Steve Madden

Madden was born in 1958 in Far Rockaway and raised in Nassau County. He briefly attended University of Miami, but left in 1977 after two years when his father said he would no longer pay tuition so that Madden could "golf year-round." Don't be mad Daddy, little Madden was just practicing to be a CEO!
After leaving college, Madden found a job as a sales rep for shoe wholesaler L.J. Simone, and worked there while sneakily learning the ins and outs of the shoe business. In 1988 Madden quit and in 1990, he got incredibly creative with company names and started up Steve Madden Inc., which he launched with $1,000 to his name and began selling his shoes to Macy's out of the trunk of his car. Three years later he opened his first store in SoHo, and later the same year the company went public.
In 1997, sales of Madden shoes topped $59 million per year, and Madden began to work on manufacturing handbags, jewelry, and blue jeans. But trouble was stirring in the form of an SEC investigation and a lawsuit by Madden's former business partner. Madden eventually resigned his CEO position, posted in $1.5 million bail (for which he handily had a Hamptons house to use as collateral), and in September of 2002 went to Floridia to serve a three-year sentence. While in jail, he remained the creative and design chief of Steve Madden Inc., with a salary of $700k a year. Not bad for a man in the slammer.
While in jail, Madden's director of operations, Wendy Ballew, came down to Florida to visit him often enough that he married her in 2005 shortly after he was released from prison.
[Image via AP]