[aflag]

Making such a bet is not a really professional thing to do. Regardless of the actual risk it introduces. If I was a manager in that company and two of my employees made such a bet I'd be tempted to fire both or, at the very least, have a very serious conversation. I think that's borderline malpractice.

[dub]

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.

[aflag]

The second paragraph seems at odds with the first. I'd describe a culture where people are making bets on whether or not you can find a bug in someone else's work is the opposite of blameless. I'd consider it quite hostile, to be honest. Specially if it's something that management is actually ok with.

I'm assuming you were at google in late 90s/early 2000s?