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Tax-Smart Charitable Giving After the OBBBA

Speakers: Larry Pon, CPA, EA, USTCP, PFS, CFP®, AEP® and Rick Peck, CFP®, ChFC®, CAP®, Impact Philanthropy Advisor
Host: Missy Davis, Financial Experts Network
Original Air Date: September 18, 2026
Run Time: Approximately 2 hours, 21 minutes
Topic Area: Charitable Planning, Tax Planning, Donor-Advised Funds, Qualified Charitable Distributions, Non-Cash Gifts, Business Owners

Key Takeaways

• Effective charitable planning begins with a client's values, causes, desired impact, community priorities, and family legacy—not simply with the available tax deduction.
• The OBBBA creates new considerations for charitable deductions, including the 0.5% of AGI floor for itemized charitable contributions, making strategies such as bunching and qualified charitable distributions increasingly important.
• Donor-advised funds (DAFs) can help clients bunch multiple years of contributions into one tax year while maintaining a regular charitable giving schedule over time.
• For clients age 70½ or older, qualified charitable distributions (QCDs) can be particularly valuable because eligible IRA distributions sent directly to charity can satisfy all or part of an RMD without increasing adjusted gross income.
• Appreciated publicly traded securities can often be more tax-efficient charitable assets than cash because clients may receive a charitable deduction while avoiding recognition of embedded capital gains.
• Complex gifts—including closely held business interests, real estate, cryptocurrency, art, and other non-cash property—require advance planning, charity acceptance, proper valuation, and careful documentation.
• Business owners contemplating a sale should begin charitable planning well before a letter of intent, binding agreement, or substantially completed transaction to reduce assignment-of-income concerns.
• Documentation is not a technical afterthought. Missing acknowledgments, appraisals, signatures, or required language can jeopardize otherwise legitimate charitable deductions.
• Philanthropy advisors can complement financial advisors, CPAs, and estate attorneys by helping clients define their charitable objectives, evaluate nonprofits, structure gifts, and navigate complex assets.
• The appropriate charitable vehicle depends on the client's objectives. DAFs, private foundations, charitable gift annuities, charitable remainder trusts, and direct gifts each solve different planning problems.

Start With the Client's “Why”

One of the central themes of the session was that charitable planning should not begin with the question, “How large of a deduction can we generate?”

Rick Peck encouraged advisors to first explore what clients actually care about:

• What values are most important to them?
• What problems would they like to help solve?
• What communities or organizations have affected their lives?
• What type of impact would they like their wealth to have?
• Are there values they want children or grandchildren to carry forward?
• What would they like their charitable legacy to look like?

Rick suggested developing an individual or family focus statement that combines a client's core values with the causes and issue areas that matter most to the family.

This can give clients a framework for evaluating charitable requests instead of responding reactively to every solicitation. It can also make multigenerational charitable planning more intentional by helping children and grandchildren understand not just where the family gives, but why.

Once the charitable objectives are clear, advisors can move to the tactical questions: which assets to contribute, which charitable vehicle to use, when to make the gift, and how to maximize available tax benefits.

Where a Philanthropy Advisor Fits

Rick explained that philanthropy advisors can fill a gap that often exists between a client's financial, tax, estate, and charitable planning.

Depending on their background and specialty, a philanthropy advisor may help clients:

• Define philanthropic goals and family values.
• Develop a charitable giving strategy.
• Evaluate nonprofits and perform due diligence.
• Determine appropriate charitable vehicles.
• Explore non-cash and complex gifts.
• Facilitate family charitable discussions.
• Coordinate with wealth advisors, CPAs, estate attorneys, nonprofit organizations, and specialized gift professionals.

Philanthropy advisors may work independently, within family offices, at financial institutions, community foundations, universities, hospitals, or nonprofit organizations. Advisors should understand the professional's role and whether that person is independent or represents a particular charitable organization.

For financial advisors, charitable conversations can also uncover planning issues that might otherwise remain undiscovered—including concentrated stock positions, business succession plans, estate planning goals, family dynamics, and assets that may be appropriate for charitable giving.

