New Update: Healthcare Costs Increasing by Over 60% in Some States. Will you be impacted?

IAC Employees: Strategic Ways to Reduce Capital Gains 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 can benefit from understanding that strategies like a Section 351 exchange, charitable donations, and tax loss harvesting may work together to help manage appreciated stock efficiently while aligning with broader long-term financial goals.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

'IAC employees should recognize that thoughtful planning with tools such as Section 351 exchanges, gifting strategies, and tax loss harvesting can help them manage highly appreciated stock while supporting both personal and philanthropic objectives.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

How a Section 351 exchange can defer capital gains on highly appreciated stock.
Alternative tax-efficient strategies such as charitable donations, tax loss harvesting, and gifting.
The role of inheritance rules, step-up in basis, and combined approaches in long-term tax planning.

A Tax-Aware Q&A on How to Manage Highly Appreciated Stock

From the Section 351 exchange to other practical approaches, this Q&A addresses key considerations IAC employees may encounter when dealing with highly appreciated shares.

Section 351 Exchange: The Fundamental Approach

Q: What is an exchange under Section 351?
A: Under certain circumstances, an investor may transfer property, such as highly appreciated shares, to a company in exchange for its stock under a provision of the Internal Revenue Code that allows the deferral of capital gains or losses.

Q: What is the primary advantage of exchanging my appreciated stock through a Section 351 exchange?
A: The main advantage is tax deferral. Gains transferred to corporations may be postponed under Section 351, though this applies only if specific diversification requirements are met, especially when transferring to investment companies like exchange-traded funds (ETFs). ¹

Q: What is meant by the “Control Test”?
A: The investor or group of investors who use their portfolio assets to fund the new entity must own at least 80% of the voting power and 80% of the total number of shares of all other classes of stock in the new company immediately after the exchange. ¹

Q: When seeding an ETF, how is the Control Test usually satisfied?
A: It is typically satisfied by either a single substantial investor making a significant asset contribution or multiple investors pooling assets to create a seeding pool for the ETF’s launch.

Q: What is the ultimate tax payment date for the deferred gain?
A: The deferred gain is recognized when the ETF shares acquired through the exchange are sold; distributions from taxable funds must also be reported in the meantime.

Other Tax-Efficient Techniques

Q: What is a straightforward method, aside from a Section 351 exchange, to sell highly appreciated shares without incurring large taxes?
A: Donating shares directly to a qualified charity is one option that some IAC employees may benefit from.

Q: What tax advantages come with donating valuable stock to a charity?
A: Subject to holding period and adjusted gross income (AGI) limits, you can bypass capital gains taxes on the appreciation and may receive an income tax deduction for the stock’s full fair market value.

Q: What is a Donor-Advised Fund (DAF)?
A: A DAF allows you to donate appreciated stock, receive an immediate tax deduction, and then recommend grants to charities over time, while the assets in the DAF grow without tax impact. ²

Q: Can I give a family member my appreciated stock as a gift?
A: Yes. In most cases, the cost basis from the donor carries over to the recipient.

Q: Why would I give a family member in a lower tax bracket appreciated stock?
A: If they sell the stock, the lower income could result in a reduced capital gains rate, potentially as low as 0% for long-term gains. ³

Tax Loss Harvesting and Other Approaches

Q: What is harvesting tax losses?
A: Selling investments at a loss to offset gains from other sales is known as tax loss harvesting, a strategy sometimes considered by IAC employees seeking opportunities to leverage bouts of market volatility.

Q: Can I deduct a certain amount of loss from my regular income?
A: Yes. If your capital losses exceed your gains, you can use up to $3,000 per year ($1,500 if married filing separately) to offset ordinary income, with remaining losses carried forward indefinitely. ⁴

Q: What is a Qualified Opportunity Fund (QOF)?
A: A QOF provides investors with tax incentives for investing in tracts of land designated as 'opportunity zones'. Capital gains reinvested in a QOF within 180 days of being realized can be temporarily tax deferred, while QOF investments helpd for at least 10 years may confer a permanent capital gains exclusion. ⁵ That said, 2025 legislation changes may prompt IRS updates to this rule.

Inheritance and Step-Up in Basis

Q: What is meant by a “step-up in basis”?
A: This adjusts an inherited asset’s cost basis to its fair market value at the time of the owner’s death, eliminating capital gains accumulated during their lifetime. ⁶

Q: If I gift shares while living, will I receive a step-up in basis?
A: No. The original cost basis transfers to the recipient without adjustment.

Determining the Right Strategy

Q: What is the best course of action for me?
A: The most suitable approach will depend on factors such as your gain size, income level, charitable intentions, and liquidity needs.

Q: Do any of these strategies call for professional guidance?
A: Yes. Given the complexity of the tax code, working with a qualified financial advisor and tax professional is strongly recommended before implementing these strategies.

Q: Is it possible to combine these strategies?
A: Yes. For example, you might execute a Section 351 exchange on part of your portfolio for tax-deferred rebalancing while donating another portion to a DAF for an immediate deduction.

Q: Is there a loophole in the Section 351 exchange?
A: No. This is a legitimate tax code provision designed for corporate restructuring and adapted for use in the ETF market. It is intended for tax deferral, not permanent tax elimination.

Featured Video

Articles you may find interesting:

Sources:

1. Kitces. ' Using Section 351 Exchanges to Tax-Efficiently Reallocate Portfolios With Embedded Gains ,' by Ben Henry-Moreland and Brent Sullivan. 12 Mar. 2025.

2. Kiplinger. “ A Donor-Advised Fund Can Give Your Charitable Giving a Boost ,” by Samuel Gaeta. 9 May 2024.

3. Internal Revenue Service. “ Topic No. 409, Capital Gains and Losses .” IRS.gov , 8 July 2025.

4. Wealth Enhancement. ' 6 Essential Tax-Loss Harvesting Tips ,' by Jim Wiley. 6 April 2022.

5. Congressional Research Service. ' Tax Incentives for Opportunity Zones ,' by Donald Marples. 26 Apr. 2022.

6. Investopedia. “ Carryover Basis: What It Is, How It Works, Gift Taxes ,” by Julia Kagan. 16 Jan. 2023.

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).