Harvey's Winston Weinberg: From Law Associate To $11 Billion Legal AI Startup CEO

Harvey CEO Winston Weinberg operates between two worlds. On one side are highly-trained lawyers who are skeptical about AI’s ability to improve their work. On the other are Silicon Valley technologists who see law as one of the fields that the biggest AI labs, Anthropic and OpenAI, can easily absorb. Co-founded in 2022, Harvey now works with more than 100,000 lawyers across 1,000 businesses, generating $200 million in revenue and recently reaching an $11 billion valuation. On The Upstarts Podcast, Weinberg talks about 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 why Anthropic is his biggest threat. Plus, he talks about his Upstart Moment: a never-before-disclosed attempt to “one-shot” company growth that saw Harvey almost merge with another company of equal size in 2024 – only to luckily pull back. 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 For more, visit https://www.upstartsmedia.com/ Season 1 of the Upstarts Podcast is presented by Mercury: https://mercury.com/ Produced & edited by Eric Johnson from LightningPod: https://lightningpod.fm/