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I think sometimes we get the order of occurence backwards as we analyze how painters became "commercially focused". The Saturday Evening Post would not have hired Rockwell had he not evidenced a high level of pre-existing ability. It soon became known by the editors that having a Rockwell cover was worth at least 100,000 in newsstand sells. So, you see, his art made them money as certainly as it made him money. As Mary pointed out so well, what difference does it make who writes the check? Good art attracts art lovers.
Michelangelo's Pieta was so awesome that it was an instant career maker. The skill evidenced by that one sculture done when he was age 23, instantly made his reputation and the Pope was not the only one to take notice. Skill first, money second.
Within every artist exists personal drives and goals. If wealth is what drives the person then they will produce shallow commercial crap like Thomas Kinkade, who now has the monetary freedom to paint whatever he wanted - yet he will continue to want money over respect till the end of his days. On the other hand, there are painters that could produce very commercial works that prefer to spend their days making serious, meaningful works even if they are not getting rich doing so.
