The Color of Money | Transformative Conversations for Wealth Building

105. Move Your Feet: How Jemila Winsey Built & Rebuilt a High-Impact Real Estate Business

Aug 13, 2025

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What does it really take to rise from homelessness to the executive suite—and then risk it all to reinvent yourself again? Jemila Winsey’s story is proof that true power comes from intentionality, relentless hustle, and the courage to pivot.

As a Nigerian immigrant, Jemila overcame early hardships to build one of North America’s largest brokerages, later stepping into a national leadership role with Real Brokerage. She breaks down the pivotal mindset shifts behind her success—why focusing on your “why” matters more than money, how to blend old-school consistency with modern tech, and why helping others win is the real prize. Jemila opens up about burnout, starting over, and leading fearlessly as the only Black executive in her company.

Whether you’re growing a business or seeking purpose in your next chapter, Jemila’s blueprint is a lesson in building legacy, staying humble, and moving your feet—no matter how many times you start again.

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