If the spirit of the holiday season moves you to be charitable, Clark has a word of advice: You may be giving money the wrong way! Most of us give by check, cash or credit card. But if you are an investor, you are better off from a tax perspective giving successful stock, mutual funds or index funds. When you donate shares instead of dollars, you get a double tax advantage. Normally you have to pay tax on investment gains when you sell. But if you donate your shares to a charity, you are exempt from the gains taxes
and you get a full charitable deduction based on the value at the time you donate. So say you bought stock for $3,333 and it's now worth three times that amount. When you donate it, all the gain is tax free and your tax deduction for charitable purposes will be $10,000.
What if your favorite charity isn't hip to stocks or you don't know which charity you like best? You can do a donor-advised fund. This kind of fund was pioneered by Fidelity Investments, but now Schwab, Vanguard and others have them too. With a donor-advised fund, you give the money to Fidelity, Schwab or whatever financial organization you choose and you get the tax benefits right then and there. Then they hold it until you decide down the road which charity or charities will get your money. You can usually arrange disbursement via the Internet. If your selected charity is already in their system, the charity will receive your money in a few hours. If the charity has to be vetted to make sure it's legit, there will usually be a 1-week delay. Remember that you won't get a tax deduction again when you disburse the money, only when you set up the fund initially. One final caveat: The IRS prohibits you from using donor-advised funds to match a pledge you made to a charity. That's because in the eyes of the IRS, the money isn't coming from you but rather from the company that set up the donor-advised fund.
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