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TIAA Employees: Strategic Ways to Reduce Capital Gains on Appreciated Stock

'TIAA employees can benefit from understanding that strategies like a Section 351 exchange, charitable donations, and tax loss harvesting may work together to help manage appreciated stock efficiently while aligning with broader long-term financial goals.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

'TIAA employees should recognize that thoughtful planning with tools such as Section 351 exchanges, gifting strategies, and tax loss harvesting can help them manage highly appreciated stock while supporting both personal and philanthropic objectives.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

How a Section 351 exchange can defer capital gains on highly appreciated stock.
Alternative tax-efficient strategies such as charitable donations, tax loss harvesting, and gifting.
The role of inheritance rules, step-up in basis, and combined approaches in long-term tax planning.

A Tax-Aware Q&A on How to Manage Highly Appreciated Stock

From the Section 351 exchange to other practical approaches, this Q&A addresses key considerations TIAA employees may encounter when dealing with highly appreciated shares.

Section 351 Exchange: The Fundamental Approach

Q: What is an exchange under Section 351?
A: Under certain circumstances, an investor may transfer property, such as highly appreciated shares, to a company in exchange for its stock under a provision of the Internal Revenue Code that allows the deferral of capital gains or losses.

Q: What is the primary advantage of exchanging my appreciated stock through a Section 351 exchange?
A: The main advantage is tax deferral. Gains transferred to corporations may be postponed under Section 351, though this applies only if specific diversification requirements are met, especially when transferring to investment companies like exchange-traded funds (ETFs). ¹

Q: What is meant by the “Control Test”?
A: The investor or group of investors who use their portfolio assets to fund the new entity must own at least 80% of the voting power and 80% of the total number of shares of all other classes of stock in the new company immediately after the exchange. ¹

Q: When seeding an ETF, how is the Control Test usually satisfied?
A: It is typically satisfied by either a single substantial investor making a significant asset contribution or multiple investors pooling assets to create a seeding pool for the ETF’s launch.

Q: What is the ultimate tax payment date for the deferred gain?
A: The deferred gain is recognized when the ETF shares acquired through the exchange are sold; distributions from taxable funds must also be reported in the meantime.

Other Tax-Efficient Techniques

Q: What is a straightforward method, aside from a Section 351 exchange, to sell highly appreciated shares without incurring large taxes?
A: Donating shares directly to a qualified charity is one option that some TIAA employees may benefit from.

Q: What tax advantages come with donating valuable stock to a charity?
A: Subject to holding period and adjusted gross income (AGI) limits, you can bypass capital gains taxes on the appreciation and may receive an income tax deduction for the stock’s full fair market value.

Q: What is a Donor-Advised Fund (DAF)?
A: A DAF allows you to donate appreciated stock, receive an immediate tax deduction, and then recommend grants to charities over time, while the assets in the DAF grow without tax impact. ²

Q: Can I give a family member my appreciated stock as a gift?
A: Yes. In most cases, the cost basis from the donor carries over to the recipient.

Q: Why would I give a family member in a lower tax bracket appreciated stock?
A: If they sell the stock, the lower income could result in a reduced capital gains rate, potentially as low as 0% for long-term gains. ³

Tax Loss Harvesting and Other Approaches

Q: What is harvesting tax losses?
A: Selling investments at a loss to offset gains from other sales is known as tax loss harvesting, a strategy sometimes considered by TIAA employees seeking opportunities to leverage bouts of market volatility.

Q: Can I deduct a certain amount of loss from my regular income?
A: Yes. If your capital losses exceed your gains, you can use up to $3,000 per year ($1,500 if married filing separately) to offset ordinary income, with remaining losses carried forward indefinitely. ⁴

Q: What is a Qualified Opportunity Fund (QOF)?
A: A QOF provides investors with tax incentives for investing in tracts of land designated as 'opportunity zones'. Capital gains reinvested in a QOF within 180 days of being realized can be temporarily tax deferred, while QOF investments helpd for at least 10 years may confer a permanent capital gains exclusion. ⁵ That said, 2025 legislation changes may prompt IRS updates to this rule.

