Hello!
Thank you for the opportunity to work together! We love hearing from so many of you throughout the year, and especially as tax time approaches. It is an honor to work with your charitable clients to maximize their community impact as well as their financial and estate planning goals.
As always, the team at the community foundation watches trends closely so that we can keep you informed of legal and policy developments that could impact your work with philanthropic individuals and families. We’re happy to share what’s trending.
–Women are increasingly shaping the philanthropic landscape—often as primary financial decision-makers and stewards of family legacy. Whether transitions happen gradually or in the wake of loss, the shift is unmistakable. Discover four practical insights to help you better serve women clients and strengthen the charitable strategies you design together.
–Two recent cases offer a timely reminder: When it comes to charitable deductions and exempt status, technical compliance is everything. Good intentions alone will not carry the day. We’re highlighting what these rulings mean for your client conversations and how proactive guidance can prevent costly missteps.
–A business sale is never just a financial transaction—it is a turning point for family identity, community presence, and long-term legacy. A case study can help illustrate how intentional philanthropy can transform a liquidity event into a unifying strategy that preserves both values and relationships for the next generation.
Thank you for your partnership. Please consider the community foundation as your first call whenever the topic of charitable giving comes up during your client meetings. We look forward to our next conversation!
THIS MONTH’S
FEATURED ARTICLES
Women and philanthropy: Four insights to inform your practice
At the community foundation, we’re honored to work with hundreds of individuals, families, and businesses who support a wide range of charitable causes. The generosity and commitment across generations and demographics inspire our team every single day.
March is an especially good time to reflect on the evolving role of women in philanthropy because it’s Women’s History Month. Increasingly, women are leading charitable decisions in their families, especially as more women are serving as primary financial decision-makers, according to Indiana University’s Lilly Family School of Philanthropy’s Women Give 2024: 20 Years of Gender & Giving Trends.
Two scenarios are driving this change:
– In many families, a leadership shift happens gradually. For example, a daughter becomes more engaged over the years in conversations about the family’s charitable giving. Or a spouse who once deferred philanthropic decisions begins to shape priorities more directly.
– In other cases, the transition is sudden and deeply personal—often following the death of a spouse or parent—when a woman assumes sole responsibility for stewarding both financial assets and charitable intent.
Here are four examples of how your awareness of these trends can play out in your day-to-day practice:
Help your clients give through thick and thin.
According to the Women Give 2024 study, over the past two decades, single women experienced a smaller decline in charitable participation than single men, and their average giving amounts held steadier or increased in certain contexts (e.g., secular causes during COVID-19). Be aware of this trend as you represent single women; it may be a priority for them to continue giving even when times are tough. The community foundation can help you develop a charitable giving plan to enable women-led philanthropy to continue through life’s ups and downs.
Discuss national trends and local needs.
According to the Women’s Philanthropy Institute at Indiana University’s Lilly Family School of Philanthropy, for the first time, between 2022 and 2023, giving to women’s and girls’ organizations surpassed 2% of overall charitable giving. This represents over $11 billion going to women’s and girls’ organizations each year. Note, however, that when adjusted for inflation, the amount actually declined between 2021 and 2023. This trend is worth mentioning to clients, especially with the help of the community foundation team to share parallel local trends and opportunities to make an impact.
Ask about all forms of philanthropy.
According to the 2025 Bank of America Study of Philanthropy: Charitable Giving by Affluent Households, 43% of affluent households volunteered in 2024, up from 37% in 2022—volunteers tend to give more and support causes more deeply, a pattern often stronger among women. Be sure to ask your female clients about causes they support both financially and through volunteerism.
Tailor advice for single women.
Research shows that participation trends vary by household type, with single women maintaining more consistent giving patterns over long periods. Pay particular attention to building thoughtful charitable giving plans for single women households. The community foundation can help maximize both impact and financial planning goals as you serve these clients.
