New Delhi: Saikat Chakrabarti likes his music “open-ended”—hip-hop, rock, and Bengali tracks feature among his many likes.
This Thanksgiving, he says, the family got together to watch “endless amounts of Sa Re Ga Ma Pa”, the popular Indian reality show for budding musicians. The show—the family tunes into the Bengali version—is a “bonding thing” with his daughter, he says.
His range in music, it appears, reflects his many influences. Chakrabarti is an Indian-origin Bengali born in Texas. He attended a majority-Black school before joining the prestigious Harvard University to study computer science. After graduation, he worked at a hedge fund firm but wound up founding fintech start-up Stripe.
The 39-year-old Democrat — who likes playing basketball and reading sci-fi and fantasy fiction by Octavia Butler, Ursula K. Le Guin and N.K. Jemisin — turned to politics with the Bernie Sanders 2016 presidential campaign. He also became the chief of staff for New York Congresswoman Alexandria Ocasio-Cortez, popularly known as AOC, two years later.
Now, the Silicon Valley entrepreneur with $50 million in equity is running for Congress from the San Francisco seat that will be vacated by seasoned Democrat Nancy Pelosi next year.
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Personal is political
Chakrabarti, in an exclusive interview with ThePrint, says that as one of the founding engineers of Stripe, his role “especially shaped his politics”.
His takeaway from earning in abundance, he says, was a nagging feeling—“What a crazy world we live in!”
“I worked hard, but most people work very hard… teachers, nurses, and doctors. Just because I joined a company early on, I was able to make all this money while everybody else can’t even afford a home… I think an economy set up like that is destined to fail,” he says.
The US used to be a society where “everyone had”, or at least the “goal was to give everyone access to the American dream”, he says, adding, “That has been thrown out. Now, we have an economy where everyone is trying to hit the lottery and make it.”
Contesting from California’s 11th District, Chakrabarti’s main opponent was going to be long-time Congresswoman Pelosi, but the race opened up for Democratic contenders after she announced her retirement. He is now up against state Senator Scott Wiener and Hong Kong-born progressive Connie Chan, and more could still put their hat in the fray.
Wiener appears to be an establishment favourite, but Chakrabarti is close on his heels.
At the workplace
Starting out his professional career at Bridgewater, Chakrabarti says, “did not suit him”.
“I asked someone at the beginning, ‘What’s the value that you find in this work?’ And they’re like, ‘Well, we create liquidity in the markets.’ I thought then that I didn’t know if that’s really for me,” he says.
But the job taught him discipline and hard work—skills that now serve him well as he runs a demanding congressional campaign.
Asked what drove the tech entrepreneur to come up with Stripe, a PayTM-like platform, Chakrabarti cites Nobel laureate Muhammad Yunus. “This is the era of microfinance loans, which lifted Bangladesh out of poverty. I thought, maybe, that would be one way to tackle some of the big problems of this world. At that point, the tech industry was still more values-driven,” he explains.
At Stripe, Chakrabarti gradually realised that he wasn’t working on the issues he wanted to.
“It’s very cheesy to say this, but I wrote a list of what I want to work on: inequality, poverty and climate change,” he says.
“That’s how I ended up working on the Bernie campaign.”
In Mamdani’s trail?
After Bernie and AOC, Chakrabarti’s campaign resembles that of Zohran Mamdani’s successful New York mayoral race.
The entrepreneur says he “loves what Zohran has established”.
“His campaign brings so much hope to people. And, it helps the campaign I am running here. Anytime someone goes up against the kind of money and attacks he faced and wins, it proves that this other model of campaigning can work—where you don’t have to rely on big donors and corporate money to win. And that lets you be free when you are elected to govern for the people,” he says.
Like Mamdani and AOC, Chakrabarti has promised to run his campaign on grassroots donations.
On Mamdani managing expectations of the Left and the Right, Chakrabarti says, “His job is to be an effective mayor. I think the best thing he can do for the Left is to show that the Left can govern.”
If elected, Chakrabarti expects similar scrutiny. “You can’t ignore any of your constituents, whether they’re Left, Right, or anybody. There are Trump voters in San Francisco. I talk to them and listen… I think, as soon as you make yourself a politician who can’t take the criticism, you’re done,” he says.
Politics of the time
The Congress aspirant admits that he has entered politics at a moment when people want to vote for anyone offering “sweeping changes”.
