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How AOC’s “humble” chief of staff got his start in Silicon Valley

Rep. Alexandria Ocasio-Cortez’s outspoken top aide, Saikat Chakrabarti, is making waves in Washington with his tough talk—but friends and former colleagues from the tech world have fond memories of working with him at Stripe and Mockingbird, the website design company he cofounded.

How AOC’s “humble” chief of staff got his start in Silicon Valley
Rep Alexandria Ocasio-Cortez, D-N.Y., leaves a news conference in the Capitol Visitor Center after responding to negative comments by President Trump that were directed at the freshman House Democrats on Monday, July 15, 2019. Her chief of staff, Saikat Chakrabarti, appears at left. [Photo By Tom Williams/CQ Roll Call]

One former colleague describes him as “smart but has very little ego.” Another praises him as “a very soft-spoken, genuine, kind human being.” And a third compliments him as being “the nicest, most purely motivated guy in the world.”

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It may be hard to believe, but they’re describing Saikat Chakrabarti, the hard-hitting chief of staff to Rep. Alexandria Ocasio-Cortez, who’s been making waves in Washington of late with his blunt rhetoric and take-no-prisoners attitude.

Over Twitter, he’s drawn ire by railing against Speaker Nancy Pelosi by name, sarcastically calling her a “legislative mastermind.” He’s labeled moderate members of his party as modern-day equivalents of the “Southern Democrats” of the 1940s, referring to the faction committed to sustaining segregation and opposing civil rights. He’s used “New Democrats” and “Blue Dogs” as seemingly disparaging terms for Ocasio-Cortez’s more centrist colleagues.

But it was when he lambasted a congresswoman for supporting a weaker border aid package that the House Democratic Caucus responded, via its Twitter account: “Who is this guy?

It’s jealousy, says political consultant Zack Exley. “They’re all just really jealous of him because he’s AOC’s chief of staff,” added Exley, a former colleague and close friend of Chakrabarti. “They’re also really angry because he, and she, speak their mind and call out bullshit when they see it.”

But, seriously, “Who is this guy?”

Saikat Chakrabarti was raised in Fort Worth by Bengali-American immigrant parents. The leap from a working-class high school in Texas to Harvard was formidable, says Exley, and the juxtaposition of the elite with the humble was likely an early shaper of his political views.

“Humbleness” is a thread that runs through all the character testimonies from friends and colleagues. That’s the quality that they say allows him to operate sanely in politics—and that allowed him to do the same previously in Silicon Valley, where he first made his mark. “I’m harping on about this humbleness, but it’s rarer here than you might think,” says ex-colleague Diede van Lamoen, of the tech world.

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Chakrabarti and van Lamoen worked together at Stripe, a payment management company whose customers now include Lyft, Target, and Unicef. Back then, Chakrabarti was one of the early engineers, and probably the third employee, recalls Ross Boucher, who was the fifth. The two were part of a team that spent seven months, before the company’s launch in September 2011, designing and building all the user-facing portions of Stripe: the dashboard, the API, the subscription features, the website itself. “I think it’s fair to say that Saikat had a significant impact on the direction of the company and certainly on its early success,” Boucher says.

The work-life balance was practically nonexistent then. Boucher and Chakrabarti would eat every meal together—in the office. They’d work out at the gym together and then return to the office. As if the burnout weren’t enough, he was also operating a separate tech company, along with Sheena Pakanati, his college friend, onetime roommate—and, oh, that fourth Stripe employee.

That company was Mockingbird, a web-based tool for designing websites and apps that the two cofounded shortly before Stripe and managed through their time there. (It’s still around, but Chakrabarti is no longer involved.) “Mockingbird, at the time, was perceived as a very high-quality product and was really respected by the market,” says van Lamoen, adding that the two articulated that they wished they’d done more with it.

But, life happened. A significant job opportunity for his wife, Kami, took the couple to London in 2013, which is where van Lamoen, then Stripe’s head of international, opened up shop as a base for global expansion. Chakrabarti continued his Stripe work in the U.K. for a few months before calling it quits. Hemingway had his Paris era. Bowie had his Berlin era. Chakrabarti had a London era, which became his soul-searching period.

The introspection resulted in a classic self-reflective conundrum: Is this really all there is? “He wasn’t satisfied by the tech scene,” van Lamoen says. “There was the sense that this doesn’t have sufficient meaning.” Besides, in the London satellite office, he perhaps no longer felt as integral to the team. And yet, he still felt the pressures of the Valley’s constraining ethos.

