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Bobby Bones Wants You to Fail

The superstar radio DJ talks hits and misses—and encourages others to embrace both—in his new book.

Written By:  Alison Abbey

Photographers:  Robby Klein

Bobby Bones is one of the most powerful and popular radio DJs in country music—or any format, for that matter—but the syndicated radio show host, who averages about five million listeners a show, won’t tell you that. Instead, the namesake of “The Bobby Bones Show” will use his trademark style of self-deprecating humor to play down his accolades. He’ll even tell you about all the times he screwed up, which he does in his new book, Fail Until You Don’t, a surprisingly fun and encouraging read, for all its talk of failure.

As he shared in his first New York Times best-seller, Bare Bones: I’m Not Lonely If You’re Reading This Book, Bones (né Bobby Estell) grew up in Mountain Pine, Arkansas. An absent father and an addict mother meant Bones spent much of his life in the care of his grandparents. He went on to become the first member of his family to graduate high school. And college.

But that rough start didn’t jilt the future star. It only emboldened him to work harder to find a way out—which he did, through entertainment. 

“It was always radio, TV, and comedy. That was it for me. But radio was what I could get on the quickest,” he says. “When I was 17, I could go beg for a job at the radio station, which I did—I got hired to clean—so, it was the easiest to get my first foot in the door.”

He paid his dues in radio, eventually moving to Austin, Texas, for an on-air gig.

“I went to Austin on a failing station and did nights. It was failing so bad that I begged to do mornings. When they hired me to do mornings, the station actually started doing pretty well and, then, eventually, thriving.”

But that doesn’t mean he had an easy time of it. With his boy-next-door good looks, black-rimmed glasses, and dappling of tattoos, Bones has always had a hard time fitting into any one genre’s mold.

“When I was doing pop, I was a bit too country. When I was doing sports, I was not athletic enough. When I'm doing country, I'm a bit too pop. It's always been the case of not quite fitting in,” he says. “But that's what makes me fit in. What I realized is that no one really fits in anywhere.”

He found his niche in Nashville in 2012, when he moved here to launch what would become the largest morning show in country radio. From there, he pushed himself into new ventures. A successful music career followed, with Bones and his band, The Raging Idiots, producing chart-topping albums in children’s and comedy formats.

Next, he took on stand-up comedy. A lifelong fan of comedians (especially talk-show host David Letterman), Bones decided to step up to the mic onstage. But, as he describes in his book, the first standup show did not go well.

>>> 20 Questions with Bobby Bones


For once, Bones let his nerves get the best of him. The audience, which he thrives on during appearances and Raging Idiots concerts, became overwhelming. And, he admits, his material wasn’t the best. Whether or not that crowd agreed, in Bones’ mind, he bombed.

But he explains in the book that one terrible first night wouldn’t stop him. Bones used the experience to fuel his comedy fire and rewrite his act. On the night-long bus ride between his first and second gigs, Bones toiled over his set, and, when he reached his next tour stop, he made strides. "I killed!" he writes in the book. "Just kidding. I didn’t. But I did better. Baby steps.”

Baby steps are a recurring theme in Bones’ life. And they may take him all the way to the White House.

“I’ve thought about running for governor of Arkansas, [which means] I will be the governor of Arkansas one day. There's no doubt in my mind. [From there], if you want to run for president, you can,” he says. “I see the small steps that it can take in order to make that happen. I, honest to God, believe I can take enough tiny steps to at least give myself a shot. Because it’s a baby-steps world.”

In Fail, Bones also shares his personal mantra, “Fight. Grind. Repeat.” Nowhere is this philosophy more evident than in his repeated attempts to find his footing on television. After more than a decade of writing scripts and pitching pilots, he’s seen his share of disappointment.

“I've probably written five pilots that didn't just fail, they were so bad that they didn't even have a chance to fail,” he says. “We did a pilot for CMT for my own talk show, and we went all the way. Then some executives got cut. The people who were championing it were let go, and we never made it. I had a show at ABC that made it to pilot and got cut. There’ve been a lot of cuts.” 

As with all of his missteps, Bones took each as a teachable moment.

“Every time I did something that wasn’t accepted or wasn’t greenlit, I understood the process a little bit better.”

Which led to his latest television achievement: This season, Bones was asked to be a mentor to the top 24 contestants on the ABC reboot of American Idol.

Initially, Bones thought he would be one of many mentors on the show and had no clue what kind of screen time he would see. With little info on the gig, he was unsure. Then he talked to new judge Luke Bryan.

“He said he loved the people, so, at that point, I thought, Maybe I want to be involved, regardless of what the role is,” he says. “I went in, and they said, ‘You’re going to mentor the top 24.’ And, it turned out, I was the only one, and I had two whole episodes. I was taken aback. And I think they were, too. I don’t think they expected me to come in and talk real life with them. I'm an idiot DJ, but I was able to come in and go, ‘Okay, I've had a real life, just like you guys. We've all had our struggles and our successes, and it's okay to talk about our struggles.’ But, also, I'm a comedian, I talk on the radio, I've done a bunch of formats, I've had a couple No. 1 records, and, so, I think they saw that I was pretty versatile.”

