Bobby Bones is a successful radio host and new American Idol mentor, but he wants you to know about his biggest failures

By Sam Gillette
March 15, 2018 08:00 AM

Bobby Bones is known for his success as a radio host, stand-up comic and, most recently, his upcoming role as mentor on American Idol — but he really wants fans to know how much of a failure he is.

In an exclusive interview with PEOPLE, the 37-year-old host of The Bobby Bones Show reveals the cover of his second book, Fail Until You Don’t: Fight. Grind. Repeat., on sale June 19.Unlike his first book, Bare Bones: I’m Not Lonely If You’re Reading This Bookwhich was an unexpected bestseller and revealed how he grew up poor in Arkansas and was raised by his single, drug-addicted mother – his new book will be motivational… by highlighting all of his biggest mistakes. It isn’t all about Bones though. Celebrity friends like Andy Roddick, Chris Stapleton, Walker Hayes and Charlamagne tha God will also share their stories of failure.

“I wrote this book to be the opposite of Instagram. On Instagram, you look and see all the beautiful things people are doing all of the time,” says Bones, who recently became the youngest inductee into the National Radio Hall of Fame. “I wrote this book to show the opposite: most of life is not about all the wins, actually most of life is the rough spots and failures that get us to the wins.”

Known for charitable work like his annual Million Dollar Show that benefits St. Jude Children’s Research Hospital, Bones explains how experiencing poverty as a child inspired his philanthropy. In his interview with PEOPLE, he also gives details about his recent stint on the set of American Idol where he serves as mentor to the top 24 contestants, explains why he’s passionate about women in country music, and the reason he wants the publication of his book to be just like Stormi Webster’s birth.

See below for the full interview.

Bobby Bones’s Fail Until You Don’t
Dey Street Books

Your last book was a surprise hit. Did that make writing Fail Until You Don’t easier or more difficult?

The first book was a life story that I was hesitant to write anyway because I didn’t feel like I had a real life story… It was a surprise hit. I had no idea that people would buy it or that it would resonate with [them]. I feel pressure to not let people down that enjoyed the first one — it’s not a sales pressure, but I don’t want people who spend 25 bucks on a book to go, “Well that was disappointing.”

What’s your biggest mistake that you write about?

I was the youngest person to ever be inducted [in the National Radio Hall of Fame) and I’m huge treat, apparently. But I got rejected from 30 radio jobs before I ever got a real radio job… So here’s this guy who’s really good at talking to people through their iPhone or their radio, but in reality, I’m quite a bad speaker. I speak in broken sentences. I have an accent. Everything that I do should be wrong but I started really young and I just learned how to learn. I would fail and I would figure out why that didn’t go right and do it again. So my main job, which I’m celebrated for, I sucked at forever.

You included your friends’ stories of failure in the book. Whose story surprised you the most?

If I asked [my friends] to give me their failure story, it was because I really appreciate what they were able to do because of that failure. There’s an artist named Walker Hayes. He’s a good friend of mine and I learned a lot about his personal struggle with addiction. Walker is close to 40 and he has his first hit just now. He’s just a guy who continues to write [and] grind it out every day.

If you see Walker now you think he’s this new artist, he’s got a hit, it all came easily to him. But he’s been dropped from two record labels… he’s just about to have his seventh kid and he’s just been slugging it out for 10 [or] 12 years. He loves [music] enough to fight through all of the bad and finally has success. Whether that was going to happen at age 29 or age 40, he wasn’t going to stop until his body stopped or he succeeded.

Walker Hayes
David McClister

What can you share about your role in American Idol?

They didn’t bring me in to be the singing coach, because I can’t sing like those guys can. They brought me in as a well-rounded mentor, [as in] I can do stand-up comedy, I do radio, TV, I perform, I play an instrument… I failed so much in all of the careers that I’m in now that I talk to people about what it’s like to not be good at it. I think the role was great, I loved working with all of the people at Idol.

Did you get any advice from the Idol alums based in Nashville?

Not so much advice about Idol, but I did use them to my advantage… As a mentor, I don’t have to know everything. All I have to do is help them learn things, so I called my friends who were on Idol and I had them talk to certain contestants because I would say, “I don’t know how to fix your problem or talk to you about that, but I know who does.”

Bobby Bones
Katie Kauss

You’re one of the few people in radio really pushing women in country. Why is that so important to you?

I was seeing on the ground floor that labels weren’t investing in females and it trickled upward because I was in radio with none to play. I know that I can’t change today, but what I can do is work on the culture for tomorrow. So I started four years ago not only yelling about it (because I’m pretty good about yelling about things and being really obnoxious), but also holding events featuring females… On my tours I would do opening acts [and] take great female artists out and highlight them. In my band [Bobby Bones and the Raging Idiots] we would take great female artists out and highlight them. So that’s been a real passionate point for me, probably because I was raised by all women for most of my life.

Has advocating for women in music taken on a new relevance with Time’s Up and other initiatives?

I’ve tried to stop yelling about it from my voice as much and propel other voices more. During the Grammys when Kesha was performing and all of the females were singing [“Praying”], it was a real moving moment. I thought let me write something about this. Instead, I went and found women I respected and retweeted them. I’m consciously trying to elevate people with an empathizing voice, more than just let myself talk.

Bobby Bones

How did growing up in poverty influence your charity work?

I lived it. It’s not fun. People have had it better, people have had it worse. [But] I don’t like thinking of anybody else having to go through similar situations.

Has anyone close to you read the book?

I haven’t let anybody read it, are you kidding me? I’ve let no one read any of it because I want it basically to be [Kylie Jenner‘s daughter] Stormi. Meaning when the baby is out, there’s the name, there’s the baby. Instagram is not changing anybody’s mind about [what] to name her, there it is. I’m ready to just have Stormi presented to the world without anybody’s opinion… I just go with my gut and about 51 percent of the time it works out for me.

Fail Until You Don’t hits shelves June 19.