You can place orders with your stockbroker to sell each individual position if you are liquidating a small portfolio of stocks.
Liquidating a large portfolio or holdings of significant amounts concentrated in single stocks is a complex task that requires special professional services of a brokerage or investment advisory firm.
One rule of thumb regarding the ownership of company stock suggests that 10-15% of your total net worth may be a suitable allocation.
10-15% allows an employee or shareholder to participate in the upside of the company should the stock appreciate and, perhaps more importantly, be somewhat insulated from the risk of total wealth destruction should the company underperform and lose its value precipitously (yes, it is possible and this can definitely happen).
Other times, the substantial allocation to one company stock is forced.
Intentional ownership can include buying stock outright, through an employee stock purchase plan, or in an employer-provided 401(k) plan.
When determining whether a closely held corporation should be liquidated, the tax consequences to the shareholders should be considered.
331, a liquidating distribution is considered to be full payment in exchange for the shareholder’s stock, rather than a dividend distribution, to the extent of the corporation’s earnings and profits (E&P).
The shareholders generally recognize gain (or loss) in an amount equal to the difference between the fair market value (FMV) of the assets received (whether they are cash, other property, or both) and the adjusted basis of the stock surrendered.
331 for the difference between the FMV and the shareholder’s basis in the stock).
As a result, the tax consequences of a subsequent sale of the assets by the shareholder should be minimal. The corporation is treated as selling the distributed assets for FMV to its shareholders, with the resulting corporate-level tax consequences.
Each of these transactions has specific rules that allow the sellers to comply with federal securities trading and tax laws.