The co-founders of Harvey, a red-hot legal AI start-up now valued at $8 billion, live together with a third roommate in San Francisco even as their company vaults them into the upper echelons of Silicon Valley wealth.
Winston Weinberg, 30, Harvey’s co-founder and chief executive, shares an apartment with his co-founder Gabe Pereyra, 34, and another roommate.
“Yes, Gabe and I still live together with one other roommate,” Weinberg said in a Monday statement to The Post.
“It’s not a statement in any way, but more of a reflection of the fact that our lives haven’t changed much – we are still focused on building a great company and putting in long hours to make that happen.”
The living arrangement highlights the grinding reality of getting by in San Francisco, where eye-popping tech valuations collide with one of the worst housing-affordability crises in the country.
“The focus of any cost of living debates in major US cities should be on the people who need it most, not on anyone lucky enough to be building a company,” Weinstein said.
“With that said, we care about this issue a lot because it impacts our employees both current and future that is the most important consideration for us.”
Harvey, which builds generative AI tools for lawyers, has become one of the fastest-rising stars of the artificial intelligence boom.
Founded in 2022, the company raised money three times in 2025 alone, with its valuation jumping from $3 billion in February to nearly three times that by year’s end.
The surge turned Weinberg and Pereyra into billionaires almost overnight.
“Yeah, sure it’s in the billions, but it’s on paper,” Weinberg recently said of his wealth to the New York Times.
Harvey is based in San Francisco, where home prices and rents have soared for years as waves of tech wealth poured into a city with chronically constrained housing supply.
Weinstein told The Post that the company plans to hire “a significant number of people” in San Francisco — along with New York City “and all of our global markets.”
As of late 2025, the median home sale price in the City by the Bay hovered around $1.49 million, up more than 10% from a year earlier. Median rents for a one-bedroom apartment topped $3,500 a month.
Even for high earners, the city’s housing market has become punishing. Years of restrictive zoning, long permitting timelines and high construction costs have limited new supply, while tech-driven job growth has fueled demand.
In 2024, only about 1,600 new homes were built in the city — the lowest number in more than a decade.
The result has been widespread displacement and deepening inequality. Non-tech workers and lower-income residents have been pushed out as prices climb, while homelessness remains stubbornly high.
More than 8,300 people experienced homelessness in San Francisco in 2024, according to the local government.
City leaders have rolled out policies aimed at easing the crisis, including rent control for some units, inclusionary zoning rules and efforts to increase density.
Late last year, officials passed a sweeping “Family Zoning Plan” designed to allow more housing in traditionally single-family neighborhoods.
The Post has sought comment from Harvey.
[Notigroup Newsroom in collaboration with other media outlets, with information from the following sources]
