Skip to Opening

Trust, Power, and Philanthropy: Moving Through Tensions and Learning in Relational Giving

Dear Reader,

What you’re holding is a reflection on a moment in time — an experiment that ran for seven years, ending approximately three years ago. It was built on aspiration as much as evidence, on a genuine desire to depart from patterns we had seen cause harm, and on the belief that if we were going to learn anything new, we had to be willing to swing far enough from the conventional to discover something different. If we had tried to be only slightly different from traditional philanthropy, we would have ended up replicating it. Systemic inertia is strong.

Traditional philanthropy, as we experienced it, concentrated decision-making at the top, kept distance between funder and community, measured what was easy to count, and asked grantees to conform to funder priorities rather than the other way around. We were departing from all of that — deliberately, imperfectly, and at times ungracefully. The learning and growth from that experiment continues. The people who moved through Wend carry its insights and its unresolved questions forward in their own work. And we share this account now because we believe the field needs honest stories, not polished ones.

This is written for people who share the aspiration not to repeat the old mistakes — who are already questioning whether a different way is possible and are asking what it costs to pursue it. We offer it as a permission slip and a caution in equal measure: try this and perhaps try it differently than we did. The trade-offs are real. The tensions are real. Account for them by name, in advance of trying them on.

You will find contradictions here. You will find unresolved questions. You will find places where we name a tension without resolving it, because it hasn’t been resolved — not by us, and probably not yet by anyone. We hope you also find kinship in that. The work of imagining a different future for philanthropy is not finished. It is, if anything, more urgent now than when Wend began.

With care and curiosity,

James and Azita

Emergence:
The Seeds of the Experiment

Guiding Principles

Wend’s team and work was organized around three principles. These were not aspirational statements kept separate from operations. They were active commitments that shaped hiring decisions, grantmaking practices, and how the organization was structured and run.

Nature as Our Guide

Transformation Through Relationship

Dignity and Wholeness of Each Individual

Nature as Our Guide

We are not separate from the world that sustains us. Life has been at this far longer than humans. Nature does not operate by the logic we have projected onto it: not competition as primary driver, not scarcity as a baseline condition, not the individual as the unit that matters. Darwin never said survival of the fittest — he said survival of the fit, meaning survival goes to the organism that fits its context. This is a claim about relationship, not dominance.

But the separation runs deep;  even the word “nature” enacts it. The moment we named the living world as something outside ourselves, we’d already reduced it to an object: something to study, control, and selectively interpret. A tree is shaped by two flows — the flow of sap and the flow of wind. Form follows flow. Wend applied this lens to its own work: attend to what is actually moving through a system, inside and out, and you begin to see why it takes the shape it does.

This principle was an invitation to follow nature in whatever way called to you, to enter the wild and refuse the separation, to attend to what is actually flowing, and to bring what you find there back into the work.

Transformation Through Relationship

Change is constant — and the transformation our world needs will not come from better strategies imposed from above. It will come from relationships.

This is not simply a claim that relationships matter. It is a claim about how reality works. We experience an objective world, a subjective interior, and — often overlooked — a relational domain that is distinct from both. A thought held alone in your mind flickers and fades; the same thought held in dialogue can be explored for hours, expanded, challenged, understood. Relationships are not just where change happens — they are the medium through which new possibilities become real.

Wend’s work was grounded in five primary relationships: self, other, community, nature, and spirit. We believed that attending to the health of these relationships — not optimizing for metrics or scale — was the most reliable path toward a more vibrant world. Data matters. Strategy matters. But both fail when not hosted in joyful, trusted relationship.

Dignity and Wholeness of Each Individual

This principle begins with love — not as sentiment, but as orientation. The dignity we speak of is not limited to humans, or even to what science calls “life.” It extends to all that has been created: the cosmos and the grain of sand, the elephant and the clump of grass. If everything is deserving of dignity, then dignity came long before humans and remains connected to mysteries we cannot fully name.

Applied to humans, this expansive dignity raises serious questions about status and power. It asks us to meet people not as means to an end, but as whole — which is to say, as containing multitudes. Wholeness is not a state to achieve but a lifelong practice: learning, reconnecting, and integrating physical, emotional, mental, and spiritual well-being.

And here we encounter paradox. Humans are capable of tremendous beauty, goodness, and love — and we are also the most violent species on this planet. Dignity does not erase this. It asks us to know ourselves fully, including the parts capable of harm, and to extend that same complex recognition to others. Transformation begins when we hold this tension rather than resolve it.

Permission Slips and Trade‑Offs

What follows is structured as permission slips — not for what Wend did, but for what we imagine the future of philanthropy can be. Each one names a departure from convention, the bet Wend made, what that bet produced, what it cost, and what we’d tell you if you were about to try something similar.

These are not endorsements of every choice Wend made. They are honest accounts of what happens when you push far enough from the conventional to learn something new. The hope is that naming them explicitly, as permissions you can consciously choose to grant yourself, makes the work of experimentation more legible, more intentional, and less lonely.

Before we begin, two threads are worth naming because they run through everything that follows.

