Mar 10, 2026
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Repair
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Bold Ventures CEO Jessyca Dudley recently joined host Michelle Renee Jackson on “Black Philanthropy: Our Stories” for a wide-ranging conversation on repair, accountability, and the future of philanthropy.
During the episode, Jessyca traced her path from public health research and sex education in Chicago to leading Bold Ventures and shared what all of this work has taught her about money, harm, accountability, and hope.
Takeaway 1: Philanthropy has two faces — and we need to understand both
Jessyca opened with a distinction that shapes much of our work at Bold Ventures: the difference between the culture of philanthropy—the deeply human, community-rooted practice of caring for one another—and the business of philanthropy, the institutionalized American system built atop concentrated wealth. Black communities, she argues, have long been experts in the former. A key challenge today is bringing that wisdom into the business of philanthropy, changing its practices to better align it with the deeper, ancient culture of philanthropy.
Takeaway 2: Repair is broader than most people assume
One of the most common misconceptions Jessyca encounters is that reparative philanthropy is only about harm done to Black people by white people. Bold Ventures holds a wider view. Wage extraction harmed all women (the pay gap is wage theft), environmental extraction harmed working-class communities of all races, and labor exploitation reached far beyond any single group. Repair, for us, is about addressing extractive systems wherever they cause harm. The harms done to Black people are undeniable. And Black people are not alone in having been harmed.
Takeaway 3: Community must be in the room where decisions are made
One of the central challenges for the practice of effective and reparative philanthropy boils down to a fundamental disconnect: The people closest to a problem are rarely the ones deciding how to address it. Bold Ventures works to change this through practices like trust-based participatory and participatory grantmaking—bringing community leaders directly into the decision-making process. The result isn't just more equitable; it's more effective, because the people who know a landscape best are finally being asked about it. These are positive steps on the path toward repair.
Takeaway 4: The long-term goal is a world where philanthropy isn't needed
Bold Ventures ultimately envisions a future where philanthropy as we know it no longer exists—because the extractive systems that made it necessary will have changed. We are seeking, as Jessyca puts it, to "stand in the gap" of that transition. Fundamentally, we don’t think justice and equity can be achieved without changes to the underlying economic structures—and to the business of philanthropy in which we currently work. This tension is one we grapple with, like so many people before us who have lived and worked—and created crucial moments of joy and progress—within systems they sought to change.
You can listen to the full podcast here:
https://www.simuel-murray.com/podcast-black-philanthropy/episode-20-1
About the Podcast: “Black Philanthropy: Our Stories”
Hosted by award-winning writer, director, and founder Michelle Renee Jackson, each episode spotlights Black and African American leaders transforming lives through giving.
