The Fundraising Masterminds Podcast Episode 90: Fueling Classical Education: A Christian School's $298K Gala [The $10M Story, Part 4 of 5] Release Date: April 23, 2025

Introduction

In Episode 90 of The Fundraising Masterminds Podcast, hosts Jim Dempsey and Jason Galasinski delve into the inspiring journey of Chesterton Academy, a Christian school in the Chicagoland area, and its remarkable fundraising achievement—a $298,000 gala. This episode is part of the "$10 Million Story" series, highlighting five different nonprofit organizations that collectively raised $10 million in 2024.

Overview of the "$10 Million Story" Series

Jason Galasinski introduces the series as a celebration of God’s work through various nonprofits. The series features stories from over a hundred organizations that participated in the Perfect Vision Dinner program, collectively raising around $10 million. Jason shares the distribution of funds raised:

• 30% went to pregnancy centers
• 25% to Christian schools
• 15% to Child Evangelism Fellowship (CEF) chapters
• 30% to other organizations

Jim Dempsey adds, “God was so gracious” (01:09), emphasizing the divine blessing behind these efforts.

Guest Introduction: Mai Wilson from Chesterton Academy

The hosts introduce Mai Wilson, the founder of Chesterton Academy of the Immaculate Heart. Mai shares her background before starting the school and the motivations that led her to establish a new educational institution centered on faith, character, and intellectual rigor.

Origin Story: Starting Chesterton Academy

Mai Wilson recounts her transition from a stay-at-home mom to founding Chesterton Academy. Concerned about her second daughter’s educational path, Mai sought a high school that offered a rigorous, integrated Catholic curriculum—something she felt was missing.

“We were recapturing what Catholic education was supposed to be.” (04:00)

Mai and her husband connected with the Chesterton Schools Network, which supported them in establishing the school. Overcoming significant challenges such as securing funding and a location, Mai highlights the importance of faith and community support:

“It just came through a series of miracles in a very short time.” (11:07)

Fundraising Challenges

Initially, Chesterton Academy modeled its fundraising efforts after a nearby successful Chesterton school by hosting galas featuring auction baskets and wine pools. Despite perfect execution, they hit a fundraising ceiling, raising the same amount as the previous year.

“We realized we had raised the same amount that we did the previous year.” (16:34)

This stagnation prompted Mai to seek a more effective fundraising strategy, leading her to Fundraising Masterminds.

Introduction to Fundraising Masterminds' Perfect Vision Dinner Program

Upon discovering Fundraising Masterminds through an email from the Chesterton Schools Network, Mai was impressed by the Perfect Vision Dinner program, particularly its departure from traditional high-pressure fundraising methods.

“When no auction baskets were mentioned... I thought, no, never again.” (17:29)

Jim Dempsey praises Mai’s understanding of Chesterton students:

“I never found a Chesterton student that I wouldn't hire tomorrow.” (09:45)

Implementation of the Perfect Vision Dinner Program

Mai embraced the mentorship program, which provided a detailed roadmap for organizing a successful fundraising dinner. The program emphasized storytelling over auction-based fundraising, allowing nonprofits to share their mission and inspire donors authentically.

“It was just month by month just to say, hey, this is what we're told to do.” (20:28)

Key strategies included:

• Table Hosting: Engaging existing supporters to invite new guests personally.
• Non-Ticketed Events: Removing financial barriers to attendance, which significantly increased participation.
• Storytelling: Focusing on conveying the school’s mission and impact to inspire donations.

Event Execution and Success

The inaugural Perfect Vision Dinner for Chesterton Academy was held during the COVID-19 pandemic with just nine students managing most classes and administration. Despite the initial scarcity and ongoing challenges, the gala was a resounding success, raising $298,000—just $2,000 shy of their $300,000 goal.

“We just trusted you guys... I was amazed because people who came before who didn't give very much gave a lot.” (27:02)

The absence of auction baskets and the emphasis on storytelling resonated deeply with attendees, fostering a genuine connection and willingness to support the school’s mission.

Impact and Future Plans

The successful gala not only provided immediate financial support but also set the stage for future fundraising efforts. Mai highlights the program's role in allowing the school to dream bigger and expand its reach within the community and beyond.

“Just telling the story, it just opened up their heart.” (27:58)

Plans include:

• Increasing Attendance: Building on the momentum to attract more guests in subsequent years.
• Sustained Funding: Ensuring the school remains fully funded and debt-free for future academic years.
• Expanding Influence: Extending the model to other Lake County schools and potentially nationwide.

Key Takeaways and Insights

1. Faith and Community Support: Trusting in a mentorship program rooted in faith can lead to extraordinary fundraising success.
2. Storytelling Over Auctions: Authentic narratives about a nonprofit’s mission can inspire greater donor engagement and generosity.
3. Innovative Fundraising Strategies: Removing financial barriers and leveraging personal invitations can significantly boost event attendance and fundraising outcomes.
4. Persistence and Adaptability: Overcoming initial fundraising plateaus requires willingness to adopt new methods and strategies.

“God rewarded us.” (36:51)

Conclusion

Episode 90 of The Fundraising Masterminds Podcast showcases how Chesterton Academy leveraged the Perfect Vision Dinner program to achieve a significant fundraising milestone. Mai Wilson's journey underscores the importance of faith-based strategies, community involvement, and innovative fundraising approaches in advancing nonprofit missions. The episode serves as a testament to the transformative power of effective fundraising, inspiring other nonprofit leaders to adopt similar strategies to fully fund their organizations.

For more information on the Perfect Vision Dinner mentorship program, visit www.chestertoniheart.org or call 815-331-8047.

Notable Quotes:

• Jim Dempsey (01:09): “God was so gracious.”
• Mai Wilson (04:00): “We were recapturing what Catholic education was supposed to be.”
• Mai Wilson (11:07): “It just came through a series of miracles in a very short time.”
• Jim Dempsey (09:45): “I never found a Chesterton student that I wouldn't hire tomorrow.”
• Mai Wilson (17:29): “When no auction baskets were mentioned... I thought, no, never again.”
• Mai Wilson (27:02): “We just trusted you guys... I was amazed because people who came before who didn't give very much gave a lot.”
• Mai Wilson (27:58): “Just telling the story, it just opened up their heart.”
• Mai Wilson (36:51): “God rewarded us.”

Connect with Chesterton Academy:

• Website: www.chestertoniheart.org
• Phone: 815-331-8047
• Location: Volo, Illinois

If you found this episode inspiring, be sure to subscribe, leave a comment, and share it with other nonprofit leaders who could benefit from Chesterton Academy’s story.