Jamaica’s Richest Woman? Trisha Bailey Shares Her Journey from Walking Barefoot to Acquiring Hundreds of Millions – Watch Interview

Jamaican-born entrepreneur Trisha Bailey has worn many hats along her journey to becoming a self-made millionaire. She has owned a recruiting business, worked as a stockbroker, and sold medical equipment before diving into the international real estate market. Bailey made her first million at age 35 and now has an estimated net worth of US$650–$700 million.

Speaking with Anthony Miller on TVJ’s Entertainment Report, Bailey said she left Jamaica because America provided better opportunities. She added that living there allowed her to fulfill her story of growing up barefoot with no electricity and running water in St. Elizabeth and becoming the successful businesswoman she is today. Though the odds were stacked against her as a black woman, Bailey stated that she remained singularly focused on her goals and blocked out the competition. In the most difficult parts of her journey, the multi-millionaire said she relied on God and pressed ahead to accomplish all that she has now. According to the entrepreneur, she developed a strong understanding of the value of saving at a young age, putting away portions of her lunch money every week, and has remained disciplined throughout her life.

Moving on to state that although she has experienced racism, she has never allowed it to slow down her progress and that it was also among the reasons why she started her first business.

“I started getting harassed, and I said okay, well now I have to create my own, and I created my own destiny,” Bailey stated. She continued by adding, “If it’s a moment where I’m experiencing the deepest level of racism… I know it’s happening, but I keep my blinders on, and I’m progressing, and I’m making changes and adjusting.”

As an experienced businesswoman, Bailey is currently investing in real estate in Jamaica and believes that the island has a lot of resources to offer. She expressed that she has no desire to be the only success story and, through her philanthropic efforts, has sent 270 Caribbean youngsters to college. Bailey recently made the largest cash donation in the history of the University of Connecticut, which she says gave her first start with a full scholarship.

“If I didn’t have the scholarship going there… I don’t know where I would be, to be honest. So that’s the reason why I chose my university that gave me the love, the support, and the boost that I needed in order to become the entrepreneur that I am today,” the St. Elizabeth native voiced.

Watch the interview below: