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Deckers Outdoor Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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'Deckers Outdoor 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.

'Deckers Outdoor 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.' Deckers Outdoor 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. Deckers Outdoor 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 Deckers Outdoor 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 Deckers Outdoor 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 Deckers Outdoor 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 Deckers Outdoor 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 Deckers Outdoor 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 Deckers Outdoor 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 401(k) plan offered by Deckers Outdoor?

The 401(k) plan at Deckers Outdoor is a retirement savings plan that allows employees to save a portion of their salary on a tax-deferred basis.

How can employees of Deckers Outdoor enroll in the 401(k) plan?

Employees can enroll in the Deckers Outdoor 401(k) plan by completing the enrollment process through the company’s HR portal or by contacting the HR department for assistance.

Does Deckers Outdoor offer a company match for the 401(k) contributions?

Yes, Deckers Outdoor offers a company match for employee contributions to the 401(k) plan, which helps employees grow their retirement savings.

What is the vesting schedule for the company match in Deckers Outdoor's 401(k) plan?

The vesting schedule for the company match at Deckers Outdoor typically follows a standard timeline, which may vary. Employees should refer to the plan documents for specific details.

Can employees of Deckers Outdoor change their contribution percentage to the 401(k) plan?

Yes, employees can change their contribution percentage to the Deckers Outdoor 401(k) plan at any time, subject to the plan’s guidelines.

What investment options are available in the Deckers Outdoor 401(k) plan?

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

When can employees of Deckers Outdoor start withdrawing from their 401(k) plan?

Employees can typically start withdrawing from their Deckers Outdoor 401(k) plan at age 59½, although there are specific rules and conditions that apply.

Are loans available against the 401(k) balance at Deckers Outdoor?

Yes, employees may be able to take loans against their 401(k) balance at Deckers Outdoor, subject to the plan’s terms and conditions.

What happens to the 401(k) plan if an employee leaves Deckers Outdoor?

If an employee leaves Deckers Outdoor, they have several options regarding their 401(k) plan, including rolling it over to another retirement account, cashing it out, or leaving it with Deckers Outdoor.

How does Deckers Outdoor communicate changes to the 401(k) plan?

Deckers Outdoor communicates changes to the 401(k) plan through official company emails, newsletters, and updates on the HR portal.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
Deckers Outdoor Employee Pension Plan Name of Pension Plan: Deckers Outdoor Corporation Pension Plan Years of Service and Age Qualification: Employees generally need at least 5 years of service to qualify for benefits. Age qualifications typically align with standard retirement ages (e.g., 65 years old). Pension Formula: Deckers Outdoor’s pension formula typically involves a defined benefit based on years of service and average salary. The formula may be calculated as a percentage of the employee’s average salary over the highest earning years multiplied by the number of years of service.
Restructuring Layoffs: In 2024, Deckers Outdoor Corporation has continued its strategy to optimize its workforce, reflecting a broader trend in the industry towards efficiency and cost management. Despite reporting strong financial performance, including a record Q2 revenue of $1.092 billion, the company has made adjustments to its workforce to align with long-term goals. These layoffs, though not publicly detailed in terms of numbers, are part of a strategic approach to maintain competitiveness and shareholder value in an uncertain economic climate.
For Deckers Outdoor, the company offers both stock options and Restricted Stock Units (RSUs) as part of its employee compensation package. Stock options at Deckers Outdoor (NYSE: DECK) give employees the right to purchase company shares at a predetermined price after a specific vesting period. RSUs, on the other hand, provide employees with company shares upon the completion of vesting conditions without requiring an upfront purchase. In 2022, 2023, and 2024, Deckers Outdoor has continued to utilize these equity compensation tools to attract and retain top talent. The stock options typically vest over several years, often linked to the employee’s tenure or performance milestones. RSUs are granted and become actual shares after a defined period, usually subject to the company's stock price performance or individual achievements. Employees eligible for these benefits at Deckers Outdoor include senior executives, key management personnel, and other employees identified as critical to the company's success. These equity awards are designed to align employee incentives with the company's long-term financial performance, ensuring that key personnel are motivated to contribute to the company's growth.
Health Insurance: Deckers provides comprehensive health insurance options that cover a variety of healthcare needs. This includes medical, dental, and vision coverage. The company also offers Health Savings Accounts (HSAs) and Flexible Spending Accounts (FSAs) to help employees manage their healthcare expenses more effectively. Mental Health Support: Recognizing the importance of mental well-being, Deckers offers free memberships to Headspace for all employees, along with an Employee Assistance Program (EAP) that provides mental health support. Additionally, virtual fitness classes are available to promote physical and mental wellness.
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For more information you can reach the plan administrator for Deckers Outdoor at 250 Coromar Dr Goleta, CA 93117; or by calling them at (805) 967-7611.

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