Financial Matters

Concentrated Stock Positions: Considerations for Corporate Executives

Building wealth through investments is a fundamental goal for many individuals, and the stock market offers an avenue to achieve that objective. Corporate executives can receive a significant portion of their compensation in the form of equity, such as stock options, restricted stock units (RSUs), or company shares. While equity compensation can be a valuable component of the overall compensation package, it can also lead to concentrated stock positions in an investment portfolio.

Understanding Concentrated Stock Positions

A concentrated stock position occurs when a large percentage of an investment portfolio, often defined as 10% or greater, consists of shares from a single company. Particularly for corporate executives, this concentration can arise from receiving equity compensation over time, exercising stock options, or simply holding onto company shares due to a strong belief in the company’s prospects. While having faith in a company’s growth potential may be admirable, it is essential to recognize the potential implications of a concentrated stock position on one’s financial well-being.

Potential Benefits

Holding a significant stake in an employer’s company can align one’s financial interests with those of the organization, strengthening the commitment to achieving corporate objectives and driving performance. If the company performs well and its stock price appreciates, the concentrated stock position could lead to substantial wealth accumulation over time. Equity compensation often comes with favorable tax treatment, such as long-term capital gains tax rates for incentive stock options or stock held for more than one year. This can enhance the after-tax returns on one’s investments. While investors who recognize a company’s growth prospects may find themselves rewarded, the risks of a concentrated stock position may outweigh the benefits.

Risks and Challenges

Concentration Risk

Concentrated stock positions lack diversification, exposing one to significant concentration risk if an employer’s stock underperforms or experiences volatility. The stock market is inherently volatile, and even the most successful companies can experience fluctuations in their stock prices. As such, a downturn in the company’s stock price could have a disproportionate impact on an investment portfolio. From a different perspective, concentration risk also presents an opportunity cost. Opportunity cost refers to the potential benefits or returns an investor forgoes by maintaining a large allocation of their portfolio in a single stock, meaning one’s portfolio may not be participating in other investments that are performing well compared to their concentrated position.

Company Constraints

Concentrated stock positions can limit the ability to access funds when needed, especially if the company prohibits or restricts the sale of its stock during certain periods. Trading restrictions and company restraints are common practices imposed on corporate executives who receive equity compensation to ensure compliance with regulatory requirements and protect the interests of the company and its shareholders. These restrictions govern when and how executives can buy or sell company stock, preventing potential conflicts of interest, insider trading, and market manipulation. Navigating these moving parts, including complex plan documents, can be difficult.

Blackout Periods: Blackout periods are specific periods during which executives are prohibited from trading company stock. These blackout periods typically coincide with the release of material non-public information (MNPI), such as quarterly earnings reports, mergers and acquisitions, or other significant corporate events. The purpose of blackout periods is to prevent executives from trading on privileged information that could give them an unfair advantage over other investors.

Insider Trading Policies: Companies often have insider trading policies in place that outline the rules and regulations governing the buying and selling of company stock by corporate executives and other insiders. Insider trading policies typically prohibit executives from trading company stock while in possession of MNPI or disclosing MNPI to others for trading purposes. Executives may be required to pre-clear any trades of company stock with the company’s legal or compliance department to ensure compliance with insider trading regulations.

Rule 10b5-1 Trading Plans: Rule 10b5-1 trading plans are pre-established trading plans that allow corporate executives to buy or sell company stock on a predetermined schedule. These plans are established when executives do not have access to MNPI, and trades are executed according to the predetermined schedule, providing a safe harbor from insider trading allegations.  Through the consistent execution of trades outlined in the trading plan, insiders can gradually reduce their exposure to the concentrated stock position without being influenced by short-term market fluctuations or personal biases.

Vesting and Holding Periods: Equity compensation, such as stock options, restricted stock units (RSUs), or performance shares, often come with vesting schedules that dictate when executives can exercise or sell their shares. Additionally, companies may impose holding periods that require executives to retain ownership of a certain percentage of their vested shares for a specified period before they can be sold. Vesting and holding periods encourage executives to maintain a long-term perspective and align their interests with those of shareholders.

Tax Considerations

Various types of equity awards, such as stock options, restricted stock units (RSUs), and stock appreciation rights (SARs), are subject to different tax treatments. The timing of taxation for equity awards can vary depending on factors like vesting schedules and exercise or settlement dates. The alternative minimum tax (AMT) may apply when exercising incentive stock options (ISOs). The AMT calculation adds back certain tax preferences, including the bargain element of exercised ISOs, which can result in higher tax liabilities compared to regular income tax calculations. RSUs are typically taxed as ordinary income upon vesting, based on the fair market value of the shares on the vesting date. Understanding the holding period and cost basis of the shares is crucial for determining the appropriate capital gains tax rate and optimizing tax efficiency. If one has accumulated many shares of employer stock over time, there could be substantial unrealized capital gains to evaluate.

