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🎙 Podcast: How Chicago’s emerging Black leaders benefit from mentorship

“It was mentorship that helped me get to that fork-in-the-road moment for myself because I had gotten to a frame of mind that there was only one route to go. And maybe sometimes there’s one route that other routes will branch off. Mentorship gave me the encouragement to step out and to build something else.”

Darius Ballinger is the founder of Chasing23, a nonprofit organization focused on building respect, unity, and a sense of empowerment among young people in Chicago by introducing them to a community of support, accountability, and hope. Following the loss of his mentor and period of incarceration, Darius launched Chasing23 to be a vehicle for positive change. By providing a comprehensive blend of mentoring, tutoring, and workforce development programming, Chasing23 supports youth of color in developing personal and professional skills, building pride and confidence, and developing goals for long-term success. Tune in to learn how Darius’ love for Chicago and his mission to create positive opportunities for youth is helping him and emerging leaders in the city “chase their 23.”

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This podcast series is supported through a grant from the Citi Foundation and is presented as part of The Inclusive Social Entrepreneurship Initiative. With the support of the Citi Foundation, Echoing Green will accelerate leaders of color and leaders who represent communities of color by providing financial and leadership development support, creating visibility opportunities to amplify their voices and stories, and connecting them to Citi employee volunteers for advising and mentorship.

For more episodes of On Course: The Podcast from Echoing Green, visit anchor.fm/echoinggreen.

Episode Transcript

Eric
Hi, and welcome to On Course the podcast from Echoing Green that explores social entrepreneurship, and the pieces of people’s lives that they tend to leave out of their bios. Echoing Green is a premier global investor in new leaders who are boldly working to change the world, providing fellowships, community, seed-stage funding, and strategic support at that critical stage where they’re just trying to get off the ground. My name is Eric Dawson. I’m a father, husband, social entrepreneur, storyteller, and I have the distinct honor of serving as a chaplain for Echoing Green. I, along with my colleagues support fellows on their spiritual and emotional well-being as they mediate between who they often feel they need to be publicly with how they often feel privately. I’m a fraud. I’m not good enough. I don’t know what I’m doing. On Course is about the journey that these leaders take from the moment they decide to act, to create to change.

Eric
Today I have the pleasure of catching up with Darius Ballinger, founder and CEO of Chasing23, a nonprofit organization focused on building respect, unity, and a sense of empowerment among young people in Chicago, by introducing them to a community of support, accountability, and hope. By providing a comprehensive blend of mentorship, tutoring, and workforce development programming, Chasing23 supports youth of color in developing personal and professional skills, building pride and confidence, and developing goals for long-term success.

Darius, one of the things, many things I admire about you is your relentless pursuit of excellence, manifested by this interview. We’ve had internet problems, phone disconnecting, and you’ve finally called in. So I just want to appreciate you and, and your commitment to telling your story because I think stories, stories really matter, right? That’s our that’s our currency for social change. And I think your story in particular is, is such an important one, because your work is so important and what I love about Chasing23 is its rootedness. Right. It’s not about a killer app, or conferences, or convenings, it’s about being rooted in a community in a group of people, in a culture and in a place and I’d just love to just start with that place. Tell us about your home. Tell us about growing up. Tell us about your roots.

