Feb 16, 2026
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Insights
In 2021, I left my job at a large philanthropy consulting firm to start Bold Ventures. It felt … well, bold. In the middle of a pandemic, in the midst of a wave of racial justice protests, I was leaving a settled path to build a company committed to revamping philanthropy in the name of equity.
In the nearly five years since, cultivating boldness has become part of my daily routine.
Today, we face new types of resistance to needed change: a landscape where hard-won progress toward justice has been rolled back, where ICE agents shoot protestors and zip-tie children, where DEI initiatives are under attack, and where the very language of equity and inclusion is increasingly contested.
For those of us committed to using wealth as a tool for transformation, the ground beneath our feet feels unstable, perhaps more unstable than ever.
Yet I've come to understand that this destabilizing disruption—destructive as it can be and is—can create new potential for change: It can help spur us to reimagine how capital flows, who holds power, and what we're actually building toward.
When old systems destabilize, we have a choice. We can work frantically to restore what was, or we can build something better together. For people who come from divested communities and backgrounds, this choice is often simple. With little nostalgia for what we know was a violent and fractious past, we look to the future.
But how do we build a better long-term future while managing short-term risk? How do we stay focused on transformation when everything feels desperate and urgent? How do we move from good intentions to meaningful action when the path forward feels unclear?
These questions have guided Bold Ventures' journey over the past five years, and they have led us to what we now recognize as our guiding practice, Reparative Philanthropy.
When I founded Bold Ventures, I knew I wanted to support philanthropy that advanced racial equity. I understood the ways traditional philanthropic practices—even well-intentioned ones—can perpetuate the very systems of harm they claim to address. But I didn’t yet have a full perspective on repair.
Working alongside clients and communities taught my team and me that effective change typically requires asking uncomfortable questions about how wealth was created and who was harmed along the way. It requires examining who holds power in philanthropic decision-making, who defines success, and who has been systematically excluded from the crucial conversations that determine the direction and pace of change.
Over five years, through partnerships with families, foundations, and donor collaboratives, we have worked to create approaches that center community wisdom, redistribute decision-making power, and measure success through the eyes of those most impacted by our work. We have learned to facilitate difficult conversations about accountability, to support participatory grantmaking that genuinely shifts power, and to help our clients navigate the tension between traditional philanthropic expectations and transformative practice.
As this work deepened, we recognized that we weren't inventing something new. We were learning to be part of something much larger: movements toward what Liberation Ventures calls a "Culture of Repair" and what the Just Economy Institute articulates as a "Just Transition." Such frameworks helped us understand our role more clearly. Bold Ventures exists to help philanthropy become a genuine tool for repair—to support those with capital in moving from extraction and control to transformation and repair.
Reparative philanthropy acknowledges a fundamental truth: Wealth accumulation in the United States has been systematically built on the extraction of resources from Black, Indigenous, and other communities of color, as well as from working-class and low-income communities across racial lines.
Enslavement generated massive capital while denying Black Americans any compensation for their labor. Land theft dispossessed Indigenous peoples of billions of acres. Exploitative labor practices extracted value while denying fair wages. Redlining blocked families of color from homeownership. Decades of underinvestment compounded these disparities.
The result is stark. The resources that built many of today's fortunes were systematically denied to the very people and communities from which they were extracted. Reparative philanthropy works to address this and ultimately transcend this injustice through five interconnected practices:
For some in the philanthropic sector, this set of practices feels almost obvious—it’s what many of us have seen work repeatedly. But for others, this set of practices will feel strange or even radical. They sit in tension with traditional philanthropy’s beliefs about fiduciary responsibility, strategic orchestration, and measurable impact. They ask everyone to think about wealth differently, as an opportunity to create meaningful connection and community through repair and accountability, a chance to build a more perfect future together.
At the moment, the most challenging part of this work is navigating the tension between short-term crisis and long-term transformation.
I've learned to look to the communities most impacted by systemic harm for help and guidance. Our own ancestors have been navigating this tension for generations. They have practiced repair, resilience, and mutual aid while managing immediate crises. They built toward liberation while surviving oppression. They have proven, repeatedly, that this can be done.
Here’s some of what we've learned through our practice at Bold Ventures:
When we let go of the need to direct every outcome, when we measure success through community-defined outcomes rather than donor preferences, the work becomes both more effective and more sustainable.
The people most impacted by systems of harm understand those systems better than external consultants. They are more likely to know what's needed, what's working, and what's missing. Our first job is to listen and resource their leadership, not to impose our own frameworks.
Transformation doesn't happen in grant cycles or strategic plan timeframes. It requires multi-year commitments, sustained relationships, and the patience to work at the pace of trust and community organizing.
Yes, it's challenging and sometimes uncomfortable. Yes, it requires confronting hard truths. But there's profound joy in creating authentic partnership, witnessing community power grow, and being part of something so much larger than ourselves.
The movement toward repair is growing. Organizations like Liberation Ventures, the Just Economy Institute, and many others are articulating frameworks for transformation. Community leaders and organizers are doing the daily work of building new systems. And many philanthropic practitioners are making progress, using trust-based approaches and participatory grantmaking, listening more closely to communities and learning from past mistakes.
At Bold Ventures, we're committed to being part of this work. We support and encourage all those who want to use wealth to interrupt harmful patterns and create pathways toward repair and a more just economy. We don't have all the answers, but we're here to serve as fellow travelers, partners, and guides.
In this difficult time—when so much feels uncertain and unstable—I find hope in Octavia Butler's reminder: "There's no single answer that will solve our future problems. There's no magic bullet. Instead, there are thousands of answers, at least. You can be one of them if you choose."
At Bold Ventures, we choose accountability, community, and repair.
We choose the long work of transformation even amid the short-term crises.
We hope you will join us.
Jessyca Dudley is the CEO of Bold Ventures and a leader focused on racial equity. Key experience: Chicago African Americans in Philanthropy, Arabella Advisors, and Joyce Foundation.
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