“That’s what got Obama in. That’s what got Trump in… Trump’s promise to ‘clear the swamp’ is not, totally, wrong. There is a swamp of corruption,” Chakrabarti says.
Apart from clamping down on corruption, Chakrabarti’s campaign has proposed a wealth tax. Healthcare, he says, is important but less popular. While single-payer insurance is a trending topic, his idea is to fill the gaps with government-provided healthcare, “like NHS in the UK or [the systems] in Sweden or in Norway”.
Chakrabarti leans towards progressive and socialist policies, but likes to avoid labels. “I’ve always campaigned with ideas first. Whenever you talk about the Left or Socialists or the Right, this, in people’s minds, frames a horse race among tribes. But when I talk about guaranteed healthcare for everyone, a public bank, or building houses to bring down costs, these are overwhelmingly popular,” he says.
But the 39-year-old concedes that several leaders, both among Republicans and Democrats, have caved in to corporate interests.
“That we have so many politicians who are sold out to corporate and lobby interests—who go in there and enrich themselves by trading stocks on insider information—is what has made people lose faith,” he says.
A generational turnover within the Democratic Party is why he wanted to run against Pelosi in the first place. Democrats, in the middle of this existential crisis, need an overhaul, he believes.
“I honestly think, in the next election cycle, and especially in 2028 (midterms), there’s going to be a chance for hundreds of new people to be running to completely sweep away what the existing Democratic party is,” Chakrabarti says.
It is necessary, he believes.
“The party polls worse than Trump now, and if we can’t replace who the party is, what it stands for, and what they’re fighting for, in voters’ minds, it is never going to be able to win an election,” he says.
Chakrabarti, in 2017, helped start Justice Democrats, a coalition of party members that recruited AOC and US Representative from Missouri Cori Bush.
His think-tank, New Consensus, has also worked on a plan called ‘Mission for America’, which he describes as the coalition’s “version of what Trump’s Project 2025 was”.
Unlike the contents of Project 2025, which advocates for several Right-wing policies such as expanding presidential powers and banning abortions, Mission for America outlines plans to build an economy around climate change and ways to narrow down inequalities.
Climate change, Charabarty says, offers new possibilities to upgrade the economy and create safer jobs. These can include manufacturing batteries, electric vehicles, and solar panels to re-employ those in legacy industries.
It’s an evolution, he says.
“At some point in America, we went off whale oil and started using fossil fuels. The whale oil industry did not like that. Then, we started driving cars. Well, the horse buggy industry did not like that… All of this doesn’t mean we don’t make progress,” he says.
And “offshore oil workers can work on wind farms” under “safer and possibly better” conditions, he adds.
But, before this, a “people’s movement” is needed to “challenge and break the stranglehold of big money (in politics)”.
Despite his reluctance to be banded together with the ‘radical Left’ in the US, Chakrabarti is vocal about his stands, a lot like Bernie and AOC.
Immigration, he believes, is a human rights issue, not an enforcement one, like the Trump administration would like others to perceive.
US’s Immigration and Customs Immigration (ICE) – the agency emboldened by Trump’s team to hunt and deport immigrants – must be abolished, Chakrabarti says. Instead, he says, it should be replaced with a “fixed legal pathway”, one not borne out of cruelty, but humanity, as it was when his own family arrived in the US from India.
Chakrabarti isn’t shy of criticising US’s foreign policies over the decades. “It has been fundamentally broken for decades now. We have a mindset that we’re the ‘police of the world’,” he says.
Trump’s policies, though, admittedly are even worse, he says. “If we continue antagonising the rest of the world, eventually America will be alone.”
And US’s continued support to Israel, Chakrabarti says, is what led to “the genocide in Gaza”.
‘Won’t tell India what to do’
What does Chakrabarti think of India?
India, it seems to him, is at a crossroads. “There are two potential futures. One version of economic growth looks a lot like what we are seeing in America—very unequal… The other path is that India realises it has control over its future. I think Indians realise this and are using this moment to create a country that lifts more people out of poverty. I have a lot of hope for India,” he says.
But the country’s “shift towards nationalism”, he says, is contrary to its founding values. “A secular, multicultural democracy… the idea of India post-revolution was beautiful”, he says.
But, as an “anti-imperialist” American politician, Chakrabarti says, he will “never say what India should do”.
Still, he has some advice. “I’d encourage India to lean into its founding values and create a society that truly works for everybody because I think India has got a rare opportunity right now to do that,” he says.
(Edited by Prerna Madan)
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