Raised in the city of Chicago, the blues capitol of the world, Jake was exposed to its lively thriving blues scene and was captivated by the romantic notion of becoming a bluesman. Dropping out of high school after the ninth grade, Jake hoboed around the United States after the example of his blues idols and his maternal grandfather, Jinx Putnam. Whenever he was back in Chicago, Jake spent his Sunday mornings hanging out at the place where many great Chicago bluesmen got their start: the Maxwell Street Market. On Maxwell Street Jake befriended the old time bluesman Maxwell Street Jimmy Davis who was to become one of his best friends and mentor. As a teenager Jake would sneak into blues clubs to hear other old time blues legends such as Homesick James and Honeyboy Edwards with whom he later spent a great deal of time playing music both on and off the stage.