The shift from tech into politics, then, appeared a push rather than a pull. “I don’t think there was a master plan,” says Pakanati of her friend’s chiseling out his new path, “but rather a series of exploratory steps.” The first of these steps would be to contact Zack Exley about joining Bernie Sanders’s 2016 presidential campaign.

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One of the first things Exley asked, as he did with every misguided naïf who inquired about hopping on board: “Why do you want to ruin your career by working for Bernie?” Half joking, but half serious, he told me, “It was understood that if you were working for Bernie, you might get blacklisted.”

Furthermore, Exley was skeptical because Silicon Valley personnel would constantly hassle him with hopeless offers. “I know exactly what you need,” they’d tell him. “You need an app that does x, y, or z, or whatever idea that’s been tried a million times and doesn’t work.” But Chakrabarti was different. He listened. He participated.

Mr. Chakrabarti goes to Washington (well, Burlington, actually)

Exley says the recent Valley dropout got to work as an organizer, sitting down with volunteers and attending events: “He really dug to figure out what we were trying to accomplish.” At that point, his tech prowess manifested for the first time in the political field, as he developed tech tools to help simplify campaign paperwork, like event invite lists. His tiny tweaks would save 100 steps, Exley says. “He did a million little things like that. And that’s what allowed everything to scale.”

Separately, Chakrabarti would team up with Pakanati again to develop Spoke, another tool that smoothed campaign organization. It’s a peer-to-peer texting tool that streamlines text message alerts for supporters and organizers. The Bernie campaign used it, and because it’s open-source software, it’s been employed on a national and global scale: to engage voters in congressional races in Alabama and Virginia, to mobilize for the Affordable Care Act, and for the vote to achieve marriage equality in Australia. In 2017, the duo transferred ownership of Spoke to the progressive advocacy group, MoveOn.org.

As with Mockingbird, there were hints of regret that they could have done more with Spoke. “Things just went in a different direction, so we didn’t end up developing the company,” Pakanati says. For Chakrabarti, that direction was moving more firmly into politics. If he was, then, in the middle of the Venn diagram that encompassed tech and progressive politics, his trajectory was taking him into the fuller circle of the latter.

With Exley, he’d go on to found two separate PACs: Brand New Congress and Justice Democrats. Exley says the brainwave for the former happened while they were lounging around in Las Vegas during the Nevada caucus, wondering what they’d do after the election. Brand New Congress, they decided, would serve as a “post-partisan” committee to endorse progressive candidates during a Hillary Clinton presidency.

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But when the election went to Trump, Justice Democrats became a better model, in that its core aim was to defeat the Republican Party—”which had gone off the deep end”—and to push for a platform that included securing the Green New Deal, living wages, and Medicare for all. The PAC endorsed 79 progressive candidates in the 2018 midterms, including the four congresswomen now known by fans and adversaries alike as “The Squad“: Ilhan Omar, Rashida Tlaib, Ayanna Pressley and Alexandria Ocasio-Cortez. Chakrabarti would become the latter’s campaign chair, and then her chief of staff.

Even if AOC’s right-hand man has physically left the tech world, his colleagues think the work ethic and discipline he developed early on make him a rare example of humility in politics. “I always joke that he was the one emotionally healthy person in politics,” Exley says of Chakrabarti’s time as executive director of their PACs. “He came from an environment where people actually did work all day, and had meetings and made decisions. And that’s not exactly how progressive campaigns always work.”

For Exley, his friend’s provocative tweets are coming from a place of deep care about the state of the country. So, why are they taking House members by surprise? “A lot of these people in Congress have just been behaving badly for so many years without anyone calling them out,” Exley says. “The people on the Hill that are upset with him can’t figure out his motives, because they’re like, ‘what’s this guy after?’ They can’t believe he just wants to make Congress work better and be less corrupt and fix stuff.”

Whatever you make of the back and forth, Chakrabarti’s transition out of tech seems to have been a singular success. “He’s one of the very few people that has broken out of tech in a structural way, gone on a completely different path, and remade a success,” van Lamoen says. “A lot of people talk about doing that. Very few follow through.”

Chakrabarti, in flawless following with his reputed affability, declined to talk because of family commitments—but was incredibly polite about it.

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