There’s a reason why Rick Ross is known in many circles as “The Biggest Boss”. The Florida rapper has accrued six number one albums on Billboard and is also the CEO of Maybach Music Group, a record label that includes artists such as Meek Mill and Gunplay. Outside of music, Ross has long established himself as a mogul, as his success in many different business ventures has led to a very lucrative life for the boss.

Perhaps Ross’ most well-known business venture is his ownership of supposedly thirty Wingstop locations around the country. Rick Ross is listed as the owner of Boss Wings Enterprises LLC along with his mother and sister. The Boss opened his first Wingstop location over ten years ago. And according to Ross, the restaurants bring him about $7 million a year. Ross also gifted one of his Wingstop locations to his son for his sixteenth birthday.

Ross also owns a number of Checkers and Rally’s restaurants. In Ross’ teens, he would save up enough money while working at a car wash to be able to eat at Checkers frequently. Because of this, Ross’ purchase of a Checkers restaurant was something of a lifetime ambition for the rapper. The Boss also purchased the Checkers location across the street from Miami Carol City Senior High School. This was his former school where he played football.