What If Philanthropy Got It Right? Robert Osborne on What if Instead?

Our guest, Robert Osborne, principal of The Osborne Group, brings 25 years of experience working with nonprofits and funders. Together, we explore:

• Why most philanthropic money never reaches grassroots, community-led organizations
• How donor-advised funds and endowments lock away billions while urgent needs go unmet
• The limits of “charity” and the need to center justice instead
• Whether measuring impact helps or distracts from real change
• And yes… how toile curtains and a fictional band called The Goody Two-Shoes Subversives tie it all together

From critique to creativity, we imagine what a more democratic, community-centered, and accountable philanthropic system could look like — and what would need to shift to make it real.


Editorial Producer: Kyriaki (Claire) Lampidou

Producer: Srijan Banik