Living Large, Room by Room
In a city where tech dreams are built, it seems even billionaires can’t escape the roommate life. Winston Weinberg and Gabe Pereyra, co-founders of the AI start-up Harvey, are living proof. Despite their company being valued at a staggering $8 billion, these tech moguls still share an apartment with a third roommate. For them, it’s not about making a statement—it’s about staying grounded while they focus on building their empire. San Francisco’s housing market, with its sky-high prices, makes this living arrangement less surprising and more a necessity.
Weinberg, at the helm of Harvey as CEO, insists their lifestyle hasn’t changed much, even as their company rockets up the valuation charts. The duo’s success story is a testament to the relentless hustle required in the tech world, where even the wealthiest are not immune to the city’s notorious housing challenges. Their choice to live with a roommate underscores the reality that, in San Francisco, wealth on paper doesn’t always translate to a mansion in the hills.
The Housing Conundrum
San Francisco’s housing crisis is as legendary as its cable cars. The city’s housing crunch is exacerbated by restrictive zoning laws and high construction costs, leaving even high-income earners scrambling for decent housing. In 2024, the city saw the construction of a mere 1,600 new homes—the lowest in over a decade. Meanwhile, demand continues to surge, fueled by tech-driven job growth, sending prices through the roof.
The median home price in the city is a jaw-dropping $1.49 million, with rents for a one-bedroom apartment averaging over $3,500 a month. It’s a brutal market that pushes non-tech workers and lower-income residents out, while homelessness remains a persistent issue. In 2024 alone, over 8,300 people experienced homelessness—a stark reminder of the inequality that plagues the city. Despite efforts like rent control and inclusionary zoning, the crisis shows no signs of abating.
Harvey’s Meteoric Rise
Founded in 2022, Harvey has quickly become a standout in the AI sector, especially with its focus on generative AI tools for lawyers. The company’s valuation soared from $3 billion in early 2025 to $8 billion by year’s end, making Weinberg and Pereyra paper billionaires almost overnight. But as Weinberg notes, their wealth is largely theoretical—tied up in the company’s success.
The founders’ commitment to their employees and future growth is evident. They’re planning to expand their workforce significantly, not just in San Francisco but also in New York and other global markets. This expansion reflects their belief in the potential of AI to revolutionize industries, even as they navigate the challenges of their home city’s housing market.
A City of Contrasts
San Francisco is a city of contrasts—where tech wealth and housing scarcity coexist uneasily. The city’s leaders are attempting to address these issues with policies aimed at increasing housing density and affordability. Yet, the pace of change is slow, and the pressure on the housing market remains intense.
For Weinberg and Pereyra, the roommate life is a reminder of the city’s challenges, even as they ride the wave of the AI boom. Their story is a microcosm of the broader issues facing San Francisco, where the dream of tech success is often tempered by the harsh realities of everyday living. In a city that never stops innovating, perhaps the greatest innovation will be finding a way to make housing accessible for all.
