Why Harvey's Hardest Problem Isn't AI—It's Multi-Entity Collaboration episode artwork

EPISODE · Nov 12, 2025 · 44 MIN

Why Harvey's Hardest Problem Isn't AI—It's Multi-Entity Collaboration

from StrictlyVC Download · host Connie Loizos & Alex Gove

In this episode, TechCrunch’s editor-in-chief, Connie Loizos, and StrictlyVC’s Alex Gove, sit down with Winston Weinberg, co-founder and CEO of Harvey, the legal AI startup that’s quietly become one of the most talked-about companies in Silicon Valley. Winston shares the origin story of how a first-year associate at O’Melveny used GPT-3 for Dungeons & Dragons before realizing it could transform legal work—leading to a cold email to Sam Altman on July 4, 2022, that changed everything. The three discuss Harvey’s rapid growth to more than $100 million in ARR, why 33% of the startup’s revenue now comes from corporates rather than just law firms, and the technical challenges of building a truly multiplayer platform that navigates complex ethical walls and permissioning across 63 countries. Winston also addresses the “ChatGPT wrapper” criticism — and he explains why he believes professional services will be less disrupted than people think. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, TechCrunch’s editor-in-chief, Connie Loizos, and StrictlyVC’s Alex Gove, sit down with Winston Weinberg, co-founder and CEO of Harvey, the legal AI startup that’s quietly become one of the most talked-about companies in Silicon Valley. Winston shares the origin story of how a first-year associate at O’Melveny used GPT-3 for Dungeons & Dragons before realizing it could transform legal work—leading to a cold email to Sam Altman on July 4, 2022, that changed everything. The three discuss Harvey’s rapid growth to more than $100 million in ARR, why 33% of the startup’s revenue now comes from corporates rather than just law firms, and the technical challenges of building a truly multiplayer platform that navigates complex ethical walls and permissioning across 63 countries. Winston also addresses the “ChatGPT wrapper” criticism — and he explains why he believes professional services will be less disrupted than people think. Learn more about your ad choices. Visit megaphone.fm/adchoices

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Why Harvey's Hardest Problem Isn't AI—It's Multi-Entity Collaboration

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This episode was published on November 12, 2025.

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In this episode, TechCrunch’s editor-in-chief, Connie Loizos, and StrictlyVC’s Alex Gove, sit down with Winston Weinberg, co-founder and CEO of Harvey, the legal AI startup that’s quietly become one of the most talked-about companies in Silicon...

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