Have you ever felt like...
"I want to give more to causes I care about. But when I sold $500,000 in stock to donate, I paid $95,000 in capital gains tax first. I essentially gave $595,000 so that $500,000 would reach the charity. And then the money was gone. I couldn't afford to do that again. Nobody told me there was a way to donate the stock directly, skip the tax, get a deduction, AND still receive income from it for the rest of my life."
$95,000
Capital gains tax on selling $500K in appreciated stock to donate
23.8%
Federal capital gains + Medicare surtax rate
$0
Income you receive from a cash donation (it's just gone)
We hear you. Generosity shouldn't cost you twice.
When you sell stock to donate, you pay capital gains tax on the sale AND lose the money entirely. That's paying twice for one act of generosity. What if you could donate the stock directly (no capital gains tax), take an immediate tax deduction worth $150,000+, AND receive income from the donation for the rest of your life? That's not a fantasy. It's a Charitable Remainder Trust (CRT), and it's one of the most powerful tools in the tax code for people who want to give generously while building wealth. Your CPA probably never mentioned it because most CPAs don't set up trusts. We do. And we connect your giving to the rest of your tax strategy so every dollar works harder.
How It Works: Donate $500K, Save $245K in Taxes, Receive Income for Life
1
Donate Appreciated Assets
Transfer $500K in appreciated stock (or real estate, crypto, business equity) directly into a Charitable Remainder Trust. You do NOT sell the stock. No capital gains tax is triggered.
2
Take the Deduction
You receive an immediate charitable tax deduction of $150,000-$200,000. The amount depends on your age: younger donors get a smaller deduction (the charity waits longer), older donors get a larger one. At 37%, that saves you $55,000-$74,000 in income tax this year.
3
Receive Income for Life
The trust sells the stock with zero capital gains tax (the trust is tax-exempt on the sale), reinvests the proceeds, and pays you 5-8% annually for life. On $500K, that's $25,000-$40,000 per year.
4
Charity Receives the Remainder
After your lifetime, the remaining trust assets go to the charity (or charities) you chose. Your philanthropic legacy continues. And your family benefits from the tax savings you reinvested through the other levers.
Same generosity. No capital gains tax. A deduction worth $55K-$74K. And income of $25K-$40K per year for life. The charity still receives the gift. Everyone wins.
Now Look at What You Keep
Sell Stock, Then Donate Cash
Appreciated stock value$500,000
Cost basis$100,000
Capital gains tax (23.8%)$95,200
Net proceeds to donate$404,800
Tax deduction value (at 37%)$149,776
Income from donation$0/year
Total tax benefit$54,617
Donate via Charitable Remainder Trust
Appreciated stock donated$500,000
Capital gains tax$0
Charitable deduction$150,000-$200,000
Tax savings on deduction (37%)$55,500-$74,000
Annual income from CRT (6%)$30,000/year for life
20-year income total$600,000
Charity receives remainderYes (your legacy)
Total Financial Benefit of the CRT vs Selling
$750K+
capital gains avoided + tax deduction + 20 years of income
Based on $500K in appreciated stock (basis $100K), donated to a Charitable Remainder Unitrust (CRUT) at age 50, 6% annual payout rate, 37% federal income tax rate, 23.8% capital gains rate. Charitable deduction calculated using IRS Section 7520 rate. Income continues for the donor's lifetime. Charity receives the trust remainder. A Donor Advised Fund (DAF) is an alternative for those who want the deduction now and grant to charities over time without the income component.
The Hidden Cost of Selling to Donate
You sell $500K in stockPay $95,200 in capital gains tax
You donate the remaining $404,800Money is gone. No income.
Your tax deduction is on $404,800Not on the full $500,000
You paid $595,200 totalFor a $404,800 donation
Generosity cost you almost $200K extra$95K tax + $500K lost asset
The Power of Donating Through a CRT
You donate $500K in stock directly$0 capital gains tax
Deduction is on the full $500,000Not the after-tax amount
Trust sells tax-free and reinvestsFull $500K working for you
You receive income for life$30,000/year at 6%
Same generosity. Radically different outcome.You give more AND keep more
This Is Real
A Taylored Tax client eliminated $1.4 million in capital gains taxes by donating appreciated assets through a Charitable Remainder Trust. They receive income for life, their chosen charities are named as beneficiaries, and the tax savings were reinvested through the other levers. Savings on this lever: $25,000/year. That's lever 6 of 7.
Taylored Tax client (identity protected). Running total: $825,000 saved across levers 1 through 6. One more to go.
