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University of Chicago Employees: Handling Single-Stock Concentration with a Section 351 Strategy

'University of Chicago employees with concentrated stock positions should understand that strategies like a Section 351 exchange can offer flexibility in managing large unrealized gains while preserving long-term planning options.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

'University of Chicago employees facing concentrated stock exposure may find that a Section 351 exchange provides an effective way to mitigate risk and maintain control over the timing of potential tax liabilities.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

When a Section 351 exchange can help diversify concentrated stock positions without an immediate tax bill.
The core eligibility rules (80% control test) and basis/step-up mechanics that drive tax deferral.
Sample case studies (James & Sarah) illustrating the numbers and outcomes.

The Strategic Potential of Section 351: An Analysis of a Multi-Stock Case in Tax-Deferred Reorganization

A sizable amount of the wealth of many high-earning professionals at University of Chicago may be invested in a small number of highly valued equities, including company shares accumulated through restricted stock units (RSUs), the employee stock purchase plan (ESPP), or equity awards earned due to long tenure. While rebalancing may seem out of reach due to the tax ramifications of selling these positions, investors can make tax-deferred contributions of appreciated assets to a new business entity through a Section 351 exchange. When an investor wants to manage several sizable, embedded gains at once, this tactic may be especially useful.

Think about James, a client with a $10 million portfolio. The value of one stock investment, which he purchased for $50,000, has increased to $1 million, or 10% of his total portfolio. At a long-term capital gains rate that can reach 23.8% for certain high-income taxpayers (20% maximum long-term capital gains rate plus the 3.8% Net Investment Income Tax), selling this position would result in a $950,000 capital gain and an estimated $226,100 tax bill. The amount available for reinvestment would be reduced by this tax.

Section 351(a) of the Internal Revenue Code provides: “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, no gain or loss shall be recognized.” Under Section 368(c), “control” generally means ownership of at least 80% of the voting power and 80% of each class of non-voting shares.

The transferor or transferors must own at least 80% of the new corporation’s stock right after the exchange to qualify for this treatment. This can be done for investors with sizable portfolios by joining a larger seeding group or acting as the principal seeder of a new entity.

In a Section 351 transaction, any built-in gains are preserved because the shareholder’s basis in the received stock typically carries over from the contributed property. If the shares are held until death, a step-up in basis under Section 1014 may eliminate the deferred gain.

Another client example involves Sarah, who has a $13 million portfolio. She owns two appreciated stocks:

Stock A: Originally $300,000, now worth $3 million.
Stock B: Initial cost basis $500,000, now worth $3 million.

At a long-term capital gains rate that can reach 23.8% for certain high-income taxpayers, the aggregate unrealized gain of $5.2 million would translate into an estimated tax of roughly $1,237,600 if sold today, which can constrain portfolio adjustments.

For employees of University of Chicago holding concentrated positions, taking part in a Section 351 exchange can reduce concentration risk and defer recognition of these gains without an immediate tax bill. If assets receive a step-up in basis at death, the deferred gain may be fully eliminated under current law, and deferral can provide flexibility in managing future tax obligations.

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Sources:

1. Internal Revenue Service. Revenue Ruling 2003-51 . Internal Revenue Bulletin 2003-21, 2003. PDF.

2. Friedel, David B., and Yaw O. Awuah. “ Sec. 351 Control Requirement: Opportunities and Pitfalls .” The Tax Adviser , 1 July 2014. Web.

3. Internal Revenue Service. “ Net Investment Income Tax (NIIT) .” IRS.gov , last reviewed 1 July 2025. Web.

4. Internal Revenue Service. Publication 551: Basis of Assets . December 2024 revision, posted 18 February 2025. PDF.

5. FINRA Investor Education Foundation (FINRA). “ Concentrate on Concentration Risk .” FINRA.org , 15 June 2022. Web.

What are the eligibility criteria for participation in the SEPP plan for employees of The University of Chicago, and how can factors like years of service and age impact an employee's benefits under this plan? Discuss how these criteria might have changed for new employees post-2016 and what implications this has for retirement planning.

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.

Can you elaborate on the spousal rights associated with the pension benefits under the SEPP plan at The University of Chicago? Discuss how marital status influences annuity payments and the required spousal consent when considering changes to beneficiary designations.

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.

How does The University of Chicago address benefits for employees upon their death, and what provisions exist for both spouses and non-spouse beneficiaries under the SEPP plan? Analyze the specific benefits and payment structures available to beneficiaries and the conditions under which these benefits are distributed.

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.

Discuss the impact of a Qualified Domestic Relations Order (QDRO) on the SEPP benefits for employees at The University of Chicago. How do divorce or separation proceedings influence pension benefits, and what steps should employees take to ensure compliance with a QDRO?

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.