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Most ultra-high net worth families have a default giving strategy: write the check. It is familiar, it is immediate, and for decades it was considered generous enough. But in a wealth landscape defined by alternative assets, generational transition, and increasing scrutiny of charitable impact, the checkbook alone is no longer a giving strategy. It is a missed opportunity – and often, a less efficient one.

I have spent more than two decades advising families, professional athletes, and family offices on holistic wealth management and strategic philanthropy. What I consistently find is that the families with the most sophisticated investment portfolios carry the least intentional giving portfolios. The two worlds exist in parallel, rarely in conversation with one another. That disconnect costs families capital efficiency, community standing, and legacy depth simultaneously.

The numbers make the case
Total charitable giving in the US exceeded $550 billion in 2023, according to Giving USA – and the trajectory continues upward. Yet at the high net worth level, the majority of that giving is still transacted in cash or publicly traded securities. This matters because cash is, in most circumstances, the least tax-efficient asset a donor can deploy.

Consider the alternative. A collector holds an asset acquired at $80,000 now appraised at $400,000. Selling that asset and donating the proceeds triggers long-term capital, gains tax before a single dollar reaches the intended beneficiary. Donating the appreciated asset directly to a qualified charitable vehicle eliminates that capital gains event entirely and may allow a deduction at full fair market value – subject to applicable AGI limitations and asset classification. The economics are meaningfully different. The impact to the receiving institution is meaningfully larger.

When the asset Is a jersey, a ring, or a game-worn pair of sneakers
One of the most underutilized philanthropic asset classes in the family office and sports wealth space is athlete memorabilia. This is not sentimental speculation. It is a Veblen goods problem – the economic phenomenon where perceived scarcity and personal connection push willingness-to-pay well above conventional market value – with a charitable solution attached.

Through my work with retired NFL and NBA athletes, I have developed a giving model that converts dormant memorabilia inventory into charitable capital. These athletes carry something most UHNW individuals do not: deeply loyal, multigenerational fan bases that span multiple cities and remain more personally connected to the player than to the franchise. A single athlete may hold devoted followings across three or more markets simultaneously – the city where he was drafted, where he became a household name, and the college town where it all began.

That geographic footprint is not nostalgia. It is an active bidder pool.

Athletes who no longer wish to retain their memorabilia – game-worn gear, signed equipment, championship-era artifacts – donate those items to GUICE Foundation, a 501 created in part for this purpose. The foundation facilitates a curated superfan auction marketed directly to the athlete's fan communities across their geographic footprint. Competitive bidding among emotionally invested fans does not follow conventional price sensitivity. The auction captures a Veblen premium – the gap between what a memorabilia dealer would pay and what a devoted fan will pay. That gap is where the charitable capital lives. Proceeds are then deployed through charitable trust structures, program grants, and vehicles aligned with each athlete's philanthropic mission.

For athletes without their own nonprofit infrastructure, GUICE Foundation serves as the receiving and operating entity – a meaningful benefit for those transferring items at effectively zero cost basis. For athletes who have established their own foundations – in one case, a nonprofit I helped structure more than twenty years ago – the model operates through their own entity with my consultative guidance. The optimal tax structure in either case should be confirmed with qualified tax counsel; the concept is replicable; the mechanics require precision.

The next generation is watching how, not just how much
The $84 trillion wealth transfer projected over the next two decades is not purely a financial event. It is a values event. The next generation increasingly demands to know not just what a family owns but what it stands for – and they are paying attention to the architecture of giving, not just the dollar amounts.

Philanthropy involving assets a family genuinely cares about creates governance infrastructure that cash giving cannot replicate. When a family co-curates a giving strategy and witnesses the community impact of that decision, they create a shared story. That story is how families make decisions together across generations rather than apart. For the athletes I work with, the memorabilia auction is not a liquidation event. It is a community activation — a transition from relevance through performance to legacy through stewardship.

What advisors must start asking
The practical shift begins with expanding the audit. When reviewing a family's charitable giving, the question should no longer be: how much are you giving? The more important questions are: what are you giving, from which asset class, at what cost basis, and toward what legacy outcome?

Alternative assets – art, memorabilia, real estate, closely-held business interests – are already in the portfolios of the families you advise. They are often highly appreciated, illiquid, and inefficient to sell. They are also ideal philanthropic instruments. A giving portfolio designed with the same intentionality as an investment portfolio changes both the scale and the sustainability of a family's impact.

The execution gap
Most philanthropic advisory engagements end at the strategy document. A consultant identifies what type of giving aligns with a family's values, recommends a vehicle, and exits. The family holds a well-constructed framework and no infrastructure to move it. 

Intent dissolves into inertia – quietly, and at significant cost to both the family's tax position and their legacy timeline. 

What changes outcomes is the execution layer. Coordinating auction house relationships, structuring charitable vehicles, marketing to fan communities across multiple cities, managing donor acknowledgment, maintaining compliance guardrails – these are not tasks a family office handles in-house. The families and athletes I work with do not manage that infrastructure. They show up, receive the recognition, and are seen – accurately – as the architects of something meaningful. The work sits behind the curtain, where it belongs.

The gap between identifying a giving strategy and executing it is where most philanthropic intent dies. Closing that gap is not a luxury service. It is the difference between a plan and an outcome.

The reframe
Your giving should reflect the same sophistication as your investing. If you would not build an investment portfolio through a single asset class with no strategic intent, why build a giving portfolio that way?

The most enduring legacies I have witnessed were not determined by the size of the gift.

They were determined by the intentionality – the right asset, at the right time, through the right structure, toward a purpose the family could name across generations. The checkbook is not going away. But for families serious about legacy, it should not be the whole answer.

About the author
Danita M Harris, CAP, is the founder of GUICE Wealth Management, GUICE Foundation ), and GUICE Privado, a luxury alternative wealth membership platform. She also serves as director of philanthropy and partnerships at the 4As . A 2025 Family Wealth Report Wealth for Good Awards honoree and FinTech Inspiring Female nominee, Danita has advised UHNW individuals, professional athletes, and family offices on alternative assets, legacy planning, and strategic philanthropy for more than two decades. She began her work with professional athletes and their nonprofit organizations in 2004 and holds deep roots in sports philanthropy through the NFL Wives Association. She is based in New York.