John Monopoly is a well-known hip hop talent scout and manager. He is a former member of the old-school Chicago prep-school krewes, "Hilltop" & "The Outcasts".

Monopoly once served as Manager for Time Exposure as well as co-promoting underground hip-hop events with Dave Dred, and Chicago Graf legend Avon under the moniker "WTTW" [Word 2 Tha Wise]. In addition, Monopoly has served as an A&R rep at Violator Management and as an executive at Jive Records, he played a key role in signing rap blue-chip prospect Dirtbag. Monopoly also teamed with DJ Whoo Kid on a joint venture with Koch Entertainment to distribute Rewind DVD Magazine as well as form The Shadyville DJ Coalition. Monopoly also runs management firm, Hustle Period. Included among Hustle Period's past and present clients are Kanye West, Shawnna, Naledge, GLC (rapper), Carl Thomas, and producer No I.D. Hustle Period officially began in August 1999 after Monopoly and VP Reno Dinero had been successful throwing house parties in their Navy Pier apartment in Chicago. Hustle Period started between founders, John Monopoly, Datu Faison and Don C, Kanye's Road manager. John has recently ventured into nightlife by opening Chicago's newest exclusive member's club, Boutique, etc.