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

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.

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 Kyle shares how early frustrations with outdated legal workflows pushed him to build internal tools, why generative AI changed everything, and what it really takes to break into the legal AI space today.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

• 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

• 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

• 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

• 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

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