J. Ivy, Jason Weaver & More Attend Powerful 'Earn Your Masters' Event

Several major names in the music and financial industries made their way to Chicago for the latest stop on the Earn Your Masters tour.

UnitedMasters founder Steve Stoute, Earn Your Leisure hosts Rashad Bilal & Troy Millings, and Ally hosted the latest installment of their event series at City Hall in Chicago on Sunday afternoon, August 5. Hosted by Kendra G, the event began with a panel discussion by Ally's The Creator Academy featuring UnitedMasters' CMO Chaucer Barnes, Head of Artist Relations Traci Tolmaire, and recording artist Jason Weaver. The actor-singer, who hails from Chi-town, spoke to the creators in the audience about the EYM competition.

"The work speaks for itself, and you know a lot of times I notice as an artist, when I have that in the forefront of my mind, competing; my ego gets involved. And through my ego I can't be my true self," Weaver said at the event.

Following the Financial Education panel, creatives and entrepreneurs from the windy city were invited to pitch their ideas to Rashad Bilal, Troy Millings, Ally's Marketing Lead for Multicultural Marketing Indya Davis, and special guest judge J. Ivy. Each participant had a chance to offer up their best proposals and qualify for a chance to win $50,000 in seed money to help bring their ideas to life. The winner will be announced at the final stop of the EYM tour in Miami during Art Basel.

"Bringing Earn Your Masters to Chicago was a game-changer for the city's creative ecosystem," Steve Soute tells iHeartRadio. "The event wasn't just about music - it was about empowering artists to become savvy entrepreneurs and build real wealth from their talent. With our pitch competition and Creator Academy, we're giving Chicago's most innovative minds a platform to showcase their vision and secure life-changing funding. Chicago has always been an epicenter for creative independence and now we're amplifying that by connecting artists directly with the business acumen they need to take their careers to the next level. This is independence in action, and it's the future of the music business."

Other highlights from the event include appearances from surprise guests like artists Xcelence and Sydny August, who showed up to lend their support. Rashad and Troy also announced their plans to launch a new financial education program made for high school students. Their new effort aims to empower students by teaching them the necessary financial literacy skills and knowledge to manage their income in the future. The program will begin at a few schools in the Bronx, with plans to expand to other schools in New York City by next year.

Rashad Bilal and Troy Millings talk about Earn Your Masters during their latest interview on The Breakfast Club. Check out more scenes from the event and watch the interview below.