The OBBBA Changes the Charitable Deduction Conversation

Larry Pon reviewed several provisions affecting charitable planning after the One Big Beautiful Bill Act.

For many taxpayers, the increased standard deduction means charitable contributions alone may still not result in an itemized deduction. That makes the timing and structure of gifts increasingly important.

For taxpayers who do itemize, the new 0.5% of AGI floor on charitable contributions creates another planning consideration. Rather than simply looking at the dollar amount contributed, advisors and tax professionals should evaluate how much of the contribution will actually produce a current-year tax benefit.

One potential response is bunching.

Instead of contributing the same amount directly to charities every year, a client might contribute several years' worth of planned giving to a donor-advised fund in one year. The client may be able to itemize in that year and then recommend grants from the DAF to charities over subsequent years.

This allows the client's charitable organizations to continue receiving support on a regular schedule even though the tax deduction was accelerated into a single year.

Qualified Charitable Distributions: A Powerful Tool for Older Clients

Larry described QCDs as one of his favorite charitable planning strategies.

A QCD generally allows an eligible IRA owner who has reached age 70½ to transfer money directly from an IRA to an eligible charity. The distribution can count toward the client's required minimum distribution while the qualifying amount is excluded from taxable income.

That distinction can be important.

Instead of taking an IRA distribution into income and then attempting to claim an itemized charitable deduction, a properly structured QCD can prevent the qualifying distribution from increasing AGI in the first place.

Depending on the client's circumstances, lower AGI may potentially affect:

• Medicare IRMAA surcharges.
• Taxation of Social Security benefits.
• Income-based deductions and credits.
• Other AGI-sensitive provisions.

Larry emphasized that the client must actually have reached age 70½ when the QCD occurs; it is not enough simply to turn 70 during that calendar year.

He also discussed QCDs from inherited IRAs. An eligible beneficiary who has reached the required age may be able to make QCDs from an inherited IRA, potentially providing an additional planning opportunity for beneficiaries subject to the inherited-IRA distribution rules.

Coordinate QCDs With Required Minimum Distributions

The Q&A highlighted an important practical point: advisors should coordinate QCDs and RMDs rather than treating them as unrelated transactions.

As a best practice, Larry suggested completing intended QCDs early enough that they can count toward satisfying the client's RMD before unnecessary taxable distributions are taken.

For example, a client who does not need an RMD for living expenses and already intends to make significant charitable gifts may be able to satisfy some or all of the RMD through QCDs rather than taking the distribution personally and subsequently donating cash.

Larry also cautioned against double dipping: an amount properly excluded from income as a QCD cannot also be claimed as a charitable deduction on Schedule A.

Advisors should also encourage clients to notify the receiving charity when a QCD is coming. Custodial checks do not always clearly identify the donor, creating the possibility that a charity may have difficulty matching the contribution to the correct donor or purpose.

QCDs and Charitable Gift Annuities

The speakers also discussed the relatively new ability to use a limited, one-time QCD election to fund certain split-interest charitable vehicles, including a qualifying charitable gift annuity.

A charitable gift annuity, or CGA, generally involves transferring assets to a charity in exchange for a contractual stream of payments to the donor or another permitted annuitant.

Larry noted that the taxation of those payments depends in part on how the CGA was funded.

For example:

• A CGA funded through the special IRA/QCD provision generally produces ordinary taxable income when payments are received.
• A CGA funded with cash may produce a combination of taxable income and tax-free return of principal.
• A CGA funded with appreciated property can potentially produce a combination of ordinary income, recovery of basis, and capital gain.

The session highlighted CGAs as a potential solution for clients who have charitable intent but would also like to retain an income stream.

Donor-Advised Funds: Flexibility With Important Tradeoffs

Larry referred to donor-advised funds as something of a “Swiss Army knife” of charitable planning, and the session explored why they have become so popular.

A client contributes assets irrevocably to a sponsoring charitable organization and receives advisory privileges over how the funds are invested and ultimately distributed to eligible charities.

The critical distinction is that once the contribution is made, the assets no longer belong to the donor.