Darius
Yeah, for sure. Thanks, man, I appreciate it. And, and third, time’s a charm. So I’m calling him and I’m calling him from the south side of Chicago. A beautiful city, a city of many different stories that have many different sides. And it’s really important that folks get the full perspective of the city of Chicago. How I grew up on the Southside of Chicago, I grew up experiencing the side and the narrative that I think that most folks know about Chicago who don’t live here, which is that it’s segregated. That is it’s, you know, riddled with crime, gangs, crooked politicians, right? This is the hustle and bustle of Chicago. Being a young boy growing up in one of these communities, there’s this notion that you want to just make it out, right? If I could just beat the streets, if I could just make it past whatever’s happening in my home, whatever’s happening on my corner, whatever’s happening in my city, if I can just get to the other side of this thing, if I can make it to a college, if I can get to a nice suburb, then life will then begin and life will happen for me and for me that’s a hard reality to accept. Because this is where I grew up, this is where I’m from and so, you know, I have a hard time believing the thing when I can very well, you know, make a difference and make a change here. This point in my life, man, I’m falling in love with the food of the city, you can ride 15 minutes and get some Caribbean food or another 15 minutes and get some pasta that’s really going to kind of get you that Italian feel. And then you can go further and you have your mag mile and you have all these, you know, famous designers Virgil from Off-White or you know, Joe Fred’s Fat Tiger Workshop, right, so all these beautiful experiences that make you say, man, I love this city and it really inspires you to be a lot more. So, I’m really rooted in in Chicago man, I’m really rooted in belief of like changing where you are. I know growing up that that was a thing, right to make it out of the hood. Now I really think that people are like, you know, you hear it and rap and pop culture like buy back to the hood make where we are a better place because this is our home.

Eric
Darius you come at your work through loss and a pretty devastating one at that from a mentor, someone who’s really important to you. Tell us about that part of your journey.

Darius
One of the most notable relationships that has kind of taken place in my life was my relationship with my homeboy Wayne, who was a good friend of mine who inspired me to start Chasing23 through just like, kind of like just a bro conversation. You know, with my my friend who I met at the age of 21, um, this guy had dropped out of high school that 18 kind of just rolled around the state, the country just kind of finding myself picked up my first charge at 19 came home after like four months, told myself I wasn’t gonna do that bad stuff anymore. Went to a college town at 20 tried to get myself together, I find myself kind of going back into the same thing that I was just going to. Then my friend named Wayne there who saw me at 20 years old, with a lot of energy and a lot of life, you know, stuff in it and just kind of putting my energy in places that wasn’t fruitful and I remember my homeboy telling me like, Man Darius you know, man, you could you could be great bro. You don’t got to settle for like, the life of crime, you don’t got to settle for like, just this one side of the story that you’ve seen coming from the Southside of Chicago, and he really encouraged me. “You survived to this point, but now I want to encourage you to live and thrive and be more and chase your 23, chase your greatness, man I’m chasing my greatness, I’m chasing my 23.” And when he said it, it was like that was nice. I liked it. That was very catchy. That was in August of 2012. Fast forward six months later. I’m going back and forth between courts. A felon, fighting another charge to know like, Man, you know, I’m gonna go to prison. and my homeboy Wayne was like, “man, nah, I don’t see that for you. I don’t see you going to prison. I don’t kind of just seeing you just filling out as like a neighborhood guy. I just don’t see that for you.” And I held on to that. I went to court in April 12, 2013. Woke up it was my 22nd birthday and I went to court this day with the full understanding that yeah, I’m gonna go to prison. You know, hopefully the state offers me a two year deal. I’ll go down, I’ll get to get time, you know, I’ll be home in 12 months, 18 months. I got to court that morning, it was a Friday and I remember the attorney coming to me and saying, “hey, you know, the state wants to work, they want to work out a deal. They’re willing to violate your probation, and continue out your probation for another two years. But you have to kind of sit in county jail for a couple of for couple of weeks. And then we’ll kind of restart this probation period for you.” And I remember leaving that court room. And just feeling like wow, like, wow, you know, okay. my homeboy said it wasn’t gonna go like that. Like, he was like, he was so confident that it wasn’t gonna go like that he had to know something, so I remember calling him to tell him that I caught that blessing. Right? They aint talk about no prison time. They talk about a couple weeks in the county. Like, that’s okay. That’s like summer camp. I can do that. Come back home. He’s like, “yea bro I’m telling you, man. See? That’s what I’m saying. You gotta chase your greatness, you gotta chase your 23.” I get a phone call the next morning and one of my homeboys was like, “hey, did you talk to Wayne? Man? I don’t know they’re saying something happened.” I’m like, okay, well, I’m not thinking nothing fatal. And so I call his phone, he didn’t answer and I remember going on Instagram and seeing a picture of my homeboy in my newsfeed. And it was like praying hands and it was like RIPs and I remember like, I was just like, it’s been seven, eight years and it’s still like wow.

