Usually when someone says this what they mean is that someone needed to sell something for a lot less than they thought they would.
More specifically, let’s say you bought something for $1, let’s pretend it’s a wheel barrow for your landscaping business. Your intention as a business is to use this $1 item to make $5 doing landscaping.
Now Let’s say your landscaping business did poorly and you needed to sell off all the things you bought. You sell the wheelbarrow for 10c. You sold that wheelbarrow for 10c per dollar you spent. “Pennies on the dollar”
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