Jessyca Dudley on Accountability, Extraction, and the Culture of Philanthropy
Philanthropy can’t free us, but it can reduce harm as we work toward something better.
This is the second installment of Builders of Justice, a series that profiles leaders who refuse to play it safe—challenging power, naming harm, and reimagining justice.
As a lecturer at the University of Chicago, Jessyca Dudley teaches her students about philanthropy’s impact and its transformative power. She also addresses its extraction.
“Philanthropy is a system that operates because of extraction,” she explains. “We don’t have philanthropy without the extraction of natural resources and without the extraction of labor from people so that a small group of people have really concentrated wealth.”
As the Founder and CEO of Bold Ventures, Dudley has dedicated over 15 years to helping families, individuals, and institutions transfer more than $50 million to BIPOC-led organizations. However, she is aware that philanthropy requires honest reflection on its origins.
“It’s a big, maybe too big of an ask to expect that a system built from those practices is liberatory,” she says. “The work that we do is sort of softening the ground or creating the pathways for bigger systemic changes that are needed so that equity and justice are possible. But personally, I don’t know that I believe philanthropy gets us to liberation.”
This type of honesty makes Dudley’s work all the more essential. In a field full of performative claims about equity while protecting concentrated wealth, she calls out the fact that philanthropy can’t free us, but it can reduce harm as we work toward something better.
The Gaps
Before Dudley entered philanthropy, she worked in public health, focusing on Black communities in research that supported young people of color’s access to reproductive healthcare. It was work rooted in relationships and understanding that the best solutions come from people with firsthand experience of the challenges being addressed.
When she entered philanthropy, she was surprised by what she found.
“There was this distance between the people who are in philanthropy and often who the foundations are serving,” she reflects. “That wasn’t my knowledge base or understanding of what I would experience coming into the work.”
The gap between those who control resources and those who need them became central to how she later built Bold Ventures. She maintained the ethos from her public health work that resources, knowledge, and education should flow in ways that empower communities rather than drain them further.
“Being a Black woman, I sort of operate with the assumption I may be excluded from places of decision making,” Dudley explains. “I know what it’s like to have your preferences, your needs, your solutions dictated to you, rather than being asked to be involved in the creation of those solutions.”
This personal experience became a method for her work. At Bold Ventures, the key question is, “Who are you accountable to?”
Accountability as Strategy
When Bold Ventures collaborates with families, individuals, and institutions, it encourages funders to shift their focus to include accountability.
“We’re asking folks to think about who are they accountable to in the work,” Dudley says. “When we ask that question, it pushes people to think about the relationships they hold, and who else needs to be a part of this work alongside them to create real accountability.”
This shift from legacy to accountability opens the door to entirely new practices. Multi-year general operating support, donor collaboratives with greater willingness to take risks and be innovative, and participatory grantmaking where communities lead decisions rather than funders.
“Sometimes that is participatory grantmaking where a funder is saying, ‘I’m not going to be the decision maker here. We’re going to actually develop a process for thinking about who would be best to determine what are the solutions and how should they be funded.’”
Dudley is careful to position Bold Ventures alongside movement leaders rather than above them. “It’s easy to get caught in the consulting trap that we have the best ideas and we have all these frameworks,” she says. “We’re very careful to position ourselves alongside movement leaders and movements and really take cues from them in the way that we advise.”
Take reparative philanthropy, a framework Bold Ventures uses in their work. “We talk a lot about reparative philanthropy, but we don’t own that. That’s not our idea. That’s really like a translation that we’ve gotten from working with movement leaders and thinking about what are they asking for and how do we translate that to donors.”
This is a clear example of honesty and transparency in action, giving credit to where ideas originate and to whom they belong.
The Culture Versus the Business
At the University of Chicago’s Crown Family School of Social Work, Policy, and Practice, Dudley emphasizes a key distinction in her teaching within the Social Sector Leadership and Nonprofit Management department. This helps students better understand what they are actually stepping into when they choose to work in this sector.
