Have you ever passed on an opportunity because you felt it was too risky, then kicked yourself later?

In the late 70’s, early 80’s I worked for Boeing Computer Services. There was an older lady I worked with, who had been there for 25 years. She sometimes told of the time when co-workers Frank and Dan Carney were approaching people asking if they would invest $500 in this pizza restaurant idea they had. Some did, my older lady co-worker said “No.” And was kicking herself to this day.

Once, around 2004, I was visiting my aunt and uncle in Seattle and my aunt showed me this closet full of fur coats, probably from the 50’s and 60’s. Real fur coats. There were, maybe, half a dozen. She asked if I wanted them. Conscious of the societal anti-animal fur movement I declined.
Now I’m kind of wondering if, from a financial point of view, I made a mistake. (Oh, BTW, she was the mother of the cousin who won $90 million on a powerball ticket!)

Conversely, have you ever taken a risk and had it pay off?