Philanthropy Is Learned / Philanthropy Needs Repair

Jessyca Dudley spends her days thinking about philanthropy from two very different vantage points.

As founder of Bold Ventures, she advises families and foundations on how to move money through a “reparative” lens. As a lecturer at the University of Chicago, she teaches the history of philanthropy and social movements, sharing with students how today's structures of giving came to be, and where they might be heading.

Earlier in her career, Dudley worked at a major foundation, while there  she realized  that "the culture of philanthropy" was very different from "the business of philanthropy." She told me that much of her work since then has been “trying to bring those things closer together” – to recenter practices of reciprocity and giving cultures that go back way farther than the modern era of institutional philanthropy, which is only half a century old.

That insight has shaped nearly everything she's done since – from launching a Black women's giving circle in Chicago, to recently co-authoring the widely shared essay Be Less WEIRD, urging donors in the Global North to look beyond familiar ways of practicing philanthropy.

We spoke with Dudley about [what it means to teach philanthropy at a moment when a new generation of donors is also learning how to give – and how history can shape both.]

You spend your time with two groups of people who are relatively new to philanthropy – college students and wealthy donors. What do they notice that philanthropy insiders might miss?

One insight that I bring to all of my work – with students or donors – is that the history of philanthropy is actually very short.

Philanthropy, as we know it today, is not that old. My students look at the history of social movements, and we spend a lot of time talking about tax policy over the past 50 years. How the United States made a series of choices – particularly under the Nixon administration – to move social services outside of government while creating a system to fund them. And how that led to what we understand as philanthropy today.

Because philanthropy isn’t that old, that means it can change. What I find most valuable about teaching is having students who can see the sector with fresh eyes. They're not yet embedded in the norms we all absorb – the assumptions we treat as inevitable, the "rules" that aren't actually rules.

That's different from how those of us inside the sector often operate. We tend to take for granted what we've absorbed over time: the assumptions, the language, "this is how it works." My students don't have the same restrictive assumptions r.

I’ve been able to bring this to my donor clients by sharing the same history. Showing them that when funders encounter cultural constraints in their work – challenges around collaboration or engaging communities – a lot of it has to do with these institutional structures that are just over sevent-five years old. Realizing that the practices they know or hear about are recent historical artifacts rather than existential truths can be liberating

By the way, I can be as guilty as anyone of accepting how things are done simply because that's how we've always done them. My students don't let me get away with that.

A lot of people see donor advising as a black box. What does your day-to-day look like with Bold Ventures, and how does your “reparative philanthropy” approach inform that?

Fundamentally, I’m helping people figure out how to use the resources they have at their disposal to help build a better future, for the communities they care about and for themselves.

What's different about Bold Ventures is that we start by talking with donors about how their wealth was actually generated.

We start by acknowledging that Big Philanthropy is an outcome of extraction. It’s the tail end of an economic system that has decided it wants profit, whether that's through paying people less than the value they create or through externalizing costs onto the environment. That's a different starting point than most philanthropy strategists take.

We ask different questions of our clients. Most donor advisors asks, "What's the legacy you want to leave?" We ask “Who are you accountable to in moving this money?” Once you ask that question, it changes everything. It changes who should be making decisions. It changes governance. It changes grantmaking.

Sometimes that means the client decides to use participatory grantmaking. But sometimes it simply means recognizing that your expertise isn't in deciding where money goes at all. One of the things we tell donors is that if you're a lawyer, be a lawyer. If you're an accountant, be an accountant. Bring that expertise to movements. Don't assume your wealth makes you the best grantmaker.

A lot of our practices grow out of that philosophy. It rare that our clients ask for a grant application or grant report. We don't ask organizations to produce grant reports. Our assumption is that organizations are already accountable to the communities they're serving. Our job isn't to create more bureaucracy – it's to help resources move in ways that strengthen those relationships and to be deep enough relatinshiop to understand the work

As one example: an individual donor came to Bold Ventures for support in transitioning from a traditional approach to giving to one focused on addressing the legacy of slavery in the United States. Their goal was to build relationships, advance repair, and redistribute wealth. They were ready to talk about the source of their inherited wealth and knew that the discomfort with that source was calling for a change. 

We began by helping this individual articulate personal values that would drive their giving – things like justice, self-determination, joy. Next we co-developed a learning plan about the history of slavery, including several dedicated learning sessions and materials that could be shared with the individual's family.

Five years in, this donor has built an entirely new set of relationships grounded in repair work – with community partners, with reparations-focused organizations, with others committed to this approach.

But perhaps most significantly, they've brought their family along. The family has collectively documented their own history: where their wealth came from, how it was accumulated, their family's specific connection to the transatlantic slave trade. 

You also publish articles, like your recent piece in NPQ arguing that philanthropy should be “less WEIRD” (less focused on Western, Educated, Industrialized, Rich, and Democratic populations and thier ideas). As someone in the media space, I’m always curious: how do you think that kind of rhetorical writing influences conversations within donor circles?

Earlier this year I was at the Global Philanthropy Forum, and I found myself wondering why we spend so much time exporting practices that we know don’t work instead of importing practices that have been working for generations across the Global Majority.

One thing I hope people take away from that piece is that many of philanthropy's best practices – participatory grantmaking, giving circles – didn’t originate in institutional philanthropy. They often came from women, communities of color, communities across the Global South.

I hope the article resonates, that it gives others something concrete to point to, validates their thinking, and gives them permission to act. Our sector often shifts based on trends and peer pressure. As more people bring diverse perspectives in, we open up what's actually possible.

That said, we tend to turn ideas into frameworks, and frameworks into dogma. So I'd rather this be an invitation than another "best practice." Best practices only work when they're grounded in deep understanding of the specific people and communities you're in relationship with. That understanding can't be templated or copied. It has to be earned through genuine connection.

What do you hope the next generation does differently?

One of my favorite things about teaching is that students push back. As an advisor, people often take what you say. In the classroom, students challenge you. They debate. They ask difficult questions. That's healthy.

I actually design my class around that. Students debate whether philanthropy should exist in perpetuity or spend down. They study social movements and trace how money changed those movements. They have to develop opinions, because if they're going to work in this sector, they need to understand where they stand.

What I hope is that the next generation enters philanthropy with a much deeper understanding of how the sector was built – and a willingness to question the assumptions we've inherited.

Because philanthropy isn't inevitable. It's a relatively recent invention. And if we understand how it was built, then we can also imagine building something different.