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Harley was born in legendary Sturgis South Dakota on June 23rd 1987.

Soon after, he moved to Rapid Valley, just outside Rapid City South Dakota, where he stayed most of his childhood. Living out in “The Valley” had it’s benefits, he grew up catching snakes and other wildlife, fishing, and growing dreams he kept to himself. 

In Middle School, Harley had a hard time singing. “I couldn’t carry a tune in a bucket with a lid,” he would say. “My father was always my biggest critic, I would go elsewhere for help cause it seemed harder to let him down. He meant well. He just wasn’t a good teacher when I was younger.” He also recalled other trials. “I remember being too scared to talk to people. I was quieter than most. In fact some people wondered if I could talk at all. I was a loner for sure. Not exactly what you look for in an entertainer.”

His grandmother taught him to dance and he soon passed that down to his baby sister. “We would steal the show from the band during the Sturgis Motorcycle Rally,” Harley recalls, “the top of her head was no higher than my belt buckle, but we’d do any move the others could do, but faster and better.” Of course this came with modifications, “She would have to jump in the air to do The Pretzel, (a move that involved a lot of twisting and turning.) To this day, we don’t do that move like everyone else. It makes it our own … and I wouldn’t change it.” Though dancing filled his musical needs, Harley couldn’t help but want more. 

“I remember writing a parody to a classic country song, Big John. It was a Burn on my Uncle Tom who was the PR for my dads band.” and it was a hit for the locals that followed this band for many years. He had a way of stealing the show every chance he got. “I even drew a picture of the band as Mt. Rushmore. It was supposed to be a T-shirt design. It read, The Wilt Brothers- Legends In Their Own Minds.” He never stopped wanting to sing, and when he reached High School, he got his chance. 

This was when he met Mr. Clayton Southwick, the choir teacher at his high school. Not only was this man a choir teacher, he was the same choir teacher that taught his father many years back. “It was amazing to me to hear those old stories about my dad when he was my age, not to mention, the amount of respect Mr. Southwick had for my father.”


So he began to learn how to sing. He wasn’t a prodigy. He had to take everything step by step and learn everything piece by piece. “I never had it easy, I had to work for everything I could get. I wasn’t the best singer and really didn’t even get that good till I was a Junior. The good that came from this is, I never got too cocky. Most singers get that way where I’m from. I never had the ‘I’m The Best’ attitude.”

“I actually gave up for awhile. I honestly believed I would never be good enough to be anything in music.” Believing he would never have the confidence, Harley quit choir after his freshman year. “I didn’t stop singing though. I couldn’t get past it. I couldn’t listen to the radio or a cd without imagining it was me on stage. I knew I had to give it another try.” This time he came in with a fire. He thought back to everything Mr. Southwick taught him and practiced. Day, night, car rides, showers wherever the opportunity came from, he sang and wrote song ideas down. 

“I believe that was my true beginning.” He recalled, “That was the threshold of my life where I was born a new man. I could see it within myself, and that gave me the strength to become the singer I knew I was born to be. I walked into the audition for Concert Choir before my Junior year and I sang like I was auditioning for the biggest record label out there."


After he finished the audition he sat down and waited for the same thing he’d heard time and time before. "I waited to be told I wasn’t good enough. That couple minutes I waited there where the longest minutes of my High School years."


After what felt like forever, Mr Southwick finished his notes and said, "Well you’ve been doing some singing this last year haven't you?" This was the first time anyone had ever recognized the effort he was putting into learning to do something everyone said he couldn’t do.” He made the cut and was in concert choir. 

Also his Junior year, he performed his original song, An American Soldier, at a school concert.

“It was amazing,” he thinks back, “this was my work, my guitar, my voice, and they were all watching me. I thought my heart was going to break my rib cage. I remember meeting eyes with an elderly woman in the front row. There were tears in her eyes. It sent a shiver down my spine to know something I wrote had touched someone so deeply.”


Since then, there was no other way to look at himself. He was an Artist, good or bad, on fan or a million, it didn’t matter. That was how he would always see himself. “I knew if I could give that feeling to any one person again, it would all be worth it. I don’t really know if any of my other songs have. Maybe my newer one, Prayer For Me, but other than that, I don’t know if I ever did what I did that night with American Soldier and that elderly lady.” 

