Understanding Wealth

[AI-assisted for speed.]

My friend and former colleague, Amanda Das, has been helping me teach the How to Raise Money workshop since its start. She shows up to wow participants with her brilliance and expertise around the systems, people, and culture that surround High Net Worth Individuals. This post is my attempt to capture and package her material.

Introduction

Every fundraiser, if they stay in the work long enough, eventually runs into the same reality: the largest pool of resources available for mission-driven work sits in the hands of very wealthy individuals. The fortunes that now shape philanthropy—the endowments, foundations, and donor-advised funds—are the product of a tax system designed to keep government small and to allow wealthy individuals to maintain control over where their money is spent. The result is that a tiny fraction of the population now exercises outsized influence over the future of American society—deciding which problems are addressed, which institutions survive, and which visions of progress are allowed to take root.

Our job, as fundraisers, is to loosen their grip.

The ways in which philanthropy has been used to maintain and preserve the privilege of the wealthy and powerful have been widely examined. Writers like Anand Giridharadas have exposed the performative and inherently conservative aspects of elite giving—how philanthropy so often functions as reputation management and social insulation rather than as a force for change.

The goal here is simpler and more practical: to understand money so that we can begin to move it toward the things that matter.

True wealth has always tried to stay hidden. Its rules are buried in expertise—financial planners, investment managers, tax attorneys—and its language is deliberately opaque. The purpose is not only to preserve capital but to make the mechanisms of preservation difficult to see. To anyone outside that world, wealth can look like alchemy: complicated, technical, and inaccessible.

But it isn’t. Once you learn how wealth actually works—how it’s structured, how it grows, and how it moves—you start to see how simple its logic really is. And once you understand that logic, you gain leverage. You gain vocabulary, confidence, and a kind of composure that allows you to engage wealthy people as peers rather than petitioners.

This post is about developing that fluency. It is not about reverence for wealth; it is about power. Wealth is one form of it—concentrated, systematized, and defended. Fundraisers operate in the space where that power can be redirected. The more precisely we understand how wealth behaves, the better we can move it—out of accumulation and into circulation, away from control and toward the collective work it was extracted from in the first place.

1. The Architecture of Wealth

The first step in developing fluency is understanding what wealth actually is—where it sits, how it behaves, and the rules that shape its movement.

1.1 Where Wealth Lives

Most of what we call wealth isn’t money in the everyday sense; it’s a collection of holdings that behave differently from cash. For most households, only about one-fifth of total net worth sits in bank accounts. The rest takes the form of securities, retirement savings, and property.

Securities include stocks, bonds, and mutual funds, as well as ownership stakes in private companies.
Retirement savings encompass accounts such as 401(k)s, IRAs, or 403(b)s—sometimes the largest pool of value for middle- and upper-middle-income families.
Property includes homes, vacation real estate, artwork, vehicles, or other tangible holdings that can be sold, inherited, or transferred across generations.

To the people who hold them, these assets don’t feel real in the way cash does. They exist as numbers—lines in a spreadsheet, future money that may or may not ever be used. That distance makes them easier to part with. Cash feels essential; it covers food, medical costs, tuition, and emergencies. It is the security blanket—the visible proof that a family is safe. Assets, by contrast, are symbols of success rather than instruments of survival. They remind their owners of what they’ve built, not what they depend on. Because of this, cash tends to be overprotected and assets underappreciated when it comes to giving.

Anything that can be owned can, in principle, be given. Financial assets can be transferred, property can be deeded or sold, retirement savings can be redirected, and art or collectibles can be donated outright. Even illiquid holdings—partnership interests, equity, or future royalties—can become philanthropic with the right structure. The barrier is rarely legality; it’s imagination.

1.2 How Wealth Is Structured

Everything that holds value can be packaged, repackaged, and restructured. Assets can be bundled together, divided into shares, or hidden inside other entities. Ownership can be brought close or pushed at a distance, made transparent or opaque. Entire industries—finance, accounting, insurance, and law—exist to perform this work. Their task is to protect capital, manage risk, and design the systems that decide who benefits and when.

Philanthropy sits inside this larger architecture. The vehicles that move charitable money borrow the same logic as any other financial structure: they define ownership, avoid taxes, and maintain control.

