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Wyn-Win Communications

Chicago based consultancy offering insightful thought leadership, strategic counsel, project management and exceptional support

Welcome to Wyn-Win Communications, where Together We Win. Wyn-Win Communications is a Chicago based consultancy offering insightful thought leadership, strategic counsel, project management and exceptional support for complex communications and community engagement programs.

07/10/2025

Today on Community Chatter, we were joined by Kenneth Speller, Board Member of 100 Black Men of Chicago, and Lisa Rollins, Regional Development Director at UNCF.

Kenneth shared details about the 23rd Annual College Scholarship Fair, happening Saturday, October 11, 2025, from 9 a.m.–2 p.m. at the Isadore and Sadie Dorin Forum (725 W. Roosevelt Rd.). The event will bring together more than 200 colleges and universities to meet with Chicago-area students, offering on-the-spot admissions, financial aid information, and guidance on the path to higher education. To register online, visit: www.100BMC.org

Lisa also provided an update on the UNCF Walk for Education, which was canceled due to extreme weather. While the walk will not take place, you can still support UNCF’s mission by registering online—your registration now counts as a donation to fund scholarships and student programs.
👉 uncf.org/events/2025-uncf-walk-for-education-chicago

Stay connected and support both organizations as they continue to empower students and strengthen communities.

24/09/2025

Today on Community Chatter, we were joined by Rael Jackson and Yvette Moyo of Real Men Charities, Inc., and Liz Abunaw, founder of Forty Acres Fresh Market, for an energizing conversation on wellness, entrepreneurship, and building stronger communities from the inside out.

We spotlighted the Grand Opening of Forty Acres Fresh Market’s first brick-and-mortar store this Saturday, September 27, from 9:00 AM to 1:00 PM at 5713 W. Chicago Ave, marking a major step forward in food access and local economic empowerment on Chicago’s West Side. Plus, we got a preview of Real Men Charities’ upcoming events at The Quarry, including the Heavenbound Sunday Jazz Brunch on October 5 and Friday Night Live kicking off October 10. From fresh food to live music and legacy, our guests reminded us what community-driven impact really looks like.

For more information on Forty Acres Fresh Market, visit their website below https://www.fortyacresfreshmarket.com/

Click below to register for Heaven Bound Sunday Jazz Brunch, October 5th.
https://events.eventnoire.com/e/jazz-brunch-heavenbound/tickets

Click below to register for Friday Night Live on October 10th.
https://events.eventnoire.com/e/friday-night-live-jazz-at-the-quarry

23/09/2025

Today on Community Chatter…

We’re talking food, family, and community power with Rael Jackson and Yvette Moyo of Real Men Charities, and Liz Abunaw of Forty Acres Fresh Market.

Catch us at 12:15 PM on Inspiration 1390AM.

10/09/2025

Today on Community Chatter, we were also joined by Kimberly Dixon-Mays, playwright and 2024 Lifeline Theatre BIPOC Adaptation Workshop winner, and Christopher Wayland, Assistant Teaching Professor of Theatre Acting at the Chicago College of Performing Arts.

Kimberly shared the inspiration behind her play RABBITS IN THEIR POCKETS—the first full production to emerge from Lifeline Theatre’s BIPOC Developmental Workshop. Inspired by A.A. Milne’s “Cherry Stones” and Br’er Rabbit folktales, the piece draws on African-American, African, and Caribbean oral traditions to explore legacy and storytelling through a powerful, cultural lens.

The play runs September 14th through October 5th at Lifeline Theatre.
General Admission: $45 | Previews: $30
Military, student, and senior discounts available
For tickets: [email protected] or call 773-761-4477

10/09/2025

Today on Community Chatter, we were joined by John Adams, Founder of the Bronzeville Trail Task Force, to discuss the transformative vision behind the Bronzeville Trail and the upcoming 2025 Installation & Awards Luncheon.

The Installation & Awards Luncheon is set for September 12, 2025, at the Hyatt Regency McCormick Place. The luncheon celebrates progress on converting the long-abandoned Kenwood “L” line into a 1.75-mile walking, biking, and running path that honors Black history, promotes sustainability, and improves community health. With $5 million committed by the City of Chicago toward this $100 million project, momentum is strong and community support is growing.

This year’s honorees include Cook County Board President Toni Preckwinkle, Dr. Maria Villalobos-Hernandez (Illinois Tech), architect Vernon Williams, R.A., and SmithGroup, recognized for their dedication to advancing this powerful community vision.

