Harvey's CEO explains his early tactic to get customers: telling lawyers how bad their arguments were

• Harvey's CEO says showing lawyers what was wrong with their arguments helped him grab attention fast.
• Winston Weinberg said it was a risky move because early versions of the tool could hallucinate.
• The legal AI sector is expanding, with Harvey valued at $8 billion following a December funding round.

Harvey's CEO says his earliest demos worked because they went straight for lawyers' arguments.

Winston Weinberg said in an episode of the "Sequoia Capital" podcast published Thursday that once he got lawyers on a call to demo his legal AI tool, he knew he had only seconds to grab their attention.

Instead of walking through features, the cofounder and chief executive of the legal AI startup pulled publicly available court filings that the lawyers had written and prompted Harvey to critique them.

"I would try to come up with prompts that were like, 'This is bad,'" Weinberg said.

"Because they're a litigator and I'm basically attacking something that they just wrote, they would instantly read the screen," he added.

Weinberg said the approach was risky because early versions of the tool could hallucinate, and a bad output could kill a conversation instantly.

"But the times that they got it right, it was over," Weinberg said, referring to moments when the analysis landed and won the lawyer's attention.

Harvey is one of the most closely watched startups in legal AI, aiming to transform how Big Law firms work. In December, the company said it had reached a valuation of $8 billion after a funding round led by A16z.

Weinberg said he relied on cold outreach in Harvey's early days, messaging thousands of lawyers on LinkedIn to secure early calls.

"I'd been practicing law for like eight months," Weinberg said of the period when he started the company. "I didn't have any connections."

The growing legal AI sector

The legal AI sector is expanding fast, and Weinberg said the scale of the opportunity is forcing constant change inside Harvey.

He said the company's rapid growth has pushed him to "reinvent" himself as a founder every few months, often rethinking leadership hires and company structure to keep up with demand.

Despite Harvey's rise to an $8 billion valuation, Weinberg has played down the idea of a single dominant winner in legal tech. In a Reddit "Ask Me Anything" session last month, he said the market is simply too large.

"There are around 10 million global legal professionals, and Harvey serves just single-digit percentage points of them," he said.

"I don't think a single player is going to capture all of the pretty enormous amount of value that will be created in the next 10 years in this space," he added.

Weinberg said the global legal market is worth roughly $1 trillion, yet only about $30 billion is spent on technology.

Investor interest has followed the shift. Legal-tech startups raised $3.2 billion last year, according to Business Insider's December analysis of Crunchbase data and deals.

AI adoption is also accelerating inside law firms. Five of the 10 largest US law firms by revenue told Business Insider in July that they were using AI in their workflows, including for document review and spotting compliance risks.