The most common philanthropic structures are:

Trusts and annuities, which hold a principal and pay income to a beneficiary for a defined period, with the remainder eventually passing to charity. Charitable remainder trusts provide income for life before transferring assets to the nonprofit; charitable lead trusts pay the nonprofit first, then revert to heirs. They balance personal security with legacy and reduce estate-tax exposure. (More on ‘tax savings’ below.)
Donor-advised funds (DAFs), which act as charitable accounts allowing assets to be transferred, invested, and distributed later at the donor’s discretion. Unlike private foundations, DAFs have no spend rules, though they do tend to be distributed faster than the endowments of private foundations. Donors receive the full deduction upfront even if the funds never leave the account. DAFs are especially popular among tech founders who experience sudden liquidity events and want the tax avoidance before they decide on priorities. They are where much of modern philanthropy now sits: fortunes captured in limbo, tax benefits claimed, generosity deferred.
Private foundations, which function as stand-alone entities controlled by the donor, family, or an appointed Board. They must distribute at least five percent of assets annually (including staff salary) and meet governance and reporting obligations, but they offer maximum control over staff, branding, and program design.
Retirement accounts, such as IRAs or 401(k)s, can also become philanthropic vehicles. At age seventy-two, withdrawals become taxable income, but directing those distributions to nonprofits offsets that liability.
Bequests, arranged through wills or beneficiary designations, represent the single largest philanthropic event for middle-class donors. They are deeply personal and often invisible until after the donor’s death.

For fundraisers, the point isn’t to master each mechanism but to recognize that every form of wealth has a shape, a rhythm, and a reason it’s held the way it is. Once you can see those patterns, you can anticipate how and when value might move.

2. The Business of Wealth

Wealth needs to be managed. Around every person of means is a network of professionals, family members, and peers whose job is to keep that money organized, protected, and compounding. Their work preserves privilege as much as it manages risk. Understanding those networks, rhythms, and practices is as important as understanding the assets themselves. They determine how decisions are made, who has access to the donor, and what kinds of influence are possible.

2.1 The Ecosystem Around the Donor

The people hired to manage wealth tend to multiply. What begins with one or two trusted professionals—an accountant, an attorney, an investment advisor—can grow into an entire network of intermediaries. Each occupies a narrow piece of the system, but together they perform a single function: keeping money in motion without letting it leave.

Their resistance to giving isn’t moral; it’s structural. Advisors are compensated as a percentage of the assets they manage, so every act of generosity reduces their income. Even when they share a donor’s values, their incentives reward preservation over redistribution.

Family dynamics reinforce the pattern. Parents, spouses, siblings, cousins, and adult children all play roles in shaping when and how philanthropy occurs. In families with generational wealth, an older matriarch or patriarch often retains final approval over large gifts. In others, a new spouse or next generation may resist giving that feels too final or too large—preferring to keep resources within the family and for their own use. Each household forms its own hierarchy, but the pattern is consistent: money rarely moves without consensus from the inner circle.

For fundraisers, this means promising conversations can stall. Advisors, family offices, and relatives are trained to slow decisions until the financial implications are mapped and the social implications are safe. Within this reality, only the principal donor can say yes, but everyone else can say no. Every advisor, family member, or gatekeeper can delay, complicate, or redirect a conversation. Each must be acknowledged and managed.

2.2 Family Offices

At a certain level of wealth, families stop hiring outside firms and begin employing those same professionals directly. The family office is the result: a private firm where every function—legal, financial, administrative, and philanthropic—is housed internally. The lawyers, accountants, investment managers, and advisors are full-time employees whose only client is the family. The office manages portfolios, property, taxes, trusts, travel, events, and reputation. In large dynasties, each branch or heir may maintain a separate office with its own staff and budgets. To say that a family “has an office” is to describe a permanent, internal infrastructure—lawyers, accountants, and advisors employed solely by and for that family.

2.3 The Calendar of Wealth

Wealth follows a predictable rhythm. Understanding that rhythm allows fundraisers to engage donors when they are in the right frame of mind—thinking about priorities, making plans, and deciding where money will move.

January–February is reflection and setup. Families look back at last year’s earnings, investments, and gifts, and sketch the year ahead—how much they hope to make, what they might change, and which priorities may move up or down. Advisors begin first-quarter planning meetings; it’s a time for thinking things through and organizing the year.

March–May is the season of strategy. Priorities begin to take shape. Families and their advisors start to look outward—meeting new people, encountering new ideas, and exploring what the year could hold. This is when to begin conversations, seed relationships, and build momentum. It is the window for co-creation, when ideas are still forming and money has not yet been allocated. The energy is exploratory, open, and social. This is when cabals form—small clusters of people who share a sense that something new might be possible.

