Booked Enterprise LLC.




Winnie Caldwell is a St. Louis, MO native. She 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 start up. Though, Winnie couldn’t stop there. Winnie also has over 3 years of experience working with youth to not only empower them but teach them how to profit via blogging/media relations. Grateful for an amazing support system on every endeavor she has approached, Winnie ensures to continuously represent her hometown gracefully. 

Winnie and son/client Sidney Keys III touring the offices of O Magazine in NYC!

Winnie and son/client Sidney Keys III touring the offices of O Magazine in NYC!


Personal Background


While climbing the Media Relations ladder, she’s also been leading a young leader. At a mere 17 years old, Winnie gave birth to her son, Sidney Keys III, 11 year old Founder of Books N Bros LLC. After overcoming adversity as a single mom, Winnie has used her testimony to assist, inspire and empower others. Outside of Sidney, Winnie always says her blog,, was her second child. Blogging pushed Winnie to travel to places she never imagined, meet people who continue to support her from all over the world and reach bounds that were never expected. And this dynamic duo's latest passion project, Books N Bros has been a testament of Winnie's connections, education and hard work. When Winnie is not networking, blogging or being a momager, she loves to travel near water for peace of mind, enjoy her favorite butter pecan ice cream and/or binge watch Netflix originals.



Over time Winnie has honed the title of being an online community influencer with a knack for leadership, community Involvement and corporate communications.

Being a naturally self - taught individual, Winnie's skills include but are not limited to: 

  • Exceptional communication and networking skills
  • Effective organizational skills
  • Successful working in a team environment, as well as independently
  • The ability to work under pressure and multi-task
  • The ability to follow instructions and deliver quality results
  • Content Development
  • Creativity and innovation
  • Public Speaking
  • Strategic thinker and self starter
  • Wordpress/Squarespace savvy
  • Advanced Libsyn user 


2016 - Present

The wire hanger by winnie - Founder

2012 – Present


2015 - 2017


2015 – 2016



I needed a press release. I didn't know where to start or what to say and that's when Winnie saved me. I told her what I wanted, and just like that...mission possible! Service was speedy and professional! I guarantee I will be working with her again.

/  Satisfied client  /


Winnie's service was the 3 P's. Professional, Prompt, and Positive. I would definitely recommend her resume revamping service to anyone looking to make a career change. Having a second eye on your resume makes all the difference in the world.

/  Satisfied client  /