In the last decade, Trisha Bailey has turned a small medical supply business in Orlando, Florida, into an empire that stretches across five states. From her years as an athlete at the University of Connecticut to her reported net worth of $700 million, Bailey’s success story is magnified by the tumultuous route she traveled.
To her many achievements, including being the wealthiest Jamaican-born woman ever, the 46-year-old entrepreneur just added the release of a memoir, “Unbroken: The Triumphant Story of a Woman’s Journey.” where she shares the darkest parts of her life boldly and poignantly. At a recent book signing in Martha’s Vineyard, many were moved to tears when she discussed passages of her book and her trauma-filled youth and adulthood.
Bailey grew up in an impoverished home in St. Elizabeth Parish, Jamaica. As a teenager she survived sexual abuse, and then, as an adult, domestic violence.
At the book signing, Bailey was emotional right along with her readers as they poured over her story. She had shared the traumas of her life with only a select few — until now. And although she said writing the book was not therapeutic for her, it was revelatory.
“The life of trauma that I was going through, I didn’t know other people didn’t live like that,” Bailey said. The more she shared about it, however, the more she learned differently, which is why she aimed for transparency.
“There were so many different incidents that happened and I was like, ‘No, that’s so embarrassing. Maybe I shouldn’t share that,” said Bailey. “But I said, ‘You know what? If I’m going to help others, I need to just tell it all.’”
She did. At 13, just a few days after arriving in the U.S. from Jamaica, she was sexually assaulted by her mother’s husband, a violation that would be repeated for years, Bailey wrote. She never told her mother, who learned of the abuse through reading the book. The man has since died.
About a year after the abuse began, as she “was going through hell at home,” Bailey wrote that she found Oprah Winfrey’s 1993 autobiography. “I saw that she was able to overcome,” she said. “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.”
One could assume that Bailey’s ability to succeed despite intense trauma is what makes her book so enticing. Another could point to her success as an entrepreneur that has earned her phenomenal wealth. Neither would be wrong.
After college, Bailey became a stockbroker on Wall Street and later a pharmaceutical sales representative. All the while, she endured at least four abusive relationships that she shielded from most family and friends.
Bailey wrote about waking up after being in a coma for eight days about 13 years ago. She could not remember what led to the near-death experience, but her last memories were of an encounter with a man she was dating while visiting Los Angeles.
When she was able to leave the hospital in L.A., she found herself disoriented in an airport while seeking a connecting flight home to Florida.
Finally, a stranger came along and aided Bailey to her gate. As harrowing as those moments were, she said they sparked an idea that would be crucial in her business journey. While sitting in a wheelchair provided by an airline, she said, she conceived Bailey’s Medical Equipment and Supplies, which launched in 2011 to distribute medical supplies to Medicare patients.
Since then, Bailey’s empire has grown exponentially. In addition to her 48 pharmacies in multiple states, she has founded 15 companies, owns real estate around the globe and has stakes in the Atlanta Hawks, Charlotte Hornets and Phoenix Suns, among other endeavors. And she has donated millions, including an undisclosed amount to UConn athletics that the school says is the largest in its history.
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