Zach Abramowitz is Legally Disrupted

What happens when a veteran litigator starts treating AI less like a chatbot and more like an operating system for his cases? In this episode, Zach speaks with Arlo Devlin-Brown, founder of TDB Law, about how AI is changing the way he actually practices law. They discuss why AI may be particularly powerful for litigators, how Arlo has built an AI-powered system that continuously tracks his cases, and why the technology is more useful for exploring arguments and strategy than simply generating finished work. The conversation also explores the future of junior lawyers, why big law’s leverage model may be under pressure, and why Arlo rejects the idea that firms should sell themselves as “AI-native” rather than simply being excellent lawyers who use AI well.
In this episode:
Why AI may be more transformative for litigation than transactional law
How Arlo uses AI as an operating system and shared memory for his cases
Why AI can make junior lawyers more valuable, not obsolete
How AI could fundamentally reshape the Big Law leverage model
Why “AI-native” law firms may be missing the point
 
Subscribe to Zach’s newsletter
https://www.legallydisrupted.com/
 
Follow Zach on X
https://x.com/ZachAbramowitz?lang=en
 
Follow Along on LinkedIn:
Arlo - https://www.linkedin.com/in/arlodb
Zach - www.linkedin.com/in/zachabramowitz
 
Engage Killer Whale Strategies
https://www.killerwhalestrategies.com

What happens when a veteran Big Law attorney leaves a traditional partnership to help build a law firm from scratch? In this episode, Zach speaks with Batya Nadler, Partner at Norm Law, about her decision to join one of the legal industry's most ambitious AI-native firms. They discuss how Norm combines experienced lawyers with legal engineers and AI agents, why repeatable legal workflows are the ideal starting point for automation, and how AI is changing, not replacing, the role of senior attorneys. The conversation also explores why client relationships remain the foundation of legal practice, what skills lawyers need to thrive in an AI-first world, and why Batya believes the future belongs to firms built around AI from day one.
In this episode:
Why Batya left Big Law to help build an AI-native law firm from the ground up
How legal engineers and AI agents are transforming repeatable legal workflows
Why senior lawyers remain essential, even as AI automates more legal work
How Norm is rethinking the traditional law firm model around AI-native infrastructure
What lawyers can do today to become AI-fluent and prepare for the future of legal practice
 
Subscribe to Zach’s newsletter
https://www.legallydisrupted.com/
 
Follow Zach on X Zach 
https://x.com/ZachAbramowitz?lang=en
 
Follow Batya
https://www.linkedin.com/in/batya-nadler-1ba85410
 
 
Engage Killer Whale Strategies
https://www.killerwhalestrategies.com

Why are some general counsel suddenly becoming the most influential executives in the C-suite? In this episode, Zach speaks with Ross McNairn, founder and CEO of Wordsmith, about why AI is fundamentally changing the role of in-house legal teams. They discuss how legal departments are evolving from cost centers into strategic operators, why generic AI chatbots aren't enough for enterprise legal work, and how the next generation of legal technology will help GCs measure ROI, manage legal operations, and reduce reliance on outside counsel. The conversation also explores why traditional CLM systems have fallen short, the emergence of legal engineering, and what the future of corporate legal teams looks like in an AI-native world.
 
In this episode:
•⁠  ⁠Why AI is turning general counsel into technology leaders inside their organizations•⁠  ⁠Why enterprise legal teams need more than ChatGPT to transform their workflows•⁠  ⁠How legal departments can finally measure ROI and demonstrate business value•⁠  ⁠Why traditional CLM systems failed and what comes next•⁠  ⁠How legal engineering is becoming one of the most important new roles in corporate legal
 
Follow Along:
Ross - https://x.com/rossmcnairn?lang=en, https://www.linkedin.com/in/rossmcnairn
Zach - https://x.com/ZachAbramowitz?lang=en, www.linkedin.com/in/zachabramowitz
 
