• A woman with short, curly black hair is smiling against a solid blue background. She is wearing a black V-neck shirt, large gAs part of Women’s History Month, we celebrate Nakisha Bailey, a 2002 graduate of Metro High School and proud alumna of Saint Louis Public Schools, a trailblazer who has shattered barriers in the music industry and is now forging a new path as a business owner and educator. Her journey is one of ambition, resilience, and creating opportunities in spaces where women are often underrepresented. She also attended McKinley Classical Junior Academy for middle school and Betty Wheeler Classical Junior Academy (formerly Kennard CJA) for elementary school, making her journey an inspiring one for SLPS students today. 

    Breaking Barriers in the Music Industry

    Nakisha began her career in New York’s fast-paced music scene, working her way up from unpaid internships to an executive role in the industry. Early on, she noticed a troubling trend—while many Black and brown professionals were assistants, few were advancing into leadership. Determined to break that cycle, she worked tirelessly, eventually earning the title of Vice President at Atlantic Records.

    "The music industry is still very male-dominated, especially in leadership roles. As a Black woman, I knew I had to be twice as good, twice as professional, and twice as prepared to be taken seriously," Nakisha says. "I wasn’t just working for myself—I was setting an example for the next generation of women in music."

    A Leap Into Entrepreneurship

    Despite reaching the executive level, Nakisha felt a pull to build something of her own. She co-founded Win Win Coffee, Philadelphia’s first Black woman-owned coffee roasting and distribution company. Starting a business in the middle of a pandemic was a major risk, but she was ready for the challenge.

    "I had spent years building other people’s success, and I wanted to see what I could do for myself," she reflects. "Running a business isn’t that different from running a label—you have to manage people, build a strategy, and make tough decisions. The biggest lesson? Bet on yourself."

    A woman with short, curly hair and clear-framed glasses is smiling while leaning on a countertop. She is wearing a black shir

    Advice for the Next Generation

    Nakisha encourages young women to take control of their own narratives. "Use your voice," she says. "Don’t wait for permission to take up space. Speak up, be present, and make sure you are heard." She also stresses the importance of taking risks, even when the path forward is uncertain. "The first opportunity might not be perfect, but it’s a step forward," she explains. "Sometimes, you have to take the leap before everything is figured out."

    Mentorship is another key factor in success. "Find mentors and allies. Women supporting women is powerful," Nakisha emphasizes. She believes in lifting as she climbs, ensuring that opportunities become more accessible for those who follow. "And if there’s no seat for you at the table, build your own. Don’t be afraid to create spaces where your voice and vision can thrive."

    Redefining Success on Her Own Terms

    Nakisha’s story is one of fearlessness and determination. Whether in music, business, or education, she proves that women can define success for themselves. Her journey is a reminder that no industry is off-limits, and that persistence, adaptability, and confidence can break down any barrier.

    For every young woman with a dream, Nakisha Bailey’s path is proof that you belong in any room you step into—and if not, you have the power to create your own.