Helping and connecting with others has always been something that has come naturally to Cynthia Jemison. The Chicago native continues to use her work as an Entrepreneur and Strategist to stay “at the intersection of culture, commerce, and impact” while finding new ways to create space and opportunities for others.
A proud graduate of Whitney M. Young Magnet High School and the Georgia Institute of Technology, Jemison began to cut her teeth in the business world, learning early lessons working with Joi Mitchell of R.U.N. Marketing and later with The Bortz Entertainment Group, where she learned to operate multi-unit businesses from the inside out. She went on to found EightyThree50 Marketing and ETF Capital, building a portfolio that bridges creative strategy, private finance, and community impact.
Today, as Founder and Chairwoman of the Hillman Recreation Foundation, Cynthia leads with purpose, designing spaces where recreation, culture, and Black excellence thrive. Jemison credits college years in Georgia and her proximity to the Atlanta University Center—and being a child of The Cosby Show and A Different World—for inspiring the Hillman Recreation Foundation’s mission of blending legacy, wellness, and community.
N’DIGO recently sat down with Jemison to learn more about the Hillman Recreation Foundation, its mission, and what the organization has in store for the near future.
N’DIGO: In one sentence, how would you describe yourself?
Cynthia Jemison: I’m a pattern-seeking visionary who looks at people, partnerships, and opportunities the way others look at puzzles or math equations—everything is just pieces waiting to be connected and solved.
Three words family and friends would use to describe you, and why?
Altruistic. Connected. Funny.
I have a big heart, and I genuinely care about people and how we can create opportunities that make life better for others. My sarcasm also precedes me, so there’s that lol
Who or what inspires you?
At this point in my life, God inspires me. When I look at the world, I see the way everything fits together—every challenge, every barrier, every trial has a purpose in shaping who we become. I believe God already has a path set for each of us, and when you align yourself with that purpose, your life starts to make more sense. For me, that means living in service, being a blessing to others because I’ve been blessed, and creating spaces that give people exposure and access to opportunities they might not otherwise see.
Please tell us all about the Hillman Recreation Foundation and its mission.
The Hillman Recreation Foundation exists to create meaningful pathways between education, industry, health, and culture. Our mission is centered around exposure and access—introducing young people and communities to industries and opportunities where they have historically been underrepresented. Through programming, events, and partnerships, we create spaces where people can experience wellness, entrepreneurship, and career possibilities that might otherwise feel out of reach.
What can you share with us about HRF’s upcoming Juneteenth celebration?
Our Juneteenth Jubilee celebration will take place on Juneteenth in Jackson Park in partnership with the historic Lakeside Lawn Bowling Club, which has been part of the community for more than 100 years. The club has been working to introduce more youth and more diversity to the sport of lawn bowling, so we’re excited to help bring new energy and new audiences to a tradition that has long existed in the park. The Jubilee will feature several curated activation zones designed to celebrate culture, wellness, and community connection, including:
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- The Recreation Green will serve as our fitness and wellness zone, where guests can enjoy a variety of recreational activities.
- The Freedom Stage will be our main performance area, featuring music performances and programming.
- The Table Talk Pavilion will host classic community games like dominoes, spades, and Ebonyopoly
- The Cookout Corner will bring the community’s flavors to life with food vendors and a cook-off competition.
- The Little Legacy Lawn will introduce youth to cultural creativity through hands-on activities like making shekere drums.
- And the Hillman Marketplace will showcase a curated Black-owned vendor marketplace, highlighting entrepreneurs and businesses from across the community.
And please tell us about this Fall’s HBCU Run & Brunch as well?
The HBCU Run & Brunch is the Hillman Recreation Foundation’s flagship event, and this year will mark our 2nd annual celebration, taking place on Saturday, September 19th.
Our partner organization this year is the nonprofit arm of Black Baseball Media, the group behind the Inaugural HBCU Baseball Classic at Wrigley Field, set to happen in May of this year. We’re also especially proud to have the support of HBCU graduate and 7th Ward Alderman Greg Mitchell in bringing it to life.
This year, we’re expanding the Run & Brunch into a full three-day weekend experience. From Friday, September 18th, through Sunday, September 20th, we have an action-packed weekend planned, including the Move & Thrive Expo, a health and wellness experience presented in partnership with Fit 4 Purpose. We’ll conclude the evening with a special fireside keynote conversation focused on wellness, purpose, and community impact.
Saturday is the centerpiece of the weekend — the HBCU Run & Brunch, featuring both a 5K and 10K race taking place within Chicago’s 7th Ward along the beautiful lakefront. After the race, the park transforms into what we call The Hillman Yard, designed to feel like an HBCU homecoming celebration where we’ll have alumni groups competing for bragging rights and the honor of influencing next year’s event theme.
The weekend concludes on Sunday with the HBCU Family Reunion, presented in partnership with Vince Bass. The gathering is designed to bring people together in the spirit of unity and connection — imagine the classic Chosen Few picnic vibe, but centered around the collective pride and camaraderie of HBCUs and PBIs.
Last great book you read?
Believe it or not, the Bible. Before last year, I had never actually read it, but once I did, I realized it’s one of the most fascinating books ever written. It has everything—action, wisdom, conflict, humor, and incredibly powerful lessons about human nature. Regardless of someone’s personal beliefs, I think anyone can gain something from the stories and principles within them.
What’s the most inspiring or motivational advice you’ve ever been given?
Years ago, someone told me that I needed to stand firm in my own stilettos if I wanted to move forward in life and business. At the time, I didn’t fully understand what she meant because I thought success always required a partner or someone else’s help. Looking back, I think what she was really saying was that you have to be grounded in who you are as a woman and in your own decisions. When you’re clear about that, everything else becomes easier.
Favorite quote or affirmation?
“Relax. Relate. Release.”
It comes from A Different World, which is fitting because the name Hillman Recreation Foundation is inspired by Hillman College from that show. But the message has always stuck with me. Life moves fast, and sometimes the best thing you can do is relax, understand what’s happening around you, and let go of what doesn’t serve you.
What’s next for Cynthia Jemison?
Right now, my focus is fully on the Hillman Recreation Foundation. We’re just getting started, and there’s so much potential ahead—from new partnerships with major organizations to opportunities that extend beyond the United States and into Africa. My goal is to continue building programs and platforms that create meaningful opportunities for communities. It may sound idealistic, but I truly believe the work we’re doing can make a real difference. And that’s the work I plan to keep doing.
For more information on the Hillman Recreation Foundation and its upcoming events, please visit them at www.hillmanrec.org/ecosystem
and connect with them on Facebook and Instagram at @HillmaRecFoundation.
