Jan 20, 2026
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Insights
Over the past few months, we have shared our approach to Reparative Philanthropy through multiple lenses. Our goal is to help the sector move in the direction of repair by asking deeper questions like, “How was wealth accumulated? Who holds power? To whom are we accountable? How do we repair harm rather than reproduce it?”
Such questions apply beyond our work with clients. Equally important is how we examine the ways we work together and show up for each other to ensure that we do not recreate exploitation internally at Bold Ventures, which requires intentional effort and regular assessment.
Below, we share some of the ways we apply the principles of reparative philanthropy to our internal culture—how we make decisions, build capacity, practice care, and navigate repair as a team.
We developed Bold Ventures’ values collectively, through conversation, reflection, and shared experience, which allows for a deeper sense of ownership. They are shared commitments we’ve made to each other that require regular reorientation and ongoing work.
By practicing the commitments we’ve made in our day-to-day interactions, we move beyond intention and into action. Our practices include structured approaches to how decisions are made, how opportunities are shared, what accountability looks like, and how to respond when things don’t go as planned.
Much of how we live our values has been relational and care-driven, while recognizing that structures are necessary to sustain their application. Building a culture of repair means not only naming what matters to us, but also developing the habits that help us return to those commitments.
Learning together is one of the intentional ways we build team capacity. It is a core part of our culture, and something we invest significant time and care in. Shared learning happens in our team meetings, co-working sessions, and team retreats. It is also supported by guided conversations and external training, as well as ongoing reflection of our client work, approaches that shape the sector, and broader ideals about our role in society.
These spaces give us more than just shared language. They have allowed us to build a shared knowledge base and develop a unified approach that shapes how we analyze problems, make decisions, and navigate complexity together. Alignment doesn’t happen by assumption; it happens through intentional conversation. Learning together gives us the space to slow down, name what we’re seeing, and situate our work within broader systems of power.
As Director Aubrey Rawlins shared, “When done particularly well, the team references content explicitly and brings issues we learn about together into the space–we develop shared understanding and can work effectively when we share a baseline of knowledge.” This baseline allows us to ground our collaboration in shared frameworks while still honoring multiple perspectives.
This sort of practice reinforces our values of shared learning and respect. It creates space for different ways of thinking and knowing, while giving us common reference points that support clarity, trust, and accountability. Over time, learning together has become a form of infrastructure for our team, a practice we rely on to build collective capacity as well as individual skills.
As we move forward, we continue to deepen how we live into the ideas and philosophies we learn together. The work is not only about acquiring knowledge, but about embedding it–allowing shared understanding to translate into shared practice.
Most decisions at Bold Ventures are made collaboratively, drawing on the collective wisdom of the team. Others are made unilaterally, based on role or responsibility, and many times land with our CEO, Jessyca Dudley. We intentionally default to collaboration when possible.
For our collaborative decisions, we use consent-based and advice process models. These allow us to move forward without requiring full consensus while still ensuring that team members affected by a decision have meaningful opportunities to shape it. As Senior Project Manager Alysha Catalano recently shared, “It feels like we have shared power in the many opportunities to be part of the conversation around a decision, and knowing that gathering our input is not just a show of sharing power but what we contribute actually translates into the decisions made at Bold Ventures.” The ability to exert real influence is central to our understanding of shared power.
From the beginning, Bold Ventures has leaned toward democratic decision-making, and we continue to refine our practice. We are still wrestling with questions like: who needs to be informed, who needs to be involved, and who ultimately decides in common decision-making scenarios?
Our team is small and collaborative, and we have not needed to formalize decision-making. Still, we are working to ensure that it has a recognizable and mutually understood shape. Developing shared language and expectation around how decisions are made helps us communicate more transparently, build trust, and reduce confusion. Continuing to build this shared muscle is an intentional part of our work for this year. Building a culture of repair means being honest about where we are still developing while committing to shaping our decision-making practices in ways that reflect our values of trust, autonomy, and respect.
Over time, small moments have allowed us to build trust. From mindfulness practices at the beginning of team meetings to intentionally making space for non-work-related connections during in-person time, we have invested in getting to know each other as people. These practices signal care for the whole human.
Structurally, care shows up in ways like the ability to take time off for expected and unexpected life needs, no-meeting Fridays, and our August closure. Seeing each other step away, rest, and tend to our lives reinforces trust and affirms care as a shared commitment.
Accountability is the flip side of trust. Much of our accountability currently operates relationally rather than through shared, explicit practices. As our CEO Jessyca Dudley recently noted, “We serve as a balance to each other, sharing perspectives and ideas that allow us to be accountable to our values.”
Of course, individual relationships vary, creating uneven relational dynamics. We are working to articulate our accountability practices in ways that better communicate how responsibility, feedback, and care intersect in our work together.
In our work to advance Reparative Philanthropy, we center the importance of repairing past historical and cultural harms. This context is less relevant to the ways we work together internally, where we're seeking to avoid the sorts of extractive practices that would necessitate repair. That said, we still think regularly about the importance of ongoing relational repair. Here, we are not talking about formal HR processes or disciplinary responses to harm. We are addressing misalignment, miscommunication, or tension between team members in a way that preserves our humanity.
To date, repair has not been something we frequently confront as a team. When challenges arise, they tend to be addressed one-on-one, based on individual relationships rather than shared team practices. While this has worked, we recognize that the absence of a collective approach to relational repair creates some limitations. Without shared language or processes, moments of miscommunication or tension risk lingering; not because of intended harm, but because there’s no clear pathway forward.
One proactive step we are exploring is the use of practices like Designing Alliances as a way to clarify expectations and establish shared agreements. This approach supports repair before it is needed by helping team members understand how to communicate, navigate tensions, and strengthen their relationships over time. We are also exploring other practices that will allow us to create a structure that supports repair without attempting to anticipate or legislate every possible scenario.
The way we work together is foundational to the work we do with clients. The practices we are developing shape how we engage partners, analyze power, and show up in moments of uncertainty.
Learning together builds shared understanding that allows us to approach client work with alignment rather than assumption. Collaborative decision-making strengthens our ability to design processes that genuinely share power between donors and communities. Practices of care, trust, and accountability influence how we build relationships that are not transactional but rooted in respect and long-term commitment. And our ongoing exploration of relational repair mirrors the questions we ask philanthropy to wrestle with: How do we respond when harm occurs? How do we remain accountable to the people and values we claim to serve?
Just as reparative philanthropy calls for reflection and adaptation, so too does our internal practice. We strive to be intentional in building structures that allow us to practice what we ask of others, and in refining those structures as we grow.
This is what it means to work at—and with—Bold Ventures. Our commitments to trust, shared learning, autonomy, and respect are not abstract. They are living practices that shape how we collaborate, make decisions, and navigate challenges together. The ongoing pursuit of internal integrity strengthens our external work—and vice versa. We believe reparative philanthropy must be embodied, and that begins with how we work together.
