Zach Abramowitz is Legally Disrupted

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

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