Jay-Z’s evolution from street hustler to bankable businessman is chronicled in Zack O’Malley Greenburg’s new book Empire State of Mind: How Jay-Z Went from Street Corner to Corner Office. While Jay-Z declined to participate in adding to the content of the  book, the work does an interesting job of explaining how the rapper earned more than all but seven public CEOs in 2010.

The book specifically points at how a failed business venture birthed the idea for Rocawear. In the early ’90s, Jay became aware of his knack for trendsetting after many of his fans showed up to his concerts wearing Iceberg Apparel clothing, a clothing line he’d referenced in his music. He later approach Iceberg about an endorsement deal when the clothing line saw a boost in sales, but was turned down. The failed prospect prompted him to start his own apparel line, Rocawear, and would pave the way for several other business endeavors.

Although much has been said about Jay-Z’s successes, the book also highlights some of his failures. His deal with Chrysler to create the “Jay-Z Jeep” fell through as did a venture with GMC Yukon for a “Jay-Z blue” painted vehicle. Greenburg says that many of the rapper’s failures are well-kept under wraps. “He doesn’t want to be seen as anything other than victorious…Even Jay-Z fails, but that doesn’t make him any less of a businessman.”