I'd rather take my chances investing in some kind of stock and make money that way than working hard to get into university and end up working for a company that exploits their employees.
この場合、次のような言い方ができますよ。
ーI'd rather take my chances investing in some kind of stock and make money that way than working hard to get into university and end up working for a company that exploits their employees.
「頑張って大学に行って最終的にブラック企業で働くなら、リスクがあっても株に投資してお金を儲ける方がましだ」
I'd rather ... than ~ing and end up ~ing で「〜して最終的に〜するより、…する方がマシだ」と言えます。
ご参考まで！
カナダ 
