Steve Madden fell in love with the shoe business in the 1970's, when he sold platform shoes at a neighborhood store in Long Island, New York; that was in high school. About 15 years later, he struck out on his own, designing and selling shoes with a high-end look at affordable prices. As his business—and his ambitions—began to grow, he got involved in a securities fraud scheme and wound up serving two and-a-half years in prison. In 2005, he returned to Steve Madden, where he helped the company grow into a business valued at $3 billion. PLUS in our post-script "How You Built That," we check back with "kid-preneur" Gabrielle Goodwin and her mom Rozalynn who invented GaBBY Bows—double snap barrettes that don't slip out of your hair.

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