Harvey's Winston Weinberg On Anthropic, Cold Emailing Sam Altman, And A 'One-Shot' Merger Near-Disaster
Fresh off an $11 billion valuation, Harvey's CEO tells The Upstarts Podcast about his Upstart Moment learning you can't shortcut your way to growth.
Harvey CEO Winston Weinberg is flying high.
His legal AI startup has overcome skepticism — both from highly-trained lawyers who think his product can’t work, and AI lab maximalists who think it can just be copied by Anthropic or OpenAI — to now work 100,000 lawyers, generate about $200 million in revenue, and as of yesterday, reach an $11 billion valuation.
But on The Upstarts Podcast, Weinberg shares a never-before-told story about how in early 2024, he and co-founder Gabe Pereyra almost crashed long before that — all because they chased a “one-shot” way to hack their way to scale.
It’s an unusual Upstart Moment, but a fascinating one. The broad strokes: Harvey was valued at about $700 million at the time, and had the chance to combine with a more traditional player with 10x the employees, but about the same valuation. Its board was nervous about it, but Weinberg and Pereyra thought it would solve many of their problems: hiring, scaling, a customer base.
They decided to agree to the deal, then finance it, in what Weinberg calls a 1980s style financial gambit. But it didn’t work. Harvey would need to take on too much debt to make it happen; the company walked away.
“I remember we had a week of just being like, ‘What is the future of our company? And how do we build this?’” Weinberg recounts on the show. But it was a bullet dodged — and a hard-earned startup lesson, he adds — Harvey has opted against acquisitions since.
“It would’ve been a huge mistake,” he says. “ I think sometimes as a founder you have the sense of ‘Oh, there’s a quick, easy way to win this.’ And you learn over time that there isn’t, that doesn’t exist.”
You can hear more of that story, as well as how a cold email to Sam Altman helped launch Harvey’s journey; why he believes lawyers are a surprise power user of AI tools; and how he’s handling a challenge from Anthropic, in the full episode.
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This season of The Upstarts Podcast is presented by Mercury.
Chapters:
00:00 Introduction
00:48 Winston's path to law
2:05 Testing GPT-3 and Sam Altman
7:45 A 'risky' demo
10:42 Investor skepticism
14:23 Near-miss 'one-shot' merger
18:50 Winston's approach to hiring
22:31 Responding to skeptics
29:23 Why you should build in public
31:02 Winning over lawyers
32:46 Anthropic and the competition
35:36 Happy customers beat Twitter love
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