Meet Ravi Gupta (Under 30 '18)


When Ravi was preparing for his first REALITY journey, he had just given notice as RePublic, an organization for which he was founder and CEO. Find out how Ravi’s time in Israel informed his next steps, putting him squarely on the path to start a whole new chapter and a whole new organization.

REALITY: Describe what you do and how you are trying to make an impact.

Ravi: When I did my first REALITY journey, I was entering my final year as founder and CEO of RePublic, a network of charter schools in the South. We were among the highest performing public schools in all of Tennessee the years that I was there, and when I took my first journey with REALITY, I had just informed my board that that would be my final year.
n 2016, I got together with some former colleagues from my work on the Obama campaign and started Arena, and organization working to support candidates around the country who are interested in serving our underserved communities and encouraging more forward thinkers to run for office.

REALITY: Who inspires the work that you do?

Ravi: I’m definitely inspired by Bryan Stevenson and his work down south with The Equal Justice Initiative. He’s done a lot to bring awareness to the history of the South.
A second person who really inspires the work that I do is Paul Farmer with everything he has done in Haiti and elsewhere, bringing awareness to HIV and tuberculosis and working to improve our healthcare systems around the world.

REALITY: What was the most meaningful moment on your REALITY journey?

Ravi: On my first REALITY journey, Forbes 30 Under 30, the highlight was definitely hiking Masada. That hour was particularly compelling; the way the story was told and how we were left with so many cliffhangers along the way was incredible. It was a mystical experience in many ways. We got to bond with people while also really grounding ourselves in the history of that amazing place.

REALITY: How have you stayed connected to Israel since your journey?

Ravi: In a lot of cases, REALITY is what brings me together with peers and colleagues because the alumni community is just so big! In addition to the people you travel with in Israel, you have this whole community of alumni who connect and collaborate back home.

REALITY: How have you shifted reality since your return?

Ravi: There’s no one moment; it’s more a series of events. I learned about all of the challenges and opportunities that people across industries were facing. After my first journey, I came home with a huge boost of energy and a new group of supportive friends to help me manage my career transition.

REALITY: How have you stayed connected to Isreal since you returned from your REALITY journey?

Ravi: I work in Democratic politics at a time when Israel is a huge topic of discussion, and now I’m at a point where I can understand the complexities of Israel in a new way each time I visit. When I’m reading the headlines and coaching candidates on the best, most ethical and responsible policies, it’s helpful for me to know some people on the ground in Israel and to have such an amazing and connected team to help me continue to understand what’s going on there.

REALITY: Since REALITY, how “do” you Shabbat? Share a short story.

Ravi: We host a lot of Shabbat dinners at my apartment. We hold a Shabbat dinner just about every other week but I think we’re still working on getting them right. There’s also lot of talk about actually “keeping” Shabbat by carrying it over to Saturday and adding more depth to what we do.

REALITY: What do you want the REALITY community to know about you?

Ravi: We’re a community that is an extension of the REALITY community in so many different ways. We learned a lot through our journeys over in Israel; as much as we like to talk about the complexities of Israel, we deal with our own complexities here in the U.S., and I want people to know that I want to start the conversation and the thought partnership on what we can do right here in the United States.

The Charles and Lynn Schusterman Family Foundation is proud to empower emerging leaders to explore their values, identity and new ways to strengthen their communities. We believe that as we work together to repair the world, it is important to share our diverse experiences and perspectives along the way. We encourage the expression of personal thoughts and reflections here on the Schusterman blog. Each post reflects solely the opinion of its author and does not necessarily represent the views of the Foundation, its partner organizations or all program participants.