Momager and Entrepreneur Manages Her 11-Year-Old Son’s Business While Building Her Brand

Winnie Caldwell is a St. Louis native and the founder of Booked Enterprise, a media company that helps clients with interview prepping, résumé revisions, and public relations needs. In addition to managing Booked Enterprise, Caldwell is also the “momager” for her 11-year-old son’s startup Books N Bros. I sat down with Winnie to discuss how she manages her son’s business, while finding time to build her brand.


Chanel Martin: Who is Winnie Caldwell?

Winnie Caldwell: If I were to describe myself, I would say that I am a storyteller—I love to talk—entrepreneur, and most importantly I am a mom. Sidney is my 11-year-old son, who founded Within my son’s company, I am not only mom, but I manage all of his PR, and I hold the given title of co-founder/program director.

Books N Bros started out as simply fulfilling a need to encourage young boys to read. With Eye See Me Children’s bookstore being the outlet that exposed Sidney to a lot of positive African American literature, Books N Bros primarily focuses on African American literature. After a few months, Books N Bros developed into a subscription-based membership business. While it is a book club for boys, serving members ages 7–13, it is also teaching Sidney entrepreneurial skills. With my assistance, we designed a membership box together and now have members nationwide from California to New York.

Members meet locally once a month to review the featured book together, receive their new membership box and extra trinkets that are included in the box (worksheets, reading supplies, snacks, a membership T-shirt, and more!). Members who are not local tune in virtually via a members-only YouTube live stream. Books N Bros has been acknowledged and featured in highly acclaimed media outlets such as HuffPost, Ebony, The St. Louis American newspaper, St. Louis Public Radio, CBS, CNN, O Magazine, and more.


How do you balance building your brand alongside your son Sidney’s brand?

Leaving my 9-to-5 in 2017, to work for my son and myself full-time, led me to a third passion, Booked Enterprise is unique because not only are my relationships and results authentically earned, but I treat each of my clients as mentees and not just another number. That is why the interview prep service is so affordable. If you’re in between jobs, it’s not very fun or easy spending money when funds are tight. I use my empathetic ability as a woman, who hasn’t forgotten her rough past, to encourage and motivate clients to the next level.

Managing my dreams with my son’s dreams is very reassuring. Being a single parent is already a unique and tough job. There are days where I’ve doubted myself, but Sidney has always been in my corner no matter the situation. When I am down, he encourages me, and when he’s down, I uplift his spirit. It also helps that we have constant faith in God that we’ll go as far as we’re supposed to. In January of 2017, I asked Sidney what he saw in the future for his business. He said he saw us speaking in front of crowds of people, traveling, meeting with authors and changing the world. By March 2017, Books N Bros had allowed us to do just that. We’ve traveled, spoken to boys about literacy, met with authors, and we’re still growing. That in itself is so encouraging.


Do you have advice for mompreneurs and momagers?

When it comes to being a mom, just be the best mom you can be to your child. Don’t try to keep up with the next mom or compete. The relationship you have with your child(ren) is authentically made for you and your family. Sidney and I tease each other, dance together, and grow together. As a momager/mompreneur, I have to stress how important it is for you to put your child first. With Books N Bros being my son’s business, I make it clear of any future opportunities that I don’t confirm or agree on anything without Sidney’s approval. I fully believe we’ll reach who we’re supposed to, exactly how and when we should. Momagers, respect your child’s comfort, mental capability, and happiness. Do what God has planned for you and you’ll see the fruits of your labor.