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:

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

In this episode:

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

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

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

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