I had a colleague who was very straight edged & by the book. He was someone who grew up in a very stable family environment and held religion as one of his core beliefs. Morally pure may be an appropriate descriptor?
Anyways, a few years back, a local media outlet ran a competition (poll) for the coolest startup office, and the award was a few cases of free beer to be delivered to that office. At that time, we really liked beer, and the beer is that much more rewarding when it's free. So what do you do when you're an engineer interested in a marketing poll? You hack the vote. This wasn't black hat, instead we just worked a means to automate the vote & make each attempt look like an individual. We were lucky at the time, it's not something you can do easily today.
So we carefully hack our way to a win, and the free beer is delivered to our office. Celebrations are had, and laughs are shared that we were able to identify the vector to exploit. We go back to our lives, but the following week our COO pulls aside one of the leads for the hack. Our morally-pure colleague had filed a complaint describing the activity as fraud. Nothing happened as a result of the complaint, but the trust with that colleague eroded as a result. He left a short time later.
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