Michelle Caldeira On How To Leave a Lasting Legacy With a Successful & Effective Nonprofit Organization

Believe in the impossible. At Uncornered, we talk about setting high expectations and low requirements. We fully expect and believe that someone who has spent time in jail can become a college graduate, community leader for good and changemaker. As a part of this series, I had the pleasure of interviewing Michelle Caldeira. Michelle Caldeira […]

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Believe in the impossible. At Uncornered, we talk about setting high expectations and low requirements. We fully expect and believe that someone who has spent time in jail can become a college graduate, community leader for good and changemaker.


As a part of this series, I had the pleasure of interviewing Michelle Caldeira.

Michelle Caldeira is the co-founder of Boston Uncornered, an organization that engages and supports active gang-involved individuals to end violence and generational urban poverty. Born in Guyana, Michelle was raised in Brooklyn, New York, earned her BA in Sociology from Binghamton University, and has spent the last 16 years in Boston. Michelle currently works remotely from London where she lives with her husband and volunteers her time on the boards of Jose Mateo Ballet Theatre and the National Youth Employment Coalition (NYEC). A still new and slow runner, Michelle has nevertheless completed 12 marathons.


Thank you for making time to visit with us about a ‘top of mind’ topic. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today?

Moving from Guyana to the US when I was 12 years old. Guyana is a small country in South America where higher education and career options are limited. So, my parents made the sacrifice to uproot their lives and move us all to America — the land of opportunity. I remember arriving on a cold February day in 1988 at JFK airport in New York City and we all piled into a one bedroom, one bathroom apartment in Brooklyn, all seven of us. My mom, dad, and five girls ranging in age from 3 to 17 years old. This is where I lived until I went away to college.

You are a successful leader. Which three character traits do you think were most instrumental to your success? We would love to hear a few stories or examples.

  1. Curiosity — Reading is one of my hobbies and I like to take in as much information as possible. This has kept me in a place of questioning and humility rather than a place of arrogance of believing I know the solution.
  2. Focus — Many, if not all of us get into nonprofit work simply to help people. When there is insurmountable pain and chaos all around, it’s hard to not to be diverted and just spend your days putting out little fires everywhere but instead staying focused on the big picture and vision, constantly going back to your strategy to see where you can improve.
  3. Humor — I think finding joy and lightness in any situation is key to pushing forward beyond pain, failure, and loss.

What’s the most interesting discovery you’ve made since you started leading your organization?

People who want to help and feel good about helping so often get pulled away from the hard thing, the thing that really will bring about systemic change. So many of us spend years, decades doing the same thing over and over again — helping people, feeling good but staying away from the most difficult intractable problems including gang violence, poverty, and homelessness.

Can you please tell our readers more about how you or your organization intends to make a significant social impact?

Boston Uncornered is on a course to END community violence. I capitalize and bold END because we actually believe it’s possible to end it, not just reduce it for a time. In our research, we’ve learned that across the country, in urban communities a small percentage of the population are involved in 60 to 70 percent of the violence that happens through small crews or social networks of disengaged/disconnected young adults (sometimes referred to as gangs), and primarily through gun violence. This community violence brings with it a high social cost — trauma from death and injury, as well as a financial cost — each shooting, fatal or non-fatal, costs cities at least one million dollars (1M dollars). A small city like Boston has more than 200 shootings each year. So, for the last five years alone, it has cost all of us one billion dollars. We’ve “spent” one billion dollars and have nothing to show for it except lives lost and a trail of trauma. Uncornered’s model, when implemented, instead gets individuals to stop shooting, get off the street corner and onto a college and career pathway. This will save lives, stop violence, and end poverty. Even as I say it out loud, it sounds big and impossible, but that is the significant impact we plan to have.

What makes you feel passionate about this cause more than any other?

I believe in the goodness of people more than anything. Also, my parents, my sisters, my extended family, both biological and chosen, were always around to support me and give me hope, love and resources. That has ensured any success I have. We created Uncornered to provide that same network of support, love, and hope for those who don’t have it.

