Is The Future of Philanthropy Impermanence? feat. Santhosh Ramdoss

What changes when we embrace impermanence instead of trying to live forever?

In this episode, Glen Galaich sits down with Santhosh Ramdoss, president and CEO of Gary Community Ventures, for a conversation about impermanence and legacy. Guided by Gary’s commitment to move all its assets into the community by 2035, Santhosh debunks the fake rule that philanthropic impact depends on institutional permanence. He invites the sector to imagine a legacy rooted in stronger systems, durable public funding, and the beauty, love, and care we leave behind. In a Break Fake Rules exclusive, Santhosh rolls out a new game, The Philanthropy Challenge, that funders can play to respond to urgent crises and see where philanthropic funds can have the greatest impact.

At the heart of the conversation is a more expansive question for wealth holders and foundation leaders: what if ending an institution is not a loss, but a strategic opening? And what becomes possible when philanthropy brings more joy, wonder, and imagination into the work of building a world that can outlast any one foundation?

💡Santhoush Ramdoss: “I think one of the practices that philanthropy does need a lot more of is joy and wonder. I think we've lost our capacity to see what's possible, and sometimes the moment of being in that wondrous possibility of what systems could be is lost.”

Learn more about Gary Community Ventures and play The Philanthropy Challenge for yourself!

Order your copy of Glen’s book, CONTROL: Why Big Giving Falls Short.

Learn about the Stupski Foundation.

Host: Glen Galaich

Guest: Santhosh Ramdoss

Executive Producer: Claire Callahan

Production Team: Podfly & Gary Community Ventures

Video Editing: Edith Belmont

Graphic Design: Middle MGMT