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Morning Speaker

Dream, Sink, Launch: The Real Entrepreneurship Journey

Kristy Jackson 

Entrepreneurship Coach

Business coach and speaker, Kristy Jackson,Ed.S. incorporates her experience and winning strategies that have set her apart as a serial entrepreneur into her new book, Dream, Sink, Launch.  Dream, Sink, Launch is a mindset and strategy guide that uses a new creative problem solving approach to innovate dreaming, flip failure into wins, and implement the appropriate action plans for success. For Kristy, business is personal, so she uses her life stories, practical advice, and dozens of work-space exercises to empower anyone who is trying to bring a dream or new idea to life. Readers will discover three big understandings:


  • Dreams require critical and creative thinking not just imagination. 

  • Sink experiences will happen, so prepare with a growth mindset, resilience, creativity, and faith.

  • A successful Launch requires creating a plan and doing your research.

Keynote Speaker
DBA: Doing Business As a Black Woman in America

Winnie Elizabeth Caldwell

Chief Operating Officer, Books N Bros

Winnie Caldwell is a St. Louis, MO native and the Co-Founder of Books N Bros. She’s also Sidney’s mom :). Winnie studied Corporate Communications at Lindenwood University and proceeded to work in a fast-paced industry blogging, content creating, teaching and empowering others in the community. Passionate about serving others, writing began as a natural fit. Winnie began blogging in 2012, which led to speaking engagements from St. Louis, MO to Washington D.C. Blogging also led Winnie to manage and build websites for others as well as teaching teens how to do so through a local financial literacy startup. Though, Winnie couldn’t stop there. Winnie also has over 5 years of experience working with youth to not only empower them but teach them how to profit via blogging/media relations.


While climbing the Media Relations ladder, she’s also been leading a young leader. The experience Winnie has garnered over the last 8 years is paying off today. Her son, Sidney Keys III, is the 14-year-old Founder of Books N Bros LLC. When Sidney had the idea to found a book club in 2016, he wanted it to be for boys as a form of social justice. Winnie took off the mom hat and put on the Communications hat.

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