E36 - Too Much FOMO: Why I'm Back on the Legal AI Startup Investor Train with Sandstone CEO Nick Fleisher

Zach announces that, for the first time since ChatGPT launched, he's investing in a legal AI startup. In this episode, he's joined by Nick Fleisher, CEO of Sandstone, to unpack why in-house legal teams, not law firms, may be the biggest winners of the AI era. Drawing on Nick's background at McKinsey where he advised law firms on AI, the conversation explores why legacy tools are failing lawyers and how AI can solve a problem that plagues in-house teams: working seamlessly with their business without slowing them down and being a bottleneck. In this episode: Why Zach decided to invest in a legal AI startup now What in-house legal teams actually need from AI Why CLM tools struggle with adoption and ROI How AI changes legal’s relationship with the business Measuring success beyond “time to contract” Why vertical legal software beats generic AI tools What makes Sandstone different from Harvey, Legora, and CLMs References: $10M Seed Round Announcement Learn More: Zach - legallydisrupted.com Nick - sandstone.com Follow Along: Zach - linkedin.com/in/zachabramowitz Nick - https://www.linkedin.com/in/nicholas-fleisher