He was such a hit that the producers asked him to return for the season finale.

“Some people have heard of me now,” he shrugs with his characteristic deprecation. “But it also opened doors in Los Angeles. They probably won’t stay open long, and I’m going to have to make some decisions, but I’m pretty excited that I get to choose. I just turned down a big show. It’s the first time I’ve ever turned down a major show. It’s pretty exciting to say no to something.”

Despite the success of his first book, Bones says he never had any intention of writing a second. 

“The first book sold; people didn’t hate it. I felt like I’d just lucked out. But, because it was a success, the book company kept making me offers. But I don’t chase money. I never had it, so I’m fine without it. I’ve found that, if I do the things I really love, the money comes, or it doesn’t, but I still love what I’m doing, so that makes me happy. So, I said no to them for a year.”

Then, he took the stage for a TED Talk, called “Winning By Losing.” The talk showcased successful people’s failures. The book company came calling again.

“They asked if I would write a book about that [topic]. And my first thought was, I don’t hate that idea. But I didn’t want to write another book. I don’t feel like I’m worth investing a week of your time into. At least with the radio show, people don’t have to pay anything to listen to me. If they’re investing their hard-earned money into me, that’s pressure to perform. I don’t want to let anyone down.”

The reluctant writer enlisted some famous friends to help take the heat off him. The book incorporates stories from stars, like Chris Stapleton, Andy Roddick, and even the governor of Arkansas, to show how failure can be fruitful. 

“I think the best way to be successful is to know where you’re the weakest,” he says. “I can’t keep sugar in my refrigerator because I’ll eat it all. There’s no sense of moderation in my life, so if I don’t put those walls up, I’m going to go outside of them.”

Bones makes it clear—in conversation and in the book—that the tips and tricks he writes about aren’t for everyone. From setting daily goals to setting boundaries, each habit is one he practices in real life.

"It's a nutty guy's version of how to be successful. I don't think anyone should take all of [my advice]—but I think some of those elements, like the discipline, the learning from when you lose—I think a lot of that you could take little parts of. But,” he deadpans, “if anyone commits to that book wholly, they’re going to go crazy.”

One thing he’s never failed to do is give back. And, naturally, even though Bones makes time for his favorite philanthropic causes, he’s quick to dismiss even the suggestion of altruistic tendencies.

“I think the reason that I get involved in things is because people got involved for me. That's really the base of it. It's not that I have this great heart—I wish it was—but I feel a debt, almost, to all the people who helped me. Without me being someone's cause, there are times where I wouldn't have had food, or Christmas presents, or rides to church camp, or things like that,” he says. “I'm very grateful to the people who did things, so I want to be that to someone. I was given opportunities, and I hope that I can give someone an opportunity to give someone an opportunity.”

When it’s suggested that his mission in itself is a charitable endeavor, Bones is, once again, defiant.

“Even the causes I choose—St. Jude for example—I was in the hospital a lot as a kid. I had to get my spleen taken out; I was very sick. So, kids in hospitals are a big thing for me. I’m on the board of Musicians on Call [an organization that brings music into hospitals] for the same reason. I know what it’s like to be a kid in a hospital for days and days, so that’s why I work with those two.”

Bones also works with animal charities, especially Austin Pets Alive! and the Nashville Humane Association, in part as tribute to his recently departed, beloved dog, Dusty. And he supports the military for what he considers to be an equally selfish reason.

“I’m so proud of my friends who have gone over and served. And I’m such a wuss. If people weren’t out protecting me, I wouldn’t be able to do what I do. I don’t have the courage to do that myself. Again, it’s such a selfish thing. I always find a way to bring it back to myself. I wish I wouldn’t, but I do.” 

And, for a man who wakes up every day at 3 a.m., Bones packs his days. He’s launched the staggeringly popular podcast, BobbyCast, where he interviews some of the biggest names in music. With more than 2 million downloads, the success of the podcast has helped pave the way for the launch of his Nashville Podcast Network, an eclectic collection of seven podcasts from hosts like Kristian Bush and Jake Owen.

In 2017, Bones was inducted into the National Radio Hall of Fame. He is the youngest inductee in the history of the institution. But, true to form, when Bones is asked about the achievement, he doesn’t brag.

“I’m not big on accolades,” he explains. “I felt awkward. Not because I didn’t feel honored, but I felt like it was a bit too early. I would’ve waited on me a bit. Let’s see if I screw this up in the next few years. I have a history of screwing up pretty bad.”



More with Bobby in the July 2018
issue of Nashville Lifestyles magazine!



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