Audacy Chief Business Officer Chris Oliviero said something at the 2026 Barrett Media Audio Summit that immediately struck me as profound. He was accepting the Jeff Smulyan Award, an honor reserved for executives who take chances most people wouldn’t.
Part of the criteria is being a “risk-taker,” and Oliviero explained what that title actually requires.
“If you’re going to be a risk-taker, you have to be comfortable with failure,” he said. He then shared one of his own career failures, and he sounded just as proud of it as he did of his many wins.
I couldn’t agree with him more.
The radio industry has plenty of leaders who are afraid to fail. They’re not even afraid to fail, really — they’re afraid to make a mistake in the first place. Maybe it’s because I make mistakes often enough that failure has become comfortable for me. There aren’t many areas where I’d suggest people follow my lead, but this happens to be one of them.
Taking a chance is almost always a good thing, even when it doesn’t feel that way in the moment. So many people treat failure like the worst possible outcome.
I used to think the same way. When someone asked about my greatest fear, I’d answer instantly: failure. In my head, failure meant losing everything. That’s not usually what failure looks like, though. It looks like admitting you made the wrong call, then pivoting toward something better.
Failure Isn’t Always the Disaster You Picture
Are there scenarios where failure turns into something dire? Absolutely, and that’s exactly why smart risk-takers make calculated, well-informed moves instead of blind guesses. I’m not suggesting companies and leaders launch “recipe-talk radio” tomorrow morning. However, I do think there’s plenty of room for companies, executives, programmers, hosts, and producers to step out on a limb once in a while.
If a risk doesn’t pay off, the stakes usually aren’t as high as you might think going in. A programming decision that flops can be corrected. A format tweak that misses can get adjusted within a quarter.
Meanwhile, a bold move that hits can reshape a station’s entire trajectory. Radio has never rewarded the leaders who play it safest; it’s rewarded the ones willing to bet on themselves.
I try to remember the quote from the philosopher, Seneca, in situations like these: “We suffer more in our imagination than in reality.”
Oliviero’s Career Proves the Point
Oliviero’s own track record backs this up. Taking risks has worked out well for him, for his career, and for Audacy as a company. That’s precisely why he stood on stage accepting an award named after one of the greatest broadcast owners the industry has ever seen. Jeff Smulyan didn’t build his legacy by avoiding risk, and the executives who earn an award in his name typically share that same instinct.
Radio’s current landscape practically demands this mindset. Between shrinking ad budgets, ongoing layoffs, and audiences fragmenting across podcasts, streaming, and social platforms, standing still isn’t really an option anymore. Executives who wait for certainty before acting will keep watching competitors move first. Meanwhile, the ones willing to test something new, even if it flops, will learn faster and adapt sooner.
So don’t be afraid to make a mistake. Don’t be afraid to take that leap of faith, whether it’s a new format, a new platform strategy, or a new voice on the air. You, your company, and the radio industry will likely be better for it. Oliviero proved that once again on that stage, and it’s a lesson worth carrying into whatever comes next.
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Garrett Searight is Barrett Media’s News Editor, which includes writing daily news stories, features, and opinion columns. He joined Barrett Media in 2022 after a decade leading several radio brands in several formats, as well as a 5-year stint working in local television. In addition to his work with Barrett Media, he is a radio and TV play-by-play broadcaster. Reach out to him at Garrett@BarrettMedia.com.
