Insight Category: Tax

How a Donor-Advised Fund Helped One Couple Give More and Pay Less in Taxes

Learn how one couple reduced their taxes, eliminated capital gains, and multiplied their charitable impact through a $300,000 donor-advised fund gift at the peak of their income year.

Total Gift
$ 299000
Total Tax Savings
$ 99000 +

A Smart Way to Turn a Financial Peak into a Kingdom Opportunity

When approaching retirement, one couple found themselves at a financial crossroads. As they entered their final year of full-time employment, deferred compensation and bonuses projected this to be their highest-income year ever.

At the same time, they held a large position in a single stock that had performed extremely well. The gains were substantial, but the future of the stock was uncertain. Should they sell and face significant capital gains? Hold and risk a market drop?

Instead, they chose a third option — one that embodied the Faith Forward Framework and their commitment to their faith and financial stewardship: They utilized our expertise to donate $300,000 of appreciated stock to a Donor-Advised Fund (DAF).

The Strategy in Action

Event
Description
Result/Benefit
Appreciated Stock Gifted
They transferred $300,000 of long-term appreciated stock into a DAF. The stock’s cost basis was only ~$25,000.
No capital gains tax due on the ~$275,000 unrealized gain.
Immediate Deduction
Because they gifted the stock directly to charity (via the DAF), they received a $300,000 charitable deduction.
Reduced taxable income in their final high-earning year.
Double Benefit
1) Avoided capital gains tax.
2) Received a full income tax deduction for the gift.
Saved roughly $110,000–$120,000 in combined federal and state taxes.
Ongoing Investment
The stock was kept invested within the DAF. It continued to grow tax-free.
The stock appreciated further, increasing their charitable capacity.
Future Giving
The couple could recommend grants from their DAF over future years — including their ongoing tithes.
They “pre-funded” years of giving while capturing today’s tax benefit.

Timing and Strategic Stewardship: Why They Gave When They Did

Charitable deductions are limited to a percentage of Adjusted Gross Income (AGI)—typically 30% of AGI for appreciated assets. In this specific scenario, the couple’s AGI was $350,000, allowing an immediate deduction of up to $105,000 (30% of AGI) in the current year, with the remaining deduction available to be carried forward for five additional years.

The strategic timing of the full $300,000 DAF gift across two tax years allowed us to maximize their stewardship by achieving the following critical outcomes:

Maximized Deductions

They optimized the allowable deduction available in each tax year.

Smoothed the Benefit

The deduction was strategically applied into retirement years when income dropped to around $200,000 per year from pensions and part-time work.

Zero Loss of Benefit

None of the substantial charitable deduction went unused, securing the greatest possible financial advantage for their mission.

Case Study Snapshot

Year
Household Income
DAF Gift Applied
Deduction Utilized
Carryforward Remaining
Tax Benefit (Est.)
Totals
$300,000 total gift
$255,000 total deduction used
~$100,000+ total tax savings
2024 (final work year)
$350,000
$150,000
$105,000 (30% AGI limit)
$45,000
~$40,000
2025 (semi-retired)
$200,000
$150,000 (remainder)
$60,000 (30% AGI limit)
$90,000
~$24,000
2026–2028
$200,000 (each year)
Deducts remaining $90,000 across future years
~$36,000

*Exact amounts depend on marginal rates and itemization.*

Why This Strategy Worked

1. They gave at the right time — capturing a major deduction during their peak income year.
2. They gave the right asset — appreciated stock instead of cash, avoiding capital gains.
3. They gave through the right vehicle — the donor-advised fund offered flexibility.
4. They gave with the right perspective — their goal was obedience and impact, not just savings.

Stewardship That Multiplies

What makes this story powerful is not just the tax efficiency — it’s the faith efficiency. Because they planned with eternal impact in mind, their generosity will continue to flow for years to come. The stock that once represented potential risk now represents potential kingdom return.

“Each of you should give what you have decided in your heart to give, not reluctantly or under compulsion, for God loves a cheerful giver.”

