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Expedia Group Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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Healthcare Provider Update: Expedia Group's Healthcare Provider Expedia Group primarily offers health benefits through a variety of healthcare providers, with specific partnerships often varying by location and employee choices. They typically utilize major insurers such as UnitedHealthcare, Aetna, and others, ensuring a broad range of options for their employees. Such partnerships supply a variety of plans catering to the needs of their diverse workforce. Potential Healthcare Cost Increases in 2026 As we look ahead to 2026, Expedia Group employees may face significant healthcare cost increases driven by a perfect storm of factors, including the anticipated expiration of enhanced subsidies under the Affordable Care Act (ACA). With some states projecting premium hikes exceeding 60%, the potential loss of these critical financial supports could result in average out-of-pocket costs spiking by 75% for many individuals. These rising costs are compounded by escalating medical expenses and aggressive rate hikes from major insurers, creating substantial financial challenges for both employees and retirees. As these shifts unfold, proactive healthcare budgeting and strategic planning become essential for employees to navigate the changing landscape effectively. Click here to learn more

'Expedia Group 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.

'Expedia Group 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.' Expedia Group 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. Expedia Group 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 Expedia Group 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 Expedia Group 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 Expedia Group 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 Expedia Group 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 Expedia Group 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 Expedia Group 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 plan does Expedia Group offer to its employees?

Expedia Group offers a 401(k) retirement savings plan to help employees save for their future.

Does Expedia Group match employee contributions to the 401(k) plan?

Yes, Expedia Group provides a matching contribution to employee 401(k) plans, subject to certain limits.

What is the eligibility criteria for participating in Expedia Group's 401(k) plan?

Employees of Expedia Group are generally eligible to participate in the 401(k) plan after completing a specified period of service.

How can employees at Expedia Group enroll in the 401(k) savings plan?

Employees can enroll in the Expedia Group 401(k) savings plan through the company’s HR portal or by contacting the HR department for assistance.

What investment options are available in Expedia Group's 401(k) plan?

Expedia Group offers a variety of investment options in its 401(k) plan, including mutual funds, target-date funds, and other investment vehicles.

Can employees at Expedia Group take loans against their 401(k) savings?

Yes, Expedia Group allows employees to take loans against their 401(k) savings, subject to the plan's rules and limits.

What is the vesting schedule for employer contributions in Expedia Group's 401(k) plan?

The vesting schedule for employer contributions at Expedia Group typically follows a graded vesting schedule, which employees can review in the plan documents.

How often can employees change their contribution amounts to the 401(k) plan at Expedia Group?

Employees at Expedia Group can change their contribution amounts to the 401(k) plan multiple times throughout the year, as allowed by the plan.

Does Expedia Group offer financial education resources for employees regarding their 401(k) plan?

Yes, Expedia Group provides financial education resources and tools to help employees make informed decisions about their 401(k) savings.

What happens to an employee's 401(k) savings if they leave Expedia Group?

If an employee leaves Expedia Group, they can choose to roll over their 401(k) savings to another retirement account, leave the funds in the current plan, or withdraw the funds, subject to applicable taxes and penalties.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
Expedia Group offers its employees a 401(k) plan and retirement savings options. Their 401(k) plan allows eligible employees to contribute pre-tax earnings, with the company providing a match for a portion of the contributions. According to the IRS limits, contributions in 2022 were capped at $20,500, in 2023 at $22,500, and in 2024 at $23,000​ (Wikipedia)​ (Wikipedia). Expedia's retirement plan is primarily a defined contribution plan rather than a traditional defined benefit pension plan​ (Wikipedia). Expedia employees become eligible for the 401(k) plan after meeting specific service requirements, and they can take advantage of company matching to boost their retirement savings​ (TIAA). For example, the plan may offer a match of up to 5% of salary depending on the employee’s contribution. Withdrawals from the plan without penalty are available after reaching the age of 59½, but hardship withdrawals are allowed under specific conditions, such as medical emergencies or home purchase
In 2023, Expedia Group announced a restructuring plan to streamline its operations and cut costs. This involved laying off around 10% of its workforce as part of an effort to improve operational efficiency and focus on its core businesses. The company cited the need to adapt to the changing travel industry landscape and economic pressures as reasons for these cuts.
Stock Option Acronym: SO Description: Expedia Group offers stock options to its employees as part of its compensation package. Stock options typically vest over a period of time, providing employees with the opportunity to purchase company stock at a predetermined price. Stock Option Availability: Available to a range of employees including executives and senior management. The options are often granted based on performance and tenure.
URL: Expedia Group Careers Details: Look for sections related to employee benefits or health insurance. The official site usually has the most current and accurate information. Glassdoor: URL: Glassdoor Expedia Group Benefits Details: Employee reviews and benefits information provided by current and former employees. Indeed: URL: Indeed Expedia Group Benefits Details: Insights from employee reviews about health benefits and other compensation aspects. LinkedIn: URL: LinkedIn Expedia Group Careers Details: Company profiles often include information about benefits and employee experiences. Forbes or Business Insider: URL: Search for relevant articles or news on Forbes or Business Insider Details: Look for any recent articles discussing Expedia Group’s health benefits or employee compensation updates.
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For more information you can reach the plan administrator for Expedia Group at , ; or by calling them at .

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