Through my study of successful businessmen, I've found a significant portion of them made their initial "small" fortune through unethical or sketchy means.
A couple of examples:
Joseph P. Kennedy, Sr: He was accused of making his fortune through insider trading before it was illegal. He is also suspected to have been involved in bootlegging during Prohibition.
Jay Gould: He was known for his role in the Erie Railroad War, where he issued fraudulent stock to wrestle control of the railroad from Cornelius Vanderbilt.
Robert Maxwell: Engaged in a massive pension fraud scheme before he became a media tycoon.
Jim Clayton: Clayton Homes faced allegations of predatory lending before it became one of the largest manufacturers of manufactured homes in America.