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Tax Strategies for University of Chicago Employees With Concentrated Stock Positions

For University of Chicago employees who have experienced significant market appreciation, the thought of rebalancing their portfolio can be daunting. The large embedded capital gains in their holdings often create a powerful disincentive to sell, leading to a 'tax-locked' portfolio. While an investor may have a well-diversified portfolio on the whole, a single, highly appreciated stock can still represent an uncomfortable level of risk. In these situations, the conventional wisdom of simply selling the position is often prohibitively expensive from a tax perspective. However, a little-known but powerful tool—the Section 351 exchange—may offer a strategic and tax-efficient solution.

Consider Michael, a successful professional with a total investment portfolio of $5 million. The majority of his assets are in a broadly diversified mix of mutual funds and exchange traded funds (ETFs). However, his portfolio also includes a single stock position valued at $500,000, which he acquired years ago for $100,000. While this single stock represents only 10% of his total portfolio, its low cost basis and unrealized gain of $400,000 make him hesitant to sell. A sale would trigger a tax bill of roughly $95,200, reducing the capital available for reinvestment and diversification. Michael's situation is common; he understands the importance of diversification, but the tax cost of achieving it feels punitive.

This is precisely the kind of scenario where a Section 351 exchange can provide a strategic advantage. This tax provision, as outlined in the Internal Revenue Code, allows for a tax-deferred transfer of property to a corporation in exchange for its stock, provided certain conditions are met. As Kevin Landis, a finanial advisor with Wealth Enhancement notes, 'A Section 351 exchange could help investors with appreciated assets achieve tax-efficient diversification.'

The core of the strategy is rooted in the tax code itself. IRC Section 351(a) states: “No gain or loss shall be recognized if property is transferred to a corporation by one or more persons solely in exchange for stock in such corporation and immediately after the exchange such person or persons are in control (as defined in section 368(c)) of the corporation.” The gain is not eliminated, but deferred, as the investor's original cost basis carries over to the new corporate shares. This is a critical distinction from a traditional sale.

For the exchange to be valid, two main requirements must be satisfied:

Diversification: The portfolio being transferred must be diversified according to the IRS's 25/50 test. This means no single holding can represent more than 25% of the total value, and the top five holdings cannot exceed 50%. Since Michael's $500,000 single stock position is only 10% of his total $5 million portfolio, his entire portfolio passes this test.

Control: The investor must have at least 80% control of the newly formed corporation immediately following the exchange. In practice, this is often achieved by multiple 'seeding' investors transferring assets at the same time to establish an ETF, or by an investor with a significant enough portfolio acting as the primary seeder of a new fund.

By working with an ETF sponsor that facilitates these exchanges, Michael can transfer his entire $5 million portfolio into a newly formed ETF. He would receive ETF shares in return, and his $400,000 unrealized gain would not be taxed. Within the ETF wrapper, the fund manager could then sell Michael's single stock and reinvest the proceeds into other securities to align with the fund's mandate. Due to the in-kind creation and redemption process of ETFs, this internal rebalancing does not trigger a taxable event for Michael. He has successfully diversified away from his single-stock risk and preserved the full $500,000 of market value.

Tyson Mavar, a Senior Vice President and Financial Advisor with Wealth Enhancement, emphasizes the importance of a holistic approach to these complex strategies. 'For clients with significant embedded gains, the goal is always to optimize after-tax returns,' Mavar says. 'A Section 351 exchange is a prime example of a strategy that, when executed correctly, can help preserve capital that may otherwise be lost to taxes, allowing it to continue working for the client over the long term.'

While the benefits are clear, it's important to acknowledge the limitations. The number of ETFs currently accepting such exchanges is limited, and these funds may have higher expense ratios than their more established counterparts. There's also the risk of an inadvertent tax treatment failure if the rules are not strictly followed. However, for an investor like Michael, the ability to defer a substantial tax bill and gain immediate diversification makes the strategy compelling. It is a powerful tool for advisors to help their clients escape the 'tax-locked' state and realign their portfolios with their long-term financial goals.

Key Resources:

IRC Section 351(a): https://www.law.cornell.edu/uscode/text/26/351

IRS Treasury Regulation 1.351-1(c)(5): This regulation details the diversification test, often referred to as the 25/50 test, which is crucial for the strategy to be valid.

Kitces.com: 'Using Section 351 Exchanges To Tax-Efficiently Reallocate Portfolios' by Ben Henry-Moreland (March 12, 2025). This article provides a comprehensive overview of the strategy's mechanics and use cases.

Cambria Tax Aware ETF (Ticker: TAX): As one of the first ETFs to publicly announce the use of Section 351 exchanges, its prospectus and fund information offer a real-world example of the strategy in practice.

