Political observers have noted the tech sector’s liberal proclivities for more than a decade, but no figure better embodies field’s growing radicalization than Saikat Chakrabarti, who helped elect Ocasio-Cortez last year and until recently served as her chief of staff. A 2007 Harvard graduate, Chakrabarti worked briefly for the hedge fund Bridgewater before relocating to San Francisco, where he co-created the web design tool Mockingbird and helped build the online payment-services firm Stripe.
But in 2015, the millionaire capitalist abandoned the startup scene to join the campaign of Vermont Sen. Bernie Sanders—the first significant democratic-socialist candidate for president in generations, and the idol of Chakrabarti’s fellow millennials. After Sanders lost the nomination, the entrepreneur and several fellow Sanders staffers started the groups Justice Democrats and Brand New Congress, which recruited Ocasio-Cortez to challenge then-Rep. Joseph Crowley.
In 2019, while still working for the rookie congresswoman, Chakrabarti donated $3,000 to Cabán’s campaign from his apartment in the West Village. He was one of many figures who did not respond to repeated requests for an interview.
He’s far from alone in his leftist inclinations, though. Tumblr founder David Karp and Edmund Resor, vice president of the software company Defentect Group—both New Yorkers—gave the maximum $2,700 to Ocasio-Cortez’s campaign last year. Ross Boucher, a colleague of Chakrabarti’s at Stripe and the co-founder of the Motorola-acquired startup 280 North, donated $1,200. Thomas Lehman, the co-founder of the website Genius, threw in $1,000, as did his fellow Brooklynite Brian O’Kelley, the CEO of AppNexus.
Crain’s found that in the most recent filing period, Ocasio-Cortez raked in thousands more from professionals in the tech industry, including from employees of Google, SpaceX, NimbleBit, IBM and ABB.
While many were based on the West Coast—the congresswoman actually received more donations from California than from New York—a number were residents of the five boroughs.
The tech industry has also smiled upon Salazar and Cabán. The largest individual donor to the former has been Christian Rudder, the founder of the dating site OKCupid, who resides in the senator’s northern Brooklyn district. Cabán attracted $55,000 in contributions from the wife of Netflix CEO Reed Hastings, $5,000 from the widow of Apple founder Steve Jobs and $1,000 from the wife of Zillow and Expedia founder David Barton. Another $5,500 for the previously unknown public defender came from Eric Silverberg, founder of the gay dating app SCRUFF, who appears to have sent two of the checks from his company’s office near Bryant Park.
One Brooklyn-based startup founder said at a fundraiser he held for Salazar last year, most of the 40 to 50 attendees hailed from his field. The entrepreneur asked to speak anonymously because he has sold his company and now holds a significant role at a multinational tech giant.
He said he does not see himself as a socialist, much less a self-proclaimed Marxist like Salazar. But he said his experience as an employer led him to favor replacing for-profit health insurance, a move he observed only socialist candidates championed until recently.
I largely agree with what democratic socialists stand for,” he said. “As an entrepreneur, I wish we had single-payer health care because then we would only have to focus on wages and not benefits.”
The techie noted that Salazar, Ocasio-Cortez and Cabán drew votes largely from Williamsburg, Greenpoint and Bushwick in Brooklyn and from Long Island City, Astoria and Ridgewood in Queens—gentrifying areas favored by the sort of affluent millennials involved in the cutting-edge economy. Compared with their counterparts on the West Coast, he argued, innovators in New York are better integrated into the urban fabric and more dependent on public resources such as the subway system.
Further, many shared their peers’ enthusiasm about the Sanders campaign in 2016—and their horror at Trump’s defeat of Hillary Clinton.
“That’s an identity thing. There’s a clustering of like-minded people,” he said. “To be told you can’t have all these things because you need to be pragmatic, only to have pragmatism lose to Trump, changed a lot of New Yorkers.”
Asked if high-earning tech entrepreneurs and employees are ready to accept redistribution of their own wealth, the Salazar donor said, “That’s a really good question—if anybody has data on the answer to that, I’d love to see it.”