Simmons, probably rap's greatest entrepreneur, lives in New York; schmoozes bankers, fashion designers, and record executives; and cuts deals with conglomerates such as Time Warner.
( ( ( ( ( Simmons , ) probably ) ( ( rap 's ) ( greatest entrepreneur ) ) ) , ) ( ( ( ( lives ( in ( ( ( ( New York ) ; ) ( ( ( ( ( ( schmoozes bankers ) , ) ( fashion designers ) ) , ) and ) ( record executives ) ) ) ; ) ) ) and ) ( ( cuts deals ) ( with ( conglomerates ( such ( as ( Time Warner ) ) ) ) ) ) ) . ) )
(ROOT (S (NP (NP (NNP Simmons)) (, ,) (ADVP (RB probably)) (NP (NP (NN rap) (POS 's)) (JJS greatest) (NN entrepreneur)) (, ,)) (VP (VP (VBZ lives) (PP (IN in) (NP (NP (NNP New) (NNP York)) (: ;) (NP (NP (JJ schmoozes) (NNS bankers)) (, ,) (NP (NN fashion) (NNS designers)) (, ,) (CC and) (NP (NN record) (NNS executives))) (: ;)))) (CC and) (VP (VBZ cuts) (NP (NNS deals)) (PP (IN with) (NP (NP (NNS conglomerates)) (PP (JJ such) (IN as) (NP (NNP Time) (NNP Warner))))))) (. .)))
Simmons lives in New York and schmoozes fashion designers. 
( Simmons ( ( lives ( in ( ( ( New York ) and ) ( schmoozes ( fashion designers ) ) ) ) ) . ) )
(ROOT (S (NP (NNP Simmons)) (VP (VBZ lives) (PP (IN in) (NP (NP (NNP New) (NNP York)) (CC and) (NP (JJ schmoozes) (NN fashion) (NNS designers))))) (. .)))