2 Corinthians 9:7

Key Takeaways

Timing matters

Give in high-income years for maximum tax impact.

Asset choice matters

Appreciated stock gifts can eliminate capital gains.

Structure matters

DAFs provide flexibility for long-term generosity.

Faith matters

Stewardship is both financial and spiritual.

Summary

Without DAF
With DAF
Stock Value
$300,000
$300,000
Cost Basis
$25,000
$25,000
Capital Gain
$275,000
$0 (eliminated)
Capital Gains Tax
~$65,000
$0
Charitable Deduction
$0
$300,000
Total Tax Savings
~$100,000+
Control of Giving
Immediate spend required
Give over time, grow tax-free
Legacy Impact
One-time
Multi-year giving from investment growth

At KERUX Financial, we help believers align their wealth with their witness — using strategies like donor-advised funds to maximize both impact and obedience.

“Command them to do good, to be rich in good deeds, and to be generous and willing to share.”

1 Timothy 6:18

The information contained herein is provided for educational purposes only and should not be construed as investment, tax, or legal advice. Past outcomes are not indicative of future results. The suitability of donor-advised funds or any charitable giving strategy depends on an individual’s unique circumstances and objectives. You should consult with your financial advisor, tax professional, and/or legal counsel before implementing any strategy discussed. Advisory services are offered through Kerux, LLC, a registered investment adviser.

Retirement Redefined: Tax Strategies for Healthcare and IRAs

Retirement planning involves many decisions, from determining withdrawal strategies to balancing tax efficiency and estate goals. Among these considerations is whether to keep funds in a traditional IRA or convert to a Roth IRA. While much attention focuses on tax implications and income needs, one critical factor often overlooked is how traditional IRAs can serve as a strategic tool for covering medical expenses, particularly long-term care (LTC).

Here, we explore how traditional IRAs can act as a built-in safety net for healthcare costs and compare their effectiveness to a Roth conversion strategy.

Traditional IRA: A Long-Term Care Safety Net

Traditional IRAs allow for tax-deferred growth, meaning contributions are often deductible, and taxes are paid on withdrawals in retirement. For retirees facing significant medical or LTC expenses, this tax structure offers unique advantages:

  1. Tax-Free Medical Withdrawals

The IRS permits deductions for unreimbursed medical expenses exceeding 7.5% of adjusted gross income (AGI). While traditional IRA withdrawals are taxable, the deduction can offset this burden. For example:

  • A retiree with high medical costs may reduce their taxable income after deductions, effectively lowering or eliminating taxes on IRA distributions.
  1. Timing Benefits for Medical Expenses

Medical expenses often increase later in life, particularly for LTC. Traditional IRAs can serve as a financial reservoir for these costs, enabling retirees to leverage tax advantages during lower tax-bracket years.

  1. Preserving Liquid Assets

By tapping a traditional IRA for healthcare expenses, retirees preserve other assets for discretionary spending or legacy planning.

Roth IRA: Flexibility Without Tax Offset

Roth IRAs, funded with after-tax dollars, offer tax-free growth and withdrawals, making them attractive for many retirees. However, their utility for covering medical costs is less pronounced compared to traditional IRAs:

  1. No Tax Offset for Medical Expenses

Unlike traditional IRA withdrawals, Roth distributions don’t qualify for medical expense deductions. This means retirees with significant healthcare costs miss out on a tax advantage available with traditional IRAs.

  1. Upfront Conversion Costs

Converting to a Roth IRA involves paying taxes upfront, potentially reducing the account’s overall value. For retirees early in retirement or with high income, the conversion cost may outweigh the long-term benefits.

  1. Prioritizing Estate Planning Over LTC Needs

While Roth IRAs are excellent for leaving tax-free inheritances, traditional IRAs may better align with personal needs if healthcare or LTC expenses are the priority.

