Season Brings New Events and New Planning Opportunities

Your September Content

Season is just around the corner, which means we have a few more weeks of calm before the storm, no pun intended. As the community is preparing for a season of events, galas, and donor meetings, no doubt you are bracing for your own year-end rush of planning opportunities with clients.

Estate Planning: Beyond the One Magic Sentence

National Estate Planning Awareness Week is coming up in October, and charitable giving has been part of its focus from the very beginning. We’re highlighting one simple sentence and a powerful question that can open an important conversation with your clients—and looking at why recent research suggests advisors should not stop with the first question.

Giving Government Securities: The Larger Lesson

Not all government securities are created equal when it comes to charitable giving. Learn why marketable Treasury securities and savings bonds can present very different charitable and tax planning considerations—and why identifying exactly what your client owns is an important first step before taking action.

We look forward to helping you and your clients turn charitable intentions into thoughtful plans throughout the busy fall planning season ahead.

Beyond the One Magic Sentence of Estate Planning

You’ve likely heard of this, and you may know that October 19 through 25 is National Estate Planning Awareness Week, which is a good time to remind yourself to ask each client a question that can open an important dialogue sometimes overlooked in the estate planning process.

Sounds simple, right? Still, advisors may not address charitable giving as consistently or thoroughly as clients would like, according to the 2026 TPI Study of the Philanthropic Conversation, which surveyed high-net-worth clients and wealth advisors, trust and estate attorneys, accountants, and other tax professionals.

Here’s what stands out in the findings:

• 80% of HNW clients agreed that advisors have an obligation to engage them in conversations about charitable activity.
• 93% of clients who discussed philanthropy with advisors considered the advisor's role important.
• 61% reported being very satisfied with charitable planning discussions. (While 99% were satisfied overall)

The key takeaway: There’s room to go deeper! Keep in mind that even clients who have never thought of themselves as philanthropists may welcome the opportunity to fully discuss and structure their charitable intentions beyond their lifetimes, such as through a charitable bequest to a favorite organization or a fund at Gulf Coast, or by naming a charity as the beneficiary of retirement assets. Raising the subject in more than a cursory way can also lead to broader conversations about family, values, getting the next generation involved, and legacy, conversations that deepen your understanding of what matters to your clients.

Using this approach also frames the conversation in a way that feels familiar, low-pressure, and normal. Rather than putting the client on the spot or suggesting that charitable planning is unusual, the wording gently communicates that many clients are thinking about similar questions: What do I want my plan to say about my values? How can I take care of family and still support the community? What kind of legacy do I want to leave? That “you are not alone” framing can be powerful because it helps the client feel part of a broader conversation instead of feeling singled out. In that sense, there is a constructive kind of herd mentality at work: When clients understand that others are also exploring charitable intentions, legacy, family, and community impact, they may feel more comfortable opening up about their own ideas, questions, and uncertainties. The question becomes less of a yes-or-no prompt and more of an invitation to talk broadly and candidly about what matters most.

If the client answers “yes,” listen closely to what they say. A smart next step in the conversation is to suggest that you involve the Gulf Coast Team as a sounding board. We’re here to help you and your client review giving vehicles and approaches that align with the client’s intentions while you continue to guide the overall legal, tax, and financial planning.

The Larger Lesson on Giving Government Securities

Every day, Gulf Coast works with attorneys, CPAs, and financial advisors to help clients support the charities and causes they care about. Often, those conversations involve gifts of appreciated noncash assets, and this is great because of the potential tax benefits. Appreciated stock may be the first noncash asset that comes to mind, but a client’s portfolio can include many other types of investments that deserve a closer look when charitable giving is part of the plan.

Government securities are a good example. Although clients may think of these investments as a single asset category, “government securities” actually encompasses a surprisingly broad range of holdings, including Treasury bills (T-bills), Treasury notes, Treasury bonds, Treasury Inflation-Protected Securities (TIPS), Series EE and Series I savings bonds, and securities issued by federal agencies and government-sponsored enterprises.

Why does that matter for charitable planning? It matters because not all government securities are created equal where charitable giving is concerned. Here are a few points to keep in mind:

• Government securities can differ significantly in how they generate income, whether they are marketable or transferable, how they are valued, and how their interest or appreciation is taxed. As a result, a charitable strategy that works for one type of government security may not work for another. And even when a government security can be transferred directly to charity, the tax results may be quite different from those associated with the more familiar gift of appreciated stock.
• This dynamic is especially striking when comparing marketable Treasury securities, which may be transferable to charity, with savings bonds, which present very different transfer and income tax issues and may be more interesting in estate planning than as lifetime charitable gifts.
• Marketable Treasury securities may be used for charitable giving, but advisors will want to look carefully at the particular security before recommending a strategy. Transfer and charitable acceptance considerations come into play, as do valuation and tax considerations. The security’s holding period, basis, fair market value, and the character of its return can all be relevant because Treasury securities may generate interest or original issue discount rather than the long-term capital appreciation that makes gifts of highly appreciated stock such a familiar charitable planning technique.
• Savings bonds present an even more distinctive situation. Unlike appreciated stock, savings bonds generally are not well suited to a straightforward lifetime charitable gift because transferring the bonds may trigger recognition of previously deferred interest. Series EE and Series I savings bonds accumulate interest that is subject to federal income tax, and many owners defer reporting that interest until the bonds are redeemed or mature. If a client simply cashes in savings bonds during life and then contributes the proceeds to charity, the client generally recognizes the accumulated interest. In other words, the strategy does not offer the same tax advantage that may be available when a client contributes appreciated publicly traded stock directly to charity.
• This does not mean savings bonds should be ignored in charitable planning. Quite the opposite: They may be especially interesting in the overall context of a client’s estate plan. This is because accumulated interest on savings bonds can constitute income in respect of a decedent, or IRD. That means leaving savings bonds to individual beneficiaries can carry an income tax consequence in addition to transferring the underlying asset. That IRD characteristic can make savings bonds worth considering in charitable estate planning because a qualified charitable organization generally is not subject to federal income tax on income it receives in furtherance of its exempt purposes. For a client who has held savings bonds for many years, this creates a good reason to identify those assets during the estate planning process and consider whether they may be better suited for charitable purposes than other assets the client intends to leave to family members.
• A common strategy for matured savings bonds is to liquidate the bonds and use the proceeds to fund a charitable gift annuity (CGA). This strategy can provide the donor with a charitable income tax deduction while also creating a guaranteed lifetime income stream. The charitable deduction may help offset the taxable income associated with liquidating the bonds, potentially reducing the overall tax impact of the transaction. Depending on the donor’s age and the applicable gift annuity rate, the donor may also be able to increase their lifetime income. Because the CGA is funded with cash, a portion of each annuity payment may be treated as tax-free return of principal for a period of time, further enhancing the tax efficiency of the strategy.

The larger lesson is one advisors encounter frequently in charitable planning: The asset matters! Two investments that look similar on a client’s balance sheet can produce very different tax and charitable planning results.

For all of these reasons and more, we welcome a call early in the process. If your client owns Treasury securities, savings bonds, or other noncash assets and has charitable intentions, please reach out before the client takes action. We are happy to work alongside you to explore whether the asset can be accepted, how a potential gift might be structured, and how Gulf Coast can help your client achieve charitable goals while you and the client’s other advisors address the legal, tax, and financial considerations.

Reading Roundup: Articles Worth a Read

Gulf Coast is happy to keep an eye out for what’s trending in the field of charitable planning, especially developments that impact your work with your charitable clients and how those clients tap into tools and resources offered at the foundation.

Check out the articles that have caught our attention recently.

Philanthropic Planning Is Wealth Management's Next Competitive Frontier, Beyond DAFs

InvestmentNews

Donor advised funds are important tools, but they are not the whole philanthropic toolbox. This article explores why high-net-worth clients increasingly expect wealth advisors to help them consider a broader range of charitable structures and how that expertise can help advisors strengthen relationships not only with clients, but also with the next generation. Gulf Coast offers a wide range of fund types and charitable planning structures to help your clients establish a lifetime and legacy giving plan tailored to their financial and charitable goals.

Donor Advised Fund Strategies For 2026

Financial Advisor Magazine

This article looks at donor advised funds through a 2026 planning lens, including how advisors can use donor advised funds as part of broader tax and charitable strategies rather than simply as repositories for year-end gifts. The bigger opportunity is to help clients coordinate the timing, assets, and ultimate purpose of their charitable giving with the rest of their financial plans.

IRS Eyes Charitable Donation Abuse in New Audits, Tax Pros Say

Bloomberg Law

The IRS is taking a closer look at charitable contributions of hard-to-value assets, including privately held business interests and art, with tax professionals reporting particular scrutiny of valuation, qualified appraisals, and substantiation requirements. For advisors, this is an important reminder that complex charitable gifts require careful planning and documentation, and that bringing Gulf Coast into the conversation early can help address the charitable side of the transaction before the client takes action.

How Advanced Charitable Exit Planning Drives AUM Growth

Financial Advisor Magazine

Business exits can be important charitable planning moments, particularly when advisors raise the subject before a transaction is already underway. This article explores how strategies involving charitable trusts, donor advised funds, and gifts of business interests can help address a business owner's tax and philanthropic objectives while also helping advisors deepen relationships and potentially retain more assets under management after the sale. As always, reach out to Gulf Coast as early as possible!

Retirees Over 70½ Can Send $111,000 a Year From an IRA to Charity Tax-Free. The Average One Donates From Checking Instead.

24/7 Wall St.

Many charitably inclined retirees are still giving from their checking accounts even though a Qualified Charitable Distribution (QCD) may offer a more tax-efficient route for eligible IRA owners. The article is a useful reminder that advisors can add value simply by asking how a client is making charitable gifts: Sometimes changing the asset or account used to make the same gift can produce a very different tax result. Gulf Coast can help your clients explore eligible ways to make QCD gifts, including, where appropriate, gifts to designated, field of interest, and unrestricted funds. Remember that QCDs cannot be made to donor advised funds.

What’s the takeaway here? 

As you skim these articles, or even just the headlines, a pattern emerges pretty quickly! Good charitable planning is about more than finding a tax break or selecting a giving vehicle; it is about helping clients make thoughtful decisions about what to give, when to give it, and what they hope their generosity will accomplish.

Gulf Coast is here as a sounding board whenever those conversations arise. Please reach out anytime!