"What If Philanthropy Got It Right?"💰| Robert Osborne - What if Instead?

In this episode of What If Instead?, hosts Mim Plavin-Masterman and Alejandro Juárez Crawford talk with Bob Osborne, Principal of The Osborne Group, a boutique consulting firm for nonprofits. With 25+ years in the field, Bob shares eye-opening truths about how philanthropy often fails to serve the communities it's meant to help—and how we can flip the script. Philanthropy Reinforces the Status Quo Donations from the top 1% are increasing, but total giving is going down. Much of the money sits idle in endowments and donor-advised funds (DAFs), gaining interest instead of creating impact. Institutions closest to the need often get a fraction of philanthropic dollars. "At its best, philanthropy should be democratic. But I don't know that it always plays out that way," Bob notes. The money often flows where it benefits the donor most—not the community. Generosity Without Impact? Bob breaks down the uncomfortable truth: decisions about funding are often far removed from the people it’s meant to serve: Big gifts often come with strings attached. Fundraisers are pressured to prioritize donor satisfaction over mission. Systemic problems stay intact because they’re not in the donor's line of sight. Worse, nonprofit organizations must tiptoe around their values just to stay funded. "You're either honest about your mission and risk losing support, or you compromise to keep the money coming." What Real Change Could Look Like Bob and his colleagues are working to shift mindsets toward community-centric fundraising: Route resources to where the need is greatest, beyond institutions familiar to donors. Redistribute decision-making power to the communities served. Don’t let funds sit: spend more of what’s already sitting in philanthropic coffers. Bob challenges donors and fundraisers alike to move from charity to impact. From wealth preservation to systemic change. "If not during a pandemic, when is the right time to spend more than 5% of a foundation’s funds?" So, What If Instead? What if philanthropy wasn’t about donor recognition or tax deductions? What if it was about solving the root causes of injustice? Bob challenges us to stop giving ourselves an A for effort, and get the whole job done. Otherwise we let ourselves off too easy "Giving money to a soup kitchen won’t end hunger. We have to be bold enough to make philanthropy unnecessary." – Bob Osborne Suggested Listening & Resources Community-Centric Fundraising: https://communitycentricfundraising.org/ Inside Philanthropy: https://www.insidephilanthropy.com/ Winners Take All by Anand Giridharadas