This is like the starving artist myth or a.k.a. "selling out" quandary. I say it's a myth because the fact it is used as a cliche in itself is psychologically damning to an artist who convinces themselves they must starve in order to keep their art "pure" and unadulterated by profit or business motivations. There's a whole body of recent books on this particular subject for artists and their basic thrust is to teach artists how to manage business or find help with business.
I remember going to a punk rock club here in my area where the band Green Day came up (played before they were famous) and the graffi in the bathroom one said "!@#$ Green Day."
The reputation people worry about within is a very small group. Often this small group is the one who supported the creative before they made it. When someone creative makes it this is seen by the smaller group as a kind of abandonment of their core belief - that one must live a modest and struggling life in order to be "real" with their creative expression.
I reject this idea that one must be poor in order to have this moral creative righteousness and feel this attitude is detrimental to creative arts.
While your question seemed to be more about money reputation I think it would help if you were more clear about it, do you mean someone who buys stocks in a weapon of mass destruction manufacturer? What kind of moral choice/reputation are you referring as an example? Or do you mean someone who straight up steals or scams?
It was deliberately open ended so that I could capture a unique perspective like yours. You made good points.