/in/zachabramowitz

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 Kyle shares how early frustrations with outdated legal workflows pushed him to build internal tools, why generative AI changed everything, and what it really takes to break into the legal AI space today.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