$8 billion AI startup Harvey co-founders still living with roommate in San Francisco’s Silicon Valley and the reason will surprise you

High-profile billionaires such as Nvidia CEO Jensen Huang, Sam Altman, the CEO of ChatGPT maker OpenAI, Tesla CEO Elon Musk have become richer- thanks to artificial intelligence boom. The AI boom has also produced a crop of new billionaires — at least on paper — from smaller startups. But the co-founders of Harvey, an AI legal software startup now valued at $8 billion, have a different story to tell. Winston Weinberg, 30, Harvey’s co-founder and chief executive shares an apartment with his co-founder Gabe Pereyra, 34, and another roommate, according to a report in The New York Post. This is despite their company placing them among Silicon Valley’s richest power players.

“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.”

Why are co-founders of Harvey staying with a roommate?

The New York Post reports 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 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. 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.”
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“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.” As of late 2025, the median home price in San Francisco stood at about $1.49 million, more than 10% higher than a year earlier. Median monthly rent for a one-bedroom apartment exceeded $3,500.

Even for top earners, housing in the city has grown increasingly unforgiving. Tight zoning rules, lengthy approval processes and soaring construction costs have choked new supply, while tech-led job growth continues to stoke demand.

Harvey is the rising star of the AI boom

Founded in 2022, Harvey builds generative AI tools for lawyers and has went on to become one of the fastest rising stars of the artificial intelligence boom. 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. But Weinberg recently told The New York Post that it is only on papers. “Yeah, sure it’s in the billions, but it’s on paper,” Weinberg recently said of his wealth to the New York Times.
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Harvey is based in San Francisco, where home prices and rents have skyrocketed for years as waves of tech wealth poured into a city with chronically constrained housing supply. But in 2024, only about 1,600 new homes were built in the city — the lowest number in more than a decade. As costs rise, non-tech workers and lower-income residents have been forced out, while homelessness remains persistently high. According to city data, more than 8,300 people experienced homelessness in San Francisco in 2024. In response, city leaders have introduced measures to ease the crisis, including rent controls on certain units, inclusionary zoning requirements and initiatives to boost housing density.