In 1996, Jay-Z and Damon Dash turned heads with their independent label, Roc-A-Fella Records. They landed a quick deal with Priority Records and Jay put out his classic debut, Reasonable Doubt. With basically no promotion, the album still managed to sell over 400,000 copies. Doing this with no outside help caught the attention of a lot of labels. A bidding war ensued, but it was won by the first rap mogul, Russell Simmons.
As many know, the deal with Roc-A-Fella and Def Jam lasted for twelve profitable years. Jay-Z had become so popular within the overall label that he was promoted to the CEO of the entire organization. While he ended up stepping down, he still contributed a lot of success to the Def Jam label. Until he arrived on the label, it was on its last leg. Not only was Def Jam in financial trouble, but such labels as Rifkind's own Loud Records were chasing it down. Had things gone just a little different, his label would have not only caught Def Jam, but they would have passed them.
Before Jay-Z and Dame Dash sat down to speak with Russell Simmons, they spoke with Steve Rifkind about possibly having a deal with his label. The turning point was when it was revealed that Loud Records was nothing more than an imprint label, itself. Meanwhile, the struggling Def Jam was a major label, which meant that there was more money to be made at Def Jam for Jay-Z and Dame Dash than there was for them over at Loud Records with Steve Rifkind. Recently, Rifkind spoke on this and how he dealt with Dame Dash. When speaking of the rap mogul, he said that he was "one cocky motherf*cker," but he said that they are good friends.