How The Wealthiest Woman In Jamaica, Billionaire Dr. Trisha Bailey, Built Her Fortune

Dr. Trisha Bailey’s story didn’t start in 2011 when she launched the first business within her billion-dollar empire. The St. Elizabeth Parish, Jamaica native’s humble beginnings failed to keep her from her present. She’s now Jamaica’s wealthiest woman and the first Black person to have a building named after them at her alma mater, the University of Connecticut. There are also many other accolades and groundbreaking achievements tied to her name.

Steadfast and determined, Dr. Bailey has journeyed through life’s ups and downs. NBC News reported that her childhood environment was impoverished, and she emigrated to the United States at 13. Then, during her teenage years, she was subjected to sexual abuse.

In college, Dr. Bailey’s athleticism and tenacity made her a track star. The latter quality also helped her in her postgraduate roles as a Wall Street stockbroker and pharmaceutical sales representative.

Unfortunately, she endured domestic abuse in her adulthood. Dr. Bailey suffered a life-changing eight-day coma and injuries in 2010—only remembering that she’d been on a date with a man in Los Angeles beforehand. Following the traumatic event, and another at an airport (where she was abandoned in a wheelchair), she entered the medical world to support those with disabilities.

The multi-industry maven founded Bailey’s Medical Equipment & Supplies in Orlando, Florida in 2011. A decade later, she was nominated for Home Medical Equipment’s Woman of The Year award. Now, her empire includes 16 businesses in pharmacy and real estate across multiple states. Her flagship business also proudly employs over 500 people, according to her website.

How Did Dr. Trisha Bailey Become A Billionaire?

In 2023, the mogul released her autobiography, UNBROKEN: The Triumphant Story of a Woman’s Journey. That year, Dr. Bailey shared her formula for becoming a billionaire with talk show host Sherri Shepherd. The entrepreneur emphasized exercising financial discipline and being financially literate. She also spoke of investing and building.

The serial entrepreneur additionally discussed her work ethic in a Sway in the Morning interview last year. She recalled working 20-hour days and not having a financial breakthrough until she made $500,000 eight months into her first business.

“I’ve always had this perseverance of resilience that everything that I touch and everything that I do, I give in everything I have,” the mother of five said. “I’m tunnel vision to the extreme. I can’t—I have this obsession about not finishing. If I start something, I must finish it, and I must excel at it.”