Saikat Chakrabarti, Part 2 (S8E6)

In Part 2, we pick up where we left off in Part 1, with that fateful visit Saikat took to The Mission. He and friends worked a lot, but didn't have a lot of money (sound familiar?). To learn The City and have some fun, they signed up for as many walking tours as they could find. After a few months living in Park Merced, Saikat relocated to The Mission—16th and Hoff, specifically. Esta Noche was nearby, and it's where he saw his first drag show. A buddy worked with Saikat to build a web wireframing tool (think the basics of web design, the skeleton of sites, so to speak). They knew some other folks in tech, naturally, and met the people who were launching Stripe, an e-payments then in startup mode. Stripe eventually hired Saikat and his friend. Saikat was the fledgling company's second engineer. He started to see tech as a force for social good, but that didn't really jell well with the work he did for Stripe. And so he quit a couple years in. The woman he was dating at the time (whom he later married) still lived in New York, and Saikat visited as often as he could. He didn't yet consider himself political, but he was thinking about issues, specifically income inequality, poverty, and climate change. In early 2015, Bernie Sanders announced his run for president in the 2016 election. Saikat hadn't heard of Sanders at that point, but he was addressing those very issues that had become important to Saikat. He signed up to be a Bernie volunteer and started on a sub-Reddit called "Coders for Sanders." But Saikat wanted "in" in. And so he got in touch with someone working on the campaign. That someone was Zack Exley, whose political biography runs deep. Exley's job with the Sanders campaign at the time Saikat got in touch was to organize all the volunteers wanting to work for Bernie but who didn't live in the first four primary states (Iowa, New Hampshire, Nevada, and South Carolina). That effort needed tech solutions, which Saikat brought. But they weren't hiring technologists at the time. Still, Exley "snuck" him on as an organizer. He expected the experience not to be a big deal. He'd work for about a year, maybe learn a thing or two. But the Bernie 2016 campaign had other ideas. "We were on the brink of actually doing these big, structural changes," he says of his time on the campaign. Coming out of that experience, he and other organizers decided to take what they had learned and start applying it to folks running for Congress, starting with the 2018 midterms. Initially, they called their effort "Brand-New Congress," and the goal was to recruit 400 people nationwide to run for office. They fell far short of that ambition, managing to get around a dozen folks to run. They wanted people from all walks of life, not just lawyers, which Congress was and is made up of primarily. And they got that, just not on the scale they had hoped. The group became Justice Democrats, which is still in existence today. They didn't have the money to spend heavily on most of their candidates, so they went all-in on someone named Alexandria Ocasio-Cortez out of The Bronx. Her brother had nominated her as part of Brand-New Congress, and Saikat had gotten to know her through the process. He saw early on what a powerful candidate she was. He moved to NYC to help run AOC's first bid for Congress as a co-campaign manager. She won, of course, and Saikat had a front-row seat for AOC's ascendancy to the national stage. He says she was her authentic self through it all. Saikat helped start a think tank coming out of the Sanders campaign as well, developing many policy positions and ideas, among them what came to be known as the Green New Deal. It was a policy platform as much as anything else. It called for a renewed and very much intensified effort to combat climate change while also creating and upgrading infrastructure. They approached every candidate running for president in 2020 asking them to sign on to a Green New Deal pledge. They all eventually did. (Biden's "Build Back Better" platform was essentially a version of the Green New Deal.) Around this same time, Saikat had signed on to be AOC's chief of staff. But Ocasio-Cortez wanted him to be her insider-type guy (I bring up Veep because, well, duh), and Saikat politely refused. He offered to help her staff up and get good people in place instead. By April 2019, having got the Green New Deal launched, so to speak, he let her know that he'd be leaving that summer, around the time his daughter was expected. That September, Saikat moved back to San Francisco. One of the first things he did was rejoin think tanks and work on filling out gaps in the Green New Deal. The pandemic hit and he dug his heels in on policy. By the time the 2024 election approached, they were ready to hand something to Kamala Harris if she were to win. Obviously, that didn't happen. He believed those who warned that a Trump victory had bad implications for democracy. But then he watched his own rep in DC, Nancy Pelosi, shrug the 2024 loss off in a "You win some, you lose some" way. He launched his campaign for that seat in Congress "by tweet" in February 2025. Turning from the national to the local, I ask Saikat what San Francisco issues are top of mind for him. He starts with the idea of meeting with and listening to San Franciscans, his would-be constituents: town halls, office hours, mass Zoom meetings … he's already doing a lot of that work. Saikat believes that to begin to effectively address issues at the local level—ICE kidnappings, healthcare, housing, transit—big changes are needed nationally. The California primary election takes place on June 2, 2026. The candidates who come in first and second place in that election will go on to compete in the Midterm election next November. To learn more and get involved, head to Saikat's website—saikat.us. Follow the campaign on Instagram and Threads.