Understanding the Options with Concentrated Stock Positions

Understanding the Options with Concentrated Stock Positions

Too much of a good thing is still too much

We regularly sit in client meetings where the central topic revolves around the precarious balance of risk and reward tied to a single, oversized stock position. In these encounters, clients often acknowledge the dangers lurking within their investment strategy, yet find themselves trapped by a web of complexities, making it challenging to take decisive action.

The reasons behind holding onto a concentrated stock position are as diverse as the individuals themselves. Some find themselves in this situation due to a windfall inheritance, exercising stock options from their company, selling a successful business, or even being part of a startup that soared to public success. The allure of price appreciation or repeated stock splits over the years, alongside accumulating shares through compensation or retirement plans, further compounds the attachment.

Adding to the problem, is that beneath the surface lies a myriad of considerations complicating the decision-making process:

  • Emotional attachments to the stock’s journey.
  • Fears of missing out on potential gains.
  • Reluctance to sell due to looming tax implications.
  • Corporate executives grappling with stringent company policies, navigating legal constraints, black out periods, and optics concerns, particularly those in high-ranking positions.

So, what avenues can one explore when confronted with such a predicament? Let’s delve into a range of strategies designed to navigate the labyrinth of concentrated stock holdings, each with its own set of advantages and caveats, urging caution and seeking guidance from financial professionals along the way.

Maintain the Status Quo

For some, inertia prevails as they choose to maintain the status quo, perhaps banking on the prospect of heirs benefiting from a stepped-up cost basis upon their demise, potentially easing the burden of capital gains taxes for successors.

Strategically Sell Shares

Employing a tactical approach, investors can leverage options like tax-loss harvesting to transition their assets while offsetting potential capital gains taxes. In addition, by writing calls on low-basis positions, they generate income to facilitate the liquidation of stock, maintaining a net cash-neutral stance on taxes.

Employ Traditional Hedging Strategies

For those keen on retaining their stock while safeguarding against downturns, hedging tactics using options come into play. Purchasing protective puts establishes a downside floor, while selling covered calls generates additional income, balancing risk, and reward.

Stock Collars

Combining the protective elements of puts with the income from selling calls, stock collars offer a comprehensive approach to limit downside risk while potentially offsetting costs, albeit with constraints and tax implications to navigate.

 Practical Pointers:

Many publicly traded companies do not allow their employees to hedge the company’s stock. Certainly, most executives will be reluctant to hedge their company’s stock due to the public nature of all company stock transactions in which they engage.

Establish a 10b5-1 Plan

Company executives who want to avoid the perception of insider trading or market manipulation can sell shares over time by using a 10b5-1 plan, providing a documented defense against any allegations of trades made to take advantage of insider knowledge.

Monetize the Position

Exploring avenues beyond direct selling, investors may consider borrowing against their stock or entering into prepaid variable forward agreements, securing liquidity without relinquishing ownership, albeit with caveats regarding taxation and structured arrangements.

Net Unrealized Appreciation (NUA)

The NUA rule provides tax advantages for retirement plan participants distributing company stock, potentially saving money, especially for those in high tax brackets.

Exchange Funds

Diversification beckons through exchange funds, allowing for instant portfolio expansion without immediate tax repercussions, albeit with due diligence required to assess costs and quality of holdings.

Charity and Income Tax Deduction Planning

If philanthropic goals are part of the overall planning objectives, donating shares to charity can offer tax advantages and fulfill altruistic aims. The use of trusts such as Charitable Remainder Trusts (CRT) can help the investor achieve diversification, income, tax planning, and charitable goals in a single strategy.


In conclusion, the journey through the maze of concentrated stock holdings demands careful navigation, with each strategy offering its own set of benefits and pitfalls. By consulting with financial professionals and weighing the nuances of individual circumstances, investors can chart a course towards financial security and peace of mind, even amidst the challenges posed by an overabundance of concentrated wealth. Remember, it’s always crucial to seek advice before taking action to avoid the burden of additional taxes.

Important Disclosures
Pallas Capital Advisors, LLC and its representatives do not provide legal or tax Preparation Advice. You should consult a legal or tax advisor regarding any legal or tax information as it relates to your personal circumstances.

These materials are provided for general information and educational purposes based upon publicly available information from sources believed to be reliable — we cannot assure the accuracy or completeness of these materials. The information in these materials may change at any time and without notice. CRN24_220



James Landry, ChFC
Chief Operating Officer, Director of Planning
Pallas Capital Advisors

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