He started his own business in 2004 under the name, Generations Music, to show he was the next “generation” of his families ties to music. This gave him a start into the entertainment world, “It was hard. I was a minor walking into clubs and bars looking for work. Most people showed me nothing more than the door.”


This was how he met everything in life, so it’s no surprise that he managed to beat it. “I kept busy enough to get experience. Luckily, the community knew my fathers name. This gave me a leg up in a lot of my trials. I don’t know for sure if it would have made a difference. A lot of my early work was gained on my own as well. Without his name, I believe I would have still did fine, but no doubt my families support was huge in the beginning.” 

In 2010 he changed the name of his business to Freeborn Entertainment, taking on a nickname given to him by some biker friends years ago. “He was a good man. I used to work as a bus boy during the Sturgis Rally when I was a young child. This biker asked me my name when I brought them ice water. I told him "Harley" and he laughed saying that is the best name a man could have. He leaned in close and tucked a $20 bill in my hand  as a tip and said, I’ll call you Freeborn, and every year he came back, he called me Freeborn. It kind of stuck, and I liked it. So I decided to use it for my business.” 

After a while, Harley grew tired of what he was doing. “I mainly did Karaoke and DJ jobs. It was good and was growing, but it wasn’t what I wanted to do. I understand that a business needs to make money and I was keeping steady work. I was becoming well known in the communities where I played, but it wasn’t what I wanted to do. I didn’t sign up to sing a bunch of cover songs and entertain a bunch of party goers.” He continued by saying, “This wasn’t even the worst of it, I’d gone through every style there was. I started out a country boy, then I tried to be what everyone else wanted to see… blamed it on being in the business of it all. I had every hairstyle imaginable, went in this big circle before finally realizing, I never stopped being that country boy, and the people that came to see me, on any level, didn’t mind the cowboy hat at all. Even if it wasn’t their choice of style. The fact is, most of them said it fit me perfectly.”

There was one thought that never left Harley’s mind, “I wanted that moment again. That moment with the elderly lady, in the front row, hanging on my every word of a song I wrote.” Realizing he hadn’t written a single song since high school, Harley made a decision. “It was time to get back to what I started out to do. If I was going to be a singer/songwriter, it was time to be a singer/songwriter. Nothing less and nothing more. I‘d rather fail at something I wanted to do, than to succeed at something that wasn’t that important to me in the first place.” 

So in June of 2012, when Harley moved to Oklahoma to start over with his wife, he decided it was time to start over with his career as well. Time to chase the dream that had never died inside him. It was time to become the Artist he always wanted to be.


“I wrote so much down there in Oklahoma many of my bigger songs came from that era."

He moved back home not long after and started a new phase of his business. In 2014 he made another big investment and ventured into recording.


“I couldn’t afford to go to a professional recording studio so instead I started investing a percentage of my business income to getting the equipment I needed to start recording myself.”


This set him into a digital world he never really knew existed “I started learning different marketing techniques and ideas about branding and creating your own style or image. I played with some ideas and found the ideas I liked best and just started implementing them. It really started making me feel more and more like I was what I set out to be. I felt like a professional artist. By 2016 I no longer listed my day job as my employment even though I still worked there. My employment was MY NAME. Harley Wilt, Singer, Songwriter, Entertainer.”

There is nothing Harley loves more in his music ventures than the people who support him. "They are my lifeblood. I know not everyone will love what I do, but the ones that do are the best a man could ask for. I don't need a record deal to know I've made it. This is my life. Hop on the ride or get out of our way."

Now his original music is available anywhere you can buy or stream music and he’s growing every day. “Every year I’m announcing changes. I believe if you’re standing still, you’re moving backwards. I have 5 kids and many fans who depend on me to move forward. I won’t let them down.” 

“I always used this catchphrase for my business, but I guess I never really lived it until now. I always believed it, but believing in something and living up to it are two different things. The catchphrase was, ‘It’s Not Just Music, It’s a Way Of Life.’”

So now Harley is starting over, once again, with a clean slate and the rear view torn off. He’s become true to himself and back to his roots. When asked how he would like me to end this biography he had only one thing to say, “To Be Continued.”

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