Andrew Simon: Building a Startup Inside Big Law

What does it take to build legal AI inside a Big Law firm with a deliberately small team?

In Episode 2 of the LegalQuants podcast, host Victor Wang talks with Andrew Simon, Chief AI & Innovation Officer at Weil, Gotshal & Manges. Andrew explains how he evaluates new legal AI products, why he thinks retrieval is one of the hardest problems in legal AI, and why Weil uses both closed frontier models and open-weight models. He describes how lawyers’ prototypes become durable applications, why the firm chose decentralized innovation, and how BenchMark grew out of a client’s question.

The conversation then turns to Andrew’s path from Big Law to a startup, supply-chain mathematics, machine learning at BCG, and Weil, before closing on machine-to-machine legal work, access to legal knowledge, raising children in the age of AI, and what he won’t hand over to it.

Andrew Simon at Weil: https://www.weil.com/people/andrew-simon LegalQuants Residency: https://residency.legalquants.com/ LegalQuants: https://www.legalquants.com/ Victor Wang: https://vic.law/

In this episode: 00:00 Welcome to the LegalQuants podcast 00:09 Meet Andrew Simon 01:12 How Andrew sizes up a new legal AI product 05:26 ROI when the technology keeps changing 06:37 Why legal retrieval is hard 10:40 Using closed and open-weight models 12:10 What happens when a new model drops 16:40 From a lawyer’s prototype to a real app 21:37 How Weil sees and supports AI use 24:14 Why Weil decentralizes innovation 27:16 Building BenchMark 31:31 How BenchMark caught on 33:07 The LASER name and the three-year goal 37:08 A startup within a Big Law firm 41:04 What Andrew looks for in a hire 44:57 Law school, Big Law, and leaving practice 49:21 Starting a beverage company 51:35 How supply-chain math led to machine learning 55:06 How Andrew came to Weil 58:38 The biggest lesson from BCG 59:26 Legal meaning, retrieval, and confidence 1:02:23 How strong a claim should a product make? 1:04:23 Agent security and machine-to-machine work 1:05:53 The case for an industry standards body 1:08:06 Where machine-to-machine efficiency matters most 1:10:27 Nonlawyers, AI, and knowledge diffusion 1:13:33 Raising kids in the age of AI 1:16:36 Parents, mentors, and curiosity 1:18:13 What he won’t surrender to AI