The first is that Wend’s strategy was relational. Not relational as a modifier on top of something else — relational as the thing itself. The bet was that relationships steeped in care, rather than transaction, could be the ground from which a different kind of philanthropy grew. That bet produced real and lasting things. It was not wrong.

Awareness of power is not the same as a mature relationship with it.

The second is that Wend and its leadership did not have an accurate orientation towards relations of  power. Power — the ability to make things happen or prevent them from happening — runs through every organization, no matter how it is structured. Wend was deeply aware of this. It saw the distortion that money creates, named the dynamics of proximity, and built real experiments to distribute decision-making more broadly.

But awareness of power is not the same as a mature relationship with it. Much of Wend’s design was also a reaction to power — a belief, often unconscious, that power itself was the problem. You can be looking right at a power dynamic and still miss what it’s doing. Care alone was not enough to hold what Wend built. What was missing was the willingness to claim power honestly and the skill to steward it well.

You’ll find both of these threads run through the eight distinct “permission slips” that we subsequently explore.

You Have Permission to Decentralize

The Departure

Conventional philanthropy concentrates decision-making at the top. Strategy flows downward. Accountability flows upward. The principal, or a small leadership team, holds authority over direction, resources, operations and evaluation.

The Bet

Wend bet that an organization could operate without a traditional hierarchy. No formal organizational chart. No people managers. Distributed decision-making. Open information flow. The underlying strategy was relational, not structural: find exceptional people, dream with them, learn with them, help them operate in the world of distributing money. The belief was that shared values, not shared structure, would hold the organization together — and that exceptional individuals, given trust and resources, would produce better outcomes than any top-down strategy could design.

What It Made Possible

The design created conditions for very different people and initiatives to coexist, influence each other, and take risks they could not have taken elsewhere. Programs iterated quickly. Individuals could pivot completely when the moment demanded it — one steward, who left political advocacy to join Wend, focused their first four years on mobility and clean transportation but sensed a major need in politics and shifted their focus back towards civic infrastructure. No conventional program structure would have permitted that.

There was responsiveness that hierarchical structures simply cannot match. When a community need emerged, a steward could act. When an unexpected opportunity arose, there was no approval chain to navigate. Wend got a lot done, and much of it would never have been approved through conventional channels.

In its early years, when the team was small and relationships were close, the model produced something rare: a quality of shared exploration and mutual trust that team members describe as generative in ways that structured organizations rarely achieve. Dreaming together, in a high-trust space, created bold and innovative ideas.

What It Cost

An ambiguous purpose — “wayfind toward a better world” — translated into individuals creating their own interpretations of what that meant. Thirteen different focus areas weren’t a focus. Team members couldn’t always connect one initiative to another; each had agency, but no shared frame held the whole together.

Minimal structure, combined with a desire to adapt quickly, sometimes felt disruptive or ungrounded. Changes came before ideas could gain traction. People flexed into projects beyond their roles based on interest, but interest didn’t always equal skill.

The lack of clear structure meant major decisions defaulted to whoever was willing to make them, which, in the absence of named leadership, was almost always the founder. This wasn’t a founder problem. It was a leadership vacuum. Decentralization without clear leadership doesn’t distribute authority — it concentrates it in whoever steps in.

There is a kind of authority that comes from having initiated something — from being the person who felt the original impulse, gathered the first people, and pointed in a direction. That authority doesn’t transfer just because you want it to. You can flatten the org chart, remove titles, and distribute decisions. But if the person who started the thing won’t name what they see and where they believe the work should go, everyone is left guessing. Abdicating that authority doesn’t distribute it. It creates a vacuum that gets filled by anxiety, politics, and proximity. In many cases, the clarity about where to go existed. What was missing was the willingness to bring it forward — because bringing it forward felt indistinguishable from the kind of control we were trying to leave behind.

One team member offered this analogy: Wend started as a test pilot environment — boundary-pushing, with failure as a learning tool. As it grew, it evolved into something more like air traffic control, managing increasing complexity. In doing so, it lost the test pilot spirit that had defined its early energy. The support system was built for air traffic control. The ambitions were still test pilots.

What We’d Tell You

Decentralize if you mean it — but know that decentralization without shared purpose produces fragmentation, not freedom. The question isn’t hierarchy vs. no hierarchy. It’s: what holds a group of people together when you remove the conventional containers? If it’s not structure, it has to be something else — and that something needs to be explicit, tended, and strong enough to bear weight.

If you started the thing, you carry something others don’t. That’s not hierarchy. It’s reality. Claiming that authority clearly, holding direction openly, and inviting others to build within it is not a power grab. It’s what allows everyone else to actually lead in their own domains. The most generous thing a founder can do is to be clear, and to let the work and the team sharpen that clarity over time.

Name the relational strategy. “Find exceptional people and dream with them” is a strategy. Own it as one. It has real advantages and real limits, and naming them is what allows you to design for both.

Also, this work required more from people as humans — not just more infrastructure, but more personal capacity for ambiguity, conflict, and self-management. If you’re going to ask that of people, name it. Build support for it. Don’t assume everyone arrives ready.