Without naming names, could you share a story about an individual who benefitted from your initiatives?

I think often about a young man who has participated in Uncornered for three years. He had been incarcerated and had been in and out of correctional facilities since his teenage years. Spending just a few minutes with him, you could see his compassion and hear his brilliance that had been buried with years of neglect and trauma. A few months into participating in the program, one of his friends was shot in front of him; he watched him die in the street. That loss brought a lot of pain, anger, and feelings of wanting to retaliate, to continue the cycle. Instead, he called his mentor who worked with him through those feelings. I remember him saying a few years later that he tried several times to get kicked out of our program, but no one would kick him out or let him leave. Hearing him reflect on that growth made me so proud. He is currently enrolled in a community college working on an Associate Degree in Business Administration.

We all want to help and to live a life of purpose. What are three actions anyone could take to help address the root cause of the problem you’re trying to solve?

  1. Change narratives you, or others, may have about why a young person may be hanging on the street corner, why they may pick up a gun and shoot another person. Shift to a narrative that an individual who makes bad, life-changing decisions may not necessarily be a bad person. And that someone who has landed in such terrible circumstances may need love, hope and belief more than anything to change their life.
  2. Learn about how structural systems that disinvest in and starve certain communities of resources have led to generations of violence and poverty.
  3. Vote for public officials that are committed to changing systems.

Based on your experience, what are the “5 Things You Need to Create Philanthropy That Leaves a Lasting Legacy?” Please share a story or example for each.

  1. Invest in a new challenge. We all know traditional youth and after school programs do good work and have an impact. We know giving to a food pantry will feel good and is needed. Make this the year that you make your traditional investment and add that same level of investment into a program like Uncornered.
  2. Time to learn, pivot, build. Philanthropy is often looking for annual success metrics for quick impact and return on investment. We’ve seen the power of giving the space and time for young people to have an inflection point, to transform. We give them resources to first breathe and survive so they can then find the hope and believe in themselves to thrive.
  3. Unrestricted support. Trust-based philanthropic investments open up opportunities for innovation. Uncornered provides a financial stipend in the form of a UBI/guaranteed income model. When we started it five years ago, we were surprised to see outcomes double immediately and have been consistent since then. Giving our students financial resources and providing the support they asked for, rather than asking them a lot of questions about what they would do with the money, has proven to be effective.
  4. Believe in the impossible. At Uncornered, we talk about setting high expectations and low requirements. We fully expect and believe that someone who has spent time in jail can become a college graduate, community leader for good and changemaker.
  5. Make a multi-year commitment. We’ve been fortunate to have several investors who said here’s a three-year investment, let’s have a regular conversation about how you’re doing and how else we can help. We are grateful for those who have trusted us to launch this big idea.

How has the pandemic changed your definition of success?

At the beginning of the pandemic, we were always asked — how are your students doing in school or how many re-enrolled for this year? My answer was typically — I don’t know but what I do know is that they are alive, they checked in with their mentor and they are safe and healthy. The pandemic has revealed so many things — good and bad — that it was easy to miss seemingly simple things and it allowed us to re-imagine success metrics. One of our students not re-enrolling for the semester but signing up to see a mental health professional has still hit a significant milestone.

How do you get inspired after an inevitable setback?

I go for a run (or a walk these days due to a knee injury). It gives me time to reflect and space to come up with ideas to try something a different way.

We are very blessed that very prominent leaders read this column. Is there a person in the world who you would like to talk to, to share the idea behind your non-profit? He, she, or they might just see this, especially if we tag them. 🙂

Madam Vice President Kamala Harris. Aside from being inspirational as a Black woman leader, she listens, has shown capacity to adjust her way of thinking, and I am encouraged by the administration’s commitment to investing in community violence models like Uncornered.

You’re doing important work. How can our readers follow your progress online?

Connect with me on Twitter @MichCaldeira and follow our organization @Uncornered_BOS. You can also visit our website www.uncornered.org.

Thank you for a meaningful conversation. We wish you continued success with your mission.

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