MediaCo Welcomes Aspilaire, Inbound from iHeart

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For seven years until last week, he was associated with iHeartMedia and some of its biggest audio brands superserving African American consumers and fans of hip-hop and R&B music. Now, he’ll be working with Victor Giacomelli and CEO Albert Rodriguez at the publicly traded owner of “Hot 97” and WBLS in New York and the Estrella Media radio and TV group.


RBR+TVBR has confirmed that Hennessy Aspilaire II will be joining MediaCo Holding, working closely with Giacomelli, the SVP of Operations at the company.

For Aspilaire, it is a reunion of sorts, as Giacomelli served as VP/Sales of iHeartMedia’s New York station group until joining MediaCo in June 2024.

On LinkedIn, Aspilaire last week confirmed that he had exited iHeartMedia, where he was a Senior Account Executive for its New York stations from February 2022 and for four years before that held a similar role at the company’s Tampa-St. Petersburg properties.

“Knowing when to leave is just as important as knowing when to stay,” he said, noting how “a few months into the job in 2018, everything changed. I closed a deal that made me more commission in two months than I had made in the entire year before. That’s when it all clicked for me … That shift forced me to adjust fast. I made dumb ass decisions … cars, jewelry, etc. Thankfully, I closed many more deals after that. But I had to learn how to manage success, avoid instant gratification, and keep building.”

That led to a promotion and the move to New York. “My first year in New York was the most uncomfortable of my life,” he revealed. “Minimal relationships and high anxiety. Imposter syndrome was real, and I almost crashed out.” But, he figured it out. Now, he notes, “This chapter is done and I’m excited for what’s next.”

For Aspilaire, that will be as a Director of Partnerships focused on live experiences and music.