Podcast

The LegalQuants Podcast

The lawyers building the frontier, showing their work.

Long-form conversations with practising lawyers who build their own AI systems, from the LegalQuants community: career stories, the work itself with screens, prompts and failures, and the takes people do not post on LinkedIn.

Hosted by Victor Wang, a former BigLaw attorney who runs an AI-powered solo practice and advises frontier AI labs on legal strategy.

New episodes every two weeks.

Episode 02 · 28 Sep 2026 · 1 h 20 min

Andrew Simon: Building a Startup Inside Big Law

In Episode 2 of the LegalQuants Podcast, Victor Wang sits down with Andrew Simon, Chief AI & Innovation Officer at Weil, Gotshal & Manges.

In this episode

  • How Andrew sizes up a new legal AI product: how was it probably built, and does the business case reach beyond a single use case?
  • Why retrieval is one of the hardest problems in legal AI, where one changed word can carry outsized weight.
  • Why Weil runs closed frontier models alongside open-weight models, and pins some small "tissue paper" apps to avoid churn when a new model drops.
  • How a lawyer's prototype becomes a real firm app, and why a working prototype is "the world's best spec document."
  • Why Weil decentralizes innovation, and the three hurdles behind "tissue rejection": understanding an idea, believing it can be built, and changing how you work.
  • How BenchMark, which analyzes a judge's public record to help litigators prepare, grew out of a client's question.
  • Why LASER stays small, what Andrew asks technical hires to explain, and what success would look like in three years.
  • Machine-to-machine legal work, the case for an industry standards body, raising kids in the age of AI, and the one thing he won't hand over to it.
Chapters

Earlier episodes

Video thumbnail for How Lawyers Built Frontier Plugins for OpenAI

Episode 01 · 25 Sep 2026 · 24 min

How Lawyers Built Frontier Plugins for OpenAI

In Episode 1 of the LegalQuants Podcast, Victor Wang joins Jamie Tso and John Hughes to unpack how the team turned legal expertise into working plugins in just a few weeks. They share the ambitious first idea, the feedback that changed their approach, and what it takes to build something lawyers will actually use.

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