We recently connected with Dr. Vondale Singleton and have shared our conversation below.

Hi Dr. Vondale , thanks for joining us today. What do you think it takes to be successful?

As someone born and raised on the South Side of Chicago—who lost his mother at 14 and overcame the odds—success for me has never been about fame, money, or status. It’s always been about **purpose, perseverance, and people**.

After losing my mother and eventually my father, I could have easily become a statistic. But one man stepped in—Steven Ray Robertson. He mentored me, believed in me, and helped me find my “why.” That relationship changed the trajectory of my life. I realized that my purpose wasn’t just to succeed for myself, but to be the consistent voice and presence for boys and young men who—like me—just needed one caring adult.

That purpose is what fueled the founding of CHAMPS Mentoring Program. It’s what still gets me out of bed every day, even when the challenges feel heavy. When you live with purpose, you’re never truly lost—you’re anchored.

Success doesn’t come easy. I’ve faced rejection, budget shortfalls, closed doors, and doubt from those who couldn’t see the vision. But every time I felt like giving up, I thought of the young men counting on me. That kept me pushing through. I often say: *You’re Born 2 Win, but you have to fight to see it.* CHAMPS exists today not because I never failed—but because I refused to quit.

I am where I am because of mentors, educators, community leaders, and brothers in the movement who invested in me. I believe iron sharpens iron. From Howard H. White at Jordan Brand to Pastor John Hannah to the young men I mentor—relationships have been my greatest currency.

I stand on the shoulders of giants, and I do everything I can to lift others up on mine.

Success isn’t a destination—it’s a decision to live out your purpose with grit and gratitude. For every young man of color wondering if he has what it takes: **Yes, you do.** You just need someone to remind you of who you are, and why you’re here. That’s what CHAMPS is about.Remember: You’re Born 2 Win—in every situation of life.

Dr. Vondale , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

Who Is Dr. Vondale Singleton?**
*Founder & CEO, CHAMPS Male Mentoring Program | MBK Chicago Backbone Director | Brilliance & Excellence- CEO| Chicago Native*

My name is Dr. Vondale Singleton, and I’m a proud South Side Chicago native, mentor, educator, and servant leader who has dedicated over two decades to empowering Boys and Young Men of Color. I’m the Founder and CEO of CHAMPS Male Mentoring Program—which stands for *Culturally Helping And Making Positive Success. I’m also honored to serve as the MBK Chicago Backbone Director, leading citywide efforts through President Obama’s My Brother’s Keeper Alliance to improve life outcomes for youth of color.

But before the titles and accolades, I was a young man navigating trauma. I lost my mother at just 14 years old—she was only 29. My father struggled to be present in my life. That kind of pain could’ve crushed me. Instead, it ignited something deeper. A mentor stepped in, spoke life over me, and helped me discover my purpose. That mentorship saved my life—and planted the seed for everything I do now.

How I Got Into This Work

I began my journey as an educator on the South Side, where I saw firsthand the challenges our young men face: broken homes, low expectations, community violence, and lack of access. I started mentoring informally, during lunch periods and after school. Eventually, it evolved into a structured, purpose-driven program—CHAMPS Mentoring launched in 2013 with a simple but powerful vision To develop young men into real leaders who are emotionally intelligent, mentally strong, and socially responsible.

What CHAMPS Does

CHAMPS is more than a mentoring program—it’s a movement. We provide:

Mentorship rooted in Brotherhood
Social Emotional Learning (SEL) & mental health support
Leadership development
Identity formation
College and career readiness
Workforce development and job placement support
Partnership activations with brands like Jordan Brand, Nike, and the Obama Foundation

Our programming serves young men ages 12 and up and meets them where they are—in schools, community centers, and even juvenile detention centers. We’ve impacted over 8,000 lives and counting.

What Problems We Solve

Our young men face systemic barriers that are generational. CHAMPS steps in to:

* Provide **positive role models** and consistent adult presence
* Address **trauma and mental health** with real conversations and resources
* Build **employable skills and leadership capacity**
* Reduce violence by offering safe spaces and structured mentorship
* Create a **community of accountability, belonging, and brotherhood**

Simply put—we help young men see who they are, believe in who they can become, and act with purpose.

What Sets Us Apart

What makes CHAMPS—and my leadership—different is that it’s personal I didn’t read about this work in a textbook—I lived it. I’ve sat in those same desks. Walked those same blocks. I’ve stared down trauma and loss. That lived experience fuels everything I do.

We combine culturally responsive mentorship with strategic partnerships, media visibility, and community engagement. We’ve been featured on **ABC, NBC, FOX, ESPN, USA Today, and even at the White House during President Obama’s administration.

