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Kemper Employees: Strategic Ways to Reduce Capital Gains on Appreciated Stock

Healthcare Provider Update: Kemper Healthcare Provider: Kemper provides health insurance through its partnerships with various insurers. Notably, they collaborate with larger health insurance companies in the industry, and specific healthcare provider information can vary by state and plan. It's essential for policyholders to check with Kemper directly or refer to their policy documentation for the most accurate healthcare provider details pertinent to their coverage. Healthcare Cost Increases in 2026: As we approach 2026, health insurance premiums across the ACA marketplace are forecasted to reach unprecedented levels, marked by increases that may exceed 60% in certain markets. The convergence of rising medical costs, potential loss of federal subsidies, and aggressive rate hikes from major insurers creates a challenging landscape for consumers. With estimates suggesting that more than 22 million ACA enrollees may face out-of-pocket premium spikes of over 75%, stakeholders are urged to consider proactive strategies for managing their healthcare expenses. Importantly, the anticipated substantial premium increases necessitate careful planning and evaluation during the upcoming open enrollment period. Click here to learn more

'Kemper 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.

'Kemper 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 Kemper 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 Kemper 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 Kemper 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.

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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 purpose of Kemper's 401(k) plan?

The purpose of Kemper's 401(k) plan is to help employees save for retirement by allowing them to contribute a portion of their salary on a pre-tax or Roth after-tax basis.

How can employees enroll in Kemper's 401(k) plan?

Employees can enroll in Kemper's 401(k) plan by accessing the company's benefits portal during the enrollment period or by contacting the HR department for assistance.

Does Kemper offer a company match for 401(k) contributions?

Yes, Kemper offers a company match for 401(k) contributions, which helps employees increase their retirement savings.

What types of investment options are available in Kemper's 401(k) plan?

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

Can employees change their contribution rate to Kemper's 401(k) plan?

Yes, employees can change their contribution rate to Kemper's 401(k) plan at any time, subject to the plan’s guidelines.

What is the vesting schedule for Kemper's 401(k) company match?

The vesting schedule for Kemper's 401(k) company match typically follows a graded vesting schedule, which means employees earn ownership of the match over a period of time.

Are there any fees associated with Kemper's 401(k) plan?

Yes, like many retirement plans, Kemper's 401(k) plan may have administrative fees and investment-related expenses, which are disclosed in the plan documents.

How often can employees access their 401(k) account information at Kemper?

Employees can access their 401(k) account information at Kemper any time through the online benefits portal or by contacting the plan administrator.

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

If you leave Kemper, you have several options for your 401(k), including rolling it over to an IRA, transferring it to a new employer's plan, or cashing it out, subject to taxes and penalties.

Can employees take loans against their Kemper 401(k) plan?

Yes, Kemper allows employees to take loans against their 401(k) plan, subject to specific terms and conditions outlined in the plan documents.

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 Name: Kemper's pension plan is known as the "Kemper Pension Plan". Pension Formula: The pension formula includes a defined benefit based on years of service and average salary. For Kemper, the formula is generally expressed as a percentage of the employee’s average salary multiplied by years of service. Years of Service and Age Qualification: To qualify for the pension plan, employees typically need a minimum of 5 years of service and must be at least 55 years old. Specific qualifications may vary. 401(k) Plan Name: The 401(k) plan offered by Kemper is known as the "Kemper 401(k) Plan". Eligibility: Employees are generally eligible to participate in the 401(k) plan after completing 30 days of employment. Kemper offers various investment options and may provide company matching contributions.

Restructuring Layoffs: In early 2024, Kemper announced significant restructuring efforts due to ongoing economic pressures and a need to streamline operations. The company plans to reduce its workforce by approximately 10% as part of this restructuring. This move is intended to enhance operational efficiency and adapt to the changing insurance market dynamics. The decision reflects broader trends in the industry where companies are realigning their resources to better cope with current economic conditions. Company Benefit Changes: Alongside layoffs, Kemper is also revising its employee benefits structure. The company is scaling back on certain benefits and altering pension plans to align with its new financial strategies. These changes come in response to the increasing costs associated with employee benefits and a need to reallocate resources to critical business areas. It’s crucial to monitor such developments as they can significantly impact employees’ financial planning, especially in light of current economic and investment uncertainties.

Kemper offers stock options and RSUs to its employees as part of its compensation package. For 2022, Kemper provided stock options and RSUs based on performance and tenure, detailed in the company's annual report (Page 45). In 2023, Kemper continued offering similar options with updated terms for new and existing employees (Page 52). For 2024, Kemper adjusted the stock options and RSU grants to align with market conditions and company performance (Page 57).

Health Insurance: Kemper offers a variety of health insurance plans, including PPO and HMO options. Benefits typically include coverage for preventive care, emergency services, hospitalization, and prescription drugs. Health Savings Account (HSA): Employees enrolled in high-deductible health plans may be eligible for an HSA, which allows pre-tax contributions to save for qualified medical expenses. Flexible Spending Account (FSA): Kemper provides an FSA option for employees to use pre-tax dollars for eligible healthcare expenses. Employee Assistance Program (EAP): Offers confidential support for personal and work-related issues, including mental health services.