The donor may recommend grants and investments, but the sponsoring organization has legal control over the charitable assets.

DAFs may be sponsored by:

• National financial organizations.
• Community foundations.
• Universities.
• Religious organizations.
• Specialized philanthropic organizations.

The speakers emphasized that the lowest-cost provider is not necessarily the best choice. Some community foundations may charge more but provide substantial philanthropic guidance, local nonprofit knowledge, or assistance with complicated gifts.

Advisors should compare fees, investment options, grant policies, minimums, complex-asset capabilities, philanthropic support, and succession provisions before recommending a DAF sponsor.

What Happens to a DAF When the Donor Dies?

A donor-advised fund does not pass to heirs like an IRA, brokerage account, or other personal asset.

Instead, donors can generally name successor advisors—often children or other family members—who can continue recommending charitable grants after the original donor's death.

Alternatively, the donor may establish instructions directing the remaining assets toward particular charities, issue areas, or endowed funds.

This creates an opportunity to integrate the DAF into broader family legacy planning.

Rick emphasized that the sponsor's agreement controls what happens when no successor advisor or charitable instructions exist. Advisors should therefore encourage clients to review the succession provisions rather than assuming the DAF will operate indefinitely according to the family's wishes.

DAF or Private Foundation?

The session compared donor-advised funds with private foundations.

Private foundations can offer substantial control, visibility, family governance, and the ability to create a long-term philanthropic institution. But that control comes with additional administration, tax rules, reporting requirements, expenses, and required distributions.

DAFs generally offer simpler administration and potentially greater privacy.

Rick and Larry also discussed situations in which an older private foundation may ultimately distribute its assets to a donor-advised fund, allowing the family to simplify its charitable structure while continuing its philanthropy.

The decision should therefore be driven by what the client actually wants: control, governance, family participation, privacy, simplicity, flexibility, or some combination of those priorities.

Appreciated Stock Can Be Better Than Writing a Check

For clients holding appreciated publicly traded securities, donating the securities themselves may be substantially more tax-efficient than selling them and donating the proceeds.

When the requirements are satisfied, a client may potentially receive a charitable deduction based on fair market value while avoiding recognition of the embedded capital gain.

That creates an opportunity for advisors to review portfolios specifically for charitable assets.

Instead of automatically funding annual charitable contributions from a checking account, advisors can ask:

“Does this client own appreciated property that would be more tax-efficient to give?”

The same concept can extend beyond publicly traded securities, although the complexity increases significantly.

Complex Assets Require More Planning

The webinar discussed charitable gifts involving:

• Closely held business interests.
• Real estate.
• Cryptocurrency.
• Artwork.
• Jewelry.
• Tangible personal property.
• Partnership and LLC interests.
• Other difficult-to-value assets.

These gifts can create significant planning opportunities, but they also create additional risks.

Before initiating a transfer, advisors should determine whether the charitable organization or DAF sponsor is willing and able to accept the asset.

The charity may need to evaluate marketability, carrying costs, environmental liabilities, unrelated business taxable income, restrictions on ownership, valuation concerns, or the cost of eventually selling the asset.

As Rick noted, sometimes a charity simply cannot afford to accept the gift.

Documentation Can Make or Break the Deduction

Larry reviewed several tax cases in which substantial charitable deductions were denied because taxpayers failed to follow substantiation requirements.

The message was straightforward: a good charitable strategy can still fail if the paperwork is wrong.

Depending on the type and value of the contribution, documentation may include:

• A contemporaneous written acknowledgment from the charity.
• A description of non-cash property.
• Confirmation of whether goods or services were received.
• Form 8283.
• A qualified appraisal.
• A qualified appraiser's signature.
• The donee organization's acknowledgment.
• Additional documentation for particularly large non-cash contributions.

Advisors should not assume that an acknowledgment letter is sufficient simply because the charity issued one. The letter and related tax documentation should be reviewed for required information.

This becomes especially important when charitable deductions reach six or seven figures.

Business Owners: Start Charitable Planning Before the Sale

One of the most important planning discussions involved business owners preparing for a liquidity event.