Eric
I know for many social entrepreneurs, our work is driven by the gifts of relationships and the sense of loss and you’ve had both in your life. I’m curious about how Wayne’s mentorship and death impacted your trajectory and your eventual launch of Chasing23.

Darius
He was a victim of a domestic violence incident. Something that was really a blindside and a traumatic experience. But it was a defining point for me in my life. Was I going to continue on the path that I was going on? Or was I going to take the advice that Wayne had given me you know, leaned into my inner voice that was telling me there was more? What was I going to do? And it was mentorship that that helped me get to that fork in the road moment for myself, because I had gotten to a frame of mind that there was only one route to go and maybe from this one route that other routes would branch off. My mentorship, put a fork in a road, my homeboy Wayne was like, you don’t have to do this. Like let me let you know that if you choose to do this, this is your choice. But I see so many other things for you. So mentorship allowed me to say, gave me this gave me the encouragement to do and to step out on something else to build something else to say that you know what Chasing23 is now today, I had what it takes in me back then to build it.

Eric
I love that image of mentorship as a fork in the road and the way you describe Wayne’s support leading you to paying it forward and leveraging mentorship as a path for other youth.

Eric
So talk about Chasing23 this idea of offering new paths, different paths to other young people describe the program, what’s the experience? What’s the vision?

Darius
Back in 2015, after going to community college for two years transformed to a four year university. You know, reestablishing myself in society as a leader, as a student leader, as a young professional. I was really encouraged to along that journey, start to bring other people along. 2015 I started to go out to high schools and really share my story. And the reason why I started to share my story is because I had a firm belief that people cannot be what they do not see. Right and so I really was adamant about young men of color young Black boys in the city of Chicago, knowing that they don’t just have to settle for the traditional life three neighborhood crime thing that that they can themselves be so much more. That we don’t just have to be, you know, entertainers or criminals that we can be thought leaders, educators, right? Like all these things, and I wanted to be a shining example for that. Having this motto of like, if it is to be it starts with me. And so I will go to the schools have these conversations and every school would be another 10 or 15 people that are bought into it, it will be the schools, the principal’s administration, everyone buying into it. After a year or so I got to a place where I said, you know, the motivational speeches are great. The the 90 minutes of inspiration is awesome. But how are we walking alongside young people as they navigate these situations? Like how are we walking alongside them? And after a year that I was really inspired to start, um, what officially is a Fellowship, a mentoring program, but we take a cohort of young people that are at a particular school, and we walk alongside of those young people throughout the course of a year. We start off at very early stages, like self awareness, who we are, you know, what things we’ve experienced, and how they shape us and how that may affect in the world, we then go into a project based learning portion of the of the program where now, you know, we’ve acknowledged kind of our immediate things, whether that interest is whether that’s mistakes or grants that we may have. And now when we’re at a project based thing, when we’re working on something where we’re putting all of our energy into maybe making an event at the school, we’re putting all of our energy into maybe designing a T-shirt brand, something that could speak to who we are, but now we’re working on those skills. And then the last portion of our program, we’re really helping young people, these young men, you know, again, start on that pathway. Yeah, we really like to be that that inspiration that jump on to get young people at least just thinking about the opportunity, right, seeing the possibility for themselves. So that last portion of our program often comes with paid work experience and civic engagement. We have a summer job program, here’s Chicago that employs a lot of young people in the city of Chicago for a period of eight weeks at a time. And again, this allows them to get that working experience. For some of our guys, it’s they stay with us. And after the project based learning and design in a T shirt company, within minutes, they want to continue to work with Chasing23 and help us do our PR or our branding, um, often times it’s giving young people different opportunities to work downtown in the government sector or working in a small business like a local restaurant and things like that. And so we really serve as a launch pad, we really are essentially what Wayne was right when guys that are like man, you know, I’m coming in his neighborhood, I’m already behind in my credits, I can’t do that, you know, this is the route that I’m going on. And we’re like standing right in front of saying, nope, nope, we got examples. You got the areas you got comments, you got all of these examples to point to that can at least get the idea out your mind that that’s the only thing that you can do. And then here’s some different avenues and opportunities that you can go. And we’re encouraging them and hoping that they continue on those pathways.

