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Casey's General Stores Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for Casey's General Stores Casey's General Stores utilizes The Retirement Group as its healthcare provider, which assists retirees and employees in navigating healthcare benefits and understanding changing healthcare costs. Potential Healthcare Cost Increases in 2026 As 2026 approaches, Casey's General Stores employees and retirees may face significant increases in healthcare costs, largely due to anticipated record hikes in Affordable Care Act (ACA) premiums. With some states predicting premium increases surpassing 60%, coupled with the expiration of enhanced federal subsidies, the potential for out-of-pocket expenses to climb by over 75% looms large. This perfect storm of rising medical expenses and regulatory changes could place additional financial strain on those relying on ACA plans, necessitating careful budgeting and planning to mitigate the impact of these changes. Click here to learn more

'Casey's General Stores employees with concentrated stock positions may benefit from thoughtful tax planning that allows for tax deferral while balancing liquidity, compliance, and long-term compounding,' Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'Casey's General Stores employees who hold highly-appreciated stock may want to consider tax-efficient strategies that help mitigate their liabilities while aligning with their overall retirement goals,' Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

How taxes can affect investment returns, particularly on concentrated stock positions.
Exchange funds and options-based strategies as methods for tax deferral and diversification.
Alternative planning techniques outside ETFs, including charitable trusts and gifting strategies.

By Carlos Hernandez, Wealth Enhancement advisor

When it comes to driving portfolio returns, many investors aim to keep management fees low by investing in low-cost index funds and exchange-traded funds (ETFs). While fees matter, however, the real culprit for lower-than-anticipated performance is taxes. ¹

Wealth Enhancement advisor Carlos Hernandez explains: 'By losing less to taxes each year, investors have access to more capital that can continue to compound over time. This makes tax deferral an important part of an effective financial plan.' Casey's General Stores employees looking for long-term growth strategies could benefit by understanding how to better manage their investment tax burdens.

Trade Money

One area where taxes can take a toll is on the sale of company stock or other concentrated investment positions. Casey's General Stores professionals looking to diversify could face significant capital gains taxes on an outright sale. One way to diversify without triggering immediate capital gains is through exchange funds. By contributing their highy-appreciated stock to a pooled fund, investors can trade their concentrated holdings for shares in a diverse basket of securities. This method can be used by Casey's General Stores employees who want to diversify while postponing taxable events.

Although this method allows for tax deferral, it also requires investors to hold the exchange fund for a period of time, typically seven years. ² This could create a challenge for investors who require liquidity. Additionally, these funds are often exclusively accessible to wealthy, accredited investors—something Casey's General Stores executives should carefully evaluate.

Funds Based on Options

Another way to mitigate taxes on the sale of highly-appreciated stock is by using options contracts. The idea is to hedge risk with put options while covering the cost of those puts by selling call options—a strategy called 'collaring'. From there, the strategy reverses, with investors selling put options and using the proceeds to buy call option on an equity or bond index. ³ If managed effectively, this helps to diversify a concentrated portfolio while still maintaining liquidity.

Given the complexity of this strategy, meticulous planning is necessary. It's generally recommended that investors work with an experienced financial advisor before pursuing this approach.

Things to Be Aware of

Although these strategies can be beneficial for Casey's General Stores employees who hold highly-appreciated stock, caution is recommended. There are costs associated with these approaches, and potential liquidity risks. Additionally, the IRS may eventually contest such arrangements because their tax status has not been thoroughly examined—something Casey's General Stores retirees should keep top of mind.

'Tax drag reduction strategies can be effective, but they must be assessed through the lens of risk, liquidity, cost, and compliance,' warns Carlos Hernandez. What is appealing in theory must hold up to inspection in the real world.

Alternative Strategies

Although they show promise, investors with highly-appreciated stock or those looking to postpone gains have other alternatives besides exchange funds or options. Other tactics could include:

- Prepaid variable forwards (subject to IRS regulations, contracts to sell at predetermined terms in the future).
- Charitable remainder trusts (CRTs), which allow investors to donate appreciated stock to a charitable trust and receive a stream of regular income in return.
- Donor-advised funds (DAFs), which provide investors with a tax deduction for the fair market value of the appreciated stock they donate.
- Other gifting techniques, such as direct donations to charity or family.
Each has its own set of guidelines, advantages, and disadvantages. To limit unnecessary taxes or violating the constructive sale regulations, careful planning is necessary for Casey's General Stores professionals managing complex portfolios.

The Bottom Line

Although the movement to mitigate the tax burden on investments is not new, the instruments are changing. Both exchange funds and options-based structures offer investors a way to manage tax liabilities, especially for Casey's General Stores employees who hold highly-appreciated stock.

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In the end, taxes are unavoidable. However, with the correct set of instruments, they can be controlled and postponed. 'The real value comes from aligning tax strategy with investment strategy,' summarizes Carlos Hernandez.

Sources:

1. BlackRock Advisor Center. ' Investing for After-Tax Returns ,' 2025.

2. Kiplinger. ' Four Clever and Tax-Efficient Ways to Ditch Concentrated Stock Holdings ,' by Robert Waskiewicz. Sep. 11, 2025.

3. Financial Planning Association. ' Tax-Efficient Ways to Diversify Concentrated Stock Positions ,' by Peter Lazaroff. Oct. 2024.

What type of retirement savings plan does Casey's General Stores offer to its employees?

Casey's General Stores offers a 401(k) retirement savings plan to help employees save for their future.

Is the 401(k) plan at Casey's General Stores available to all employees?

Yes, the 401(k) plan at Casey's General Stores is available to all eligible employees.

Does Casey's General Stores provide matching contributions to the 401(k) plan?

Yes, Casey's General Stores provides a matching contribution to the 401(k) plan, subject to certain conditions.

How can employees at Casey's General Stores enroll in the 401(k) plan?

Employees at Casey's General Stores can enroll in the 401(k) plan by completing the enrollment process through the company's HR portal.

What is the minimum age requirement to participate in Casey's General Stores' 401(k) plan?

The minimum age requirement to participate in Casey's General Stores' 401(k) plan is typically 21 years old.

Can employees at Casey's General Stores take loans against their 401(k) savings?

Yes, employees at Casey's General Stores may have the option to take loans against their 401(k) savings, depending on the plan's provisions.

What investment options are available in Casey's General Stores' 401(k) plan?

Casey's General Stores' 401(k) plan offers a variety of investment options, including mutual funds, target-date funds, and other investment vehicles.

How often can employees at Casey's General Stores change their 401(k) contribution amounts?

Employees at Casey's General Stores can typically change their 401(k) contribution amounts on a quarterly basis or as specified in the plan documents.

What is the vesting schedule for employer contributions in Casey's General Stores' 401(k) plan?

The vesting schedule for employer contributions in Casey's General Stores' 401(k) plan may vary, but employees usually become fully vested after a certain number of years of service.

Are there any fees associated with Casey's General Stores' 401(k) plan?

Yes, there may be administrative fees and investment-related fees associated with Casey's General Stores' 401(k) plan, which are disclosed in the plan documents.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.

Casey's General Stores recently announced a restructuring plan that includes a reduction in workforce and changes to employee benefits. The company is also revising its pension plan to address financial pressures.

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For more information you can reach the plan administrator for Casey's General Stores at One SE Convenience Blvd. Ankeny, IA 50021; or by calling them at +1 515-965-6100.