Andrew Jordan & the $50K Basketball Game: How a Small-Town Educator Thinks Like an Entrepreneur

Andrew Jordan didn’t take the usual path to becoming a recognised voice in school leadership. He didn’t come from a big city, a high-powered policy background, or a famous education think tank. Instead, he started in Stockton, Illinois—a small town where Friday night football is everything, and community events are often held in the school gym.

As a high school quarterback, Andrew learned early how to read people, make quick decisions, and bring others with him. These lessons stuck. They would eventually shape the way he leads—not just classrooms, but entire school systems.

Today, Andrew is the Superintendent of Donovan CUSD #3, but his career began in the classroom. He moved through roles as Assistant Principal and Principal before stepping into the top spot. Along the way, he earned multiple degrees from Northern Illinois University, Western Illinois University, and the University of Illinois at Springfield. He’s known for securing over $270,000 in competitive education grants, including the Stronger Connections Grant and the High-Impact Tutoring Grant, both of which delivered real results for students.

He doesn’t just lead from an office. Andrew once turned an unused library into a modern student media centre and helped run a tutoring programme that measurably raised student performance. He’s also served on state education committees and worked with the Illinois Masonic Student Assistance Program, which delivers over $80,000 worth of free training to schools every year.

But ask Andrew what he’s proudest of, and he won’t mention titles or awards. He’ll tell you about the Stockton 3-on-3 Basketball Tournament—a community event he ran for 15 years that raised more than $50,000 for student-focused projects.

Part educator, part entrepreneur, part coach—Andrew Jordan is proof that big impact often starts in small towns.

Can you tell us a bit about yourself and what you do?

I’m a public school superintendent in rural Illinois. I’ve worked in almost every part of a school—teacher, assistant principal, and principal. Now I lead the whole district. My job is part operations, part mentorship, part community-building. I also spent time running two businesses and a 3-on-3 basketball tournament that raised money for student programmes. I care about getting things done, not just talking about them.

How would you describe your personal or professional vibe in 3 words?

Hands-on, resourceful, and relentless. I like solving problems myself, whether that means moving furniture to redo a student space or writing the grant to fund it. I don’t give up when the answer is “no”—I just look for another way.

What’s one fun fact about you most people don’t know?

I helped run a business that timed running races all over the Midwest. We’d show up before sunrise with gear, wires, bibs, and timers. I’ve timed thousands of runners across the finish line—and learned that the logistics of a school aren’t so different from a 5K.

What’s your favorite TV show right now?

Hard Knocks. It’s raw, focused, and full of people trying to prove themselves. As a former athlete and current educator, I love watching how teams are built from scratch and how people handle pressure. There’s a lot of crossover with how schools function.

What’s your most-used social media app these days?

Facebook, mostly for staying in touch with parents and the community. It’s where I post updates about our schools and see what’s going on in town. It’s less about scrolling and more about connecting.

What was the first social media app you ever joined?

MySpace! I had no idea what I was doing. It was all just profile songs and top 8 drama, but it felt like a big deal at the time.

Are there any influencers or creators you never miss content from?

Honestly, I follow education professionals more than traditional influencers. I keep up with Dr. Joe Sanfelippo—he shares real advice, not just buzzwords. I also watch what other rural superintendents are doing. We’re in the same trenches.

Are there any must-follow accounts or pages for people in your industry?

Yes—@PrincipalKafele on X is a good one. His posts are short but powerful. Also, the Illinois Principals Association posts great resources. If you’re in education and want quick, useful tips, both are worth following.

Do you listen to any podcasts related to your field or niche?

Yes. The School Leadership Show is solid. It’s made for working principals, not academics, and covers everything from hiring to community engagement. I also listen to Transformative Principal—it’s got short, smart interviews with people actually in the field.

What’s the best advice you’ve heard from a podcast or interview?

“Start where you are, use what you have, do what you can.” I think Arthur Ashe said it first, but I heard it on a leadership podcast. I’ve built entire student programmes off that one mindset. If you wait for perfect, you’ll never start.

If you could collab with any influencer or celeb, who would it be?

JJ Watt. He’s an athlete, but he gives back constantly and cares about youth development. I’d love to partner with him on something sport-based that teaches leadership and character in schools.

What’s a habit, hack, or tool you swear by for staying informed or inspired?

I keep a whiteboard next to my desk that just says “Who did you help today?” It keeps me focused when the admin stuff starts piling up. Also, I write everything down. Pen and paper. If I don’t write it, it doesn’t happen.

Follow Andrew Jordan on LinkedIn.

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