$8 billion AI startup Harvey co-founders still living with roommate in San Francisco’s Silicon Valley and the reason will surprise you
“Yes, Gabe and I are still living with another roommate,” Weinberg told The Post on Monday. “This isn’t a statement by any means, but rather a reflection of the fact that our lives haven’t changed much; we’re still focused on building a great company and are putting in long hours to make it happen.”
Why are Harvey’s co-founders staying with a roommate?
The New York Post reported that the living arrangement of Harvey co-founders Winston Weinberg and Gabe Pereyra highlights the high rising cost in San Francisco, where eye-popping tech valuations are colliding with one of the worst housing affordability crises in the country. “The focus of cost-of-living discussions in major U.S. cities should be on the people who need it most, not on those lucky enough to start businesses,” Weinstein said. Weinstein told The Post that the company plans to hire a “significant number of people” in San Francisco, as well as in New York City “and in all of our global markets.”
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“However, we care deeply about this issue because it affects both our current and future employees, which is the most important consideration for us.” As of late 2025, the median home price in San Francisco was approximately $1.49 million; This was an increase of over 10% from a year ago. The average monthly rent for a one-bedroom apartment exceeded $3,500.
Housing in the city has become increasingly brutal even for the best earners. Strict zoning rules, lengthy approval processes and rising construction costs have choked off new supply; Technology-led job growth continues to drive demand.
Harvey is the rising star of the AI boom
Founded in 2022, Harvey develops productive AI tools for lawyers and has become one of the fastest rising stars of the AI boom. The company raised money three times in 2025 alone; Its valuation nearly tripled from $3 billion in February to year-end. This increase turned Weinberg and Pereyra into billionaires almost overnight. But Weinberg recently told The New York Post that this is only on paper. “Yes, it’s certainly in the billions, but it’s on paper,” Weinberg recently told the New York Times.
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Harvey is based in San Francisco, where home prices and rents have been rising rapidly for years as waves of tech wealth have flowed into a city with a chronically limited housing supply. But in 2024, only 1,600 new homes were built in the city; this was the lowest figure in more than a decade. As costs rise, non-tech workers and low-income residents are being laid off, while the homelessness rate remains high. More than 8,300 people experienced homelessness in San Francisco in 2024, according to city data. In response, city leaders have implemented measures to alleviate the crisis, including rent controls on certain units, inclusionary zoning requirements and initiatives to increase housing density.
