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DISH Network Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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Healthcare Provider Update: DISH Network Healthcare Provider and Cost Projections for 2026 DISH Network provides healthcare benefits to its employees through Cigna. As for the healthcare landscape moving into 2026, significant increases in costs are anticipated for many American consumers and employers. Health insurance premiums for Affordable Care Act (ACA) marketplace plans are expected to rise sharply, with projected hikes averaging around 20%, and some states nearing 66%. Contributing factors include the expiration of enhanced federal premium subsidies and the ongoing rise in medical expenses due to inflation and increased utilization of healthcare services. Consequently, a substantial portion of the population could face out-of-pocket premium increases exceeding 75%, making effective budgeting and proactive healthcare strategies essential for managing these impending costs. Click here to learn more

'DISH Network 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.

'DISH Network 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.' DISH Network 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. DISH Network 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 DISH Network 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 DISH Network 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 DISH Network 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 DISH Network 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 DISH Network 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 DISH Network 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 savings plan does DISH Network offer to its employees?

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

Does DISH Network provide any matching contributions to the 401(k) plan?

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

What is the eligibility requirement to participate in DISH Network's 401(k) plan?

Employees at DISH Network are eligible to participate in the 401(k) plan after completing a specified period of service, typically within the first year of employment.

Can employees at DISH Network choose how much they want to contribute to their 401(k) plan?

Yes, DISH Network allows employees to choose their contribution percentage, up to the IRS annual limit.

What investment options are available in DISH Network's 401(k) plan?

DISH Network's 401(k) plan includes a variety of investment options, such as mutual funds, target-date funds, and other investment vehicles.

How often can employees change their contribution amount in DISH Network's 401(k) plan?

Employees at DISH Network can change their contribution amount at any time, typically through the online benefits portal.

Is there a vesting schedule for DISH Network's matching contributions in the 401(k) plan?

Yes, DISH Network has a vesting schedule for matching contributions, which means employees must work for a certain period before they fully own those contributions.

Can DISH Network employees take loans against their 401(k) savings?

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

What happens to the 401(k) plan if an employee leaves DISH Network?

If an employee leaves DISH Network, they can choose to roll over their 401(k) balance to another retirement account, cash out, or leave the funds in the DISH Network plan if eligible.

Does DISH Network offer financial education resources for employees regarding their 401(k) plan?

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

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
DISH Network offers a comprehensive 401(k) plan to its employees, focusing on flexibility and growth. The plan allows employees to contribute between 1% and 50% of their eligible pay, with the company providing a 50% match on contributions up to $5,000 annually. In addition to this, DISH Network may offer profit-sharing contributions, decided annually by the Board of Directors, which could significantly boost retirement savings. Eligibility for the 401(k) plan requires employees to be at least 19 years old and to have completed 90 days of service. Employees are automatically enrolled with a 3% contribution to a Target Date Freedom Fund unless they choose to opt out. The vesting for company contributions and profit-sharing increases by 20% annually, achieving full ownership after five years of service. DISH Network's pension offerings include profit-sharing, which directly contributes to the 401(k) account, rather than a separate pension plan. There is no separate traditional pension plan mentioned; rather, the focus is on 401(k) contributions and profit-sharing, indicating that the company's retirement benefits are structured to maximize tax-advantaged savings through these defined contribution plans.
Layoffs and Restructuring: In 2023, DISH Network continued its restructuring efforts, which began in 2020, resulting in several rounds of layoffs. These actions are part of DISH’s broader strategy to reduce operational costs amid declining business performance and increasing debt levels. As of mid-2023, the company had laid off approximately 3,000 employees. DISH Network is also under financial pressure due to its costly expansion of the 5G wireless network and has been considering a merger with EchoStar to address these challenges. The impact of these layoffs is significant given the broader economic and investment environment, as the company’s financial instability could have long-term consequences on its workforce and operations. This news is crucial to monitor because of the ongoing economic uncertainty, rising interest rates, and potential implications for DISH’s debt refinancing​
DISH Network offers stock options and Restricted Stock Units (RSUs) to its employees as part of its compensation package. Specifically, in 2023, DISH Network granted significant equity awards to key executives, including stock options and RSUs with vesting periods designed to retain top talent. For example, Mr. Hamid Akhavan, the newly appointed CEO, received an annual award of 750,000 RSUs with a one-year vesting period and a one-time award of 2,000,000 stock options with three-year ratable vesting. Similarly, other executives like Mr. John W. Swieringa, received 500,000 stock options and 200,000 RSUs, each with a five-year ratable vesting beginning in 2025. These stock options and RSUs are typically made available to senior executives and key management personnel at DISH Network. The terms of these equity awards, including vesting schedules and eligibility, are outlined in the company’s SEC filings, such as the 10-K Annual Report and specific 8-K filings related to executive compensation agreements.
DISH Medical Plan (DMP): The primary health insurance plan offered by DISH, which includes a range of healthcare services, preventive care, and access to prescription drugs through OptumRx. Health Savings Account (HSA): Employees can contribute to an HSA, which DISH supplements with free contributions, allowing for tax-advantaged savings for medical expenses. Flexible Spending Accounts (FSA): These include a Health Care FSA, Dependent Care FSA, and Transportation FSA, offering employees additional ways to manage and save on healthcare and related expenses. Employee Assistance Program (EAP): Provides confidential support for various personal and work-related issues, including mental health, with up to five free counseling sessions per issue per year.
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For more information you can reach the plan administrator for DISH Network at 9601 S Meridian Blvd Englewood, CO 80112; or by calling them at (303) 723-1000.

https://www.thelayoff.com/dish?page=2#google_vignette https://www.kiplinger.com/taxes/tax-planning/604591/net-unrealized-appreciation-a-hidden-tax-strategy https://retirement.tips/blog/net-unrealized-appreciation-nua-explained/ https://fortunefinancialadvisors.com/business-retirement-plans/introduction-to-nua-a-tax-saving-strategy/ https://cordcuttersnews.com/dish-is-reportedly-issuing-another-round-of-layoffs-as-cord-cutting-grows-5g-focus/ https://www.nerdwallet.com/article/finance/layoffs-2024 https://kpmg.com/us/en/home/insights/2023/11/tnf-notice-2023-75-pension-plans-cost-of-living-adjustments-2024.html https://www.401kmaneuver.com/5-major-changes-coming-to-your-401k-in-2024/ https://last10k.com/sec-filings/dish/0001558370-24-004386.htm https://www.sec.gov/Archives/edgar/data/1001082/000110465923088624/tm2323111d3_425.htm https://www.principal.com/ https://www.fidelity.com/ https://www.independentactuaries.com/2024-plan-limits/ https://www.milliman.com/en/insight/2023-lump-sums-defined-benefit-plans-much-lower-as-interest-rates-rise https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-defined-benefit-plan-benefit-limits

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