Collect money from rackets to earn a good amount of money. Your underbosses control rackets and collect money directly from them. You will need to visit your underbosses to get the money. There is a cap on the amount they can hold for you at a time. If you do not collect it, they will stop bringing money in from the rackets. Keep visiting your underbosses on a regular bases to collect the money. The cap will increase with game progression. Progressing through the story and having all three underbosses to command will unlock new ways to earn money, like Stealing Dead Drops and Following Bagmen. However, this method will not become available until you progress through the main storyline to meet Donovon on a bench in Barclay Mills. Progressing through the main storyline is important, especially getting closer to Vito Scaletta. Reach $140,000 to unlock the ability to hire someone to collect the racket money. This will allow you to Steal Dead Drops and Follow Bagmen instead of worrying about collecting racket money.