Harvey's CEO, Winston Weinberg on How Model Performance is Plateauing & Two Key Rules for Effective Deal-Making

20VC

Jan 19, 2026

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Winston Weinberg is the CEO and Co-Founder of Harvey, the leading professional services platform engineered with AI for law, tax, and finance. Winston has raised over $980M for Harvey from Sequoia, a16z, GV, Elad Gil and more with a last round price of $9.2BN post-money. Before founding Harvey in August 2022, Winston was an attorney at O'Melveny & Myers LLP, specializing in antitrust and securities litigation.

In Today's Episode We Discuss:
  • #1 Thing Every Founder Needs to Do Everyday

  • Must Do Daily Routines and Productivity Tips for CEOs

  • How to Get Sequoia and a16z Term Sheets

  • Why VCs Suck at Helping Companies Hire?

  • What No One Understands About Enterprise AI Adoption

  • AI's Impact on Professional Services

  • Future of Law Firms: Do They Die?

  • What Everyone Should Know That No One Tells You About Hiring in Europe

  • I Have Massive Trust Issues…

  • Biggest Lessons on Effective Deal-Making

  • Cold Emailing OpenAI and It Leading to a Term Sheet

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