How to Save Like an Optimist, Invest Like a Pessimist

The Motley Fool is a private company that nobody's really invested in other than its employees. The investors at our company are optimists, and the people who work right alongside them are also optimists. So save like an optimist, invest like a pessimist? What happens? I see someone who goes bankrupt and is bitter about it because they didn't have any fun going bankrupt.