Gold Watch

Lupe Fiasco's The Cool Lupe Fiasco
Sounds like 50 (as in 50 cent) was on a world tour when he was young. Lupe's saying he's at the same stage as 50 at this point.
"Fall of Rome" and "Head Porter" are both clothing designers. Lupe is referencing his fashion.
Mont Blanc is a brand of luxury pen and Moleskine a brand of notebook. I assume he's saying he likes to write his rhymes with these.
"I've always been amazed that people forced to live in the worst parts of town go to bad schools and who have it the hardest are always the first to step up" People from bad soul testing neighborhoods usually have a strong backbone