A stock where you are playing with "house money" is no more or less risky than one where you have a loss or are even. The only difference is emotional.
I guess, but capital preservation. Live to trade another day..etc..I find it way easier to go long on freebies.. a selfie mind trick ,lol.. besides I assume having a (very) high level of competency/experience in a particular industry facilitates "staying long"..