Subscribe to Zach’s newsletter
https://www.legallydisrupted.com/
 
Engage Killer Whale Strategies
https://www.killerwhalestrategies.com

Why would top venture capital firms invest $60 million into an immigration law startup at a $750 million valuation? In this episode, Zach speaks with Dan Mishin, founder and CEO of Manifest, about his vision for transforming one of the most complex and underserved areas of legal practice. They discuss why immigration law became the company's first focus, how AI is helping lawyers process cases faster and more accurately, and why Manifest is building far more than a traditional law firm. The conversation explores the challenges facing both lawyers and clients in the immigration system, the opportunity to create AI-native legal infrastructure, and what happens when software, operations, and legal expertise are combined into a single platform.
 
In this episode:
Why investors valued Manifest at $750 million after its first major funding round
How AI is transforming immigration law through speed, accuracy, and automation
Why Manifest is building legal infrastructure, not just another law firm
The hidden operational problems holding back many legal practices
How AI-native platforms could help lawyers serve more clients at lower cost
 
Learn More:
https://www.legallydisrupted.com/
 
Follow Along:
Dan - https://x.com/mishindan1, https://www.linkedin.com/in/danielmishin
Zach - https://x.com/ZachAbramowitz?lang=en, www.linkedin.com/in/zachabramowitz
 
Subscribe to Zach’s newsletter https://www.legallydisrupted.com/
 
 
Engage Killer Whale Strategies
https://www.killerwhalestrategies.com

As AI capabilities accelerate, how should law firms and legal departments prepare for a future where agents can perform increasingly complex legal work? In this episode, Zach speaks with Max Junestrand, CEO and co-founder of Legora, about the rapid evolution of legal AI and what it means for the future of legal services. They discuss the recent wave of law firms building their own AI initiatives, why legal teams are adopting AI faster than many realize, and how firms can rethink their business models in an agent-driven world. The conversation also explores the role of legal-specific AI products, the growing importance of transformation partners, and why Max believes legal AI represents a trillion-dollar opportunity.
 
In this episode:
Why law firms are investing heavily in AI
How legal teams can prepare for a future where AI agents perform increasingly complex work
Why legal-specific AI products still matter in a world of Claude, GPT, and other frontier models
How AI is changing the economics of legal services and creating new opportunities for firms
Why Max believes legal AI could become a trillion-dollar market opportunity
Subscribe to Zach’s newsletter
https://www.legallydisrupted.com/
 
Follow Zach on X
https://x.com/ZachAbramowitz?lang=en
 
Follow Max on X
https://x.com/MaxJunestrand
 
Engage Killer Whale Strategies
https://www.killerwhalestrategies.com
 
 
 

What happens when a former lawyer looks at the biggest names in legal AI and decides he can build a competing product in two weeks? In this episode, Zach speaks with Will Chen, founder of Mike, an open-source legal AI platform that has quickly gained attention for challenging conventional wisdom in legal tech. They discuss why some lawyers are frustrated with existing legal AI products, the rise of vibe coding, and how AI is making software development more accessible than ever. The conversation also explores open-source legal AI, the growing movement toward law firms building their own tools, and why some believe the future of legal technology may be far more decentralized than today's market leaders expect.
 
In this episode:
Why Will believes many legal AI products are little more than thin wrappers around frontier models
How vibe coding is enabling lawyers to build software without traditional engineering backgrounds
The case for open-source legal AI and local-first deployment in law firms
Why more firms are exploring building their own AI tools instead of buying them
How AI could lower the barriers to starting a law firm or legal tech company
Learn More:
https://www.legallydisrupted.com/
 
Follow Along:
Will - https://x.com/willchen500, https://hk.linkedin.com/in/will-chen-0bb0a477
Zach - https://x.com/ZachAbramowitz?lang=en, https://www.linkedin.com/in/zachabramowitz

