Estate planning pitfalls – If the wealth is in a single stock

Estate planning and investment risk management go hand in hand. After all, an estate plan is effective only if you have some wealth to transfer to the next generation. One of the most effective strategies for reducing your investment risk is to diversify your holdings.

However, it’s not unusual for affluent people to end up with a significant portion of their wealth concentrated in one stock. There are several ways this can happen, including the exercise of stock options, participation in equity-based compensation programs, or receipt of stock in a merger or acquisition.

Ease risk by diversifying

To reduce your investment risk, the simplest option is to sell some or most of the stock and reinvest in a more diversified portfolio. But this may not be preferable if you don’t want to pay the resulting capital gains taxes. Or it may not be an option if there are legal restrictions on the amount you can sell and the timing of a sale. And in some cases, you may simply wish to hold on to the stock.

To soften the tax hit, consider selling the stock gradually over time to spread out the capital gains. Or, if you’re charitably inclined, contribute the stock to a charitable remainder trust (CRT). The trust can sell the stock tax-free, reinvest the proceeds in more diversified investments, and provide you with a current tax deduction and a regular income stream. (Be aware that CRT payouts are taxable — usually a combination of ordinary income, capital gain and tax-free amounts.)

Ease risk without selling the stock

What if you don’t want to sell the stock? You have a few options, including:

• Using a hedging technique, such as purchasing put options to sell your shares at a set price.
• Buying other securities to rebalance your portfolio. Consider borrowing the funds you need, using the concentrated stock as collateral.
• Investing in a stock protection fund. These funds allow investors who own concentrated stock positions in different industries to pool their risks, essentially insuring their holdings against catastrophic loss.

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