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​Ravi Gupta ’05 is a busy guy. In addition to being co-founder and managing partner of Arena, which supports progressive political candidates and reforms, and producing a politics podcast, and signing with a talent agency for a potential TV project, he’s about to launch Second Chance Studios, a nonprofit digital studio that employs formerly incarcerated people.

It’s a long way for someone who admits he wasn’t a great high school student himself. “I barely got into ��ñ��,” he says jokingly. Gupta, who grew up in Staten Island, blossomed once he entered the college environment. After becoming more politically aware in a post-Sept. 11/ Iraq War world, he joined and eventually became captain of the ��ñ�� Speech and Debate Team. He was on a pre-med track until he was encouraged to sign up for a program to teach English language classes in Ghana.

“At that point, I got totally sucked back into politics,” he says, and attended Yale Law School after graduating from ��ñ��.

After two years at Yale, he put his law degree plans on hold to work on Barack Obama’s first presidential campaign. Gupta started as a fundraiser, then worked his way up to running field offices during the primaries. During the general election, he was assistant to David Axelrod, then chief strategist to the campaign.

When Gupta returned to law school after the election, he thought he’d buckle down and finish his degree, until Susan Rice asked if he’d work with her in her new role as ambassador to the United Nations.

“She agreed to let me shuttle back and forth,” he says. Gupta completed his law degree while serving as her assistant and as a junior speech writer.

The experience was invaluable, Gupta says, but he found himself wanting to make a difference outside of government. He left politics to open a series of charter schools in Tennessee with law school classmates who had been interested in education reform. By 2011, Gupta had already received the University Medal.

The medal, the highest honor the University bestows, is awarded in recognition of distinguished service to the University, to higher education and to the larger community.

Gupta returned to the political world after the 2016 presidential election to co-found Arena. The organization not only supports progressive political candidates, but also “trains people who have been overlooked and underutilized” to work on campaigns for these candidates and eventually be on staff if they’re elected, Gupta says.

In New York, Arena helped with the successful election campaigns of U.S. Rep. Antonio Delgado, from the 19th congressional district and the first person of Black or Hispanic descent to be elected to Congress from upstate New York; and U.S. Rep. Ritchie Torres, representing the 15th congressional district and the first openly gay Afro-Latino member of Congress. In 2020, Arena raised more than $6 million and helped elect 27 candidates.

In 2017, Gupta and Jason Kander, a former secretary of state of Missouri and former member of the Missouri House of Representatives, launched Majority 54. It’s a podcast designed to help the 54% of Americans who did not vote for Donald Trump in the 2016 presidential election communicate with the 46% who did.

“Our whole mission is to talk to people in their lives who have different political beliefs, and have good conversations,” Gupta says, adding that his own family is politically split.

Over the winter, Gupta developed a TV pilot and signed with the Creative Artists Agency (CAA) for it and other potential projects. Given the fickleness of the entertainment industry, he’s mum on the details except to say the project is based on his experiences growing up in Staten Island.

But up first for Gupta is Second Chance Studios, which will open in June. Like Arena, it’s designed to help people find their potential, but instead of budding politicians and political wonks, the nonprofit focuses instead on the formerly incarcerated.

Annually, about 8,500 New Yorkers are released from prison, and 53% of those released are rearrested each year. That number drops to 31% for those who are employed after they’re released. The goal of Second Chance Studios isn’t just to give them jobs, but to set them up for new careers.

The idea for Second Chance Studios came from a connection Gupta made with Coss Marte, who founded the NYC-based fitness studio CONBODY after serving time in prison himself. Marte employs formerly incarcerated people and has a zero recidivism rate.

Fellowships are a year long and participants “run the studio,” Gupta says, while receiving training, coaching and mentoring in a “new media” field, such as digital advertising, video production or podcast recording.

“We want to learn in this first cohort what kind of range of skills and profiles really succeed in this world,” Gupta says. “If somebody already comes in with a high-skill background, how will they do compared to somebody who didn’t graduate from high school and college? We don’t want to exclude people from the program before we know what’s possible.”