leave money on the table
v. phr.— «The ideal offering, investment bankers say, is one that rises to a small premium. A small price rise presumably gives the initial investors confidence in the company, and also confirms the sagacity of the corporate officers and underwriters involved in setting the offering price. The company thus does not feel that it left “money on the table.” By that criteria, the Genentech offering was not successful.» —“A ‘Hot’ Offering Retrospective” by Karen W. Arenson New York Times Dec. 30, 1980. (source: Double-Tongued Dictionary)
Further reading
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While reading Great Expectations (Bookshop|Amazon) by Charles Dickens, a listener in Arlington, Texas, is surprised when one of the characters inherits some money, which Dickens describes as a cool four thousand. Were they really using cool that way...