Click here for tickets: https://www.eventbrite.com/e/bronzeville-trail-task-force-inc-2025-installation-and-awards-luncheon-tickets-1478938738579?aff=oddtdtcreator

26/08/2025

The annual UNCF Chicago Walk for Education is coming up and it’s shaping up to be quite a party!

Today on Community Chatter, Al Orendorff, filling in for Wynona Redmond, welcomed UNCF Development DIrector Latina Brooks, who talked about UNCF’s 42nd annual Walk for Education. The Walk will be on Saturday, September 13, 2025, starting at 9 a.m. at Jean Baptiste Point at DuSable Lake Shore Drive and 39th St.

Walkers can either take part on their own, join a team or form their own team. You can walk, run, bike or skate. There’ll be plenty of music, dancing, food and fun for the whole family. Funds raised by the walk will be used to support scholarships, programs, and vital resources that open doors and empower young minds across Chicago.

You can register in advance to either walk or sign up to be a volunteer online (at UNCF.org) or onsite. In-person registration starts at 7 a.m. with warm-ups kicking off at 8.

Let’s walk for a future where every child can access a quality education. Your support helps shape a brighter future for the next generation!

13/08/2025

On today’s , we spoke with Karl A. Brinson, a lifelong West Side resident and President of the Chicago Westside Branch NAACP. A dedicated community leader and member of the Moore Park Advisory Council, Karl has spent decades advocating for equity, justice, and opportunity in Chicago.

He joined us to share details about the Freedom Fund Concert Fundraiser on Saturday, Sept. 20, 2025 at the Kehrein Center for the Arts, featuring the incomparable Terisa Griffin. This inspiring evening of live music and community will unite voices for justice.

🎟️ Tickets: www.bit.ly/CWB25Tickets

02/08/2025

What a powerful discussion at the Black Women's Expo! Our 'Y'all Gone Make Me Find My Mind' panel, led by Dr. Carol L. Adams, tackled critical mental health issues. Huge thanks to all the amazing panelists! The Expo continues today and Sunday!

More details to come.

01/08/2025

Wyn-Win Communications and Dear Me Care Circle are proud to present three transformative sessions at the 30th Annual Black Women’s Expo in Chicago! Join us this weekend, August 1–3, at McCormick Place as we uplift, inform, and inspire.

➡️ Hear directly from extraordinary leaders and change-makers at:

🥼🩺 Ask the Doctors: Prioritizing mental health for Black families on Friday, August 1, 3–4 p.m.

🛐 Faith Is Our Super Power!: Conversations on faith, resilience, and winning the cancer battle on Saturday, August 2, 1–3:30 p.m.

💡 Help Yourself: Balancing caregiving and self-care on Sunday, August 3, 2–3:30 p.m.

Check the flyers below for full speaker lineups. We can't wait to see you there!

23/07/2025

Today on , we welcomed Rev. Frank Walton, Intentional Interim Minister at Hyde Park Union Church!

HPUC is celebrating 150 years with a free Ghanaian choral concert on Saturday, July 26 at 5 p.m., led by acclaimed composer James Varrick Armaah. The church—now a Chicago Landmark—also continues to serve the community through its food pantry and recent $500K tower restoration.

Learn more & RSVP at www.hpuc.org.

16/07/2025

Today on Community Chatter, we were joined by Merry Green, Founder of the Black Women’s Expo (BWe NEXT), and Keiana Barrett, CEO of the Business Leadership Council, to highlight the incredible milestone of the 30th Annual Black Women’s Expo—the longest-running expo for Black women in the country.

This year’s event celebrates three decades of empowering, educating, and elevating Black women through conversations, commerce, and culture. From beauty and wellness to financial literacy, entrepreneurship, and advocacy, BWe remains a powerful platform where Black women connect, grow, and lead.

For more info on the Black Women's Expo and its events, visit https://bwenext.com/,

02/07/2025

Today on Community Chatter, I was joined by our Marketing Communications Coordinator, Ronnita Dumas, to talk about the work we do at Wyn-Win Communications to engage communities and support impactful causes.

We discussed our partnerships with organizations like HSI, working with Donald Dew and Lisa Rollins, and our ongoing work with UNCF to help the next generation access higher education without the burden of student debt—something Ronnita has experienced personally.

She also shared her journey in communications and reflected on meeting Rev. Jesse Jackson during our time working with Rainbow PUSH Coalition, a moment that continues to inspire our commitment to purpose-driven work.

To learn more about Wyn-Win Communications, visit wyn-win.com,

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