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Politics & Policy

Tech exec challenges San Francisco’s lone Democratic Socialist supervisor

Bilal Mahmood stands on a balcony.
Tech entrepreneur Bilal Mahmood will challenge Supervisor Dean Preston in what will be a closely watched November race. | Source: Michaela Vatcheva for The Standard

One of the worst-kept secrets in local politics is finally out in the open, as tech entrepreneur Bilal Mahmood confirmed to The Standard in an exclusive interview that he will file paperwork this week to challenge Supervisor Dean Preston in November’s election.

Mahmood said he will formally file papers with the San Francisco Department of Elections on Thursday, setting the stage for what could become the most closely watched local contest outside of the mayor’s race due to the candidates’ radically different visions for the city and the crises playing out in District 5. Issues around homelessness, public safety and drugs—particularly in the Tenderloin neighborhood, which became part of the district in 2022—are in some ways emblematic of problems San Francisco is facing on the whole.

“If we can solve the challenges of District 5, we can solve the challenges of the entire city,” Mahmood said. “And that, to me, is why this district is important.”

Bilal Mahmood sits in front of City Hall.
Bilala Mahmood, pictured near Civic Center, said that District 5's challenges are emblematic of the city as a whole. | Source: Camille Cohen/The Standard

Mahmood, 36, previously ran for state Assembly in 2022, finishing with a surprisingly strong third-place showing in the primary despite never running for elected office. Since then, he has spent time meeting with local officials and community stakeholders, as well as writing about San Francisco’s excessive red tape. He also spearheaded an initial effort to lure universities into creating campuses and housing in vacant Downtown commercial towers.

While the District 5 race would seem to be a clear case of a moderate Democrat challenging a progressive incumbent—Preston’s 2019 election victory made him the first Democratic Socialist to win a supervisor seat in almost 40 years—Mahmood has said he wants to move away from the divisive rhetoric on both sides. He also distanced himself from Mayor London Breed.

“I don’t have her endorsement,” Mahmood said. “I’m not seeking it either.”

Mahmood, who attended Stanford University and the University of Cambridge before working as a policy analyst in the Obama Administration and launching a career in tech, said he is running for supervisor because City Hall is “fundamentally broken.” Bureaucracy, he said, has led to corruption and a sclerotic hiring process that leads to staffing shortages in public safety, while a broken permitting system has hampered development. 

Preston, a former tenants rights attorney who has opposed new housing developments and called for defunding the police, has contributed to the problems, said Mahmood, who moved to the Tenderloin last year and has been a renter in the city since 2014.

“He’s consistently blocked housing, and he’s not been collaborating with the community,” Mahmood said. “If you talk with most community members here [in the Tenderloin], they don’t see him.”

Over the last year, Preston has increasingly become a target of moderate political groups in the city. The supervisor, who owns a home by Alamo Square, has framed his reelection as a battle for the soul of San Francisco, saying the opposition he is facing is part of a “billionaire backlash” funded by wealthy tech executives. Preston often attributes much of the city’s problems to income inequality and capitalism. He did not respond to a request for comment for this story.

Dean Preston listens during a meeting.
Supervisor Dean Preston, the Board of Supervisors' lone Democratic Socialist, is facing opposition from moderates in his November reelection. | Source: Justin Katigbak for The Standard

“What is wrong with the district right now is that Dean is too focused on pointing fingers and making excuses for why things don’t work, rather than finding solutions and results,” Mahmood said. “You have a supervisor that’s saying the way we bring economic opportunity and solve the public safety crisis by ending capitalism. Even if you believe that to be true, that’s not going to happen overnight.”

In September, Elon Musk tweeted that he would contribute $100,000 to helping oust Preston in reply to a tweet by Y Combinator CEO Garry Tan, who has been one of the supervisor’s fiercest critics. Musk then went a step further by saying Preston “should go to prison” for legislation he had written, prompting the supervisor to call Musk a fascist.

Meanwhile, the moderate political group GrowSF, which is led by two former tech workers, announced last summer that it had raised more than $300,000 for its “Dump Dean PAC.”

Spending by independent groups will likely focus on the policy differences between the two candidates, but Mahmood said he also intends to show the difference in their lived experiences.

Mahmood is the son of Pakistani immigrants, and his first visits to what is now District 5—which also includes the Haight, Japantown, the Western Addition and NoPa—began when he was a boy growing up in the Peninsula. Shalimar, a Pakistani and Indian restaurant on Jones Street in the Tenderloin, was the only restaurant in the Bay Area that served his family’s native dishes at that time. The restaurant remains his favorite to this day. 

“I think [the Tenderloin has] the best food in town, specifically some of the best ethnic cuisines,” Mahmood said, before quickly adding that restaurants in Japantown are also at the top of his list.

While the supervisor race won’t be decided until November, Mahmood is also appearing on the March ballot for a seat on the San Francisco Democratic County Central Committee. Officials fundraising numbers aren’t due to be reported until the end of this month, but Mahmood said he had raised more than $200,000 in that race.