Once you become friends with Brucie you will gain the ability to call him for street races after you complete the initial story related race mission with him. Afterwords when you call him, he will send you on nine different street races around Liberty City which are listed below. The races are repeatable, so simply race and win a total of twenty races to unlock this achievement.
1) South Broker
2) Airport Run
3) Dukes Boulevard
4) South Algonquin
5) Star Junction
6) Road to Bohan
7) North Alderney
8) Elevated
9) South Alderney