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Over time, if you are anything like me, you learn to stop abruptly once you feel the pain of a cut, so they rarely go all that deep. After a few days, they heal up fine with no scarring.

I agree...

You must not be shaving your chin/mustache area I presume? If so, you are taking to the straight razor freakishly fast. If not, try shaving those areas and see how you fare. The "fool's pass" and...

Nothing brings on nicks and blood moreso than cockiness and speed. It's a bad combo from my experience. And, this is even after the 100 shaves. :)