June–August is the season for broadening relationships. Attention shifts toward travel, friends, and time away. Formal discussions lose traction, but social ones gain importance. This is a good time to learn more about donors personally, to ask broader questions, and to round out the relationship beyond the immediate project or gift. It’s a chance to build familiarity and ease—trust that will carry into fall.

September–November is execution. The decisions that were considered and debated over the summer are finalized once families return from travel. Many donors come back ready to move, so the first few weeks of September often act as a starting pistol on a sprint of work. This is when proposals, budgets, and schedules are completed; when lawyers, accountants, and managers step in; when paperwork, contracting, and financial planning all converge. Communication strategies and launch plans take shape alongside the legal and administrative work. For fundraisers, this period is a sprint of precision and follow-through—confirming the commitments that were built over the year and ensuring the implementation process runs smoothly.

December is reactive. Donors make quick, opportunistic gifts to clear liquidity or meet obligations before year-end. These gifts can be large but are rarely transformative. The window for shaping intent has already closed.

For fundraisers, the implication is straightforward. If you want to influence a major gift, start in March. If you arrive in December, you’re asking for what’s left in the account.

3. The Culture of Wealth

Wealth creates its own culture—a set of instincts, preferences, and beliefs about how the world should work. Understanding that culture—how it thinks, what it values, and what it chooses to preserve—is essential to understanding how wealth behaves.

3.1 Life at the Top of the Pyramid

The wealthy live at the top of the pyramid of need. They are free from the necessity of thinking about survival and comfort, which allows their attention to turn elsewhere—to meaning, legacy, aesthetics, permanence, and systems. Their giving tends to follow that same path. They want to shape ideas, build frameworks, design systems, imagine the future, and give form to the values that define them. It’s about altering the system itself—while preserving the parts of it that advance their ideology. Philanthropy becomes the medium for those ambitions.

For fundraisers, that means meeting them at altitude. Conversations about impact have to take place in the same register—systems, identity, imagination. The goal isn’t to mirror their perspective, but to bridge it: to connect their desire for scale with the public work that gives it purpose.

3.2 The Ideology of Intelligence and Control

This sense of elevation feeds a deeper ideology. Capitalism intentionally conflates wealth with intelligence. It teaches those who succeed within it that their success is proof of superior judgment. Over time, that belief hardens into certainty: the wealthy come to see themselves as best equipped to decide how resources should be used. Philanthropy extends that logic. It becomes a stage where they direct capital according to their own sense of what matters, confident that personal judgment is more effective—and more legitimate—than public decision-making.

That belief is most visible in how the wealthy talk about taxes. The phrase “tax savings” is treated as neutral, even virtuous, but it’s a sleight of hand. There is no such thing as tax savings. It is tax avoidance, reframed to sound prudent. The money is not being saved—it’s being redirected from collective use to private control. Imagine a donor who bought Apple stock for $10,000 a decade ago. Today it’s worth $40,000. If they sell it, they owe capital-gains tax—roughly 25 percent—on the $30,000 profit, leaving about $32,500. If they donate the stock directly to a nonprofit, they avoid the tax entirely, and the charity receives the full $40,000 instead of $32,500. The donor hasn’t saved $7,500; they’ve simply decided that they, not the public, will determine where that money goes. It feels intelligent, efficient, even moral—but it’s a transfer of authority from the state to the individual.

This belief spans ideology. On the right, it sounds like resistance to “big government.” On the left, it becomes discomfort with funding war or corporate welfare. Both start from the same assumption: that private individuals make better moral choices than public systems.

The culture around wealth is designed to preserve that authority. Politeness keeps donors comfortable, discretion keeps them unexamined, and deference keeps everyone else in their place. Fundraisers working inside that environment face a choice. We can reflect the expectations of power, or we can hold our ground and keep the conversation honest. Every exchange with wealth tests that balance—how much truth we’re willing to risk to move the money.

Conclusion

Fundraisers operate inside a contradiction. We work within the same structures that concentrate power, using their own tools to push resources outward. That tension isn’t a flaw in the profession; it’s the defining condition.

Fluency is what makes it possible. Fluency isn’t approval—it’s comprehension. It’s the discipline of knowing how to move inside a world without internalizing its values. We read the room, learn the language, and stay clear on what we’re there to do once the door opens. Equal footing is a deliberate stance. Confidence and calm build credibility; deference erodes it.

At the top of wealth’s pyramid, philanthropy is how meaning and control converge. Fundraising, at its best, is the act of undermining that control—how private purpose begins to serve something public again. The work is neither pure nor comfortable, but it is necessary. The point isn’t to stay unmarked; it’s to keep capital moving out of private hands and into collective purpose.