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How Harvey’s 31-Year-Old CEO Winston Weinberg Is Reshaping Big Law with A.I.

Winston Weinberg explains how Harvey scaled to $8 billion while navigating rising competition and redefining legal work in the A.I. era.

Winston Weinberg understands what junior associates at law firms need because he was once one of them. In 2022, the then 27-year-old was working at O’Melveny & Meyers when he began experimenting with OpenAI models alongside his roommate, Gabe Pereyra, then a research scientist at Meta. After realizing A.I. could streamline inefficiencies in the legal sector, the two cofounded Harvey, a startup built for lawyers.

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Since then, Harvey’s tools have become a must-have for Big Law, used by more than half of the AMLaw 100 firms. Clients include powerhouse firms like Paul, Weiss, as well as in-house legal teams at PwC and KKR. Three years in, Harvey serves more than 1,000 customers across 6o countries. “Demand broadly for A.I. for legal is at an all-time high,” Weinberg told Observer over email.

Silicon Valley has taken notice, too. After Weinberg cold-emailed the OpenAI Startup Fund, it became Harvey’s first institutional investor. The company was most recently valued at $8 billion following a $160 million round in 2025—a year when it raised capital three times—and closed with more than $190 million in annual recurring revenue.

Harvey has continued to expand through a partnership with LexisNexis, integrating its legal content and citations, and by working with leading law schools at Stanford, NYU and UCLA to bring A.I. into legal education. Last month, it even came full circle, partnering with Suits actor Gabriel Macht—the man behind Harvey Specter, the character that inspired the startup’s name—in what Weinberg........

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