Making Cents of Service: Mentoring the Philanthropic Investment Club

A small investment portfolio has become a powerful tool for teaching students about stewardship, philanthropy and servant leadership.

Sep 25, 2026  |  By Jennifer Cookston, The Webb School of Knoxville

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Webb School of Knoxville boasts an array of extracurriculars outside the usual sports and drama: not just chess but also knitting, mahjong, mountain bike mechanics, and a hot sauce club to name a few. This is one of the many special aspects of Webb that drew me to the school after spending almost two successful decades at my previous independent school. Upon arrival at Webb in 2023, I learned I would be inheriting club advising duties from the previous business officer, and I eagerly embraced the opportunity.

The Philanthropic Investment Group (PIG, for short) is a student-run upper school club that teaches financial literacy while supporting local charitable causes. The club started with a small but generous donation, which serves as the basis for the portfolio, which now is over $20,000. While not huge, it generates enough earnings to make philanthropic contributions twice a year.

How It Works

The club meets 10 times throughout the year for 30 minutes a meeting, and around 20 students participate regularly. Students present stock recommendations, review portfolio performance, vote on investment strategies, and introduce charitable organizations for consideration. Presentations are typically delivered in our “Visualization Lab,” which has a wall of screens and stadium-style seating.

And in addition to making two significant investments each year, PIG members choose two to three smaller charitable efforts, such as school bake sales or walk-a-thons, to support throughout the year.

While PIG meetings do not allow for an in-depth exploration of every topic, the goal is to give students a well-rounded foundation in finance that they can build upon long after they leave Webb.

Guest speakers help PIG members connect classroom concepts to real-world careers and experiences. For example, our finance committee's investment chair has spoken about private wealth management as a career path. Advancement team staff and alumni have discussed the relationship between wealth, philanthropy and community impact. While PIG meetings do not allow for an in-depth exploration of every topic, the goal is to give students a well-rounded foundation in finance that they can build upon long after they leave Webb.

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The Advisor's Role

For the most part, PIG is entirely student-led, and my role is simply to facilitate discussion and provide context when needed. I’ve served a direct role in a couple key areas.

First, I encourage students to think critically about their investments and gather credible information to deepen their understanding. Questions include: What is happening in the global economy that could impact this stock’s performance? Does the organization have a strong administrative structure? How can you use Form 990 filings to assess financial health and transparency of a not-for-profit organization? How much of each donated dollar directly supports the mission? These short lessons help students become more informed investors and philanthropists.

Students serve as chairs and co-chairs of both the investment and philanthropic side of the club, and they take ownership of the club’s direction and key decisions. I have helped establish succession planning in the annual activities, drawing from my own experience working with Webb’s governance committees. Students now formally nominate their peers, and the current chairs and co-chairs play an active role in identifying and mentoring future leaders. This process helps students develop an always-looking-forward mindset, which I believe is important.

At a school with more than 70 extracurricular activities, I am always looking to differentiate our club. I’d like to think that the spirit of setting aside resources and being wise would be enough to keep students coming back to the PIG club, but in case it’s not, there are always donuts!

Real Impact

The fund has made a notable difference in communities around the school.

As the reserves become stronger, so does the potential to expand that impact and provide greater opportunities.

September 2024 saw an extreme case: Hurricane Helene swept through the southeastern United States and left a trail of destruction throughout East Tennessee, including areas outside Knoxville. Local nonprofits faced enormous challenges as they strove to meet the urgent needs of affected families. PIG provided supporting funds, and being involved in that process and witnessing the tangible difference those investments made was deeply impactful to both the students and me personally.

Watching the portfolio grow into something truly self-sustaining is the greatest reward. As the reserves become stronger, so does the potential to expand that impact and provide greater opportunities. It serves as a reminder that investments are more than a financial asset: they are tools for sustaining a school’s mission, creating opportunities and ensuring resilience.

In an ideal world, free of competing priorities, it would be wonderful to see the investment club evolve into a full-fledged class where students can dive deeper into financial literacy, philanthropy and investment strategy. But until someone invents a way to add more hours to the day, I’m excited to continue the next chapter of PIG and see what our students accomplish in the 2026-27 school year.

webb school of knoxville

Author

Jennifer Cookston

Jennifer Cookston

Chief Financial Officer

Webb School of Knoxville

Knoxville, TN

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