Losing Your Shirt

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Dictionary Says

Definition of 'Losing Your Shirt'

In the investment world, this expression is used to describe a very bad investment that causes an investor to lose everything he or she has invested (and more, in some cases).
Investopedia Says

Investopedia explains 'Losing Your Shirt'

This is a terrible position to find yourself in. The phrase suggests that the investor not only loses all he or she has invested, but is also in such dire straits that he or she has to sell the "shirt off their back."

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