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As we all know, you get to deduct charitable gifts from your taxable income. We also all know that 501(c)(3)’s don't pay taxes. So, let’s say that you have $30,000 of income that will be taxed at 35% for a total tax burden of $10,500, and you would like to make a charitable gift of that $30,000 to get your deduction, save $10,500 of tax liability, and support a cause you know will really do some good. And in this instance, you don't have an extra $30,000 of cash in your checking/saving account to make the gift. First, I am going to tell you the wrong way to make that gift. Step one: Sell $35,000.00 worth of some of that stock that has appreciated 300 percent Step two: write your favorite charity a check for $30,000. Wait, why did I have to sell $35,000.00 worth of stock to make a $30,000 gift? Because you're going to realize an additional 4-5k thousand dollars of capital gains tax liability on the sale. So you sold, $35,000 worth of stock to make a $30,000 gift and now only get $6,500 in tax savings. That $30,000 gift had a net cost to you of $28,500.00. Now, here’s the right way. Give the charity $30,000 worth of highly appreciated stock. Let the charity sell the stock for cash (because you didn’t sell it, you don’t have capital gains liability). You gave away $30,000 worth of stock and get a $30,000 deduction, saving you $10,500 worth of taxes. The net cost of that $30,000 gift is $19,500. When the charity sells that stock, it pays no taxes and can put all $30,000 to work making the world a better place. 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