Eric
I love it and I love this idea of creating possibilities, right? Because as you and I both know the cruelest thing we do to young people in this country is we destroy a sense of hope. Right? A sense of possible. Darius I’d love for you to tell a story of hope, a story of possibility. Tell the story of a young person you’ve connected with, through Chasing23 that’s been an inspiration to you.

Darius
I think about Kaywan, who is one of my first young people that came into my program. You know, as you know, as a practitioner, when we start these programs, right, like the first, those first 10, 20, 40 people we come in contact with we like those are the ones we hold on to because that says scale and grow we get disconnected. But Kaywan was one of my first guys in my first cohort in 2015. I have my own lived experiences that I that I’ve lived through and overcame, but it was a totally different experience for me to lean into others experience. Kaywan had been in Inglewood for all of his life. And this is all that he knew. Kaywan man has literally lived through a lot of the things that I had hoped to prevent for him. My success story for Chasing23 isn’t like oh man, I took a gangbanger who was selling crack and he graduated from a two year four year and now he’s like, he’s working at Deloitte. Like, my success story is like Kaywan, so he’ll call me like he called me earlier this year, we got a job in the midst of the pandemic, and everything was going on and he’s like, you know, what, even though I had a baby, and even though I caught a case, as I got with you, like, I’m still I still feel like, there’s hope for me, I still know that my story is not over. Like your story didn’t end at that. So I knew that my story is not ending and know that a story that you tell a funder is really like, well, I thought the program is to prevent that. And it is, but also it’s to spark this, this sense of hope, and a sense of agency. When I look at the heart of Kaywan I could say, maybe I didn’t give you a thing right then and there, but like, what’s in you is stuck with you, and you’re gonna take it wherever you go.

Eric
I love it. So Darius, you named your organization Chasing23. What was the origin of that? What’s the name?

Darius
Yeah. I mean, I think Chicago, you can take a stab at what that 23 means. But it’s essentially chasing greatness. I mean, it is man. It is the bat light for Gotham City. It’s ambition and charisma mixed together, it’s hustle and passion all together. It’s a belief that really that man, all that is to be is within me and if we start within ourselves, we have so much in us and that was a lot of just the conversations I had with my homeboy and I mean, again, like I say, when Wayne brought it up that we will look at somebody like Michael Jordan, he like laid it all out on the court. Right? Like he put it all out there for the game of basketball. How, as individuals, can we take on that same theme but if you’re not playing basketball? What does it mean to leave it all on the line for yourself, for your family, for your community for your work? Like, how does that feel? And so that, you know, it’s a spark of inspiration, that it does something like what Nike does, right? How Nike can inspire what brands can do, Chasing23 aspiring that same sense of agency of hope and resilience?

Eric
So Darius, what’s your 23? What’s success for you?

Darius
That’s a great question. I’ll say that you know, success has always been a holistic thing. It’s not the one thing, it’s the whole thing. As much as I can, is live up to my fullest potential that success. The imprint that I’ll make on my children’s lives, in their lives, that will be a measure of success. And, you know, from there, whatever I can, can give out into the world that that that is a benefit and that he will have impact. I will measure and success. Yeah, that’s that I think that’s the best way to the route. I think success is such an interesting thing. Now, now that I’ve established some level of success, and I’ve done some level of things, success is interesting. I think happiness, joy, peace, like all of these other words, I want to try to attribute to now because I think success is success is really interesting. You know, success, oftentimes is just getting to something that you wanted. But once you get that thing, how you feel matters. So like you said, you can fail a bunch of times and give them something and then be successful. And then like, what if that what you succeeded for ain’t really your happiness at all. That wasn’t what I was really going for. Right? And that could come out of a place of lack. Right? But if you started with abundance, like you moved out of that abundance, that’s a that’s a totally different way to approach life. So I think success is, you know, just constantly living in an unraveling it isn’t experiences a moment of success or a feeling of success that I would like to attribute? There’s some kind of destination once I make it there. I’ll be happy also accountants.

