Dr. Trisha Bailey, a trailblazing entrepreneur and philanthropist, shares her inspiring journey from a challenging childhood to becoming a self-made billionaire. In an exclusive interview, Dr. Bailey discusses her raw and unfiltered story, captured in UNBROKEN: The Triumphant Story of a Woman’s Journey, aiming to empower others to overcome obstacles and embrace resilience.


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Growing up in a modest environment, Dr. Bailey’s early years were marked by humble beginnings in Woodland, St. Elizabeth, Jamaica. Despite the daily trek to school, she found contentment and never felt deprived. Dr. Bailey recalls a supportive family environment, which included wisdom from her grandmother about dreaming big. She remembers her fondest moments and happy places being a family farm, where she collected carrots, potatoes, and more.

“My grandmother used to walk 25 miles with a donkey to the market, and she’ll work for eight hours to sell the items,” Dr. Bailey said. “And then she walked back 25 miles. She literally was an angel that walked on earth. She passed away when I was 30.”

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Dr. Bailey’s fond memories of her grandmother are attributes she could associate with her hometown of Jamaica, calling the people of her beloved home country “loving beyond imagination” and possessing a high work ethic.

Dr. Bailey migrated to the United States at age 13, sharing a 600-square-foot, one-bedroom apartment with her sister, mother, and her mother’s husband. They believed they had made it at that moment due to the American luxuries of indoor toilets, running water, and a television. Dr. Bailey also revealed she wanted to be a teacher, then principal, elevating to superintendent, but that would shift to finance and entrepreneurship. Dr. Bailey highlights that her success is rooted in the discipline that her grandmother taught as a child.

Since her beginnings in Jamaica, Dr. Bailey’s life and career have made her a mother, entrepreneur, philanthropist, and author. The memoir details her journey as a young girl emerging from poverty. Dr. Bailey entered the finance world, becoming one of the youngest stockbrokers at 22 and establishing Bailey’s Medical Equipment & Supplies in 2011, initiating a journey that would transform her into the CEO of 16 companies and a member of the billionaire’s club. She now owns a stake in three professional sports teams and numerous real estate properties.

“In my book, it is as raw as it can get,” Dr. Bailey says. “It goes through all my personal traumas, it goes through every step and every obstacle I’ve had in building my empire. It teaches you how to become a billionaire, but it also, and most importantly, teaches you how to overcome trials, and areas in your life when you’re at your darkest moment.”

She adds, “I advocate for people who are dealing with depression and various mental health issues, to find therapy, find ways to heal yourself. The same way that you eat healthy. You should also take care of your own mind, and in ‘UNBROKEN,’ you will be inspired.”

The UNBROKEN memoir has been celebrated by luminaries like Rick Ross and Nate Burleson, echoing the power of her real-life story. You can learn more about the memoir and see reactions below. UNBROKEN: The Triumphant Story of a Woman’s Journey is available on Amazon.