How Bobby Bones Authenticity Built A $100 Million Dollar Radio Empire

The BobbyCast starring Bobby Bones

iHeart

When you’re called “the most powerful man in country music,” served as a mentor on American Idol, competed on Dancing with the Stars, and now have a multi-million dollar deal with Netflix for The BobbyCast as well as a $100 million dollar overall talent deal with iHeart all for doing radio, then a lot of people might make a lot of assumptions about you. But if you’re Bobby Bones, the youngest inductee into the Radio Hall of Fame (at age 37 in 2017), you deal with it by outworking all of them and making authenticity an ethos. “I don’t think I’m lucky by any means,” he told me as part of our Zoom interview, by which he means his intense work ethic got him to where he is today, “but I am fortunate. My dad worked at a sawmill his whole life, and now I have a company and a team that’s supported me even when things happen like getting fined a million dollars by the FCC.” It’s a funny story that he can laugh at now, but couldn’t laugh about at the time. And he put that aforementioned team together by himself, built around people he liked and wanted to work with that do a great job, which he called “the greatest gift to being a professional”.

Bobby might as well have been talking about his origin story in radio here as he related to me how at five or six years old, while being raised by his grandmother, he knew he wanted to work in radio and do standup comedy. That feeling never left him, and by the time he was about 18 years old he begged a local radio station for a job, and they let him clean up the lobby and work the control board for Rick Dees’ Weekly Countdown. When someone was fired for stealing equipment, they felt they had no one to turn to in order to fill a crucial time slot and they put him on the air—and Bobby Bones was born (real last name Estell). But if they hadn’t liked Bobby being around and he didn’t do a great job with what they gave him, then that opportunity would never have happened.

And still to this day despite the fact that he’s known the world over by his stage name and not his last name by birth, he still thinks about it.

 ”The irony of it all is”, he says, “I’ve spent my entire career trying to be as honest and authentic, not relatable, but at least truthful as possible, and to do that with a fake name has always felt disingenuous.”

A lot of people talk a big game about being authentic, but I don’t think I’ve ever talked to someone that’s worked so hard to truly live it out publicly through a variety of fields.

“I love sports and it’s hard for me not to talk about sports on my rain radio show (The Bobby Bones Show), but fortunately I have other outlets and do a sports podcast with former quarterback Matt Cassell (Lot’s to Say). If I were to start doing content on everything that I personally consume, I’d probably be talking politics, but I don’t because I’m disciplined enough to know what people come to me for.”

If you didn’t know, people come to him (I think) because they love country music, pop culture, and nostalgia, as well as his willingness to be so open and talk about anything that people treat him as a friend or family member. I was watching a recent episode of The BobbyCast and he was asking a married woman if her kids belonged to her husband and she responded “Oh Bobby” in the same way you might address your brother or sister for pulling a prank on you.

This is a man that puts himself out there professionally so much that he says if not for his wife he probably would have live streamed his daughter’s birth (back in March).

And in fact he still says that nothing is off limits, but between being married and a few security scares he says that “some of the more personal stuff will have to be time shifted.”

Looking back on his origin story I realized that his authenticity was baked in from the beginning because he said the radio station gave him two options for on air names for what became his big break – Bobby Z or Bobby Bones and he went with Bones because it least sounded like a human or “maybe a pirate or a dentist doctor.” And in that most vulnerable of moments when he was just a kid trying to make it into his dream of radio he didn’t just pick whichever one sounded cooler, he picked the one that sounded human.

 I never wanted to be an abbreviated personality. I wanted to be somebody that had a great voice and did traditional radio talk.

Like anybody thrown into the proverbial fire that lived, Bones figured it out along the way. “ I tried so hard to be that guy. I would affect my voice, and I would try to emulate other DJs like Rick Dees, or Casey Kasem, they all had that great DJ voice, and I couldn’t do it. So the way that I found to be successful wasn’t because I had some idea of, oh, this is how I’m going to do it. It was mostly out of necessity, because I couldn’t get it to work the way that I was trying to do it.”

What Success Looks Like Now

He says that success now looks like “being able to say no to something, because at first he would say yes to almost everything, first to pay the bills, and then for himself to prove his worth. But he offers a major caveat to that, “I’ve never been money motivated, and I think the advantage of coming from so little is I never had to leave comfortable, so I never had anything to lose, ever.”

Now If you heard someone say they never had a dad, their mom was a drug addict, and they were raised by their grandmother in a trailer park then you would probably think that the fact that they stayed out of jail was a pretty good accomplishment, let alone being a content making machine for radio. For the record he offers up therapy and his incredible amount of hours of being on the air live for dealing with anger about his past and the imposter syndrome he used to live with.