10/14/2026
You don’t have to choose between holding a concentrated stock position forever and selling it outright.
I talk to a lot of people with a significant portion of their net worth tied to one company. It may be a business they built, stock accumulated over a long career, or a position they’ve held for so long that selling feels like giving up on a decision that worked.
They understand the risk. They also understand the capital gains tax waiting on the other side of a sale. So the position stays in place year after year, and doing nothing becomes the decision. Meanwhile, one company continues to have an outsized impact on a family’s financial future.
There are several ways to approach this without simply selling the position and paying the tax all at once. You can hedge some of the downside while creating liquidity, build capital losses elsewhere in the portfolio to offset gains as you sell, or use certain tax strategies to defer gains and potentially reduce the overall tax impact. In many cases, the best answer isn’t one strategy, but a combination of several over time.
None of these are one-size-fits-all. The right approach depends on the stock, cost basis, size of the position, liquidity needs, and what the family is ultimately trying to accomplish. Each strategy has its own trade-offs and requires coordination across investment, tax, legal, and risk planning.
The question underneath all of it is pretty simple:
How much of your family’s future do you want one stock to control?
If one stock represents a large share of your wealth, it’s worth understanding what options exist before deciding to do nothing.
Disclosure: For informational purposes only. This content does not constitute personalized investment, tax, or legal advice. Investment and tax strategies involve risks, and their suitability and outcomes depend on individual circumstances. There is no guarantee that any strategy will reduce risk, defer taxes, or achieve a particular result. Consult a qualified professional before making investment or tax-related decisions.
Full disclosures: https://mrmcpas.com/legal-disclosures/
