Sep 24, 2025

Understanding Reparative Philanthropy: A Conversation with Jessyca Dudley

This week, Bold Ventures announced its commitment to Reparative Philanthropy. We sat down with founder and CEO Jessyca Dudley to discuss what this approach means and how Reparative Philanthropy differs from traditional giving.

Let's start with some basics. What's the difference between reparative philanthropy and regular philanthropy?

Traditional philanthropy too often treats symptoms while maintaining existing power structures. Reparative philanthropy addresses root causes by redistributing both resources AND power to communities most impacted by systemic harm. Reparative Philanthropy is ultimately about transforming systems, not just funding programs.

Is Reparative Philanthropy exclusively about racial issues?

No. While racial repair is central to Reparative Philanthropy, this approach also addresses class-based extraction and other forms of systemic harm. It recognizes both that racialized exploitation has been a defining feature of our economic system and that wealth concentration has harmed many communities.

For someone interested in this approach, where should they start?

Start with the question: "To whom am I accountable?" Think carefully about the communities that were—or are—harmed by the accumulation of wealth and power that benefits you. Then listen deeply to those communities. Look for immediate opportunities to shift power or resources to them and to thereby join in community and repair with them.

Also, look for others making similar journeys! This work can't be done alone or in isolation.

What does reparative philanthropy actually look like in practice?

Often, today, it looks like multi-year unrestricted funding, community members making final funding decisions, funders supporting organizing and advocacy, and all of us measuring success through community-defined outcomes rather than donor preferences. 

In the future, it looks like a more just and equitable world and a functioning multiracial democracy.

Some critics might say this sounds like guilt-driven giving. How do you respond?

This isn't about guilt—it's about accountability and community. Understanding how wealth was created helps us use it more intentionally. Guilt is paralyzing; accountability is empowering. We're asking: How can we use our resources to interrupt harmful patterns instead of perpetuating them? How can we use our wealth to create more community rather than to deepen division and despair? Answering these questions is about remaking community together. This is how we can actually work together to create a more perfect future.

How is reparative philanthropy different from reparations?

Repair and reparations work together but operate differently. Reparations are comprehensive political and economic demands for systemic redress at the scale of nations and institutions. Repair is more local and relational, built on grounded trust and specific relationships. Both are essential, and understanding the distinction helps funders act with integrity and engage productively.

What advice do you have for someone whose board or family isn't ready for this approach?

Start where you can and build understanding over time. Share stories of transformation, invite community voices into conversations, and demonstrate impact. Change often happens gradually, but it has to start somewhere. We can help you navigate these conversations.

How can foundations balance fiduciary responsibility with community control?

Fiduciary responsibility doesn't require maintaining all decision-making power. Many foundations have successfully shared power while meeting legal obligations. It's about expanding your understanding of accountability beyond just financial stewardship to include community impact and voice.

What happens when things go wrong? What if foundations make mistakes?

Just to be clear: You WILL make mistakes. We all do. The key is building relationships of trust where mistakes can be acknowledged, learned from, and repaired. Community partners typically appreciate transparency and accountability more than perfection, just like you do.

How should organizations measure success differently under this approach?

Move beyond traditional metrics like "dollars deployed" to include power built, relationships transformed, community-defined outcomes achieved, and systems changed. Ask communities how they measure success and use their frameworks alongside, or even in place of, your own.

Finally, what about donor intent and family legacy? How do you address concerns that this approach abandons family values?

Reparative philanthropy can honor family values while transforming how they're expressed. Many families find that this approach actually deepens their legacy by addressing root causes rather than just symptoms and by connecting the past and the present to a vision of a more perfect future. Reparative philanthropy is about evolving and deepening your impact, not abandoning your values.

To learn more about Bold Ventures' approach to Reparative Philanthropy, sign up for our newsletter or contact us directly. 

Browse

More Articles

Sep 24, 2025

Understanding Reparative Philanthropy: A Conversation with Jessyca Dudley

Aug 14, 2025

Facilitating All Together Bold: Reflections on Designing, Adapting, and Engaging in a Learning Community

All Together Bold (ATB) emerged as an idea to respond to the need for spaces in the social sector where individuals working towards racial, cultural and...