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Why Radio Host Bobby Bones Ran Negative Ads Against Himself It's hard to cut through the noise.

By Jennifer Miller

Opinions expressed by Entrepreneur contributors are their own.

Zack Massey

A few years ago, anti-Bobby Bones billboards started popping up around Nashville. "Go Away Bobby Bones," they said. Who put them up was a mystery -- "Was it a record label that didn't appreciate his style, an artist he had offended?" asked the Tennessean -- but the intended target was clear: Bobby Bones was about a year into airing his country music morning show on local radio.

So who was behind the ads? Bones was. He'd scrapped his way into a radio career and had learned that sometimes the least-expected decisions have the greatest payoff. Today, with an audience of 5 million people (and a new book, Fail Until You Don't: Fight. Grind. Repeat), his is the most popular syndicated country morning radio show in America. Entrepreneur spoke with him about how he fought for his audience, often by taking unexpected, controversial -- and of course, entrepreneurial --chances.

Related: Why Failure Is Your Best Teacher

In your mid-20s, you came out of nowhere to start a morning show. How did you manage that?

I didn't have a syndication company, so I had to start my own, with my own money. I had to pay for the tech, the producer and the phone line out of pocket. The equipment I was using was meant to be for local station broadcasts. Nobody was using it to transmit longer than 100 miles. But I made it work for 1,000 miles. There was a latency to it and other issues. But we managed to syndicate our entire show through one market.

So you were really bootstrapping?

I had to spread my show, because no one else was going to do it for me. I lost money for years. I found a Wichita station that had lost its morning show. I said we'd fill in for free. I felt I had to establish myself before I could charge. In a year, we went to number one in Wichita, then other stations started picking us up. We went from three to five. Only after I gained five to seven markets did Clear Channel decide to syndicate the show. Over a decade, I grew my audience until I had the number one morning radio show in Austin.

Clearly, something about you appealed to listeners. What was it?

I've always been the guy that doesn't fit into a specific place. I like pop, country, hip-hop. I originally thought that was a weakness -- the fact that I never truly identified with any single format. In fact, that's become my strength. It's what separates me from the pack.

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How did you come to realize that your weakness was a strength?

By totally changing the culture of country radio from conservative cowboy hats and belt buckles to something a lot more progressive.

By progressive you mean --

I came to Nashville in 2013 and started playing hip-hop on a country music show.

And conservative Nashville just went along with that?

It was blasphemous to anyone in country radio, and I was doing it frequently. There was a small, vocal part of the listenership that didn't like it, but there were other options for them. In the end, more people came to us than left us. The other thing is that the people aren't the industry. I was going to represent the people. That's how I came to understand that my "weakness" was really a strength. No one just listens to one type of music. My first year in Nashville, I was there to say: I'm a human being and not the product of a format.

You actually make it sound kind of easy.

It wasn't. It was precarious. Pushback was heavily from industry: in their blogs, newsletters, magazines.

How did you handle the blowback?

Before I started, I knew there'd be fails and setbacks. But when you know they're coming -- when you prepare yourself -- it's not a surprise. It sucks, of course, but you don't have to jump off a cliff. I kept reminding myself to wait it out. And, luckily, it caught on.

It must have also required some humility.

It's always disheartening when you're doing something that you've been successful at and it's not working. I'd spent my late 20s and early 30s developing a show, and being myself, and being a big success in 25 cities. In Nashville we were starting over.

Related: Embrace Your Setbacks -- and Use Them to Your Advantage

What's your advice for entrepreneurs who don't know if they're moving in the right direction?

If you commit to a direction, even if you're going the wrong way, it's better than wandering around some middle ground. I'd committed to a vision, and I stuck with it. You can look at the data -- and I do -- but you've got to trust your gut.

Did you ever find yourself moving in the wrong direction?

Originally, I got irritated with the old guard and started pushing back and fighting just to let them know I understood their challenge. I was bullheaded. Looking back, I shouldn't have been so aggressive. I should have been talking about the positive direction we were going instead of screaming about everything that was wrong with their format. Calling attention to the negative was a waste of time.

Also, unlike the status quo, I didn't want to befriend anyone in the artist community, because I wanted to be objective. But I've had to bend that rule and even break it. Some artists are just too good people. So that's an example of conforming to something I said I'd never do.

You tried some creative marketing tactics to win over Nashville, like putting up negative billboards about yourself. Why did you think that getting people to criticize you would help you?

I was wondering how to get people to notice me, and with all the noise -- social media, radio and TV -- it's hard to cut through. So I bought four billboards in town, and they said "Go Away Bobby Bones." My thinking was, people would have one of three reactions: "I agree." "I disagree." Or "Who the hell is he?" All three are good because at least they see something is happening. And if you look at the news cycle, negative stories get the most clicks. My marketing advice: Do something to create drama. We love drama.

What's your advice for entrepreneurs who are trying to introduce a new product or supplant a well-liked one?

You really have to find what makes you special, and even though it may not seem to be working right away, you have to commit. Brand awareness is a marathon. So find out what separates you from the rest and dig in. If you love it, you'll work hard at it, and if you work hard, that's where the success comes from. And even if you're not successful, worst-case scenario is you did something that you love and you put your all into it.

Jennifer Miller is the author of the novels The Heart You Carry Home and The Year of the Gadfly.

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