Cinderella –
Think about it this way. When you outdo someone in some way or win something, you feel happy, right? Your ego is fed, and you feel a strong sense of self-worth. Someone who has had to overcome trials and tribulations in order to do what is right and good may have had the pain of all those trials and tribulations, but their ego might be soaring through the roof. Then you have someone who grew up that way. Do you feel like you just achieved a major accomplishment when you daven an entire shemoneh esrei? Maybe yes, but if not – this is my point. Someone born into it does not have the added help of ego in the most basic things. The tzadik ben tzadik is the one who goes to daven, doesn’t get prodded on by his ego, and works to do it lishmah anyway! That is greatness. Of course, the ba’al teshuva can achieve greatness in his/her own way. But there is a huge possibility for true greatness to be achieved by someone born into it as well, precisely because it “means less” to them.