To be honest, I didn’t encounter the expression “Don’t Leave Money On The Table” until I was working for a very small startup about 5 years ago. The expression struck me as amusing since who would be silly enough to or wealthy enough for that matter to just leave money behind?
It brought to mind the image of robber barons lighting cigars with $100 bills.
Working for a tiny startup company gave me unique access to the CEO and strategy meetings that usually focused on sales and marketing. They weren’t the typical discussions centering around technical issues that I was used to participating in as an engineer.