PayPal has attained mythic status in some corners of Silicon Valley.. The money transferring service spawned the careers of a generation who went on to start and bankroll some of tech’s most successful startups, among them YouTube, Yelp and Tesla. A 2007 Fortune Magazine article, featuring a photo of the PayPal Mafia in gangster gear, cemented its place in Silicon Valley lore. 

Since then, some PayPalniks have become as famous for their right-wing politics as for their business accomplishments. Billionaires Elon Musk, David Sacks and Peter Thiel became enthusiastic supporters of President Donald Trump, reaping the rewards for their financial support from this most transactional and corrupt of presidential administrations.

Until his recent falling out with Trump, Musk had carte blanche to slash away at government expenditures, often to devastating effect. Sacks, as Trump’s Artificial Intelligence and Crypto Czar, holds a position that will allow him to grant favors to those burgeoning industries (including, notably, himself). The linking together of Artificial Intelligence, a real thing that will change much about our world and crypto, which is little more than a high tech Ponzi scheme, reveals quite a bit about this administration and its PayPal associated cheerleaders. Thiel, for his part, has become an ambassador-without-portfolio, perhaps the most influential of the techies who paid their way into Trump’s inner circle.

In contrast to household names like Musk, Thiel and perhaps Sacks, Jeremy Stoppelman, a onetime PayPal vice president and current , has preferred to be more discrete about his political activities. Quietly, Stoppelman has become one of San Francisco’s most influential political donors, recently making headlines as a leading donor to the effort to oppose the recall of District 4 Supervisor Joel Engardio. 

To date, the Stoppelman has donated $175,000 to the Stand with Joel campaign, ranking him second only to Chris Larsen ($200k), the crypto billionaire who has flooded San Francisco with police surveillance cameras. Larsen likes Engardio’s consistent support for the long-troubled San Francisco Police Department. Stoppelman is a fan of Engardio’s embrace of YIMBYism, the belief that removing obstacles to residential development, including effective environmental and labor protections, will — magically — result in plentiful housing at all price points. 

YIMBYs want to increase the city’s density. The Westside, including the Sunset which Engardio represents, is a neighborhood, largely, of single-family homes. For YIMBYs like Stoppelman, it is ripe for re-development. They have been ardent supporters of Mayor Lurie’s upzoning plan which would allow for the easier demolition of existing construction and will inevitably result in displacement, especially of tenants living in rent-controlled apartments, and mom-and-pop business leasing storefronts along commercial corridors. 

To that end, Stoppelman was the biggest contributor to Proposition K, donating $350,000 to the November 2024 ballot measure that closed a portion of the Upper Great Highway. Closing the north-west corridor would create desirable beach-front property for market-rate and luxury housing, transforming a sleepy corner of San Francisco into what critics say will be Miami Beach. Prop K was largely backed by YIMBY tech interests, such as Stoppelman, Y Combinator Partner Emmet Shear ($75k), and Crypto company Solana Labs’ Director Anatoly Yakovenko ($50k) – however, it was opposed by about two-thirds of Engardio’s constituents, leading to recall on the September 16th ballot.

Stoppelman was also the seed funder for Sonja Trauss, the so-called mother of YIMBYism. In a 2022 San Francisco Standard interview, he gushed about his first meeting with Trauss. “It was an exciting moment . . . Not to use too cheesy of an analogy, but it was like meeting a great entrepreneur at the start of their endeavor. It told her maybe the day after the meeting, ‘I’ll get behind you, what do you need?’ So, I’ve continued to support her work all the way through the present.” 

Since then, Stoppelman has spent generously to further YIMBY causes. A staunch ally of notable YIMBY champion, Scott Wiener, in 2018 he backed the state senator’s bid to increase housing near commercial corridors, controversial legislation that wrested planning decisions from local jurisdictions. To that end, Stoppelman donated $100,000 to California YIMBY to promote Wiener’s bill. Days after it failed, Stoppelman hosted Wiener and Trauss at a meeting at Yelp headquarters, an event co-sponsored by the California Association of Realtors.

In 2022, Stoppelman donated $100,000 to the November 2022 YIMBY-backed ballot initiative called “Affordable Homes Now.” Proposition D offered short-cuts for developers who build “affordable” rental housing. It defined affordability as an apartment affordable to individuals or families making up to 140% of San Francisco’s median income, which would be nearly $153,000 for an individual, or just over $218,000 for a family of four, in 2025. The measure was defeated.

At a recent meeting at the Harvey Milk Democratic Club, Engardio attempted to explain Stoppelman’s continued support.  “He likes closed streets; that’s his thing,” Engardio said. Gentrification is also Stoppelman’s “thing.” The city they envision will be hospitable to the well-compensated techies in their employ and not to the working people who serve them.