Career Risk

When a significant portion of one’s wealth is tied to a single company, adverse events such as poor financial performance, leadership changes, or industry downturns can not only erode the value of their investment portfolio but also jeopardize their job security and future prospects within the company. Executives and employees with concentrated stock positions may face pressure to deliver strong financial results to support the stock price and investor confidence. In extreme cases, prolonged declines in the company’s stock price could lead to job loss, diminished career opportunities, and financial hardship, highlighting the importance of diversification and risk management in mitigating career risk associated with concentrated stock positions.

Mitigating Risks

For a corporate executive with concentrated stock, implementing long-term diversification strategies can be crucial to managing concentration risk, protecting wealth, and gaining liquidity. We believe a well-diversified portfolio contains a broad range of asset classes, where no single stock comprises more than a few percentage points of the total portfolio. A prudent approach involves gradual diversification over time, balancing the need to reduce exposure to single-stock volatility while maximizing the potential benefits of holding company shares. Executives can establish a systematic plan to diversify their holdings by setting predetermined milestones or triggers for selling shares, such as reaching specific price targets, vesting schedules, or time intervals. By gradually selling shares and reinvesting proceeds into a diversified portfolio of assets, one may be able to achieve a more balanced and resilient portfolio over the long term.

In crafting a diversification strategy, one should remove emotion from their decision-making process, focusing instead on objective analysis and adherence to predetermined goals and risk parameters. We believe this disciplined approach becomes crucial in navigating the volatile nature of the market, ensuring that strategic decisions are driven by rational assessment rather than impulsive reactions to market fluctuations and trying to time the market.

When facing the task of selling a concentrated stock position, corporate executives can employ several strategies to spread out the associated tax burden over time. One approach is tax-loss harvesting, where executives strategically sell other investments with losses to offset capital gains from selling the concentrated stock. If the employer stock itself is held at a loss, these shares could be sold at a loss to offset other capital gains in current or future years. Additionally, executives can consider gifting shares to family members in lower tax brackets, effectively transferring the tax liability to individuals with a lower tax rate. Another tax-efficient option is gifting highly appreciated shares to charitable organizations, which not only allows one to support charitable causes but also provides a tax deduction for the fair market value of the donated shares as well as avoiding capital gains altogether. Charitable gifting can also be accomplished by gifting stock to a Donor Advised Fund, which can offer more flexibility as the donor as well as tax advantages.

Seeking guidance from financial advisors and tax professionals who specialize in executive compensation can offer valuable insights and customized diversification strategies. These professionals can provide personalized recommendations tailored to one’s financial goals, risk tolerance, and tax situation. By adopting a thoughtful and systematic approach to diversification, executives can protect their wealth, enhance portfolio resilience, and build a solid foundation for financial security in the years ahead.

Managing concentrated stock positions can be complicated. At Schultz Financial Group, we consider your personal circumstances and financial goals in order to make appropriate recommendations. Contact us today so we can discuss your goals and how to help achieve them with your concentrated stock position.

  • Schultz Financial Group, Inc. (“SFG”) which is a registered investment adviser, drafted this blog post for its website and for the use of its clients or potential clients. Any other distribution of this blog post is strictly prohibited. Registration as an investment adviser is not an endorsement by securities regulators and does not imply that SFG has attained a certain level of skill, training, or ability. While the content presented is believed to be factual and up to date, it is based on information obtained from a variety of sources. SFG believes this information is reliable, however, it has not necessarily been independently verified. SFG does not guarantee the complete accuracy of all data in this blog post, and it should not be regarded as a complete analysis of the subjects discussed. All expressions of opinion reflect the judgment of SFG as of the date of publication and are subject to change. This blog post does not constitute personalized advice from SFG or its affiliated investment professionals, or a solicitation to execute specific securities transactions. SFG is not a law firm and does not intend for any content to be construed as legal advice. Readers should not use any of this content as the sole basis for any investment, financial planning, tax, legal or other decisions. Rather, SFG recommends that readers consult SFG and their other professional advisers (including their lawyers and accountants) and consider independent due diligence before implementing any of the options directly or indirectly referenced in this blog post. Past performance does not guarantee future results. All investment strategies have the potential for profit or loss, and different investments and types of investments involve varying degrees of risk. There can be no assurance that the future performance of any specific investment or investment strategy, including those undertaken or recommended by SFG, will be profitable or equal any historical performance level. Any index performance data directly or indirectly referenced in this blog post is based on data from the respective copyright holders, trademark holders, or publication/distribution right owners of each index. The indexes do not reflect the deduction of transaction fees, custodial charges, or management fees, which would decrease historical performance results. Indexes are unmanaged, and investors cannot invest directly in an index. Additional information about SFG, including its Form ADV Part 2A describing its services, fees, and applicable conflicts of interest and Form CRS is available upon request and at

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