Philanthropy Puzzler: Lemonade Out of Lemons | Sharpe Group
Posted August 11th, 2023

Philanthropy Puzzler: Lemonade Out of Lemons

Question: I have a donor who is considering making a noncash gift at year-end. In addition to giving highly appreciated securities, what are other options I should discuss with them?           

Answer: Even the shrewdest investor occasionally buys a stock that turns out to be a “dog.”  Continuing to hold declining stock, hoping for an upturn, may prove disappointing.  Often, it’s smarter financially to cut their losses and sell the “loser.” A really good idea for loss investments: Sell the stock and give the proceeds to charity.  They’ll receive the capital loss deduction and a charitable deduction if they itemize.


The “Philanthropy Puzzler” features gift questions fundraisers may encounter in the field, followed by solutions from our panel of experts. If you would like to send us your own “puzzler,” please email us at with “Philanthropy Puzzler” in the subject line.

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