School Fundraiser Success: How a Chicago Dean Raised $6K in 4 Days

In just four days, a middle school on Chicago’s South Side raised more than $6,000 through a school fundraiser with Double Good — a simple, turnkey fundraising solution any organization can launch in minutes. The impact? School-wide excitement, boosted attendance, and a transformed the student experience.

At the center of it all: Dean Henigan, a former teacher-turned-dean who believed that joy could be the foundation for cultural change. By pairing creativity with purpose, he turned a first-time school fundraiser into a movement — one more way for his students to feel proud of themselves and their community.

A Fresh Approach to School Culture Through Fundraising

From the start, Henigan made it his mission to rebuild the school’s culture with joy at the center. He launched initiatives that focused on student engagement and motivation, like the “Dean Depot,” a student store where kids could redeem “Dean Bucks” for snacks, school supplies, and small prizes.

These incentives weren’t just about rewards; they were about recognition. They reinforced positive behavior, created daily moments of joy, and added something positive for students to look forward to each day. Even attendance began to improve. “I knew kids needed to be held accountable, but they also needed to be celebrated, and that’s what changed everything,” said Henigan, reflecting on the culture shift at his school.

Popcorn with a Purpose - An Easy School Fundraiser

One of the most powerful additions to the school year was the introduction of a Double Good fundraiser—something the school had never tried before. Inspired by another school in his network that had raised $37,000, Henigan launched the effort with one goal in mind: create more opportunities for students.

Over just four days, students sold more than $13,000 through their Double Good pop up stores, raising over $6,000 for the school.

But it wasn’t just the number that made the fundraiser special. Henigan turned the event into a full-on school competition. Daily updates were shared in student group chats. The top 10 sellers earned out-of-uniform privileges for the rest of the year, were awarded crowns and scepters, and received 200 Dean Bucks and access to exclusive field trips. Suddenly, students weren’t just selling popcorn—they were part of something bigger.

Lessons in Leadership and Giving Back

The fundraiser didn’t just benefit the students. Henigan made sure to thank the entire school community by distributing donated Double Good popcorn to both staff and the top student sellers.

The result? A simple, joyful fundraiser that brought the whole school and community together.

What began as a way to raise funds quickly became a catalyst to reignite students’ pride in the school. Henigan’s belief in the power of joy, and his commitment to mentorship and representation, transformed the student experience.

Surpassing all the goals he set for his students, Dean Henigan knows that anything is possible when an entire school comes together around something positive. And for this Chicago middle school, it's just the beginning.

Want to make your next school fundraiser simple and joyful?