Longview Advantage ETF (Ticker: EBI): Another example of a new fund launched via Section 351, demonstrating the increasing adoption of this strategy by ETF sponsors.

Other ideas if you own a highly appreciated stock

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Articles you may find interesting:

- Donating highly appreciated stock to a public charity.

- Contributing appreciated stock to a Donor-Advised Fund (DAF).

- Gifting highly appreciated stock to a family member in a lower tax bracket.

- Upstream gifting of appreciated stock to an older family member for a step-up in basis.

- Using tax-loss harvesting to offset capital gains.

- Entering into a variable prepaid forward contract.

- Reinvesting capital gains into a Qualified Opportunity Fund (QOF).

- Holding the stock until death to receive a step-up in basis for heirs.

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Eligibility Criteria for SEPP: Employees at The University of Chicago become eligible to participate in the SEPP upon meeting age and service requirements: being at least 21 years old and completing one year of service. For employees hired after the plan freeze on October 31, 2016, these criteria have been crucial in determining eligibility for newer employees, impacting their retirement planning as they do not accrue benefits under SEPP beyond this freeze date.

In what ways does the SEPP (Staff Employees Pension Plan) benefit calculation at The University of Chicago reflect an employee's years of service and final average pay? Examine the formulas involved in the benefits determination process, including how outside factors such as Social Security compensation can affect the total pension benefits an employee receives at retirement.

Benefit Calculation Reflecting Service and Pay: The SEPP benefits are calculated based on the final average pay and years of participation, factoring in Social Security covered compensation. Changes post-2016 have frozen benefits accrual, meaning that current employees’ benefits are calculated only up to this freeze date, affecting long-term benefits despite continued employment.

How can employees at The University of Chicago expect their SEPP benefits to be paid out upon their retirement, especially in terms of the options between lump sum distributions and annuities? Analyze the advantages and disadvantages of each payment option, and how these choices can impact an employee's financial situation in retirement.

Payout Options (Lump Sum vs. Annuities): Upon retirement, employees can opt for a lump sum payment or annuities. Each option presents financial implications; lump sums provide immediate access to funds but annuities offer sustained income. This choice is significant for financial stability in retirement, particularly under the constraints post the 2016 plan changes.

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Spousal Rights in SEPP Benefits: Spouses have rights to pension benefits, requiring spousal consent for altering beneficiary arrangements under the SEPP. Changes post-2016 do not impact these rights, but understanding these is vital for making informed decisions about pension benefits and beneficiary designations.

As an employee nearing retirement at The University of Chicago, what considerations should one keep in mind regarding taxes on pension benefits received from the SEPP? Explore the tax implications of different types of distributions and how they align with current IRS regulations for the 2024 tax year.

Tax Considerations for SEPP Benefits: SEPP distributions are taxable income. Employees must consider the tax implications of their chosen payout method—lump sum or annuities—and plan for potential tax liabilities. This understanding is crucial, especially with the plan’s benefit accrual freeze affecting the retirement timeline.

What resources are available for employees of The University of Chicago wishing to understand more about their retirement benefits under SEPP? Discuss the types of information that can be requested from the Benefits Office and highlight the contact methods for obtaining more detailed assistance.

Resources for Understanding SEPP Benefits: The University provides resources for employees to understand their SEPP benefits, including access to the Benefits Office for personalized queries. Utilizing these resources is essential for employees, especially newer ones post-2016, to fully understand their retirement benefits under the current plan structure.

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Posthumous Benefits: The SEPP includes provisions for spouses and non-spouse beneficiaries, detailing the continuation or lump sum payments upon the death of the employee. Understanding these provisions is crucial for estate planning and ensuring financial security for beneficiaries.

What factors ensure an employee remains fully vested in their pension benefits with The University of Chicago, and how does the vesting schedule affect retirement planning strategies? Consider the implications of not fulfilling the vesting criteria and how this might influence decisions around employment tenure and retirement timing.

Vesting and Retirement Planning: Vesting in SEPP requires three years of service, with full benefits contingent on meeting this criterion. For employees navigating post-2016 changes, understanding vesting is crucial for retirement planning, particularly as no additional benefits accrue beyond the freeze date.

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Impact of QDROs on SEPP Benefits: SEPP complies with Qualified Domestic Relations Orders, which can allocate pension benefits to alternate payees. Understanding how QDROs affect one’s benefits is crucial for financial planning, especially in the context of marital dissolution.

How can employees at The University of Chicago, who have questions about their benefits under the SEPP plan, effectively communicate with the Benefits Office for clarity and assistance? Specify the various communication methods available for employees and what kind of information or support they can expect to receive.

Communicating with the Benefits Office: Employees can reach out to the Benefits Office via email or phone for detailed assistance on their SEPP benefits. Effective communication with this office is vital for employees to clarify their benefits status, particularly in light of the post-2016 changes to the plan.