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Startup Impresses Lawyers By Brutally Roasting Their Own Legal Work

Startup Impresses Lawyers By Brutally Roasting Their Own Legal Work
Photo by Amina Atar on Unsplash

KEY POINTS

  • •Winston Weinberg launched Harvey by cold-messaging thousands of lawyers and showing the AI tearing up their own filings.
  • •Harvey reached an $8 billion valuation after a December funding round despite early AI versions hallucinating risks.
  • •The legal AI market is booming with $3.2 billion raised last year and major firms already using AI workflows.

Winston Weinberg, fresh out of law school after just eight months, decided his winning pitch for $8 billion-valued Harvey AI was to attack lawyers by roasting their own court filings on video calls. Forget warm intros; he cold-LinkedIn-messaged thousands of unsuspecting litigators to 'critique' their work, knowing early AI tools hallucinated like a stoner at Comic-Con. Harvey bent Big Law firms with juicy burns so precise, lawyers couldn’t look away, despite risk of erroneous clapbacks killing deals instantly. With $3.2 billion cash flooding legal AI last year and 5 of America’s biggest firms already hooked on AI, Weinberg reinvents himself every few months to keep up before his startup dethrones itself at the $8B throne.

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Source: Businessinsider | Published: 1/19/2026 | Author: Lee Chong Ming