Inheritance and Step-Up in Basis

Q: What is meant by a “step-up in basis”?
A: This adjusts an inherited asset’s cost basis to its fair market value at the time of the owner’s death, eliminating capital gains accumulated during their lifetime. ⁶

Q: If I gift shares while living, will I receive a step-up in basis?
A: No. The original cost basis transfers to the recipient without adjustment.

Determining the Right Strategy

Q: What is the best course of action for me?
A: The most suitable approach will depend on factors such as your gain size, income level, charitable intentions, and liquidity needs.

Q: Do any of these strategies call for professional guidance?
A: Yes. Given the complexity of the tax code, working with a qualified financial advisor and tax professional is strongly recommended before implementing these strategies.

Q: Is it possible to combine these strategies?
A: Yes. For example, you might execute a Section 351 exchange on part of your portfolio for tax-deferred rebalancing while donating another portion to a DAF for an immediate deduction.

Q: Is there a loophole in the Section 351 exchange?
A: No. This is a legitimate tax code provision designed for corporate restructuring and adapted for use in the ETF market. It is intended for tax deferral, not permanent tax elimination.

Featured Video

Articles you may find interesting:

Sources:

1. Kitces. ' Using Section 351 Exchanges to Tax-Efficiently Reallocate Portfolios With Embedded Gains ,' by Ben Henry-Moreland and Brent Sullivan. 12 Mar. 2025.

2. Kiplinger. “ A Donor-Advised Fund Can Give Your Charitable Giving a Boost ,” by Samuel Gaeta. 9 May 2024.

3. Internal Revenue Service. “ Topic No. 409, Capital Gains and Losses .” IRS.gov , 8 July 2025.

4. Wealth Enhancement. ' 6 Essential Tax-Loss Harvesting Tips ,' by Jim Wiley. 6 April 2022.

5. Congressional Research Service. ' Tax Incentives for Opportunity Zones ,' by Donald Marples. 26 Apr. 2022.

6. Investopedia. “ Carryover Basis: What It Is, How It Works, Gift Taxes ,” by Julia Kagan. 16 Jan. 2023.

How does TIAA-CREF's current approach to retirement benefits reflect the changing landscape of retiree health care support, and what implications does this have for employees planning for their retirement? How can TIAA-CREF employees leverage available resources to ensure that they are maximizing their retirement readiness?

TIAA-CREF is adapting to the evolving landscape of retiree health care by integrating defined contribution retirement and health care plans, thereby increasing benefits while maintaining cost control. This shift is crucial for employees planning for retirement as it allows for more predictable and sustainable benefits management. Employees should leverage TIAA-CREF’s educational resources, online tools, and direct consultation with wealth advisors to maximize their retirement readiness, ensuring they understand how to optimize their savings and benefits.

In what ways has the transition from traditional defined benefit plans to defined contribution plans impacted TIAA-CREF employees in terms of financial security during retirement? What strategies can employees employ to manage their defined contribution savings effectively to ensure they meet their retirement needs?

The transition from defined benefit plans to defined contribution plans at TIAA-CREF has significant implications for financial security during retirement, potentially increasing the responsibility on employees to manage their retirement savings. Employees can enhance their financial security by taking advantage of TIAA-CREF's automatic enrollment, lifestyle funds, and matching contributions strategies. Additionally, they should consider utilizing financial planning services offered by TIAA-CREF to effectively manage and plan their retirement savings.

TIAA-CREF promotes a robust wellness program alongside its retirement benefits. How can the wellness initiatives offered by TIAA-CREF contribute to an employee's overall preparation for retirement? What measures should employees take to integrate wellness into their retirement planning?

