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IAC Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for IAC IAC, officially known as IAC/InterActiveCorp, is known for its diverse portfolio of subsidiaries across various industries, including media, technology, and telecommunications. The primary healthcare provider associated with IAC is UnitedHealthcare, which is the health insurance division of UnitedHealth Group. UnitedHealthcare provides a range of healthcare plans and services, including individual and family coverage through platforms such as the Affordable Care Act (ACA) marketplace. --- Potential Healthcare Cost Increases in 2026 As the healthcare landscape evolves, significant premium hikes are expected for ACA marketplace plans in 2026, with some states reporting increases exceeding 60%. This surge in costs is attributed to rising medical expenses, the potential expiration of enhanced federal subsidies, and aggressive rate hikes from major insurers like UnitedHealthcare. A staggering 92% of policyholders may face an out-of-pocket increase of over 75% if subsidies are not renewed, highlighting a challenging financial outlook for millions relying on affordable healthcare options. It's essential for consumers to be proactive in managing their healthcare decisions amidst this anticipated landscape. Click here to learn more

'IAC 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.

'IAC 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.' IAC 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. IAC 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 IAC 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 IAC 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 IAC 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 IAC 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 IAC 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 IAC 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 IAC 401(k) plan?

The IAC 401(k) plan is a retirement savings plan that allows employees to save a portion of their paycheck before taxes are taken out, helping them prepare for retirement.

How can I enroll in the IAC 401(k) plan?

Employees can enroll in the IAC 401(k) plan by accessing the enrollment portal through the company’s HR website or by contacting the HR department for assistance.

Does IAC offer a matching contribution for the 401(k) plan?

Yes, IAC provides a matching contribution to the 401(k) plan, which helps employees maximize their retirement savings.

What is the eligibility requirement to participate in the IAC 401(k) plan?

Employees are generally eligible to participate in the IAC 401(k) plan after completing a specific period of service, as outlined in the plan documents.

What types of investment options are available in the IAC 401(k) plan?

The IAC 401(k) plan offers a variety of investment options, including mutual funds, target-date funds, and other investment vehicles to help employees diversify their savings.

Can I change my contribution rate to the IAC 401(k) plan?

Yes, employees can change their contribution rate to the IAC 401(k) plan at any time by accessing their account online or contacting HR.

What happens to my IAC 401(k) account if I leave the company?

If you leave IAC, you have several options for your 401(k) account, including rolling it over to a new employer’s plan or an individual retirement account (IRA).

Are there any fees associated with the IAC 401(k) plan?

Yes, there may be administrative fees and investment-related fees associated with the IAC 401(k) plan, which are detailed in the plan documents.

How can I access my IAC 401(k) account information?

Employees can access their IAC 401(k) account information through the online portal provided by the plan administrator.

What is the vesting schedule for IAC's matching contributions?

The vesting schedule for IAC's matching contributions is outlined in the plan documents, and it typically requires employees to work for a certain number of years before fully owning the match.

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

Pension Plan: Since IAC does not have a traditional pension plan, this section is not applicable. 401(k) Plan: Employees are generally eligible for the 401(k) plan if they have completed 30 days of service. Specific eligibility details such as age or years of service for the 401(k) plan are not explicitly outlined, but employees must be employed at the time of plan entry.

Restructuring and Layoffs: In early 2024, IAC announced a significant restructuring plan aimed at streamlining its operations and improving efficiency. This move involves laying off approximately 15% of its workforce across various divisions. The decision is part of a broader strategy to refocus the company’s resources on core businesses and enhance profitability. The restructuring is being closely watched as it reflects IAC's response to economic pressures and evolving market demands. This is crucial to understand given the current economic volatility and potential impacts on job security and company performance. Changes to Benefits and Retirement Plans: IAC has also revised its employee benefits and retirement plans as part of the restructuring. The company has updated its 401(k) match program and introduced new guidelines for pension contributions. These changes aim to align benefits with the company’s revised financial strategy and address recent tax reforms affecting corporate pensions. Understanding these changes is important for employees and investors, as they reflect broader trends in corporate benefit adjustments amid economic uncertainties and regulatory shifts.

Stock Options and RSUs: IAC typically grants stock options and RSUs to key employees and executives. Stock options allow employees to purchase IAC stock at a set price, often with a vesting schedule. RSUs are granted as shares of IAC stock that vest over time or upon achieving certain performance targets. Eligibility: Stock options and RSUs at IAC are generally available to senior management, key personnel, and high-performing employees. The specific terms of these grants vary based on the employee’s role and tenure at the company.

IAC provides comprehensive healthcare benefits including medical, dental, and vision coverage. They offer plans through major providers, with a focus on flexibility and employee choice. The company also includes mental health resources and wellness programs. Terms and Acronyms: PPO (Preferred Provider Organization), HSA (Health Savings Account), FSA (Flexible Spending Account), EAP (Employee Assistance Program).