As is the case when you are working with any charitable client, our team is honored to be your partner. Whether your client is establishing a new structure, building a comprehensive strategy around an existing donor-advised or other type of fund, or navigating inherited philanthropic responsibilities, we are here to help ensure their giving reflects both enduring legacy and evolving purpose.
Documentation is no joke and coffee is not milk: Two important tax rulings
At the community foundation, we value the role you play in helping individuals and families make the most of their charitable giving. That’s why we’re committed to providing regular updates on legal and policy developments that may impact your clients.
In two recent rulings, the underlying message is consistent: Courts and the IRS continue to apply the technical requirements governing charitable deductions with precision. Your clients’ good intentions are not enough.
Strict substantiation: A familiar but critical reminder
Gibson v. Commissioner serves as yet another reminder that it is really important for your clients to substantiate their charitable deductions. Time and again, both the IRS and the Tax Court have disallowed a taxpayer’s deduction because rules were not followed. In Gibson, a married couple claimed nearly $194,000 in noncash charitable contributions related to donated personal property. The court did not dispute that tangible items were transferred to a charitable organization. Instead, the deduction failed because the taxpayers did not satisfy the detailed substantiation requirements—specifically, contemporaneous written acknowledgments and qualified appraisal standards.
No matter how strong a client’s desire to make a difference through charitable donations, technical compliance drives deductibility. Form 8283 thresholds, appraisal rules, and acknowledgment language are not administrative formalities; they are statutory requirements. The Gibson case provides a practical example to share with clients who may be inclined to “drop off” significant in-kind gifts without first consulting their advisory team.
Here’s the key takeaway: Even though you as an attorney, CPA, or financial advisor may fully understand the importance of following the rules, you still need to remind your clients regularly. You don’t want a client to ask “Why didn’t you tell us?” when they learn the hard way that they should have kept better records.
Exempt status is not forever
The lesson in Milk Saving Starving Children Foundation v. Commissioner is that if you say you’ve got milk, you’d better have milk! In Milk, the Tax Court upheld the IRS’s revocation of 501(c)(3) status for an organization that failed to operate exclusively for charitable purposes and conferred impermissible private benefits. The organization’s stated mission—to distribute milk—was in fact charitable. Over time, though, its operations drifted away from distributing milk to operating a coffee shop and hosting a golf tournament.
Here’s why we’re sharing this case:
- The Tax Court’s written opinion in Milk provides a terrific overview of the legal principles behind one of the cornerstones of tax-exempt status: a charity’s ongoing activities must further its exempt purposes. As you bring new attorneys, CPAs, and financial advisors into your practice, the Milk case is simply terrific for training purposes.
- As it applies to your client work, remember the Milk case when a client expresses interest in supporting a lesser-known or newly formed organization. Please reach out to the community foundation in these instances because our team can provide insight on any charitable organization, whether well-established or new—and offer safeguards through field-of-interest funds and other vehicles.
Thank you for the opportunity to work together to serve your charitable clients! Our goal, as always, is to serve as a practical resource—helping you ensure that your clients’ charitable intentions are fulfilled with clarity, compliance, and confidence.
Case study: Business owners exit with a family legacy
As an attorney, CPA, or financial advisor, you probably work with several clients who own a family business. You’ve likely also considered that there may be a role for strategic philanthropy in family business succession planning to help clients get ready for an eventual exit. But so what? How does strategic philanthropy actually play out in conversations with a real client?
Here’s a case study to illustrate a scenario similar to what you might experience in your own practice.
When Mark and Elaine come into your office to update their estate and financial plans, retirement is only part of the future picture they’d like to discuss. At 66 and 64, they are financially secure—but the larger question looming in the background is the future of the family business. After three decades of ownership, they are beginning to explore a sale within the next few years.
