As in to keep a low profile. Remaining opportunistic while those without foresight jump without looking and mostly fail and settle for less, in reference to business ventures, sex, and and all things green.
"How you living papi?..."
"...You know honey, I stay shy."

"Yo son, there's all types of ladies out tonight..."
"...Yeah true, but some be rollin' wit VD. I'm a stay shy and bag a clean mommy"

"Look man these Enron cats be climbin in leaps and bounds..."
"...Listen kid, sit tight and stay shy cause dem boys is twisted"
by Jaime C July 25, 2005
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