Bailey founded her own Bailey’s Medical Equipment and Supplies to provide equipment to Medicare patients. At age 46, Bailey now boasts acquisition of 47 pharmacies scattered across America. Her portfolio also includes 15 companies she founded, stakes claim to real estate properties and from knowledge gleaned on Wall Street is credited with investments in the Atlanta Hawks, Charlotte Hornets, Phoenix Suns, and a sprawling property in Orlando, Florida where she is envied as owner of a stable of horses. That Bailey is also the mother of five girls. She made the journey from Woodland, St. Elizabeth, Jamaica at age 13, to arrive in Hartford, Connecticut and later attended the University of Connecticut.