From Legacy to Leadership: How Cheris Monique Built Multiple Empowerment Businesses by Honoring Family Traditions While Creating Her Own Path
Some entrepreneurs are driven by market opportunity. Others are called by purpose. For Cheris Monique, the founder of multiple empowerment-focused businesses spanning early childhood education to adult transformation, her entrepreneurial journey has always been guided by something deeper than profit: a natural inclination to help others rebuild, rise, and realize their dreams.
As a certified Family Life Educator, confidence coach, and seasoned entrepreneur, Cheris has built a multi-generational empire of empowerment. For over 30 years, her Jumping Jacks Learning Center has served the Wilmington, Delaware community, earning recognition from the Wilmington City Council for its exceptional commitment to children and families. But her impact extends far beyond early education.
Through RAM Role Model Society, she empowers girls ages 7 to 18 to build confidence through creative outlets like modeling, fashion, and photography. Her Rebuild Your Life brand helps women and adults reignite dreams they may have put on hold. And through her YouTube show “Steel Toes to Stilettos,” she reaches millions with motivational content about resilience and transformation.
Cheris’s ability to reinvent herself across industries—from education to entertainment, where she’s appeared on shows like “One Life to Live” and “Law & Order” and walked in New York Fashion Week—is grounded in a powerful belief: it’s never too late to start over. Her journey represents a unique approach to entrepreneurship, one that honors family legacy while carving new paths.
What makes her story particularly compelling is how she’s woven together multiple businesses that serve different life stages while reinforcing a single mission. Rather than diversifying for the sake of growth, she’s created an ecosystem where each venture strengthens the others, proving that purpose-driven businesses can be both financially successful and deeply meaningful.
In this conversation, Cheris shares how she’s built sustainable revenue streams across multiple generations, the importance of honoring those who came before while creating your own legacy, and why she believes empowerment isn’t just a calling—it’s a business model that works.
What inspired you to found your businesses and what were the main challenges you faced?
By nature, destiny, and passion, I’ve always been drawn to encouraging and empowering others to reach their goals, embrace self-sufficiency, and live unapologetically. Every day, I naturally step into the role of mentor, counselor, or coach—whether it’s offering a listening ear or following up with advice that leaves people feeling lighter and more confident.
My work spans across all ages and stages of life. I started with my early education program, serving infants, toddlers, and preschoolers—a family legacy inspired by my mother and aunt, who both owned childcare businesses. Carrying that torch was important to me, not just as a profession but as a way of honoring them.
From there, I created RAM Role Model Society, an empowerment program for girls ages 7 to 18. The mission is to build self-esteem and confidence through creative outlets like modeling, fashion, and photography—tools that give young women the courage to see themselves beyond limitations.
And lastly, there’s my Rebuild Your Life brand and community, which empowers women and adults to chase the dreams they may have put on the back burner.
Through this work, I’ve learned that consistency, truly understanding my audience, creating effective marketing strategies, and offering a product that meets real needs are the keys to not only sustaining my businesses but also growing them financially.
Did you start the venture alone?
I can’t say that I started everything on my own. Everything is connected to a person or a purpose. My childcare center is an extension of the legacy my mother began over 25 years ago. It just felt right to pick up where she left off, so she can finally rest when she’s ready.
Everything else is part of the purpose and plan for my life. Throughout my journey, there have been people who poured into me and believed in me. Those individuals are an important part of my story — but at the beginning and end of the day, it’s up to me to keep it going.
What’s your business model, and how have you grown your revenue?
My business model is built around multi-generational empowerment—serving people at every stage of life through different platforms and programs. Jumping Jacks Learning Center provides early childhood education, creating a foundation for young minds while generating steady revenue through tuition and educational services.
RAM Role Model Society operates as a specialized empowerment program for girls, combining creative workshops, mentorship, and confidence-building activities. This creates both direct revenue through program fees and indirect value through community building and brand recognition.
Rebuild Your Life functions as my flagship empowerment brand, offering coaching, workshops, content creation, and speaking opportunities. This diversified approach includes my YouTube show “Steel Toes to Stilettos,” which builds audience engagement and creates multiple revenue streams through content monetization, coaching packages, and corporate speaking engagements.
The key to my financial growth has been understanding that each venture serves a specific audience need while reinforcing my overall mission of empowerment. By maintaining consistency across all platforms, deeply understanding my audience at each life stage, and ensuring my marketing strategies reflect real value, I’ve been able to create sustainable businesses that grow together rather than compete with each other.
