FAQs on RMDs: What Overstock.com Employees Need to Know

Healthcare Provider Update: Healthcare Provider for Overstock.com Overstock.com provides its employees with health insurance options through major insurers offering Affordable Care Act (ACA) plans, including well-known providers like UnitedHealthcare and Anthem. Potential Healthcare Cost Increases in 2026 In 2026, employees at Overstock.com are expected to face significant increases in healthcare costs, driven by anticipated premium hikes in the ACA marketplace. Projections indicate that some states might see premium increases exceeding 60%, exacerbated by the potential expiration of enhanced federal premium subsidies. As many employees may bear a larger share of healthcare expenses, it is crucial for Overstock.com workers to stay informed about their benefits and explore strategies to manage rising costs. The combination of inflated medical expenses and changing employer strategies could lead to a challenging healthcare landscape, stressing the importance of proactive financial planning. Click here to learn more

'RMDs may feel restrictive, but for Overstock.com employees they also create structured opportunities to rebalance portfolios, manage taxable income, and strengthen long-term planning.' – Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

'By treating RMDs as a planning tool rather than just a tax requirement, Overstock.com employees can use them to create flexibility in withdrawals and align retirement income with broader financial goals.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. Which retirement accounts are subject to RMDs and recent legislative changes.

2. Strategies that Overstock.com employees can use to manage the tax impact of RMDs.

3. How market conditions and long-term planning interact with RMD requirements.

By Wealth Enhancement Group's Brent Wolf

RMDs, or required minimum distributions, are a critical consideration for retirement income planning. Because they are required, they are sometimes seen as burdensome, but they also offer opportunities for careful money management. For Overstock.com employees, understanding how RMDs work and incorporating them into a broader strategy can help improve portfolio efficiency and mitigate long-term tax impacts.

Accounts Subject to RMDs

Traditional tax-deferred retirement accounts, which are funded with pre-tax contributions and grow tax-deferred, fall under RMD rules. These include SEP IRAs, 403(b) plans, 401(k) plans, 457 plans, and traditional IRAs. Once individuals reach a certain age, withdrawals are mandatory. Roth accounts stand out as exceptions. Roth IRAs remain permanently free of RMDs, while Roth 401(k) plans are also exempt under recent legislation. For Overstock.com workers nearing retirement, this exemption may enhance the role that Roth accounts can play as long-term planning tools, since assets can continue growing without taxable withdrawals.

Changing Ages for RMDs

The age at which retirees must begin taking RMDs has shifted in recent years. For decades, it was 70½. It later increased to 72, and then to the current age of 73. Beginning in 2033, the starting age will move again to 75. For Overstock.com retirees, these adjustments provide more flexibility and open a wider window to implement strategies such as Roth conversions, systematic withdrawals, or portfolio rebalancing before RMDs take effect.

Why RMDs Are Often Disliked

RMDs are unpopular among retirees who don't require the funds for their current living expenses because they trigger taxable income. This added income can push retirees into higher tax brackets, raising their overall tax burden. For Overstock.com employees with substantial retirement savings, RMDs can also affect Medicare costs through higher income-related monthly adjustment amount (IRMAA) surcharges. In many cases, RMDs represent a significant annual tax consideration for households.

Techniques to Manage RMDs

Although RMDs for traditional accounts cannot be fully eliminated, several approaches can help reduce their taxable impact:

• Pre-Retirement Diversification:  Spreading savings across Roth accounts, taxable brokerage accounts, and traditional retirement plans may lower future RMD obligations.

• The Early Retirement Window:  For those who stop working before 73, the years between retirement and the first RMD are often lower-income years—ideal for Roth conversions or accelerated withdrawals at more favorable tax rates.

• Qualified Charitable Distributions (QCDs):  Starting at 70½, IRA owners can direct RMD distributions directly to qualified charities, rather than taking them themselves, reducing taxable income while meeting RMD requirements and achieving charitable goals.

• Still Working Past 73:  Employees still working at Overstock.com after age 73 may be able to delay RMDs on their active employer plan.

• Legacy Planning:  Roth conversions, even after RMDs start, can lower the taxable inheritance left to beneficiaries, aiding in estate planning.

Market Conditions and RMDs

A common question is whether market downturns affect RMD amounts. The answer is no—RMDs are based on account balances as of December 31 of the prior year. Short-term fluctuations do not alter the required withdrawal. While Congress has occasionally suspended RMDs during crises, such as in the pandemic, these suspensions remain rare.

Turning RMDs Into Opportunities

Although RMDs are mandatory, they can be reframed as tools for portfolio management. By selling from overweighted positions, retirees can meet their RMD while also rebalancing. For Overstock.com retirees with large equity allocations, this may mean using withdrawals to trim stock-heavy portfolios in favor of diversification.

Additionally, funds withdrawn through RMDs need not sit idle. If not required for daily expenses, they can be reinvested into a Roth IRA (subject to eligibility) or taxable brokerage account. This reinvestment can help maintain long-term portfolio growth.

Conclusion

While RMDs are often viewed as mandatory tax obligations, Overstock.com employees can approach them strategically. Diversifying account types before retirement, making use of early retirement years, using QCDs, and considering Roth conversions all provide ways to manage the impact. When integrated into a broader financial plan, RMDs can serve as both compliance and opportunity—helping retirees sustain portfolio health, mitigate taxes, and extend financial growth into the future.

Custodians typically calculate RMD amounts and provide reminders, but the responsibility to take the correct distribution rests with the account holder. By anticipating these requirements and using them to rebalance or reinvest, Overstock.com retirees can approach RMDs as part of a proactive retirement strategy.

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Sources:

Internal Revenue Service.  Publication 590-B: Distributions from Individual Retirement Arrangements (IRAs).  U.S. Department of the Treasury, Mar. 19, 2025. pp. 6–7, 37.  https://www.irs.gov/publications/p590b

Myers, Elizabeth A.  Required Minimum Distribution (RMD) Rules for Original Owners of Retirement Accounts.  Congressional Research Service, 29 Aug. 2024. p. 1.  https://crsreports.congress.gov/product/pdf/IF/IF12750

Centers for Medicare & Medicaid Services.  Medicare Costs 2025.  CMS Product No. 11579, Dec. 2024. pp. 2–3.  https://www.cms.gov/newsroom/fact-sheets/2025-medicare-parts-b-premiums-and-deductibles

Social Security Administration.  Form SSA-44: Medicare Income-Related Monthly Adjustment Amount — Life-Changing Event.  SSA, Dec. 2024. pp. 1, 5–7.  https://www.ssa.gov/forms/ssa-44.pdf

Financial Industry Regulatory Authority.  Thinking About Rolling Over Funds From Your Thrift Savings Plan? Consider This.  FINRA, Nov. 2024. p. 2.  https://www.finra.org/investors/military/retirement/roll-over-tsp