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How The EdHub STL Fellowship Saved My Life (and My Son’s Business)

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by Tyler Mathews in EdHub STL, Stories
September 16, 2019

By Winnie Caldwell

“Comparison is the thief of joy” (Theodore Roosevelt). This is a popular quote many may be familiar with and many startup organizers may need to be a bit privier to.

The summer of 2016 changed my family’s life. That summer, I was referred to visit EyeSeeMe Children’s Bookstore, so I took my son on a surprise visit there. We were in awe to see so many Black figures in a variety of ways. It was mind-blowing for us as we lived in a segregated are of St. Louis County at the time. We were only familiar with seeing books highlighting Black figures like Dr. Martin Luther King, Rosa Parks, and maybe Michael Jordan. EyeSeeMe exposed us to the multi-layers of Black people like never before. The proud mom, small business supporter, and inspired black girl in me was so enthralled that I was excited to share this moment via Facebook Live. In only two days and 65,000 viewers later, our lives were changed.

Sidney, cofounder of Books N Bros (third from right)

We went from supporting a local Black-owned bookstore as residents, to my son, Sidney Keys III, becoming inspired to start his own initiative, Books N Bros book club. I was working with teenagers at my 9–5 during that time and learned to trust youth to lead, so I asked what he wanted. “I want to make friends. I want to introduce African American books to other boys. I want reading to be fun!” Expressed 10-year old Sidney.

Now, three years later we have led over 300 members, internationally, all boys, between the ages of 7–13, to be excited about African American literacy.

We had what felt like rock star moments as we graced red carpets from LA to NYC for our efforts. Oprah Winfrey personally sent a video to congratulate Sidney and other celebrities followed suit. We were on a high. We were excited. We became known as a powerful mother and son duo that could not fail.

Then, the rock star status slowed down. We had the highest number of members ever and I was the running machine. I quit my job to answer the high demand we’d just experienced. I worked from home diligently. I lost a ton of sleep. I answered thousands of emails daily. I sabotaged myself. Due to this thing called pride, I didn’t know how to come up for air. I sunk into this other thing called imposter syndrome, with a dose of anxiety, and a lot of depression. What everyone didn’t know is that I’d lost motivation, I was struggling financially, and spiritually as I was the backbone of my power duo family.

After a lot of pitfalls and struggles, I was introduced to the upcoming EdHub STL Fellowship. I’d been aware of Cortex for years but never felt like it was accessible to me until EdHub STL invited organizers and aspiring startups to apply who explicitly work to empower underserved families through education. Cortex as an infrastructure is inspiring but there is a larger issue in the Midwest area as Black and Brown communities not only feel underserved, but more so unseen. EdHub STL created an outlet for Black and Brown organizers to be seen, to excel, and to align with allies to create better systems for our future in education. I was inspired. I applied.

I am proud to say that Sidney and I are alums of the first EdHub STL cohort. EdHub STL saved my life.

Winnie Caldwell and Sidney Keys III

I was able to work outside of my home in open spaces to take my mind off personal problems and dive into creating further possibilities for our members. I’m thankful for the Fellowship office space as it granted me a safe space to vent with other Fellows. The access to have extra storage space for books, materials (as we didn’t have enough storage space at home), and the daily boost that we were doing great things.

Throughout the Fellowship my skills were sharpened thanks to several educators and mentors that facilitated weekly sessions with us. Sidney and I had the opportunity to visit schools with the other Fellows to ensure students of St. Louis had the same opportunity as children in other regions. I was stretched to think beyond the red-carpet experiences and into the role of a change maker.

Sidney Keys III visiting Roses in Concrete Community School.

Sidney Keys III visiting Roses in Concrete Community School

I am proud to say I have developed personal strategy to combat that entrepreneurial slump I experienced. I cultivated relationships that have helped take Books N Bros to greater heights. We now have help to operate more efficiently as an organization without so much physical demand of me. We successfully hosted our first fundraising gala at Innovation Hall with enough donations to grant 13 boys full year scholarships for a free experience in Books N Bros. We also won second place in the 4 Hands Pilsner Scholarship.

Thank you to the entire EdHub STL and Venture Cafe St. Louis family as we’ve grown with you and propelled to higher heights with the help of your resources and experts.

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