Strange that he always lose. Never seen such a guy that has a terrible luck. Maybe winning in gambling is not for him? And the reason why he keeps on gambling is maybe not because of the profit this time but because he only want to have fun.

When you use gambling for entertainment, you won't mind losing but he better tell that to the people around there so that they will worry less. In the case of the worker that is concerned at the gambler, if I am the owner and I found that out I think I will feel touched. I will give that worker a special treatment among my other workers because I like the attitude that he is showing towards our customers.