Reps Up Entertainment was basically seen previously as a street movement that gained traction in the Scarborough Area of greater Toronto, the Kingston-Galloway District. Whereas, the original founders of the Reps Up entity is seen as Raynford Humphrey (P Reign) as well as his elder brother, popularly known as Gillatein. In order to incorporate a stronger yet critical component of the organization's growth, another performer, whose ties with Gillatein and P Reign, Anon "The Great" was seen as the primary individual that facilitated the Montreal flagship of the venture. Whereas, P Reign's original birthplace, which is the New Burgundy section of Montreal, Canada, was therefore considered to be a critical market to base ventures with responsibilities handed down to Anon.

​

Despite of the Reps Up Entertainment being seen as it's own venture, the organization has been provided great opportunity of exposure to the masses through the growth of appeal of rap artist Aubrey "Drake" Graham, with Graham's underground roots in accordance to other upcoming artists, whereas the traction of his latest work in 2008, being So Far Gone, Graham was able to sign with Young Money Records through Cash Money Records. Whereas, a companion that was close to both P Reign and Drake, who was prominently known as "Hollywood," with his organization being Ethnicity Inc. worked within beneficial means. Whereas, "Hollywood" is seen by many to be the bridge between Reps Up Entertainment and October's Very Own (Aubrey Graham's venture). As a result, the underground ventures of Reps Up Entertainment had reached the mainstream, whereas continous exposure resulted in the mass appeal of P Reign of the music industry within the United States.