Eric
I think there’s a real tension for social entrepreneurs as they’re coming up as struggling between, you know, making it out of versus making it better. How have you navigated between that choice or is even a choice.

Darius
It’s a choice is a choice, man, man, when the pandemic started as civil unrest started, it was, it was that idea of like, man, you know, look at all this work we did in the communities and like all these relationships and like, like, once all of these, like external forces started happening, it really started to put pressure on a theme that was so precious and so sacred is so like, so special. And it, and it challenged, you know, me in a way to where, you know, you think about like, man, you know, and what I’m doing matters, like it is it I probably would better serve like, healing through racism, structural oppression, my personal adversity, and then going back to hope, I was like, pulling out six covering wounds, while like covering other people while, like, you know, making space and people who got roles who don’t care about the service a lot. It was a lot in that process. And it’s a process that I’m still in but I think that at the heart of at the heart of social entrepreneurs at the heart of folks that want to be change agents is that you know, through that adversity through all of those challenges, the real you will show up and so again, if there’s a commitment to make things better, that that commitment will never go away. How you approach it, your understanding of it will change but I mean anything that you’re really committed to man you don’t really know you’re committed to it until it gets rough You know, they’re like when you work it out like day one that is not you did nothing on day one like you may not even celebrate it you need to wait like day 21 day 49 where you like got up when you didn’t feel lucky when it kicked in to start when because then you’re getting there right like that early outset it does nothing and so for me that that’s the part route now of like, being in it and and kind of appreciating every moment of it again versus just like I’m fixing things and then it’s going to be all fixed because you know inequality kind of know structural oppression like these things didn’t get fixed and one night and one RFP and one grant cycle.

Eric
Exactly, and I think Darius, that that’s such a powerful point because the stories that we’re given as social entrepreneurs is one of linear exponential change. This step follows that step, follows that step. But it’s not a straight line is it? It is a journey as you described.

Eric
So Darius, what’s next for you?

Darius
I’m going to continue I’m continuing to live and to be open. I’m somebody who has been on both spectrums of life. And I say that, you know, graciously. We’re just, you know, talking about opportunity, I had already this year to testify before Congress on behalf of police accountability, and police reform. And you got that experience. And I remember going, speaking, and then flying back and then being back in neighborhoods and thinking like, wow, what, such a profound calling that I have in my life that I was like, literally in the halls of Congress, speaking to, you know, legislators and policymakers about the lived experiences of the people that I was like walking down the street with later on that day. And it was literally like I literally testifying to Congress at 10 o’clock, and then like, that seven o’clock that evening, I was like, walking back into my building past the liquor store past, everybody on the corner. And was just like wow, man, this is just a lot to take in. And in and again, it makes me you know, think about just where my space is and where my role is in this work as I as I move forward. But you know what, for me, I think that is yet to be revealed. I think what I can speak to is sticking to my commitment, in terms of bettering myself, being better for my family and be better for my community. Like if I if I think if I say to those, those things, those priorities that was for me was it will kind of like present itself right in front of me. And when the tides ready, I stepped right into.

Eric
For those who are listening and inspired by your work how can they learn more?

Darius
They can follow me at chasing23.org or they can reach out to our organization. Always give us support. Time, talent, treasure is always helpful. They can find me I’m out I’m out about I do speaking training I’m really here as kind of folks see fit and then on social media man I’m on a lot of different social media channels Twitter, LinkedIn thanks to Echoing Green and a lot of other great projects you could just kind of Google my name now and I’ll come up.