TIAA-CREF’s wellness programs are integral to helping employees prepare for retirement by promoting physical and financial well-being. Engaging in these wellness initiatives can lead to reduced long-term health care costs and improve overall health, which is vital for a secure retirement. Employees should actively participate in these programs and integrate wellness into their retirement planning to ensure they remain healthy and financially prepared for their post-working years.

As employees approach retirement, understanding health care costs becomes essential. What resources does TIAA-CREF provide to help employees estimate their future health care expenses, and why is it crucial for employees to factor these costs into their retirement planning?

TIAA-CREF provides several resources to help employees estimate future health care expenses, which is essential for comprehensive retirement planning. Utilizing tools like health savings accounts and retirement health savings plans can aid employees in planning for these costs effectively. Understanding the specifics of Medicare and supplemental insurance options available through TIAA-CREF can also help employees make informed decisions about their health care in retirement.

Facing the challenges of an aging workforce and rising health care costs, how is TIAA-CREF adapting its retiree health care strategies to remain sustainable? What can current employees learn from these changes as they prepare for their future?

Facing an aging workforce and rising health care costs, TIAA-CREF is adapting its strategies by shifting towards health reimbursement arrangements (HRAs) and providing access to Medicare Advantage plans through private exchanges. These changes help sustain the financial viability of retiree health benefits. Employees should stay informed about these shifts and plan accordingly to utilize the evolving benefits effectively as they prepare for retirement.

The retirement health savings plan (RHSP) at TIAA-CREF offers unique benefits. How does this plan specifically support employees in managing their health care costs post-retirement, and what should employees consider when contributing to this plan while employed?

TIAA-CREF’s RHSP offers unique benefits by allowing employees to save for health care costs with tax advantages. Understanding and contributing to this plan during their employment can significantly aid employees in managing health care expenses post-retirement. Employees should consider maximizing their contributions to take full advantage of TIAA-CREF’s matching offerings and the tax-free growth of these assets.

TIAA-CREF has moved towards providing financial support for retirees through health reimbursement arrangements (HRAs) instead of traditional retiree health benefits. What should TIAA-CREF employees know about the HRA structure, and how can they plan to utilize these funds effectively to cover medical expenses in retirement?

TIAA-CREF’s move to provide financial support through HRAs instead of traditional health benefits requires employees to understand the structure and benefits of HRAs. Planning how to use these funds effectively, including covering medical expenses and insurance premiums in retirement, is crucial. Employees should educate themselves about the terms and optimal uses of their HRA to maximize its value for their retirement health care needs.

Considering recent changes in accounting standards like FAS 106, how has TIAA-CREF adjusted its benefits structure? How can employees understand the implications of these standards when it comes to their retiree benefits and overall financial planning?

With changes in accounting standards like FAS 106 affecting the reporting and funding of retiree benefits, TIAA-CREF has adjusted its benefits structure accordingly. Employees need to understand these changes and their implications on their retiree benefits to plan their finances and retiree benefits more effectively. Awareness of these accounting standards and proactive engagement with HR can help employees navigate these changes.

The rising costs of health care naturally impact retirement planning. How is TIAA-CREF preparing its employees to navigate these rising costs in their retirement? What proactive steps should employees take to mitigate health care costs during their retirement years?

TIAA-CREF is preparing employees for rising health care costs by providing tools and resources to estimate and manage these expenses effectively. Employees should proactively use these resources and consider increasing their health savings contributions to mitigate the impact of medical inflation on their retirement savings.

If TIAA-CREF employees have further questions or need detailed information regarding their retirement benefits, what is the best way to contact TIAA-CREF for assistance? What resources are available through TIAA-CREF's communication channels to ensure employees have comprehensive support during their retirement planning process?

For TIAA-CREF employees seeking further assistance or detailed information regarding their retirement benefits, contacting TIAA-CREF through their dedicated support channels, including customer service lines and online portals, is advisable. Utilizing workshops, webinars, and one-on-one advisement can also provide comprehensive support and guidance in navigating retirement planning effectively.