The first part of your conversation is very familiar: income projections, portfolio sustainability, and how the family business’s corporate structure could evolve to allow Mark and Elaine to step back from day-to-day operations. If you are their financial advisor or CPA, you might run the models, stress-test assumptions, and outline what taxes and retirement could look like if a liquidity event occurs. If you are their estate planning attorney, you might review the company’s legal structure and emergency transition plans.
In any case, you know the numbers are strong. A sale would more than fund Mark and Elaine’s lifetime needs. But as your conversation deepens, a more complex issue surfaces: what does succession look like—not just operationally, but reputationally and relationally?
“Our two adult children are not active in the business,” says Mark. “A third-party sale is inevitable, and we are fine with that financially, but it’s a gut punch emotionally.” A concerned expression crosses Mark’s face as he considers his feelings about a sale to non-family members. “The company’s name carries a lot of weight in the community,” he says. “For years, the business has been closely associated with the family’s identity and local impact. So what happens to that identity if we sell?” Mark wonders aloud.
Elaine’s concern is more inward-facing. “I really want our children to stay aligned after a liquidity event. For so many years, company events and trips have been where we’ve all gathered. I hate to think of that ‘glue’ disappearing in an instant.” Elaine says she has seen other families fracture after a business sale. “They barely see each other anymore,” she remarks.
This is where you introduce a broader planning lens. You validate that a business sale is not only a financial event. It is deeply personal and public at the same time. “How the family positions itself before, during, and after that transition can shape both community legitimacy and internal unity for decades,” you say. “So you both are spot on with your concerns.”
You suggest that philanthropy—structured intentionally before a sale—can serve as a bridge. What you mean is that Mark and Elaine could explore the option to transfer shares in the business to a donor-advised fund at the community foundation well in advance of any potential transaction. Then, when the business is sold, a portion of the proceeds lands in the donor-advised fund.
The tax advantages of the transaction are meaningful. By donating a portion of closely held stock before a legally binding sale process begins, Mark and Elaine are eligible for an income tax deduction, subject to AGI limitations, based on the stock’s fair market value at the time of the gift. Later, when the business is sold, the proceeds on the shares held by the donor-advised fund are not subject to capital gains tax.
Still, you emphasize that tax efficiency is only one layer.
Creating a donor-advised fund before the sale allows the family, working together, to articulate a charitable mission while the business is still operating. It signals continuity: although ownership may change, the family’s commitment to the community does not.
You suggest to Mark and Elaine that the community foundation team join the next meeting. Of course, you remain responsible for facilitating the transaction and coordinating with other advisors. But the community foundation’s philanthropic advisors can facilitate conversations that go beyond the corporate, legal, financial, and tax aspects, leading a dialogue focused on questions that will shape the family’s philanthropy plan, such as:
What causes reflect the values that built the business?
How should the family’s name be represented post-sale?
What governance structure will guide the next generation’s involvement?
You also share with Mark and Elaine that the community foundation can host structured family meetings, provide community needs assessments, and introduce best practices for multigenerational philanthropy. Importantly, this gives the children a meaningful role before liquidity occurs. Instead of simply awaiting proceeds, they begin working together to recommend grants, evaluate impact, and represent the family publicly.
In effect, philanthropy becomes a training ground for shared decision-making—without the operational risk of running a company.
Mark and Elaine love this suggestion. “Let’s do it,” Elaine says. “This plan makes us feel like a future sale is less like an ending and more like a pivot.”
Mark and Elaine’s situation is one of many examples of cases where a family business may eventually change hands. But through an intentional philanthropic structure—designed in coordination with the community foundation—the family’s influence, values, and unity continue. Please reach out to our team anytime. It is our pleasure to help you serve your charitable clients through all stages of their lives.
The team at the community foundation is honored to serve as a resource and sounding board as you build your charitable plans and pursue your philanthropic objectives for making a difference in the community. This newsletter is provided for informational purposes only. It is not intended as legal, accounting, or financial planning advice. Please consult your tax or legal advisor to learn how this information might apply to your own situation.