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Cintas Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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Healthcare Provider Update: Healthcare Provider for Cintas: Cintas Corporation typically collaborates with various health insurance providers to offer employee benefits, but a specific single healthcare provider isn't disclosed in their publicly available information. Typically, large employers like Cintas may operate with several health insurance options, allowing employees to choose their preferred plans from major insurers. Potential Healthcare Cost Increases in 2026: As we approach 2026, Cintas may face substantial increases in healthcare costs, reflecting broader trends projected across the industry. Factors such as the impending expiration of enhanced federal premium subsidies and escalating medical costs could push premiums sharply higher, potentially affecting employee coverage and benefits. With many insurers reporting significant rate hikes-some exceeding 60%-companies like Cintas may need to strategically manage these financial pressures to maintain competitive employee offerings while safeguarding their bottom line. By proactively addressing these challenges, Cintas can better prepare for the potential financial implications of rising healthcare expenses in the upcoming year. Click here to learn more

'Cintas 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.

'Cintas 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:

  1. How taxes can affect investment returns, particularly on concentrated stock positions.

  2. Exchange funds and options-based strategies as methods for tax deferral and diversification.

  3. 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.' Cintas 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. Cintas 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 Cintas 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 Cintas 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 Cintas 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 Cintas 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 Cintas 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 Cintas 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 is the purpose of the Cintas 401(k) Savings Plan?

The Cintas 401(k) Savings Plan is designed to help employees save for retirement by allowing them to contribute a portion of their salary on a tax-deferred basis.

How can Cintas employees enroll in the 401(k) Savings Plan?

Cintas employees can enroll in the 401(k) Savings Plan through the company’s benefits portal or by contacting the HR department for assistance.

What types of contributions can Cintas employees make to the 401(k) Savings Plan?

Cintas employees can make pre-tax contributions, Roth (after-tax) contributions, and may also be eligible for employer matching contributions.

Is there a company match for contributions made to the Cintas 401(k) Savings Plan?

Yes, Cintas offers a company match on employee contributions, which helps employees save more for retirement.

What is the maximum contribution limit for the Cintas 401(k) Savings Plan?

The maximum contribution limit for the Cintas 401(k) Savings Plan is determined by IRS regulations, which can change annually. Employees should check the latest guidelines for the current limit.

When can Cintas employees start contributing to the 401(k) Savings Plan?

Cintas employees can typically start contributing to the 401(k) Savings Plan after completing their eligibility period, which is outlined in the employee handbook.

Can Cintas employees change their contribution percentage at any time?

Yes, Cintas employees can change their contribution percentage at any time through the benefits portal, subject to certain restrictions.

What investment options are available in the Cintas 401(k) Savings Plan?

The Cintas 401(k) Savings Plan offers a variety of investment options, including mutual funds, target-date funds, and other investment vehicles to suit different risk tolerances.

How often can Cintas employees review their investment choices in the 401(k) Savings Plan?

Cintas employees can review and adjust their investment choices in the 401(k) Savings Plan at any time, allowing them to align their investments with their retirement goals.

Are there any fees associated with the Cintas 401(k) Savings Plan?

Yes, there may be fees associated with managing the Cintas 401(k) Savings Plan, including administrative fees and investment fund expenses. Employees can review the fee structure 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.
Cintas offers a competitive benefits package that includes a pension plan and a 401(k) plan for its employees. The Cintas pension plan, named the "Cintas Retirement Plan," is available to employees who meet specific years of service and age qualifications, typically requiring several years of service and reaching a certain age threshold. The pension formula used in the Cintas Retirement Plan is based on years of service and final average pay. For the 401(k) plan, Cintas offers the "Partners' Plan," which includes a company match for employee contributions. Employees must be active and have completed at least 1,000 hours of service during the fiscal year to be eligible for the company match. The 401(k) plan allows employees to contribute pre-tax dollars, and Cintas provides additional catch-up contributions for employees aged 50 and above
ERISA Settlement: In 2023, Cintas settled a class-action lawsuit for $4 million, addressing allegations of excessive 401(k) plan fees and mismanagement. The settlement includes non-monetary relief, such as conducting a record-keeping review within five years. This is important due to current economic, investment, and political environments impacting employee retirement plans. 401(k) Plan Management: The company faced criticism for high-priced, actively-managed investment options and excessive recordkeeping fees, which led to a significant financial burden on plan participants. This news highlights the necessity for vigilance in managing employee benefits amidst fluctuating economic and political conditions
2022 Stock Options and RSUs Cintas Corporation offers stock options to its employees as part of its long-term incentive plan. The stock options, denoted as CTSO, typically vest over a four-year period. Employees are granted the option to purchase shares at a predetermined price, incentivizing long-term employment and performance. Restricted Stock Units (RSUs), referred to as CTRSU, are also awarded to employees, converting into shares upon vesting. Eligibility for these stock options and RSUs is determined by employee rank and performance metrics. 2023 Stock Options and RSUs In 2023, Cintas Corporation continued to provide stock options (CTSO) and RSUs (CTRSU) with slight modifications to the vesting schedule to align better with market practices. The RSUs vest over a three-year period, with one-third of the units vesting each year. Both the stock options and RSUs are designed to retain key talent and align employees' interests with shareholders. 2024 Stock Options and RSUs For 2024, Cintas Corporation has introduced performance-based RSUs (PCTRSU) alongside the existing stock options (CTSO) and RSUs (CTRSU). These performance-based RSUs vest based on the achievement of specific financial targets over a three-year period. This addition aims to enhance motivation by linking rewards more directly to the company's financial success. Eligibility remains based on job level and individual performance.
Cintas offers a comprehensive range of health benefits to its employees, aimed at promoting overall wellness and providing financial protection. Key benefits include medical, dental, and vision coverage, as well as health savings accounts (HSAs). The company emphasizes preventive care through initiatives like biometric screenings and the LiveWell program, which offers premium discounts for healthy behaviors. Notably, Cintas provides competitive pay and retirement plans alongside these health benefits, making it a rewarding workplace. Recent updates include adjustments in premium rates and expanded eligibility for wellness programs​
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For more information you can reach the plan administrator for Cintas at 6800 Cintas Blvd Mason, OH 45040; or by calling them at (513) 459-1200.

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