“We talk a lot about the difference between the culture of philanthropy, which so many of us grew up with, that’s really about sustaining ourselves and our communities and the kinds of practices you find in religious communities and cultural communities,” she explains. “Which I think is very different from the business of philanthropy, which again, built on extraction, built on a set of narratives around the idea that those who have generated great wealth are best positioned to dictate to others how they should live and how they should become upwardly mobile.”
Many of us are familiar with the culture of philanthropy. Community change, social justice, service—these are common themes. However, the business of philanthropy is quite different. It serves as a way to preserve wealth, built on stories about who deserves resources and who has the power to decide who does.
“If you’re operating in the space of philanthropy without understanding those underlying messages, there’s only so much you can do,” Dudley says. “You may be working within a space that you don’t have a full understanding of its culture.”
She admits she didn’t fully grasp this when she first worked at a foundation. “I was totally guilty of this when I was in my role in a foundation, did not understand enough about the history of philanthropy to understand why it was so challenging to sometimes do the work that I wanted to do.”
Her curriculum now includes the history of philanthropy—covering the industrial age, the first significant period of wealth concentration in the U.S., and the tax policies that shaped the structures we navigate today. She invites guest speakers from across the sector so students can understand the real-world experiences of working in philanthropy across different identities. She prepares them for the crucial decisions they’ll face about their relationships with social movements when philanthropy becomes involved, which can shift decision-making and control.
Within six to eight months of her foundation role, Dudley was ready to leave. What kept her going were relationships with other Black women in philanthropy who helped her map her own power and understand her ability to influence. “I had not been in roles where really understanding my power and my ability to influence had been so critical to the work,” she recalls.
Understanding the difference between the culture and the business of philanthropy transformed how she taught, how she survived in the sector, and ultimately how she built Bold Ventures.
The Contradictions We Name
The contradictions in this work are many and layered. There’s the basic contradiction of a system built on oppression pursuing liberatory goals. There’s the contradiction between what institutions claim and what they actually do. And there’s the personal contradiction of controlling resources while trying to stay true to your values.
Dudley doesn’t shy away from any of them.
“I think there is the tension of trying to do good work in a system that is built on oppression,” she acknowledges. “If we’re operating in philanthropy without naming that, we’re not really engaging with the true nature of our sector.”
Then there’s the misalignment between stated values and actual practice. “There’s a misperception that the majority of philanthropic dollars are benefiting communities of color, because we have a narrative that people of color can only be receivers of philanthropy, when we actually know the majority of philanthropic dollars are going to white-led organizations.”
This matters symbolically and materially. If your budget doesn’t align with your values, the work you want to do, or the outcomes you claim to want, then what are you actually funding?
And it’s not just grantmaking. “The majority of money in philanthropy is actually in investments and not in the grantmaking,” Dudley points out. “Are your values showing up in the investments? Or is it possible they are undermining the values-driven work that you’re doing on the grantmaking side with how your investments are set up?”
Private foundations are required to donate 5% of their assets. The question is what the other 95% is doing and whether it’s undermining everything that 5% is trying to build.
What It Takes
When I ask Dudley what it will take for philanthropy to move from reform to liberation, she says the efforts she provides aren’t easy and require work.
“I think we’ve got a lot further to go,” she says. “I don’t think it’s ever going to be perfect. But I do think that takes real honesty about how this sector was created, what its limitations are, who it is, and just really getting real about that.”
The honesty she’s calling for involves examining the systems that created philanthropy and questioning why it’s even needed right now. It means confronting what she calls “strong American cultural narratives” about people without wealth, and the perceived morality—or lack of it—that prevents the sector from trusting communities with resources.
“If we show up as a sector that does not trust people for a systemic reason that they do not have wealth, there’s real limits to what we can do,” Dudley explains. “Really starting to understand those narratives that drive our sector and working to challenge them and understanding how they show up in our own perceptions and work with money, how they show up in our institution’s practices and work with money is really critical.”
At Bold Ventures, this is reflected in how the team functions internally. They share decision-making regarding which projects to pursue. The entire team takes August off to reconnect with family and engage in activities unrelated to work. No client-facing work on Fridays, so there’s actually time to focus on the work instead of just talking about it.