What I’m Most Proud Of

I’m most proud of the transformations—the young man who goes from skipping school to standing on stage as a college-bound leader. The father who learns to show up differently for his children. The mentees who now mentor others.

I’m also deeply honored to have received numerous recognitions—including two Emmy Award nominations, the Chicago Defender Men of Excellence Award, and recently, an Honorary Doctorate for my contributions to mental health and social entrepreneurship.

But honestly? My proudest moments are quiet ones—when a young man looks me in the eye and says, “Because of CHAMPS, I believe in myself.”

What I Want You to Know

If you’re reading this, here’s what I want you to take away:

CHAMPS isn’t a program—it’s a calling.
We don’t just mentor—we change lives.
We’re not here to react—we’re here to reimagine what’s possible.

Whether you’re a parent, partner, funder, policymaker, or someone who just cares—we invite you to walk with us.

Because in every young man, there’s greatness.
And we’re here to remind him: You’re Born 2 Win.

We’d love to hear a story of resilience from your journey.

One of the most defining moments of my life—and the one that shaped my resilience—was losing my mother when I was just 14 years old. She passed away at the young age of 29, leaving behind a son who was angry, confused, and searching for answers. At that age, I could’ve easily gone down the wrong path. Many expected me to.

What people didn’t see was the emotional toll—the silent nights, the unanswered questions, and the feeling of being invisible in a world that kept moving without her. I didn’t just lose a parent—I lost my foundation.

But here’s where the story shifts.

God sent someone into my life—a mentor named Steven Ray Robertson. He saw something in me that I couldn’t yet see in myself. He not only helped me get into college—he led me to Christ. He showed up consistently, listened without judgment, and spoke life into my potential. That relationship was the seed that would later grow into CHAMPS.

Years later, after becoming a husband, father, educator, and leader—I experienced another heartbreak. My father, whom I had reconnected with as an adult, passed away. That loss, too, hit hard—but it also solidified something deeper in me: the call to stand in the gap for young men who don’t have access to a father or role model. I had to become what I once needed.

And through it all—I kept showing up. Even when it was hard. Even when doors closed. Even when funding didn’t come through. Even when I questioned if I was enough.

CHAMPS was born out of that fire. What started as lunchtime mentoring at school has become a movement that has now impacted over 8,000 boys and young men of color across Chicago.

Resilience isn’t just about surviving the storm. It’s about building something from it. I didn’t allow pain to define me—I used it as fuel to walk in purpose.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

Reputation isn’t built overnight. It’s built in the trenches—moment by moment, relationship by relationship, and year after year of showing up when it’s not convenient, when there’s no spotlight, and when nobody’s clapping.

What helped me build my reputation in the urban mentoring space boils down to a few key principles:

1. Consistency Over Everything
In communities where systems have failed us, consistency is currency. I made a decision early on that I wasn’t just going to pop in for photo ops or during grant season—I was going to stay planted. I’ve been mentoring for over 20 years and leading CHAMPS for more than a decade. Through joy and heartbreak, I’ve stayed present.

Young men in Chicago know this: I’m going to show up. Not just for the wins, but in the courtrooms, hospital rooms, and classrooms. That consistency builds trust—and trust builds reputation.

2. Leading With Authenticity
I don’t lead from a pedestal—I lead from experience. I’ve faced the same trauma many of our young men deal with: losing my mother at 14, navigating fatherlessness, and growing up in environments that didn’t always believe in my worth. That gives me credibility in spaces where surface-level talk won’t cut it.

When I say “Born 2 Win,” it’s not just a slogan—it’s a lived testimony. I’ve modeled vulnerability, faith, and accountability. That transparency opens doors that titles can’t.

3. Building Something Bigger Than Me
The CHAMPS Mentoring Program was never about building my name—it was about building a movement. From the very beginning, we focused on developing young men into leaders, not just participants. That approach has created a ripple effect. Mentees have become mentors. Young men have become fathers, business owners, and agents of change.

When people see results—real transformation—they pay attention. And when those results are consistent, your name starts to carry weight.

4. Collaborating Without Competing
In the urban mentoring space, ego can get in the way. I made it a point to collaborate, not compete—with schools, city leaders, community orgs, and brands like Jordan Brand, Nike, and the Obama Foundation. I understood that to have a citywide or nationwide impact, we had to lock arms.

Being a bridge builder in a city known for division has helped position CHAMPS as a model for mentoring that works.

Contact Info:

• Website: https://www.champsmentoring.com
• Instagram: https://www.instagram.com/champsmentoring
• Facebook: https://www.facebook.com/champsmentoring
• Linkedin: https://www.linkedin.com/company/champsmentoring/
• Twitter: https://www.x.com/champsmentoring
• Youtube: https://www.youtube.com/champsmentoring

Image Credits

Sterling Gilmore