From $2M single-stock risk to strategic opportunity
A client’s large holding of a single stock was causing outsized risk in her portfolio. She also needed help with tax planning and budget management.
A large portion of the client’s portfolio was tied up in a single, highly appreciated stock. While selling outright could have reduced risk, it may also have triggered significant tax consequences. At the same time, the client wanted confidence that her income and assets would support her lifestyle throughout retirement.
At-a-glance
Need for reliable retirement income with tax consideration
Concentration‑aware investment strategy paired with cash flow and tax planning
The team designed a coordinated strategy that addressed the concentrated position alongside the client’s broader planning needs.
Covered call: Designed to reduce concentration risk, generate income, and provide a buffer against modest share price declines.
Cash flow planning: Our Dynamic Cash Flow Illustration mapped out her expenses for the next 20 years
Tax planning: Guidance on withdrawal strategies, Roth conversions, and charitable gifting
By taking a more strategic, integrated approach, the client was able to address the risks tied to her concentrated stock position while creating a clearer picture of her retirement finances. The combination of income generation, cash flow planning, and tax awareness helped bring greater structure to her long‑term plan.
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This case study is based upon real clients. This content is for illustrative purposes only, may not be representative of any future experience of our clients, and is not intended to provide specific recommendations to any individual. The writer of a covered call option forgoes, during the option’s life, the opportunity to profit from increases in the market value of the security covering the call option above the sum of the premium and the strike price of the call but retains the risk of loss should the price of the underlying security decline. Traditional IRA account owners have considerations to make before performing a Roth IRA conversion. These primarily include income tax consequences on the converted amount in the year of conversion, withdrawal limitations from a Roth IRA, and income limitations for future contributions to a Roth IRA. In addition, if you are required to take a required minimum distribution (RMD) in the year you convert, you must do so before converting to a Roth IRA. Investing involves risk, including possible loss of principal. All investment strategies carry risk, and transactions in options may carry a high degree of risk. Options derive their value from underlying equities or indices, and the derivative value is directly related to the underlying security, thus they carry many, if not more, of the same risks as the underlying equity or index. This information is not intended as a recommendation. The opinions are subject to change at any time and no forecasts can be guaranteed. Investment decisions should always be made based on an investor’s specific circumstances. Investing involves risk, including possible loss of principal.