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 Kyle shares how early frustrations with outdated legal workflows pushed him to build internal tools, why generative AI changed everything, and what it really takes to break into the legal AI space today.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

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

In this episode:

Will LLMs Kill LegalAI or Legacy SaaS

Vibe coding vs enterprise software