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.