Your wealth grew
in one direction.
Does your risk too?

What it is: Sell shares over time and offset the gains with losses harvested elsewhere in your investments.

Who uses it: Anyone without trading restrictions, especially when the cost basis is not far below today's price.

Tax treatment: Capital gains tax generally applies and can be spread across years and tax brackets.

Watch for: A sale gives up future appreciation of the shares sold, and harvested losses are limited by tax rules such as the wash sale rule.

What it is: A written instruction, set up in advance, that tells your broker when to sell.

Who uses it: Mostly executives, board members, and other employees who learn company news before the public. Company policy decides who may use one.

Tax treatment: Ordinary sale tax rules generally apply to each trade as it executes.

Watch for: Waiting period before the first trade: for executive officers and directors, the later of 90 days after the plan is adopted or two business days after the company discloses its financial results (Form 10-Q or 10-K) for the fiscal quarter in which the plan was adopted, never more than 120 days; for everyone else, 30 days. A plan can serve as a legal defense to insider trading claims if the SEC's conditions are met. It is not a guarantee, and it does not replace Section 16 reporting or Rule 144 limits.

What it is: A put sets a floor under your stock's price. Selling a call pays for it but caps your gains.

Who uses it: Investors with a large position who want protection without selling. It needs options approval, and your company may restrict hedging by executives and directors.

Tax treatment: No sale means no immediate tax, but the tax code treats some hedges that lock in your gain as an immediate sale (IRC §1259). Structure matters.

Watch for: You give up some upside, and it does not generate cash.

What it is: A bank pays you cash today, a portion of what your shares are worth. Later you settle with shares, within a set range.

Who uses it: Usually owners of very large positions, often executives and founders, who want cash but cannot or prefer not to sell.

Tax treatment: Tax is usually put off until settlement, but how the contract is set up matters a great deal.

Watch for: You give up some upside. Fees and the bank's credit apply.

What it is: Investors pool their single stocks into one fund, and each owns a slice of the whole mix.

Who uses it: Investors whose stock has grown a lot and who can lock up money for years. Each fund sets its own eligibility rules, so check its offering documents.

Tax treatment: Contributing generally does not trigger tax right away. After about seven years you can take out a basket of stocks that keeps your cost basis, so tax is delayed, not erased (IRC §704(c)(1)(B), §737).

Watch for: Fees apply, and you cannot easily withdraw.

What it is: A charitable savings account: you give shares, take the tax benefit now, and recommend grants over time.

Who uses it: People who already give to charity and own stock that has grown in value.

Tax treatment: Giving shares generally avoids tax on the gain, and a deduction may apply, within income-based limits.

Watch for: The gift cannot be taken back, and the sponsoring charity has the final say.

What it is: A trust that pays you income for up to 20 years or for life. What is left goes to charity.

Who uses it: People who give to charity and want income from stock that has grown. Usually set up with an attorney.

Tax treatment: The trust can sell the stock without immediate tax, but you are taxed on the payments as you receive them.

Watch for: It is irrevocable and files a tax return every year.

What it is: Keep the stock, and build the rest of your investments to balance it.

Who uses it: People who are not ready to touch the position but want the rest of the household balance sheet more balanced.

Tax treatment: No tax event on its own.

Watch for: The position itself stays exposed to that company's risks.