Rashida Gayle – In the BIG League

AS a child growing up in Jamaica, Rashida Gayle liked to imagine that she would grow up to become either the next Oprah Winfrey or a gynaecologist — such was her passion for representing and helping people, especially women, to access the opportunities and resources they deserve. Today, she is neither Oprah nor a doctor, but she is still in the big leagues. Now living and working in the United States, Rashida is the first and only black woman to independently represent both National Football League (NFL) and Major League Soccer (MLS) athletes, and was named a 2021 Forbes 30 under 30 and 2021 Atlanta 500 awardee .

“I had no idea I would end up working in sports or entertainment,” Gayle, 29, told All Woman right off the bat. “But my parents always kept a very sports-heavy home, even after we moved to the States. We always watched the Olympics and soccer and football, so of course you know Usain Bolt was like a national hero in our household. I’ve always been in the sports world through my parents.”

Such was her fondness for sports that Gayle found herself volunteering to help manage her high school’s football team. When she went off to college, she worked part-time in the sports marketing department for the three years of her tenure.

“That shaped my future in sports marketing,” she said in reflection. “Being able to leverage the relationships that I built going to university put me in a really good position career-wise to begin my journey.”

But, she did not immediately see the good position that she was in. After graduating from Florida State University, the young woman found herself job hunting unsuccessfully in one of the toughest and most male-dominated industries.

“Being a woman in a male-dominated industry is hard in itself, because you’re not typically in the room, especially in a high position. Put being black on top of that,” she said frankly. “In Jamaica we have more classism, but in America we have racism. Sometimes you are slighted because of the colour of your skin. You can be as rich as you want to be, but some people will still not like you just because of your skin.”

Because of how competitive the sport industry is, both on the field and in the boardrooms, it’s standard practice for a graduate to work for a few years for free before starting in even an entry level role, Gayle said. But after a few internships, Gayle’s indomitable Jamaican entrepreneurial genes kicked in, and she decided to start a business.

“I started my first company, RG Management, in the fall of 2014, three or four months after I graduated. It was made official in 2015,” she shared proudly. “I leveraged the relationships I had from working in sports in college and the business grew until after a few years it was acquired by a firm in New York.”

Gayle has been a serial entrepreneur since, and through her flagship firm, Twenty Six Marketing Agency, she has helped athletes, entertainers and influencers to cash in on their talents and provide them with the representation needed to secure multimillion-dollar deals.

One of the biggest challenges that the CEO faces is one she has to overcome constantly — being confident and bringing her A game day in, day out.

“It’s really convincing yourself everyday that it’s worth it — that you’re worth it… That the vision that you see is going to come through and there is a light at the end of the tunnel,” she said with conviction. “Sticking to the plan is definitely the most difficult because you have your days where you wonder why you started a company, and I think no matter what, other challenges exist, that’s always gonna play a role in your life, and it’s not something you can run away from. The external factors, you just deal with them as they come, but internally, you are fully responsible for how you shape yourself to be successful.”

Gayle revealed the two main sources of her confidence and motivation: being a fool — foolish enough to believe that she can accomplish anything she desires — and her team.

“I have such a good team around me, and I’d be damned if I didn’t put out a hundred per cent effort for my team. They work so hard, and it is essential for me to produce for them as well,” she said graciously. “I have a partner, who started with me from the beginning, and my vice-president of strategic partnership as well. Just seeing them do well in their roles brings me so much joy.

“ Forbes was great. It was a high and it was phenomenal. It was a dream come true. But that’s a short-term feeling of accomplishment. What brings me the most joy, long-term, is when I see the people within my company do well and accomplish their goals,” she added.

Twenty Six is just over a year old, and Gayle is planning to increase in skills and knowledge as her business increases in size.

“We’re really young, but we’ve done really well from a growth standpoint,” she assessed. “We have a number of clients from a variety of sports and industries. My short- and long-term goal is to scale and grow the company, and be a force in the entertainment industry.”

And, she has not given up on her childhood dream of women empowerment. Gayle also co-founded Bloom, a non-profit organisation geared towards helping professional women connect with each other, receive mentorship, and catalyse their growth and development.

But even as she continues to sprout branches and bloom, the young woman vows to never neglect her Jamaican roots.

“I came home to Jamaica since the pandemic happened, and I spent two weeks here because I had to quarantine,” she said joyfully. “As a child, with my parents living in Jamaica, my parents always ensured that we travelled to different places on the island, and that is still something I enjoy doing. I also love to eat, especially Jamaican food. My favourite food is plantain. I can eat it with anything at any time of the day.”

She also loves to give back to the country that has given her so much.

“Jamaica means a lot to me and my family,” Gayle said solemnly. “Eventually I want to be active in our economy and our policies, but not necessarily in a political way. I want to have an impact and give back to our community. That’s what’s most important to me.”