Key Considerations for Your Retirement Plan

When deciding between a traditional IRA and a Roth conversion, consider:

  1. Tax Brackets Now and in the Future
    • If you anticipate being in a lower tax bracket later in life, a traditional IRA may maximize your tax efficiency, especially when combined with medical deductions.
  2. Projected Healthcare Costs
    • For retirees expecting significant LTC needs, the built-in flexibility of a traditional IRA can outweigh the predictability of a Roth IRA.
  3. Estate Planning Goals
    • If leaving a tax-free legacy is a priority, Roth IRAs are advantageous. However, for those focusing on personal healthcare, traditional IRAs provide a direct solution.
  4. Conversion Timing and Costs
    • Assess whether the upfront tax hit of a Roth conversion is justified, especially if future medical expenses could reduce taxable income through deductions.

Balancing Healthcare and Tax Strategies

For retirees anticipating substantial medical or LTC costs, maintaining a traditional IRA can be a powerful strategy. By leveraging tax deductions and strategically timing withdrawals, traditional IRAs effectively function as a healthcare reserve.

On the other hand, Roth IRAs offer unmatched tax-free growth and withdrawal flexibility, making them ideal for estate-focused retirees or those with fewer medical needs.

Ultimately, the decision between a traditional IRA and a Roth conversion is personal, requiring a careful evaluation of healthcare projections, tax considerations, and financial goals. A consultation with us at Abound Financial can help retirees craft a plan tailored to their unique needs.

Traditional IRA as an LTC Strategy

A traditional IRA is not a substitute for long-term care insurance but can act as a practical alternative for retirees comfortable self-insuring against LTC risks.

Example: Nursing Home Costs and Tax Efficiency

  • Scenario: John, age 75, withdraws $100,000 annually from his $500,000 traditional IRA for nursing home care.
  • Income: Social Security and pension income total $50,000, placing him in the 12% tax bracket.
  • Medical Deduction: LTC expenses far exceed the 7.5% AGI threshold, allowing him to deduct $96,250.
  • Outcome: After deductions, John’s taxable income remains low, with an effective tax rate of only 6.45% on his IRA withdrawal.

Using the traditional IRA, John minimizes taxes while covering his medical expenses efficiently.

Comparison of Results: Traditional IRA vs. Roth IRA

Factor Traditional IRA Roth IRA
LTC Withdrawal $100,000 $100,000
Effective Tax Rate on Withdrawal 6.45% (after deduction) 0% (tax-free)
Total Tax Paid $6,450 $0
Net After-Tax Withdrawal $93,550 $100,000
Roth Conversion Cost (at 65) $0 $110,000 (one-time)

 

Analysis

  • Maximizing Tax Savings with a Traditional IRA:
    John leverages the medical expense deduction to significantly reduce his tax burden on withdrawals from his traditional IRA. With an effective tax rate of just 6.45%, this strategy makes the most of his medical expenses and allows him to preserve more of his retirement funds.
  • The Cost of a Roth Conversion:
    If John had converted his traditional IRA to a Roth at age 65, he would have faced an upfront tax cost of $110,000. This substantial expense reduces the overall retirement nest egg, especially if John doesn’t live long enough to fully capitalize on the tax-free growth of the Roth IRA.
  • Lost Deduction Opportunity:
    Using a Roth IRA for LTC expenses eliminates the opportunity to offset taxable income with the medical deduction. While Roth distributions are tax-free, they don’t provide the same tax relief when paired with high medical expenses.

Conclusion

For retirees like John, who anticipate significant long-term care expenses, the traditional IRA can be a more effective choice. By taking advantage of the tax-deductible nature of medical expenses, John minimizes his overall tax liability while addressing healthcare needs.

This strategy is particularly beneficial for retirees with high medical costs and those in moderate-to-lower tax brackets. By contrast, the upfront conversion cost of a Roth IRA may outweigh its benefits in scenarios where medical deductions provide meaningful tax relief.

There is no one-size fits all answer when it comes to your particular needs. Connect with one of our advisors today if you’d like to plan for your financial future!

This is a hypothetical situation based on real life examples. Names and circumstances have been changed. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. To determine which investments or strategies may be appropriate for you, consult your advisor prior to investing.
This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific tax issues with a qualified tax advisor.