Diana Jackson Didn’t Just Build a Business. She Built a Movement

Diana Jackson

Some people are born into legacy. Others build it piece by piece, setback by comeback. Diana Jackson is the latter. The Far Rockaway native and founder of A Wise Choice Entertainment did not just create a business. She built a movement rooted in resilience, community, and an unwavering belief in what is possible when faith leads the way.

Born in Queens, New York, raised in West Palm Beach, Florida, and proudly of West Indian descent from Saint Vincent and the Grenadines, Diana's story defies the ordinary. A Black woman raised by a single mother, she carved her path through trials most people would buckle under. Homelessness, loss, and adversity were chapters in her journey, but never the final pages. Through prayer, determination, and her refusal to give up, Diana transformed her vision into reality. What started as a dream became A Wise Choice Entertainment. The company blends artist management, promotions, marketing, event planning, entertainment consulting, and travel into one of the most dynamic platforms in the industry.

"Being independent was the key," she says. "I wanted control over my life. I wanted to be able to say, this is mine."

And it is. A Wise Choice Entertainment was established in the 20th century, built on a foundation of research, wisdom, and guidance. It has since grown into a full-spectrum brand that serves artists, creatives, and dreamers alike. From organizing concerts to planning girls’ trips, booking travel to managing talent, Diana’s company provides seamless experiences. Her travel branch, A Wise Choice Enterprises, helps clients book trips through a personalized platform, blending entertainment and leisure with style and care.

Running a company of this scope is never easy. "You have to go through trials and errors, losses and gains," Diana says. "I had a lot of losses. But I never gave up. Giving up is not a part of my vocabulary."

That grit, quiet, powerful, and deeply personal, is what sets Diana apart. RDC Magazine is honored to feature her not just for her business acumen but for her unstoppable spirit. She represents what entrepreneurship looks like when it is built not on privilege but persistence.

A Wise Choice Entertainment is not just about putting on a great show. It is about making sure every artist and every client is taken care of. Diana prides herself on her commitment to excellence. "If the artist is well taken care of, they will give you their all. That is how events become unforgettable," she explains.

When Diana reflects on her journey, what excites her most is not only what she has built but what is ahead. Since launching AWCENT in April 2013, she has never lost sight of the larger vision. "This is just the tip of the iceberg," she says. "The best is yet to come."

That sense of purpose has helped her push through every challenge. Diana credits her faith in God, her persistence, and her support system for keeping her grounded during tough times. "There were moments I wanted to quit," she says. "But I had friends who believed in A Wise Choice Entertainment even more than I did. They would not let me stop."

That support, combined with her lived experience, shaped her leadership style. "No one can see your vision as clearly as you," she explains. "You have to roll up your sleeves and get involved in every part of your business. That is the only way to make it work."

In addition to her work in entertainment, Diana Jackson is the powerhouse behind Women Making Positive Changes, Inc., a nonprofit organization she founded in 2016 to meet urgent community needs and uplift underserved populations. What began as a grassroots effort has evolved into a transformative force for good—driven by compassion, resilience, and a commitment to providing real solutions. The organization is currently developing Leonora’s Place, a 36-unit affordable housing complex that will serve homeless individuals, youth, battered men and women, veterans, and low-income workers in Palm Beach County, Florida, and South Atlanta. This visionary development is designed to do more than just provide shelter—it’s about building holistic support systems. Each unit will come equipped with modern amenities like in-unit washers/dryers and Wi-Fi, while the property will feature an on-site playground, electric vehicle charging stations, a daycare center staffed with licensed childcare professionals, and a community room. Beyond housing, residents will receive personalized support, including help securing jobs, transportation through local partnerships with Palm Tran and MARTA, and assistance with scheduling medical appointments. Women Making Positive Changes also partners with CarePortal to fully furnish homes for homeless families—providing everything from diapers and clothes to furniture and kitchen appliances—ensuring that each family has the essentials for a fresh start. Through Diana’s leadership and tireless efforts, Women Making Positive Changes, Inc. is not just meeting the moment—it’s changing lives. Learn more or get involved at wmpcinc.org.

"It is about more than business," she says. "It is about being a light. A bridge. A second chance."

Her values were shaped early by her mentor and mother, the late Vivian Leonora Jackson. "She taught me to work hard, to carry myself with etiquette, and that your first impression is your best impression," Diana says. "I promised to make her proud."

She has. Along the way, she has been supported by an extraordinary circle of loved ones and colleagues. She gives heartfelt recognition to Gary Moore, Tara Rousseau, Sean Allick, Charles Newkirk, Antoinette Williams-Gordon, Geneva Miller, Tonia Jackson, Anton McCarthy, and her mentor Leonardo Bennett, who introduced her to outdoor concert tour life through The FunkFest. She also credits her reality TV clients, including Mrs. Deborah Bryant, known as Momma Dee, Brisco, and Miss Clemie Shaw, known as Ms. CeeCee, for their support and belief in her mission.

When Diana is not making power moves in business, she is soaking up the energy of South Florida. If a friend visits, she curates the perfect week. Monday night at Blue Martini in Brickell. Tuesday is dinner at Rocco’s Tacos and comedy at Thirty 1 Lounge with host Larry Dogg. Wednesday brings a stroll through Wynwood, lunch at Dukunoo Jamaican Kitchen, and dinner at Victory Lounge. Thursday might include Topgolf and R&B throwback vibes at Studio 183 in Miami Gardens. Friday is for happy hour at Dave & Buster’s and a set at the Improv in Dania Beach. Saturday calls for poolside luxury at Daer Dayclub at the Hard Rock. And on Sunday, she closes the week with brunch at Mango Café and nightlife at Club LIV on South Beach.

Through it all, Diana stays grounded. Her story is not about hype or spotlight. It is about faith, legacy, and refusing to give up. She has proven that you can come from humble beginnings and create a brand that not only thrives but transforms lives along the way.

At RDC Magazine, we believe stories like Diana’s are essential. They remind us what can happen when you trust your path, honor your roots, and lead with heart. Diana Jackson did not wait for opportunity. She built her own. She did not just dream. She dared.

A Wise Choice Entertainment is not only a business. It is a message.

And Diana Jackson is only getting started.