From Roommates to Billionaires: Harvey's Founders Gabriel Pereyra and Winston Weinberg on Building AI Infrastructure for Law

Jan 20, 2026

Guest

Gabriel Pereyra

Guest

Winston Weinberg

Winston Weinberg and Gabriel Pereyra, co-founders of Harvey, transitioned from roommates in a San Francisco apartment to leaders of an $8 billion legal AI powerhouse. They share their unique journey, including the challenges of gaining traction with law firms and the pivotal role of GPT-4 in enhancing their platform. They discuss the complexities of scaling infrastructure while ensuring data security and ethical compliance. Additionally, they highlight their ambitions to create an essential AI operating system for the legal industry and plans for future growth in corporate legal teams.

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ANECDOTE

Founders Still Roommates

Winston and Gabriel still live in the same apartment they started Harvey in, with minimal furniture and a mattress on the floor.
Their lifestyle hardly changed despite becoming billionaires on paper and massive company growth.

INSIGHT

GPT-4 Sparked A Strategic Pivot

Early access to GPT-4 delivered a reasoning leap that made complex legal workflows feasible.
That capability shift redirected Harvey from consumer access-to-justice ideas toward big law adoption.

ANECDOTE

Cold Outreach Led To A&O Breakthrough

Harvey founders sent tens of thousands of LinkedIn messages and got few responses until an intro led to an in-person demo with Allen & Overy.
A&O's endorsement triggered a flood of law firm interest that overwhelmed their four-person team.

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Gabriel Pereyra and Winston Weinberg started legal AI company Harvey in 2022 as roommates in a San Francisco apartment. Pereyra had been working on AI research at Meta and Google, while Weinberg was a first-year litigation associate at O'Melveny & Myers. Today, they still share that same apartment, but their company has grown into a global enterprise serving more than 1,000 law firms and corporate legal departments and valued at a whopping $8 billion.

In this episode of LawNext, Pereyra and Weinberg take us back to Harvey's earliest days, when they were sending thousands of LinkedIn messages trying to get anyone to look at their product. They share the pivotal moment when early access to GPT-4 transformed what they could build, the breakthrough that came when Allen & Overy became their first major client, and how they have evolved from building an AI assistant for individual lawyers to constructing what they call "essential infrastructure" for legal work.

With host Bob Ambrogi, they discuss Harvey's vision for becoming an AI operating system that integrates across the entire legal tech ecosystem, their focus on memory and agentic AI that can handle complex multi-step workflows, and the massive infrastructure challenges of deploying AI at scale across global law firms while maintaining ethical walls and data security.

Pereyra and Weinberg also reflect candidly on how two founders with no management experience have learned to scale a company now employing hundreds of people — more than 20 percent of whom are lawyers — and what it is like to go from struggling startup to being featured in The New York Times as AI billionaires while still sleeping on a mattress on the floor.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.
Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner).
Eve, taking care of the tasks that slow you down so you can operate at your highest potential

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