How did Harvey become the defining company in legal AI and where does the industry go from here? In this episode, Zach speaks with Winston Weinberg, founder and CEO of Harvey, about the company’s rapid rise at the center of the legal AI boom. They discuss how law firms are actually adopting AI, why legal workflows are uniquely suited for large language models, and what it takes to build products trusted by the world’s top legal organizations. The conversation also explores the evolving relationship between lawyers and AI, the challenges of scaling legal technology, and why the next generation of legal professionals may work very differently than the last.
In this episode:
How Harvey became one of the most influential companies in legal AI
What law firms are actually looking for when adopting AI tools
Why legal work is especially well-suited for large language models
The biggest challenges in building trusted AI products for lawyers
How AI could fundamentally reshape the future of legal practice and legal careers
Learn More:
Winston - https://www.harvey.ai/blog/author/winston-weinberg
Zach - https://www.legallydisrupted.com/
 
Follow Along:
Winston - https://www.linkedin.com/in/winston-weinberg
Zach - linkedin.com/in/zachabramowitz

What happens when you rebuild a law firm from scratch in the age of AI? In this episode, Zach speaks with Logan Brown, founder of Soxton, an AI-first law firm serving startups as an on-demand, AI-powered general counsel. They discuss how Soxton is rethinking legal services from the ground up, why fixed pricing and automation are expanding access to legal help, and where traditional law firms still have the edge. The conversation also dives into the explosion of new startups, the rise of AI-driven litigation, and whether Big Law is facing a slow but inevitable transformation.
In this episode:
How AI-first law firms are redesigning legal services and pricing models
Why startups are delaying hiring in-house counsel with AI-powered alternatives
Where traditional law firms still win—and where they’re most vulnerable
Why AI could drive both more startups and more litigation
How legal careers and firm structures may fundamentally change in the next decade
Learn More:
Logan - https://fortune.com/2026/04/05/logan-brown-soxton-founder-2-5-million-ai-powered-law-firm-started-da-office-12-years-old/
Zach - https://www.legallydisrupted.com/
 
Follow Along:
Logan - https://www.linkedin.com/in/logan-brown-03765552
Zach - linkedin.com/in/zachabramowitz
 

Money is pouring into legal AI,  but how do top-tier investors actually evaluate the space? In this episode, Zach speaks with Keith Rabois, Managing Director at Khosla Ventures and one of the most successful investors of the past two decades, about how he thinks about legal tech in the age of AI. They discuss why elite founders are suddenly flocking to legal, the risks facing application-layer startups, and what separates real opportunities from hype. The conversation also explores why Rabois invested in Spellbook, why he’s skeptical of some of the biggest names in legal AI, and how changing incentives across law firms and in-house teams are reshaping the market.
In this episode:
Why top VCs are following talent, not verticals, into legal AI
The biggest risk facing legal AI startups: speed of replication and weak moats
Why in-house legal teams may be a better market than Big Law
What makes Spellbook compelling, and why contracts are the real opportunity
How AI is challenging traditional software economics and long-term value
Learn More:
Keith - https://www.khoslaventures.com/team/keith-rabois
Zach - https://www.legallydisrupted.com/
 
Follow Along:
Keith - https://www.linkedin.com/in/keith
Zach - linkedin.com/in/zachabramowitz
 

Is the legal AI race still a two-horse battle, or has a new contender changed everything? In this episode, Zach speaks with Richard Tromans, founder of Artificial Lawyer, about the rapid rise of Claude and what it means for the broader legal tech ecosystem. They unpack how frontier model providers are reshaping the market, why law firms are experimenting with multiple AI tools at once, and whether general-purpose AI could start replacing legal-specific platforms. The conversation also explores shifting buying behavior in law firms and in-house teams, the real “moats” in legal AI, and why recent hallucination controversies may say more about legal workflows than the technology itself.
In this episode:
Why Claude is suddenly at the center of the legal AI conversation
How general-purpose AI tools could disrupt legal tech spending
The real competitive moat in legal AI: brand, trust, and distribution
Why law firms are adopting multiple AI models instead of picking one
What AI hallucination cases reveal about legal workflows - not just the tech
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