Eric
What does it feel like to say that all?

Darius
I grew up man, I grew up lonely. You know, I didn’t have my pops. My mom worked a lot. I had a big void in my life I feel very just kind of like that I’m just here and there was a point in my life where I was like, Nah, man, you somebody and then I went back into this phase like I don’t matter be now that again, this is this is always what I was hoping always when I was I was getting that it gets all of the other things that have come along in association with it it’s kind of like that thing that you know you just be mindful of what you pray for because you might just get it. So I’m grateful I’m grateful that what I believed as a young boy has come into fruition in my adulthood and I just hope that that and continue to work on just you know better than that now as I’m going to do it and I have a broader understanding of life and my purpose.

Eric
So Darius, we’re gonna move into our fast questions. These are a set of quick questions for a phrase or one or two sentence response. Ready?

Darius
Okay. Yeah.

Eric
If you could sit down with yourself 15 years ago, what would you tell your younger self?

Darius
Man, you got so much ahead of you. There’s so much more ahead of you. And I’ll say switch it up, I’ll say switch it up earlier. Make the necessary changes now because everything that you think you can be you actually will become.

Eric
if you get sit down with yourself 15 years from now, what would you want to ask?

Darius
Wow. Wow, what would I want to ask? Oh, man, I just, I just commend him. I don’t know. I think I’d be an awe. I’d just sit and watch. 15 years from now. My boy could grow, my relationships have been established for a while so I’d just be in awe. I think I just marvel at who I’ve become kind of just, you know, understanding what all it took to get to that moment.

Eric
Who would play you in the movie of your life

Darius
Who could play me? Denzel Washington because he’s just so in the character, he’d be able to get into my character with all the energy.

Eric
And what was that movie be called?

Darius
Part of a chasing

Eric
If you could do anything else in the world that you wanted to do with your time, except what you’re doing right now, what would that be?

Darius
I like to get a lot into the arts, Arts and Media, like fashion. Definitely, like just not so much heavy political science, structural racism, oppression, like I would get to like more of just like the beauty of like living life in experiencing and enjoying all of life, while still fighting the good fight.

Eric
As you stumble, as we all do, what’s the most important thing for helping you get back up?

Darius
Grace . Whenever I stumble or fall know that I’ve stumbled before in life, and that I’ve gotten up. Some of the times that I’ve gotten up, have not been on my own, so I give myself some space and not be an expert or a leader or a thought leader. But to be a servant, to be a vessel, and to have this kind of larger, things are bigger than me perspective.

Eric
Darius, I’ve loved our conversation today and actually I want to end with that word “love.” I feel like it’s one of those words that we don’t spend enough time on, we don’t pay attention to, we don’t lift up. As I hear your story, if I had to pull a thread through it, it is this brave, fierce, revolutionary idea of the power of love. Whether you and Wayne, whether that’s you and your family, you and your program. If I had to distill the power of what you do, that would be the word I would use. At the end of the day what we all need, but particularly those, and particularly too for young people, that those young people who are told again and again in ways subtel and not so subtle that they’re not worthy. The best and maybe the anecdote to that is to love them. Is to offer them that commitment that they are enough, that they are loved. I admire you for the work that you do, but also for the man you are and how you move through the world. Thank, thank you for sharing your story.

Darius
Eric man, and I appreciate you all the time. Every time we connect, it’s a divine connection, and so I’m grateful for everybody at Echoing Green. And a man you know, everybody that’s listening to this to this recording man, I just wanted folks to be encouraged and inspired. I am just one person who took my lived experiences and stepped out and said, Man, you know, I just want to make the world a better place. And, and just believe that and here I am years later, that’s coming into fruition and very, like small relationships and on larger and larger scales. And so I just hope everybody to be encouraged and go out there and chase their 23 because the world needs all of us.

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