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

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:

• 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

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.