Bailey was raised in St. Elizabeth Parish, Jamaica. She didn’t come from a household with stable earnings and she experienced sexual trauma from her mother’s husband after moving to the United States at 13 years old. At the time, her only hope while “going through hell at home” was Oprah Winfrey’s 1993 autobiography.
“I saw that she was able to overcome,” Bailey said, according to NBC News. “I was able to see this woman on TV and it gave me life. She gave me hope. And I wanted to be able to touch other young women to show them what to look for, to show them how to build themselves up.”
Despite her troubled past, she became the first in her family to graduate from college. She earned a bachelor’s degree from the University of Connecticut in 1999, her website reads. Bailey later obtained a master’s degree in business administration and a doctorate in management and organizational leadership.
Bailey’s career trajectory began as a stockbroker on Wall Street before she pivoted to become a pharmaceutical sales representative. She still endured trauma during this time from multiple abusive relationships, once waking up from a coma after eight days in a Los Angeles, CA, hospital.
Although the memory is souring, for Bailey, it instilled a vision inside of her. While on a connecting flight to go to Florida, Bailey recalls feeling “invisible to the world.” She was seated in a wheelchair and unable to speak following her coma.
It was during this moment she conjured the idea to enter the medical equipment industry.
“I was wheelchair bound, my larynx was clipped, so I was not able to speak. When I got to Atlanta, the flight attendant escorted me off the aircraft, placed me in a corner for my connecting flight for two hours. I sat there and I cried and tried to find someone to help me to get to my next destination. After two hours, a young girl came and helped me, and during that moment, I realized that the disabled was invisible to the world and because of that, I started Bailey’s medical equipment and supplies,” she explained in a video. “I wanted no one else in the world to ever feel the way that I did as a young girl sitting there in a wheelchair, crying, desperately needing help, needing someone to care, needing someone to assist me. So that’s my motivation for starting Bailey’s medical equipment and supplies.”
Bailey’s Medical Equipment and Supplies was launched in 2011 to provide assisted living facilities, group homes, individual patients, and contract facilities free pharmacy deliveries, the company’s website reads.
It has since expanded to 46 pharmacies across various states, per NBC News.
Its success only scratches the surface for Bailey, who has also conquered the real estate industry, owning over 50 commercial and residential real estate properties from the United States to Jamaica, per her website.
Plus, Bailey reportedly has stake in the NBA’s Atlanta Hawks, Charlotte Hornets and Phoenix Suns, according to NBC News.
“I know that my business success is not normal,” Bailey told NBC News. “I know it is a blessing from God, like my entire life. But having grace and being kind and caring and loving blesses your business. If you’re someone who’s doing the wrong things, morally corrupt, your business may miss being blessed because God is in the middle of all those things.”