“We work hard, we set a high bar for our work, and we also need to do things that are not work,” Dudley says.
The team also spends significant time discussing how doing this work impacts them, particularly for those who didn’t grow up with wealth. “Being in proximity to this kind of wealth, sometimes being exposed to conversations that can be really challenging, particularly if they’re about communities that you are in fact a part of, takes a toll,” she reflects. “We spend a lot of time as a team just doing our own inner work and doing that as a team together.”
They discuss how they are affected, the solutions they desire, and how they want to present themselves, so they show up as their most whole and best selves.
This is what it looks like to build differently.
The Future We Can See
If Dudley could give every foundation in the country one lesson—or two—from Bold Ventures’ work, they would be these:
First: “Really thinking clearly about who your decision makers are, and if you can shift those decision makers to have greater impact. So many foundations are just talking to themselves or talking to academics; they’re not actually talking to the folks who will benefit from those resources.”
Second: “Really understand where is your money and where is it moving to? Does your budget align with the values that you have, the work you want to do, the outcomes that you want to have? And same thing for your investments.”
These are straightforward recommendations, but they require the honesty Dudley has emphasized throughout our discussion. Honesty about who has power, who gains from existing arrangements, and who suffers from them.
When I ask what a truly liberated future for philanthropy looks like, Dudley speaks plainly.
“I mean, I think if we’re truly liberated, there’s no philanthropy, because we wouldn’t have concentrated wealth. We wouldn’t have a system where you are either a worker or an owner, because we would have real ownership that is equitable and distributed.”
Short of that? “Moving big capital, moving it in an urgent way, and moving it to the scale of the challenges that it’s trying to solve. I think too often, we are risk-averse and hesitant to move the type of capital that’s really needed to make change. And at this point, we know what it takes to pass policy, we know what it takes to do narrative change, and we need to move resources at the scale of what those challenges take.”
We understand what’s necessary. The real question is if we’re ready to take action.
The Power of Transparency
Near the end of our conversation, Dudley returns to something that matters deeply to her: making this work more transparent.
“I think that there’s such an opaqueness around how philanthropy works that so many of us have the same experience that you described, we sort of show up in the work, and we’re a little bit blindsided by it,” she says. “How can we do more to sort of open the space up? I think philanthropy has benefited from being opaque and not really sharing how decisions are made.”
The secrecy isn’t accidental. It protects power, prevents accountability, and keeps people from understanding the system well enough to challenge it.
“If folks know more about how philanthropy works, then they can hold us accountable as a sector,” Dudley says. “And I think that’s really important.”
This is why transparency—through writing, teaching, and revealing processes and contradictions—matters so much. It might not change philanthropy on its own, but it creates the conditions for accountability. And as Dudley has shown throughout her career, accountability is where real change starts.
Not every answer lies in philanthropy. Not every solution can be funded. The true power resides in building community through relationships, earning trust, and participating in movements.
Jessyca Dudley has built a career helping philanthropy minimize harm while promoting liberation. She’s upfront about the sector’s limitations and honest about its extraction practices. She’s dedicated to transparency, accountability, and amplifying the voices of those most affected by the issues philanthropy aims to address.
The work needed is to become serious about understanding what this sector is built on. It’s shifting who makes decisions and where money actually flows. The work is developing internal practices that mirror the world we want outside. It’s being honest about limitations while still moving resources at the necessary scale. The work is about accountability. And she’s guiding the next generation to approach this work with eyes wide open, asking honest questions about power and wealth, and understanding clearly what this sector is and isn’t.
Jessyca Dudley (she/her) is an experienced social sector leader and strategic advisor who has supported individuals and organizations in shaping their strategies, implementation, and learning to advance racial equity. As Founder and CEO of Bold Ventures, she has directed over $50 million to BIPOC-led organizations, creating equity-centered funding strategies that disrupt traditional philanthropy and support divested communities. With a Master of Public Health from the University of Illinois Chicago and a Bachelor’s in Women’s Studies from Skidmore College, she champions a strategic, evidence-based vision for equitable capitalism.
Learn more about Bold Ventures at alltogetherbold.com.