On the Kenya Keynote Tour, during a visit to a Masai village, one of Kenya’s most revered tribes known for their resilience, cultural heritage, and warrior traditions—Roosevelt was recognized for his impactful presence. He was honored with a Masai name, Tipilit, meaning “the ultimate leader.” The name Tipilit suited him perfectly. With his tall frame, commanding voice, and impeccable style, he embodies leadership at every turn. Yet, his fellow speakers saw that his quiet moments and genuine warmth showed an entirely different side to the powerhouse he portrayed on stage.
Roosevelt’s on-stage presence was unforgettable, using structured acronyms, succinct phrases, and rapturous encouragement to inspire students and team members alike. Each talk was a blend of wisdom and humor, with messages like “this is a writer downer” sticking in the minds of students long after the sessions ended. But beyond his impactful teaching style, Roosevelt connected deeply with his audience by acknowledging their shared heritage. As a successful entrepreneur who proudly claims his “blackness,” he symbolized achievement for the Kenyan youth, reminding them that “Africa is the Motherland” and encouraging them to take pride in their roots.
For Roosevelt, this message wasn’t really about race; it was about the power of history and culture. Most of the students in Kenya have never left Kenya, let alone Africa. For them to hear that Roosevelt traveled almost 30 hours across the world, left his family, and put aside his business to be there with them, made them feel special and loved. Williams wanted to ensure that they understood why. It’s because he knows a secret that not many around the world are willing to admit. Africa is rich. It’s rich in land resources, hospitality but more importantly in talent. Roosevelt stood tall as a booming reminder of the subtle but obvious oppression and corruption that is riddling the country, urging the youth to take back their futures.
Fatherhood and Family Values
Kenya in particular is also rich in family. As a father, Roosevelt also carries this message of confidence into his own home. His six-year-old daughter is often a source of joy and pride for him, and he didn’t miss an opportunity to brag about her to the team on the tour. For Roosevelt, family is central, and he believes in nurturing his daughter’s confidence from an early age. He frequently spoke about teaching her decision-making skills, ensuring she understands her worth and feels empowered to approach life with self-assurance. His parenting philosophy reflects the same principles he brings to his professional life, ensuring that his legacy of leadership and positivity is passed down to the next generation.
The Quiet Leader
Though Roosevelt’s stage presence was bold, offstage, he was a gentle observer. On the tour bus, he often spent hours in reflective silence, taking in the Kenyan landscapes as they passed. But he made a unique impression on his teammates through small gestures of kindness. At each hotel, Roosevelt left a trail of roses for the crew to find—a tribute to his namesake, “Roosevelt,” which means “rose field.” The roses became symbols of his gratitude and a reminder of the contrast between his powerful public persona and his reflective, nurturing side. His thoughtful actions and encouraging words added an unforgettable warmth to the tour, making him a cherished presence.
Despite his reserved temperament offstage, Roosevelt Williams III is well-known for his vibrant and impeccably styled suits, which tend to match his louder on-stage personality and have become something of a signature look. Whether in plaid, bold colors, or intricate patterns, each suit reflects his personality—confident, approachable, and full of character. To perfectly intertwine his quiet yet bold demeanor, Roosevelt adds a personal touch to every outfit by placing a single rose in the front pocket of his jacket, a nod to his namesake, symbolizing both his connection to his heritage and his thoughtful approach to life. His fashion sense, combining elegance with flair, leaves an impression everywhere he goes, making him a memorable figure both on and off the stage.
Celebrating Others
Roosevelt’s commitment to uplifting others was evident not only with the youth on the Kenya Keynote Tour but also with his fellow speakers. He was quick to offer encouragement, often complimenting each person in ways that showed his keen observational skills. Whether it was a subtle nod to someone’s strengths or an enthusiastic cheer, Roosevelt played the role of “hype man” for the entire team, especially during moments of exhaustion. His ability to lift spirits and recognize everyone’s unique contributions reflected his deep belief in the power of community and shared success.
This commitment to celebrating others also shines through at YBNB’s annual Black and Gold Gala, a grand event Roosevelt hosts to spotlight Black excellence. The 2024 gala earlier this month was its 4th year of celebrating excellence in the local San Diego community, especially for Black business leaders. Roosevelt sees the Black and Gold Gala as a bridge between his mission and his community, showcasing achievement, creativity, and ambition in an unforgettable evening of celebration and connection.
For Roosevelt, the gala is a cornerstone of YBNB’s mission, where Black professionals and young entrepreneurs inspire each other. It reflects his belief in community-driven success and his commitment to providing future generations with positive role models. His dedication to nurturing talent and promoting excellence was evident in every detail of the event, from the recognition awards to the show-stopping fashion shows.
Tipilit: The Ultimate Leader
Roosevelt Williams III’s time in Kenya provided a glimpse of a leader who combines strength with humility, commanding presence with genuine empathy. His organization, Young Black and N’ Business, embodies his mission to uplift communities and create opportunities for economic growth, mentorship, and self-empowerment. Following the tour, Roosevelt formalized his support for Kenya by inviting several community leaders to join the YBNB network, providing them with mentorship and ongoing resources. By publicly honoring these locals, he solidified YBNB’s commitment to fostering a global network of black entrepreneurs.
Roosevelt’s journey on the Kenya Keynote Tour reflects his belief that true leadership is as much about quiet support as it is about public influence. His Masai name, Tipilit, or “the ultimate leader,” encapsulates not only his achievements but also the values he lives by. Through his powerful words, structured teaching, and thoughtful gestures, Roosevelt Williams III exemplifies a legacy that transcends borders—a leader dedicated to uplifting others, with a rose for every step of the journey.
Jenny Carrington is a dancer, writer, philosopher, and yogi. After successfully walking across the United States from Delaware to California (over 3,000 miles), she now focuses on social activism.