A business owner may want to contribute some ownership interest to charity before a sale, potentially creating a charitable deduction and avoiding capital-gain recognition on the donated interest.

But timing is critical.

If the sale has progressed too far before the charitable transfer occurs, the IRS may apply the anticipatory assignment-of-income doctrine and treat the donor as though the donor sold the asset and then contributed the proceeds.

The speakers therefore emphasized beginning the charitable planning process early—ideally before the transaction has progressed to binding commitments or a virtual certainty of sale.

Advisors need to consider:

• Whether a letter of intent has been signed.
• Whether a binding sales agreement exists.
• How far negotiations have progressed.
• Whether significant contingencies remain.
• Whether the charity truly controls the donated interest.
• Whether the charity is obligated to participate in the sale.
• Whether the receiving organization will accept the business interest.
• Whether a qualified appraisal is required.

For closely held businesses, this is an area where financial advisors, CPAs, attorneys, valuation professionals, philanthropy advisors, and the charitable organization should coordinate well before closing.

Charitable Remainder Trusts for Larger Planning Opportunities

For larger appreciated assets, Larry discussed charitable remainder trusts as another potential planning vehicle.

A CRT can accept appreciated property, sell and diversify the property within the trust, provide an income stream to designated beneficiaries, and ultimately transfer the remainder to charity.

However, CRTs involve substantially more complexity than a DAF or direct charitable gift, including trust administration and annual tax reporting.

Larry suggested that the economics generally become more compelling with larger transactions rather than creating a CRT for a relatively modest contribution.

The client also needs genuine charitable intent. A CRT should not be viewed simply as a technique for avoiding capital-gain tax.

Choosing the Right Charitable Vehicle

There is no universally “best” charitable structure.

Instead, advisors should match the strategy to the client's goals.

A direct charitable gift may be appropriate when simplicity is the priority.

A donor-advised fund may work well when clients want flexibility, privacy, bunching opportunities, investment growth, and family successor advisors without operating a private foundation.

A private foundation may make sense when family governance, control, visibility, and a long-term philanthropic institution are important.

A charitable gift annuity may appeal to clients who want to make a charitable gift while retaining an income stream.

A charitable remainder trust may be appropriate for larger appreciated assets when diversification, income, and charitable legacy goals come together.

The planning process should begin with the client's objectives and then work backward to the appropriate vehicle—not the other way around.

Practical Application for Financial Advisors and CPAs

Charitable planning creates an opportunity to move beyond the annual question of “How much did you give to charity?”

Consider adding charitable planning questions to regular client reviews:

• What causes and organizations matter most to you?
• Are you currently giving primarily with cash?
• Do you own appreciated securities that could be donated instead?
• Are you age 70½ or older and giving to charity while also taking IRA distributions?
• Would bunching several years of contributions into a DAF improve the tax result?
• Do you have concentrated stock, real estate, business interests, or other appreciated assets?
• Are you contemplating selling a business or other highly appreciated asset?
• Would you like children or grandchildren involved in your charitable legacy?
• Do your current estate documents and beneficiary designations reflect your charitable intentions?
• Are your charitable gifts being properly documented?

These questions can uncover opportunities that cross tax planning, retirement planning, investment management, estate planning, business succession, and family legacy planning.

The larger lesson from Larry Pon and Rick Peck was that tax efficiency should support philanthropy—not define it. Start by understanding what the client wants to accomplish. Then bring together the appropriate assets, charitable vehicles, tax strategies, and professional expertise to help accomplish those goals.

Compliance Note

This webinar was provided for educational purposes and discussed federal tax and charitable planning concepts that may depend on a taxpayer's individual circumstances. Tax laws, deduction limits, QCD limits, charitable contribution rules, proposed legislation, and other provisions may change.

Charitable strategies involving donor-advised funds, private foundations, charitable gift annuities, charitable remainder trusts, closely held business interests, real estate, and other non-cash property may involve significant tax, legal, valuation, and administrative requirements. Financial professionals should review current law and applicable IRS guidance and coordinate with qualified tax, legal, valuation, and charitable-planning professionals before implementing a strategy.