E36 - Too Much FOMO: Why I'm Back on the Legal AI Startup Investor Train with Sandstone CEO Nick Fleisher
Zach Abramowitz is Legally Disrupted · Jan 14, 2026 · 50:36
Zach Abramowitz is Legally Disrupted
Zach Abramowitz is Legally Disrupted · Jan 14, 2026 · 50:36
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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:
Learn More: Zach - legallydisrupted.com Nick - sandstone.com
Follow Along: Zach - linkedin.com/in/zachabramowitz Nick - https://www.linkedin.com/in/nicholas-fleisher
Episodes: Zach Abramowitz is Legally Disrupted
