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Booking Holdings Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for Booking Holdings Booking Holdings does not operate a single healthcare provider but typically offers its employees access to a variety of healthcare options, including employer-sponsored health plans that may consist of multiple insurers. Their healthcare plans usually allow employees to choose from a network of providers, which may include large insurers like UnitedHealthcare, Anthem, and Aetna, depending on the specific offerings in different locations. Potential Healthcare Cost Increases in 2026 As Booking Holdings prepares for 2026, employees should brace for potentially significant increases in healthcare costs. With anticipated record hikes in Affordable Care Act (ACA) premiums-some states projecting raises of over 60%-financial pressure on employees may surge. The expiration of enhanced federal premium subsidies combined with ongoing medical inflation, particularly in pharmaceuticals and hospital services, could lead to out-of-pocket costs rising dramatically. In this landscape, employees must proactively assess their healthcare options to mitigate these rising expenses. Click here to learn more

'Booking Holdings 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.

'Booking Holdings 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.' Booking Holdings 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. Booking Holdings 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 Booking Holdings 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 Booking Holdings 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 Booking Holdings 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 Booking Holdings 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 Booking Holdings 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 Booking Holdings 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 Booking Holdings offer to its employees?

Booking Holdings offers a 401(k) retirement savings plan to its employees.

Does Booking Holdings provide matching contributions for its 401(k) plan?

Yes, Booking Holdings provides matching contributions to eligible employees participating in the 401(k) plan.

What is the eligibility requirement for Booking Holdings employees to participate in the 401(k) plan?

Employees of Booking Holdings are typically eligible to participate in the 401(k) plan after completing a specified period of employment.

Can employees at Booking Holdings choose how their 401(k) contributions are invested?

Yes, employees at Booking Holdings can choose from a variety of investment options for their 401(k) contributions.

What is the maximum contribution limit for employees participating in Booking Holdings' 401(k) plan?

The maximum contribution limit for employees in Booking Holdings' 401(k) plan is determined by IRS guidelines, which can change annually.

How often can employees at Booking Holdings change their 401(k) contribution amounts?

Employees at Booking Holdings can typically change their 401(k) contribution amounts on a quarterly basis or as specified in the plan details.

Is there a vesting schedule for the employer match in Booking Holdings' 401(k) plan?

Yes, Booking Holdings has a vesting schedule for the employer match, which determines when employees fully own the matched contributions.

Can employees take loans against their 401(k) savings at Booking Holdings?

Yes, Booking Holdings allows employees to take loans against their 401(k) savings, subject to specific terms and conditions.

What happens to my 401(k) savings if I leave Booking Holdings?

If you leave Booking Holdings, you have several options regarding your 401(k) savings, including rolling it over into another retirement account or cashing it out, subject to taxes and penalties.

Does Booking Holdings allow for after-tax contributions to the 401(k) plan?

Yes, Booking Holdings allows for after-tax contributions in addition to pre-tax contributions within the 401(k) plan.

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

Booking Holdings announced a restructuring plan that includes significant layoffs. The company is streamlining its operations to reduce costs amid a challenging economic environment.

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For more information you can reach the plan administrator for Booking Holdings at 800 Connecticut Ave Norwalk, CT 6854; or by calling them at +1 203-299-8000.