We caught up with the brilliant and insightful Calvin King a few weeks ago and have shared our conversation below.

Calvin, thanks for joining us, excited to have you contributing your stories and insights. Along with taking care of clients, taking care of our team is one of the most important things we can do as leaders. Looking back on your journey, did you have a boss that was really great? Maybe you can tell us about that boss and what made them a wonderful person to work for?

Throughout my life, I’ve been blessed with some incredible leaders—my parents, my older brother, teachers, coaches, mentors, and former bosses—all of whom played a vital role in shaping who I am. But if I’m being honest, the best boss I’ve ever had is… me.

That might sound a little unconventional, but hear me out.

Each of those early influences poured into me a common truth: I am responsible for my thoughts, my beliefs, my decisions, and ultimately, my outcomes. That mindset—that I am the one who holds the keys to my growth and integrity—has guided me through every season of life. As a student. As a partner. As a parent. And especially now, as an entrepreneur and founder of Free Lunch Academy.

Over time, I’ve come to hold myself to a standard that often exceeds what others might expect. I’ve learned the value of doing the right thing, even when it’s hard—and especially when no one’s watching. That kind of self-leadership has taught me to lead with transparency, fairness, and a level of honesty that starts with self. It’s not always easy, but it’s always worth it.

So when I think about the most impactful leader in my journey, I give credit to the village that raised me—but I also honor the version of myself that chose to listen, evolve, and lead with intention. That version? He’s the best boss I know.

Calvin, 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?

For those who haven’t heard of me before, my name is Calvin Leroy King III. I’m a father, founder, creative visionary, and proud product of purpose. I wear a few hats—some corporate, some community—but the role I hold closest to heart is that of Founder and Executive Director of Free Lunch Academy, a social impact organization I launched to use the power of performance and storytelling to educate, empower, and elevate youth across Chicago and beyond.

My journey into this work didn’t begin with a business plan—it started with a calling. After a career in corporate sales and marketing, I realized I had a deeper desire to create spaces where young people could develop the emotional intelligence and communication skills that school often overlooks. I wanted to help them not only navigate life’s challenges, but also rise above them with confidence and character. That’s how Free Lunch Academy was born.

At our core, we offer social-emotional artistic learning experiences—live stage plays, interactive workshops, and youth-led creative residencies—all designed to prevent bullying, promote healing, and build community through the arts. Our flagship production, Be A Buddy Not A Bully, has toured over 500 schools and impacted more than 100,000 students across the Chicagoland area. And we’re just getting started.

What sets us apart is our unapologetic commitment to culturally relevant, emotionally resonant programming. We don’t just come into schools and talk at students—we meet them where they are, speak their language, and co-create experiences that stick with them long after the final curtain call. Our work is trauma-informed, compassion-led, and built on the belief that every child deserves to feel seen, heard, and safe.

I’m most proud of the transformation we’ve witnessed—not just in our students, but in entire school cultures. We’ve helped students find their voice, redirected young people away from violence, and brought families, educators, and communities together around healing conversations.

If there’s one thing I want people to know about me and Free Lunch Academy, it’s this: we’re not just building better students—we’re nurturing better humans. Our work is about planting seeds of empathy, expression, and excellence in the next generation. And in a world that often feels divided, I believe that’s the kind of leadership we need more of.

Have you ever had to pivot?

One of the biggest pivots in my life happened when I walked away from a promising corporate career to chase purpose over a paycheck.

I had started out in tech sales with a Fortune 100 company, climbing the ladder, checking all the boxes, and doing everything “right” by societal standards. On paper, it looked like success—but something in my spirit felt unsettled. I found myself questioning if I was using my gifts in a way that truly mattered. Was I building someone else’s dream at the expense of my own? Was I showing up in the world the way I was meant to?

That inner tension eventually became impossible to ignore. So, I pivoted.

I left the comforts of corporate life and leaned fully into my passion for youth development, emotional wellness, and the performing arts. That leap of faith gave birth to Free Lunch Academy—a space where I could fuse creativity and character education in a way that felt real, relevant, and necessary.

It wasn’t an easy transition. I had to learn how to lead a nonprofit, build community trust, secure funding, and reintroduce myself to the world—not as a corporate climber, but as a creative disruptor, educator, and change agent. But every challenge refined me. Every closed door redirected me. And every student we’ve impacted since that pivot has affirmed that I made the right move.

That shift taught me that pivots aren’t failures—they’re faith in motion. Sometimes the plan has to change so the purpose can come alive. And for me, it did.

Can you share one of your favorite marketing or sales stories?

One of my favorite marketing stories isn’t from a traditional boardroom—it happened on the South Side of Chicago, in a school auditorium packed with students, teachers, and a principal who, to be honest, didn’t want us there.

We had pitched Be A Buddy Not A Bully to this particular school for over a year. Every email went unanswered. Every phone call? Sent to voicemail. But I believed in what we were doing so much that I refused to let the “no” be final. So, one day, I pulled up to the school with a tablet in hand, cued up with footage of our stage play, and asked the security guard if they could pass a message to the principal.

He gave me five minutes.

I remember walking into that office with a mixture of determination and humility. I said, “I know we’re not on your radar yet, but we’re on your students’ side. And I’d love a chance to prove it.” Then I hit play. That short video showed our kids acting, crying, laughing—and most importantly, learning. It was raw. It was real. And something shifted in the room.

She booked us on the spot.

When we finally performed at the school, the same principal who had once dismissed us stood up at the end, teary-eyed, and said, “I had no idea how much we needed this.” That single event led to a district-wide referral and opened doors we’d been knocking on for years.

What made it special wasn’t just landing the “sale”—it was knowing that the “yes” didn’t come from clever copy or a big ad spend. It came from showing up, standing firm in our mission, and being willing to put the product—our impact—in the room.

That’s the kind of marketing I believe in. Bold. Honest. Human.

Contact Info:

• Website: https://www.freelunchacademy.com
• Linkedin: https://www.linkedin.com/in/calvin-king-b58aa69/

Image Credits

Ollie Photography