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Leading with Integrity through Philanthropy: Q & A with Board Chair Rob Tolleson

Rob Tolleson and his wife, Charisse, have been volunteers since they joined the Flintridge Prep community in 2017. Rob is owner and President of Reyn Spooner, a leading Hawaiian apparel brand based in Honolulu. He joined the Flintridge Prep Board of Trustees in 2020 and was named Board Chair in 2022. The Tollesons’ daughter, Emeline ’21, attends Wake Forest, and son Henry ’23 attends Northeastern. Their youngest son, Ridley, will graduate from Flintridge Prep in 2025. We talked to Rob about his love for the Flintridge Prep community and what philanthropy means to the Tolleson family.

Rob Tolleson and his family


We often talk about a culture of philanthropy. What does this mean to you, and why is it so important to Flintridge Prep?

I have learned that the more I give, the more I get back. This is true for giving, but it’s true for dedicating time to volunteering, as well. Charisse and I are really happy that we have made that investment, because we feel like we’ve gotten it back tenfold. We’ve made a ton of friends, and the more time I’ve spent with faculty and staff, the more I have realized what a special place it is.

Why is the Annual Fund so important for non-profit independent schools like Flintridge Prep?

What I learned is that there’s a gap between the annual operating budget of schools and what tuition covers. At Flintridge Prep, typically, the gap between our tuition revenue and our budgeted expenses is about 18%. As a board, we set tuition every year, and we do our best to not charge any more than we absolutely have to. We understand the burden on families. We are an outstanding school, and we’ve invested even more in recent years in wellness and other programs to make the experience as exceptional as possible. I feel a responsibility to try to close that gap by contributing to the Annual Fund for each child we have in the school at the time.

Do you look at investing in a school as a long-term commitment?

I do. You don’t always see the benefit while you’re there, but you’ve enjoyed these facilities and this programming because of previous donors. So now it’s our turn, and it’s our responsibility. Together we drive the future of the school through gifts and time. Giving back is not a transactional relationship. That is what separates Flintridge Prep. I think that’s pretty special.

The school has the responsibility to steward resources so that they benefit students as much as possible. It is the responsibility of community members to be stewards of the school by contributing to the Annual Fund and, if they can, to endowment and capital campaigns, because that’s how strong communities survive and thrive. Without those funds, we would still provide a fantastic education, but we would have to make harder choices about the opportunities students can take advantage of. We don’t ever want to put two very important causes next to each other and have to choose one.

Can you talk a little about comprehensive campaigns that include Annual Fund, capital, and endowment giving?

The most successful campaigns include both capital gifts to build or refurbish spaces and gifts to endowment to perpetually fund all the great programs that happen inside those spaces. Our campus is what it is because previous generations of families gave, so we see it as our turn and our responsibility to invest in the future of Flintridge Prep. We helped when we were approached about the capital campaign for the Bachmann Collaboration Building. And we’ll continue to help out in the next capital campaign.

We have a benefit coming up this spring. Can you talk about benefit giving?

The benefit reminds you of what a great community we have. It’s an opportunity to support a specific program or project.

What is the difference between Annual Fund and Endowment giving?

While the Annual Fund invests in the current year and helps close that budget gap, endowment is something that helps drive the school’s future, because gifts to endowment are invested. Each year we take a percentage out of the endowment to help fund the school. These funds are a very important part of annual spending while also building an annuity for the future. Endowment gifts can be broad and fund a variety of projects, or they can be focused on specific programming that donors have a passion for. Either option is a source of perpetual funding that takes pressure off the annual budget. The strongest schools generally have the largest endowments; they’ve seen the most support from their community over the years building an endowment to invest in the future.