When I worked at Google back in the day, we used to make dollar bets all the time. You'd tape the signed dollars you won to your monitor.

A willingness to take pride in your work and to not take it too seriously when smart, well-intentioned people make mistakes (e.g. blameless postmortems) is part of the culture difference that led to Google's engineering becoming so exceptional and innovative vs the more corporate, don't-rock-the-boat, fear-driven culture that the traditional businesses had at the time.