Orlando-based entrepreneur, richest Jamaican woman in the world, chronicles abuse and poverty in new memoir

August 27, 2023  -An article by NBC News shares the story of Trisha Bailey, a Jamaican entrepreneur whose remarkable success story brims with inspiration and impact.

Trisha’s remarkable journey began in the impoverished settings of St. Elizabeth Parish, Jamaica. This Jamaican-born entrepreneur transformed a small medical supply venture in Orlando into a sprawling empire that spans seven states.

NBC News states that Bailey’s net worth is estimated at a staggering $700 million, positioning her as the wealthiest Jamaican-born woman in history.


Unbroken: A memoir of triumph and transparency

Bailey recently unveiled her memoir, “Unbroken: The Triumphant Story of a Woman’s Journey.”  Within its pages, she courageously recounts the myriad challenges she faced, from a traumatic childhood marked by sexual abuse in Jamaica to harrowing experiences in her adult life, including domestic violence and a mysterious coma.

Writing the memoir was not a therapeutic experience for Bailey but was illuminating. It showcased her belief in the power of raw honesty to resonate with and aid others.

Oprah’s influence and the birth of an idea

Upon her arrival in the U.S. as a teenager, Bailey’s life took several unexpected turns. During her most challenging times, she drew inspiration from Oprah Winfrey’s 1993 autobiography, seeing in Oprah’s story a beacon of hope.

This inspiration, coupled with a pivotal moment of vulnerability in an L.A. airport, led Bailey to conceptualize Bailey’s Medical Equipment and Supplies.

Founded in 2011, the company has become a cornerstone of her thriving business empire.


Beyond business: A global footprint

The NBC News article shares that the success of Bailey’s medical supply business was just the beginning.

Today, she has a significant presence in multiple sectors. Apart from her 46 pharmacies spread across various states, Bailey’s business ventures include 15 different companies, a vast global real estate portfolio, and stakes in NBA teams such as the Atlanta Hawks, Charlotte Hornets, and Phoenix Suns.

Beyond her commercial successes, Bailey has made sizable philanthropic contributions, including a generous donation to her alma mater, the University of Connecticut, which is the largest the institution has ever received.

Unwavering strength in the face of adversity

Bailey’s personal growth is underscored by the traumas she has battled.

Instances of abuse and trauma pepper her narrative, yet her spirit remains undeterred. Friends, like Rhoan Stewart, find her strength both astonishing and moving, with many struggling to reconcile her cheerful demeanor with her tumultuous past.

Bailey’s healing journey was greatly aided by Eye Movement Desensitization and Reprocessing therapy, a method that allowed her to confront and move beyond her traumatic experiences.

Kathy Jackson, a close friend since their time together at UConn, emphasizes Bailey’s unwavering spirit and generous nature, as seen through her charitable donations exceeding $10 million in Florida alone.

Bailey looking forward

As Bailey embarks on her book tour this September, she radiates a contentment that is truly infectious.

“I am truly the happiest I’ve ever been,” she said. “I didn’t even know people could be this happy, to be honest.”

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