Usher Helped Launch My Journalism Career. Two Decades Later, I Brought Him to The Shade Room.

A newspaper contest, a 150-word concert review, and a $15-a-week writing gig started it all for AC at just 15 years old. More than two decades later, I found myself executive producing a surprise with the very artist who helped set my career in motion.

Whenever someone asks how I got my start in media, I usually fast-forward to radio.

My internships at WGCI and B96 in Chicago. My first paid radio gig in Detroit. Even my one-day internship with Mancow, which is a story for another day. 😂

But if we’re going all the way back, the story starts with a newspaper, a contest, and Usher.

Before the titles, there was a 150-word review

I was a high school freshman who actually enjoyed reading the newspaper on the daily. 👵🏼📰

One day, while flipping through The Herald News in Joliet, Illinois, I spotted a contest to become a guest music critic for the paper’s weekly Teen Scene feature. The assignment? Attend Usher’s 8701 Evolution Tour and write a concert review in 150 words or less.

I entered, won one of five spots, went to the show, and submitted my review. It ran in the June 5, 2002 edition, with my name and photo. My first published byline.

And then came the real plot twist.

The editor offered me a regular spot on the Teen Scene staff, writing weekly reviews of new music releases and concerts. My salary? A phat $15 a week.

Listen, you couldn’t tell teenage me NOTHING. Forget my shift as manager at McDonald’s; I was officially a paid music critic. 😂

From $15 a week to a career in media

That first assignment started a career that has taken me through radio, television, publishing, podcasting, digital media, and eventually executive leadership.

I’ve worked across dozens of brands at Urban One and Reach Media, made many celebrities a household name, helped build and launch iHeartPodcasts, and today lead content across social, editorial, and video at The Shade Room.

Different platforms, different chapters, same curiosity about the stories and cultural moments people actually care about.

And, apparently, a running Usher theme.

First, I finally got to thank him

Nearly 20 years after that concert review, I met Usher aboard Tom Joyner’s Fantastic Voyage. I got to tell him the story and thank him for unknowingly helping launch my career.

I’m sure he meets people with stories like mine all the time. But for me, it was a full-circle bucket-list moment. One I never could have pictured when I was 15 and sending a 150-word review to a newspaper editor.

I thought that was the full-circle ending. Turns out, there was another chapter.

Then Usher showed up in my work again

In 2023, The Shade Room shared the story of fans from Oakland who went through a whole series of travel nightmares trying to make it to Usher’s Las Vegas residency. Snow, road closures, scrambling to get there—after all that effort, they still missed most of the show.

The story struck a nerve with our audience. And then Usher himself commented on our post.

He offered to bring them back to see the full show. It was the kind of genuine, unexpected celebrity response that can make a social post take on a life of its own.

The internet already had a great moment. But I saw the possibility of creating something even more meaningful.

So I personally reached out to Usher’s team to see whether he’d be open to taking it a step further. I secured the talent booking, flew our TSR Studios team and Thembi—host of Stepping Into The Shade Room—to Las Vegas, and executive produced the surprise as Head of Content at The Shade Room.

Not just covering the moment. Building the moment.

A surprise for another Usher fan

We brought the fan onto Stepping Into The Shade Room to tell her story. And then Usher walked out.

Her reaction was everything. What began as a frustrating trip to see her favorite artist became a surprise meeting with him, captured for our audience in a special interview.

It was also one of those rare times when the story behind the camera meant as much to me as the one in front of it.

Years earlier, I had been the teenage Usher fan whose concert experience turned into an unexpected career opportunity. Now I was helping create an unexpected experience for another Usher fan, through a platform whose content I lead.

And yes, I joked at the time, “Are y’all with Make-A-Wish? Because Usher doesn’t really do press.” 😂

All of this while covering Davis–Garcia fight week in Vegas—and still making it back home for my daughter’s soccer game. A win on both fronts.

Watch: Usher’s Stepping Into The Shade Room surprise

Watch the full surprise interview on YouTube →

Why I still keep the receipts

I still have the original newspaper clipping. I still have the editor’s letter telling me I’d won the contest, asking for a review of 150 words or less, and confirming when it would be published.

Not because I thought my teenage concert review was some groundbreaking piece of criticism. I was 15. Let’s be serious. 😂

I keep them because they remind me that careers don’t always begin with a big title or a carefully mapped-out plan. Sometimes they begin with a tiny assignment, an unexpected invitation, and somebody giving you a chance.

That $15-a-week opportunity gave me my first byline and the confidence to keep going. A teen who was on the brink of emancipation, no Mimi, needed.

And more than two decades later, I got to turn a moment involving that same artist into a memorable experience for someone else.

From a 150-word review to executive producing an Usher surprise.

Not bad for a girl who liked reading the newspaper. ♥️

---

AC Trybula (Ashley Trybula, also known as ACThePlug) is a media executive and Head of Content at The Shade Room. She writes about storytelling, content, culture, audiences and the business behind the scroll.