AI Founders Worth Billions Are Choosing To Share Apartments In San Francisco. Here's Why

The ongoing housing crisis in San Francisco has led even newly minted AI billionaires to maintain modest living arrangements. According to the New York Post, Winston Weinberg (30) and Gabe Pereyra (34), co-founders of the legal AI startup Harvey (currently valued at $8 billion), continue to live together with a third roommate in San Francisco. Weinberg told The Post that the arrangement reflects their continued focus on building their company, noting that while their net worth is in the billions, it is currently "on paper".

"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," he said.

"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. 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," he added. 

Harvey, the generative AI startup building tools for lawyers, has quickly emerged as one of the breakout successes of the AI boom. Launched in 2022, the company saw rapid growth in 2025, raising funds three times in the same year. Its valuation soared from $3 billion in February to nearly triple that by the end of the year. The explosive rise catapulted its co-founders, Gabe Pereyra and Winston Weinberg, into the billionaire club in a matter of months.

The AI boom has produced several other young billionaires, including the 22-year-old founders of Mercor, valued at $10 billion as of late 2025.

San Francisco Housing Crisis

San Francisco's housing crisis is a pressing issue, with skyrocketing rents and home prices forcing many residents out. Despite impressive tech sector valuations, living in the city has become increasingly difficult, even for high-income earners.  By late 2025, the median home price in San Francisco reached approximately $1.49 million, a 10% increase from the previous year. Meanwhile, the median monthly rent for a one-bedroom apartment has topped $3,500.

Buyers working in AI accounted for more than 25% of all home sales in the city during late 2025, up from just 10% in 2024. To combat the crisis, some AI startups like Cluely have begun leasing luxury apartments for employees to ensure they can live near the office, with some units costing up to $12,000 monthly.

A mix of factors has worsened the crunch - from restrictive zoning laws and costly, delayed permitting processes to high construction expenses. Meanwhile, strong job growth in the tech industry continues to drive demand.

City officials have introduced various measures to address the crisis, such as rent control for select units, inclusionary zoning to mandate affordable housing in new developments, and policies to support higher housing density. 

However, in 2024, only about 1,600 new housing units were completed, the lowest in over ten years. The housing shortfall has triggered displacement, pushing lower-income and non-tech workers out of the city. Over 8,300 people experienced homelessness in 2024.