In an era marked by job uncertainty, rising costs, and rapid technological change, more people—especially young leaders—are choosing entrepreneurship as a pathway to ownership, independence, and generational wealth.
For Keeana Barber, Founder and CEO of WDB Marketing, this movement isn’t a trend. It’s a calling she recognized long before it became mainstream.
Twenty years ago, following the tragic loss of her brother, Bobby Barber, Keeana made a life- changing decision.
“My brother was killed in November 2004,” she recalls. “I wanted to build something in his honor—something that would last.”
At just 22 years old, fresh out of college, Keeana took over her brother’s promotions business. What began with hosting events soon evolved into a full-service branding, printing, and marketing agency—now known as WDB Marketing. Two decades later, the company has supported more than 5,000 businesses and become a cornerstone of Chicago’s entrepreneurial ecosystem.
After ten years of serving thousands of entrepreneurs, Keeana saw a deeper opportunity.
“God placed us in a unique position,” she says. “We were connected to so many business owners,
dreamers, and innovators. I wanted to create something that brought those networks together.”
That vision became LEGACY.
Building More Than a Moment—Building a Movement
LEGACY stands for Leadership, Education, Growth, Advocacy, and Youth. More than an awards show, it is a platform designed to develop entrepreneurs, deploy capital, and create long- term opportunity.
“I thought about what I needed when I started,” Keeana explains. “Mentorship. Access to real accountants. Real legal advice. A support system. That’s what we set out to create.”
In 2016, WDB launched the first LEGACY Awards Weekend. What started as a gathering of like-minded entrepreneurs has grown into a nationally recognized, three-day experience attracting more than 1,000 business owners annually.
Now, as WDB Marketing celebrates 20 years and LEGACY marks its 10th anniversary, the platform stands as one of Chicago’s most impactful entrepreneurship initiatives.
A Weekend Designed for Impact
LEGACY Awards Weekend unfolds over three powerful days:
Friday: Legacy Talks & Business Mixer The weekend begins with a high-energy summit and networking mixer, featuring expert panels and thought leaders focused on building sustainable, legacy-owned businesses.
Saturday: The LEGACY Awards Gala
The signature event brings together nearly 800 entrepreneurs, executives, sponsors, and community leaders for an unforgettable evening of celebration and connection.
One of the most anticipated features is the Black-Owned Restaurant Showcase, highlighting approximately 15 local restaurants during the reception.
“We’re celebrating, we’re connecting, and we’re supporting our community through food,” Keeana says. “Come for the community—stay for the food.”
The evening also includes live entertainment, music, and the presentation of LEGACY Awards—honoring outstanding business leaders and rising entrepreneurs.
Investing Directly in the Next Generation
At the heart of the Gala is the Young Entrepreneur Pitch Competition.
Each year, three finalists take the stage to present their businesses in front of a live audience. Attendees vote in real time, helping determine the winners.
The total prize package exceeds $25,000 and includes:
$5,000 in direct capital for first place
Professional marketing and printing services
Legal and accounting support
Financial consulting and mentorship
Ongoing access to WDB’s business network.
Second and third place winners also receive funding and services.
“Money matters,” Keeana says. “But access, guidance, and community—that’s what changes lives.”
Many past winners have gone on to scale their businesses, secure major partnerships, and appear on regional and national media platforms—extending the impact far beyond one night.
Sunday: Community, Connection, and Reflection
Sunday brings the community back together for an all-you-can-eat brunch with a live DJ—a space to reflect, reconnect, and turn new relationships into long-term partnerships.
“It’s where business turns into family,” Keeana shares.
Powered by Community
LEGACY Awards Weekend is promoted through social media, partner organizations, community leaders, and WDB’s extensive database. But its most powerful ambassadors are its alumni.
Past finalists and winners return year after year—mentoring new participants, serving on committees, and sharing how LEGACY helped transform their journeys.
“They don’t just win and leave,” Keeana says. “They stay connected. They build the next generation.”
A Room Where Generations Meet
One of LEGACY’s most powerful features is its diversity of experience.
First-year startups sit beside 40-year-old companies. Young founders network with corporate executives. Nonprofits collaborate with for-profit innovators.
“It’s about putting everyone in the same room,” Keeana explains. “That’s where growth happens.”
Affordable ticket pricing ensures accessibility, keeping the event inclusive while maintaining its high-level experience.
More Than an Event—A Full-Service Ecosystem
Behind the scenes, WDB Marketing and co-founder James Wheeler power the experience through in-house branding, production, and design.
From stage backdrops and signage to apparel, programs, and digital media, WDB delivers every visual element.
Their philosophy is simple: “We Print Everything.”
And they do—signage, banners, step-and-repeats, uniforms, marketing materials, and more—ensuring every LEGACY experience reflects excellence and professionalism.
Looking Ahead
LEGACY Awards Weekend 2026 will take place March 13–15.
Young entrepreneurs under 25 with established for-profit or nonprofit ventures may apply for the pitch competition through February 15.
But for Keeana Barber, the mission goes far beyond one weekend.
“This is about building ownership. Building confidence. Building wealth. Building legacy,” she says. “We’re not just celebrating success—we’re creating it.”
After 20 years of business and 10 years of LEGACY, WDB Marketing continues to prove that when vision meets purpose, communities rise—and futures are built.
