Concentration and conviction are not the same thing.
An executive or founder may know the company better than almost anyone. That knowledge can support genuine conviction.
But when salary, future equity grants, career opportunity and personal net worth depend on the same company, concentration risk extends beyond the brokerage statement.
Taxes make the decision harder—not irrelevant.
Large embedded gains can create a powerful reason to postpone diversification. Selling may trigger substantial tax. Holding avoids the immediate tax bill, but preserves exposure to the underlying asset.
The better comparison is the cost of creating liquidity versus the economic risk of continuing to hold the position.
The objective does not have to be an immediate exit.
Planning can begin by defining liquidity needs, future vesting, charitable or estate objectives, risk tolerance and the minimum level of diversification the household actually needs.
That framework can turn an emotional sell-or-hold question into a staged wealth decision.
Optionality is a form of wealth.
A concentrated position can create enormous wealth on paper while limiting flexibility.
Creating optionality means building enough liquidity and diversification that the family’s future does not depend on a single outcome.