I’m pushing 70 now, and after decades as a financial advisor, I’ve seen a lot—market booms, busts, and everything in between. But one thing that’s never lost its shine for me is helping people give in a way that’s smart and meaningful. There’s a strategy I’ve been guiding clients through for years: donating appreciated assets—stocks, real estate, or other holdings that have grown over time—to charity. It’s a move that’s good for the heart, great for the tax bill, and, frankly, a bit of a gem whether you’re driven by faith or just love a solid plan. Let me walk you through it, because I think it’s something worth understanding, no matter where you’re coming from.
Turning Growth into Good
Imagine you’ve got a piece of your portfolio that’s done well—say, some stock you picked up years ago for $5,000, now worth $25,000. It’s the kind of growth many of us dream about, and I see it all the time with clients—assets like stocks, a rental property, or a fund that’s quietly ballooned over the decades. For me, it’s a nod to stewardship—Scripture says, “To whom much is given, much is required” (Luke 12:48)—but it’s also just practical. Selling that stock outright means facing capital gains tax—15% or 20% for most, depending on your bracket.1 That’s $3,000 or $4,000 of that $20,000 gain heading straight to the IRS.2
Here’s where it gets interesting, and it’s something I’ve been showing clients for years: give that asset directly to a charity instead. Don’t sell it—transfer it as is. The IRS says you skip the capital gains tax entirely.3On top of that, if you itemize, you can often deduct the full market value—$25,000 in our hypothetical—not just what you paid way back when.4 The charity gets the whole amount to use, you save on taxes, and it’s like the numbers and your values line up perfectly.
A Win That Feels Right
I’ve always believed giving should feel like a double blessing—for the giver and the receiver. Take that hypothetical $25,000 stock. If you give it to a cause—a church, a food bank, maybe a school program—they sell it tax-free and put every dollar to work. You deduct the full value on your taxes, dodge the capital gains hit, and know you’ve stretched your resources further. It’s a strategy that works whether you’re moved by generosity, fairness, or just wanting to outsmart the system a little. I’ve been at this long enough to know a good idea when I see one, and this is one I keep coming back to.
Stories That Stick
In my line of work, you collect stories. Many years ago, I considered myself skilled at sifting through reports on common stocks to identify those with strong potential for growth. One of my selections was a stock I bought for $25 per share, which quickly soared to over $100 per share, reaching a total value exceeding $20,000. When it came time to decide whether to sell, I did some research and discovered that the company was donating to an organization whose values conflicted with both my client’s morals and my own. Neither of us wanted to continue holding the stock. The solution? We made an in-kind donation of the shares to a food bank. They promptly sold the stock, using the proceeds to further their mission. This approach eliminated capital gains taxes on over $15,000 in profit, supported a worthy cause, and allowed us to divest from a company we no longer wished to back. It was a genuine win-win-win.
Something to Chew On
I’ve been doing this long enough to know the details matter—deduction limits (usually 30% of your adjusted gross income for appreciated assets), picking a qualified charity, timing it right.5 It’s not a one-size-fits-all thing, and I always tell my clients to sit down with their tax person (which should be one of our tax people if you’re looking!). But the heart of it? That’s straightforward: give what’s grown, skip the tax sting, and watch it do more.
After nearly 70 years on this earth and countless client meetings, I can say this: it’s a rare day when your wallet and your purpose line up so neatly. Whether you see it as a nod from Proverbs— “A generous person will prosper” (11:25)—or just a darn good tactic, it’s been a privilege to share it. What’s your take? Ever thought about giving this way? I’d love to hear your story.
Citations
[^1]: IRS, "Topic No. 409: Capital Gains and Losses," updated regularly, www.irs.gov.
[^2]: Tax Foundation, "2025 Federal Income Tax Brackets and Rates," projected annually, www.taxfoundation.org.
[^3]: IRS, "Publication 526: Charitable Contributions," updated regularly, www.irs.gov.
[^4]: IRS, "Publication 561: Determining the Value of Donated Property," updated regularly, www.irs.gov.
[^5]: IRS, "Charitable Contribution Deductions," ongoing guidance, www.irs.gov.