Most people give generously. Far fewer give strategically. The difference can be substantial — for the causes you care about and for your own financial picture.
There’s a version of charitable giving that most people never discover. Not because it’s complicated or reserved for the ultra-wealthy — but because nobody ever sat down with them and asked the right questions.
In Episode 20 of Quarter Over Quarter, Don Drury and Tom Moran are joined by Michael Mongin — an attorney and advisor at Moran Wealth Management — for a conversation about charitable planning that goes well beyond writing a check. They cover donor-advised funds, private foundations, charitable remainder trusts, qualified charitable distributions, and something far less talked about: the risk of giving too much.
What follows is a road map, not a prescription. The strategies that make sense for you depend on your situation — but understanding what’s available is the first step.
The First Question That Changes Everything
Before any structure is discussed, before any tax calculation is run, Mongin asks every new client one question: do you have a charitable inclination?
If the answer is yes — even loosely — then the planning conversation can broaden significantly. If the answer is no, or not yet, these strategies don’t belong in the conversation. Tom Moran put it plainly: charitable planning isn’t a tax strategy you adopt because your accountant suggested it. It starts with a genuine desire to support something beyond yourself. The tax efficiency follows from that; it doesn’t lead it.
That distinction matters because people who approach this backwards — leading with the tax savings — often end up disappointed. The numbers may not meet expectations, the commitment to a cause isn’t there to sustain it, and what should have been meaningful ends up feeling transactional.
Four Tools in the Charitable Planning Toolkit
The episode walks through the primary vehicles available and how they differ in control, cost, and application.
Donor-Advised Funds (DAFs)
Mongin describes a donor-advised fund as a “rent-a-foundation” — and it’s an apt frame. You open an account, make a contribution (which is your tax deduction), and then advise the sponsoring organization on where those dollars go. Fidelity, Schwab, and community foundations all offer them, often with low minimums. Someone else handles the compliance. You handle the giving.
One often-overlooked feature: there’s no minimum annual distribution requirement. You can contribute a larger amount in a high-income year and distribute the funds over many years. Front-load the deduction, stretch out the giving.
Private Foundations
When control and continuity matter — particularly across generations — a private foundation becomes worth the added complexity. You’re essentially creating a nonprofit, which comes with IRS compliance obligations, annual filings, and often a foundation administrator. The cost threshold Mongin referenced has moved: what used to be a five-million-dollar starting point is now closer to ten.
The tradeoff for that complexity is complete control and the ability to involve family. More on that shortly.
Charitable Remainder Trusts (CRTs)
A CRT occupies different territory than a DAF or foundation. Rather than being purely charitable, it’s a split-interest arrangement: you get an income stream for a period of time, and a charity receives what’s left when the trust ends.
This structure is particularly relevant for someone holding highly appreciated stock who needs retirement income but doesn’t want to trigger a large capital gains event by selling. The appreciation is essentially spread over time rather than hitting all at once. The income coming back is taxable — the episode explains the “worst to first” ordering of how it’s characterized — but the tax is deferred and arrives gradually. For someone who is charitably inclined but also needs cash flow, this can do a lot of work.
Qualified Charitable Distributions (QCDs)
For IRA owners who are 70½ or older and subject to required minimum distributions, the QCD is one of the cleanest giving tools available. In the episode, Michael Mongin cites the 2025 QCD limit as $108,000 — transferred directly from an IRA to a qualifying charity and excluded from reportable income entirely (note: IRS limits are indexed and subject to change; confirm current thresholds with your advisor or at IRS.gov). It doesn’t show up as income; it’s simply excluded. That means it reduces AGI in a way a standard charitable deduction cannot, which can have downstream effects on Medicare premium thresholds, Social Security taxation, and other income-sensitive calculations.
And it doesn’t have to be the full $108,000. If someone has been giving $20,000 a year to their church or favorite causes, routing that through a QCD instead of writing a check out of a savings account accomplishes the same philanthropic goal with significantly better tax treatment.
What Appreciated Stock Changes About the Equation
One of the more practical segments of the episode walks through a scenario that plays out repeatedly in Mongin’s practice: a client with a concentrated position in something like Nvidia — low cost basis, significant appreciation, and a charitable history of $10,000 a year.
The instinct is to write a check. The better move, in many cases, is to contribute the appreciated shares instead. If you were going to give $10,000 a year for the next decade, you could fund a donor-advised fund with $100,000 of that stock today. You get a deduction for the full fair market value. The fund sells the shares — no capital gains tax. You start distributing from the fund annually. And you’ve reduced a concentrated position in your portfolio in the process.
In the right circumstances, a single decision like this may address several goals at once — charitable giving, a potential deduction, deferred or reduced capital gains exposure, and portfolio concentration risk. The actual tax impact depends on individual planning factors, but the illustration points to the kind of interconnected thinking that sits at the center of these conversations.
Philanthropy as a Family Value — Not Just a Transaction
Some of the most compelling material in the episode doesn’t involve tax rates at all.
Don Drury shares how families he’s worked with have used a private foundation to involve children and grandchildren in the giving process — not as passive beneficiaries, but as active stewards. Annual family meetings. Each grandchild researches a cause, prepares a presentation, and makes a case for funding it. One grandfather, Mongin recalls, insisted that segment go first — before any other business. He wanted his family’s charitable mission front and center, not an afterthought.
What gets built through that process isn’t just a tax-efficient structure. It’s a shared language around values, stewardship, and what the family stands for. That tends to outlast the money.
A Note on Overgifting — Because It Happens
Tom Moran raises a point near the end of the episode that doesn’t come up in most conversations about philanthropy: the risk of being too generous.
Some clients, he notes, are so philanthropically inclined — and so generous with their children and grandchildren — that an advisor’s job becomes making sure they don’t inadvertently compromise their own financial security in the process. Generosity that creates dependency or depletes retirement resources isn’t really generosity in the long run.
Charitable planning, when done well, sits inside a comprehensive financial plan — not adjacent to it. The goal is for clients to give with confidence, knowing the math supports both their legacy intentions and their own long-term needs.
What This Means for You
The full episode covers considerably more ground than any summary can — including how multiple structures can be layered together in the same year for clients navigating a liquidity event, a business sale, or a significant change in income.
If you’ve been giving generously and wondering whether there’s a more intentional way to structure it — or if you’re sitting on a concentrated position and haven’t thought about philanthropy as part of the solution — this episode is worth your time.
Listen on
Apple Podcasts or
Spotify, or reach the team at
moranwm.com to start a conversation about how charitable planning might fit your situation.
