A man speaks, gesturing with his hands; behind him are images of a woman with Chinese text, the Golden Gate Bridge, and a website that says, “Let’s do nothing together”—all subtly hinting at the intersection of human connection and AI.
San Francisco’s political experiment with the technology has only just begun. But it’s already permeating civic discourse. Illustration created by Brandon Pho.

The dialog is in Mandarin, and unmistakably AI-generated. A mom juggles groceries in the kitchen with tough news: Her son is leaving San Francisco. But why? New girlfriend? No, mom: New wealth tax.

“The company doesn’t want to stay in California anymore,” says the AI-generated son, hauling his boxes into an AI-generated moving truck.

The video, released in May, is the first AI-generated ad produced by Y Combinator CEO Garry Tan’s political dark-money group, Garry’s List.

Under the banner of “Garry’s List Studios,” the ad discloses its use of AI and lists its top funders as Tan, billionaire Ripple co-founder Chris Larsen and Govern for California, another political group that’s friendly with tech executives.

In May, Garry’s List spent $51,000 on TV ad buys for AI videos, according to a spokesperson and financial disclosures.

The initial video urged residents to vote “No” on Prop. D, the “overpaid CEO tax” shot down by 53 percent of city voters in the June primary. Another AI video, posted to Instagram later that month, did the same, but aimed at Spanish speakers.

A third video endorsed Phoebe Maffei for San Francisco Superior Court Judge (she won with more than 57 percent of the vote). The fourth and most recent video, also posted to Instagram, is an AI-generated promo for Garry’s List itself, vowing to decipher political issues for voters to the tune of an upbeat pop song.

Tan, the venture capitalist who amassed a tech-friendly political following for bashing progressives for years, said he’s exploring further use of the tool. 

“We are currently doing the research to determine which races we will engage in this November, and how,” said Sam Singer, Tan’s spokesman, in a statement.

“With this new tool, Garry’s List takes documents and proceedings that are technically public but nearly impossible for most people to follow and turns them into ads that make the issues not just accessible but understandable, and we hold ourselves to that same standard in how we communicate.”

Tan’s allies are encouraged. 

“Short-form content is in,” said Griffin Lee, an organizer with ConnectedSF who aligns with Tan on many issues. “These videos have the best shot at engaging more Gen-Z and millennials.”

Tan’s opponents are bemused.

“It’s great. Please keep doing it,” said progressive San Francisco political consultant Daniel Anderson. “It seems like there are two things people love: Political ads and AI slop. I can’t imagine people will be moved on either front by these ridiculous videos. As far as I’m concerned — go for it, Garry’s List. Go nuts.”

San Francisco’s political experiment with AI is just beginning. But it’s already permeating civic discourse. In this year’s congressional race to succeed Rep. Nancy Pelosi, Sen. Scott Wiener is marketing a Claude-powered AI chatbot designed to mock his opponent, Connie Chan, over her stances on housing and transit. 

On social media, dueling factions of the city’s housing debate are generating AI images of San Francisco neighborhoods to start discussions about development restrictions, or simply to wind each other up. 

In this year’s Los Angeles mayoral primary, AI videos boosted the unsuccessful campaign of Republican reality TV star Spencer Pratt, turning his message into bite-sized short-form video stories. 

Tan has toyed with AI in politics for some time now. Garry’s List is a media venture on top of a political machine. AI-generated art often adorns the Garry’s List website, appearing above written posts that urge techno-optimism and tough-on-crime action. 

People who sign up with Garry’s List are promised their own “political AI” agent to answer questions personalized to the user’s elected representatives, district, and policy positions. Tan also used AI to build the website, prompting a spat online with critics he called “Luddites” over the site’s page speed.

“Cautiously — there can be positives here,” said Mindy Romero, a political sociologist and founder of the Center for Inclusive Democracy.

“It means a local campaign that doesn’t have money, that might be on the side of the public who would’ve really struggled to get their message out without money, can all of a sudden get up to scale in a way they couldn’t in the past.”

At the same time, Romero warns: “If you start to create AI-generated videos that are using somebody else’s likeness, then the purpose is to manipulate, which is dangerous and anti-democratic because people need truthful and accurate information.”

As a 501(c)4 nonprofit, Garry’s List can also spend money directly on candidates and ballot measures, print voter guides, host in-person events, take out ads and run educational political programs. 

The group spent $76,000 against the failed CEO tax measure this year, including the $51,000 TV ad buy. The group also gave $15,000 to Neighbors for a Better San Francisco, a moderate political pressure group that spent $860,000 against the CEO tax and bankrolled the 2022 recall of progressive District Attorney Chesa Boudin.

Garry’s List also gave a maximum donation of $39,200 to California gubernatorial candidate Xavier Becerra after Becerra bested Tan’s favorite, San Jose Mayor Matt Mahan, in the June primary. 

The Garry’s List ads mark another San Francisco experiment with AI in politics — at least in Tan’s own circles, for now.

“I think the people that will engage with these videos are people who already follow Garry,” said Griffin Lee.

Brandon Pho covers tech and power in San Francisco.

He has reported on communities up and down California since 2018.

Right before joining Mission Local, he sparked a California lawsuit against the federal government after obtaining and publishing the blueprints for a secret Bay Area ICE facility.

He likes the TV series ‘Columbo’ and lives under the panoptic surveillance of his two cats near Mission Dolores.

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4 Comments

  1. Garry Tan is an unmitigated public menace, much like the idea of AI in all things.

    Regulate these paid lying machines and tax the Billionaire bullsh*tter class 100%.

    There’s a reason why they back Weiner BTW obviously he’ll do anything for money, anything they tell him to as long as the check is big enough.

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  2. It all makes sense now. Of course Tan and co are the ones pushing the “do nothing” narrative about Chan. Gary Tan is one of the top ten most annoying and unhelpful SF transplants.

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    1. Of all the annoying things he has done (and it is a long list of extremely annoying acts) moving to San Francisco after being born somewhere else has got to be dead last. This “transplant” shit is so tired.

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      1. Fair enough. It’s true that a lot of the San Franciscans we most revere were transplants, like Harvey Milk. And if you zoom out, everyone here who isn’t Ohlone is a, erm, transplant. So yes, Garry Tan’s politics would be just as terrible if he had grown up here, that’s not the issue.

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