Wally Wilson | Crain's Nashville

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Wally Wilson


Wally Wilson – a songwriter, record producer and entrepreneur – has worked with artists such as Trisha Yearwood, Lonestar and Rascal Flatts. His most recent undertaking is Skyville Live, an online series celebrating the hot new musical talent. 

The Mistake:

Underestimating the height and complexity of the barriers to independent labels in terrestrial radio. 

I've worn a lot of different hats in the music business, and 15 years ago or so I started a publishing company along with a couple of other guys called Skyline Music Publishing. We were growing and did fairly well, and as the business changed, we changed. In 2009, one of my partners, Paul Worley, had a lot of success with Lady Antebellum and other people in developing acts.

We discovered this act with three girls that were really good and became known as Stealing Angels. We tried to get them a record deal, but couldn't. We believed so much in them that we decided to create a record company. I came up with this name, Skyville Records, and hired the very best promotions staff. 

We put out these records and made a great video of this group and put them on a radio tour. We did everything you should do.

I ended up spending a lot of my own money and tons of my partner Glen Morgan's money on this project. We found out that it is virtually impossible to break down the barriers that exist in the current system of terrestrial radio when it comes to having an independent label. It's only been done maybe twice in 25 years or so.

We got burned there and we had to shut the label down.

We kept developing acts, but out of the ashes of that came Skyville Live. As much as Nashville has live music everywhere, it's very difficult to find young acts a place to go and perform. We would take these acts and take a space out at the Basement and we called it Skyville Live, and everybody got a chance to play.

We decided that if we got an iconic and mainstream act and some up-and-coming artists, we could have a cool show and put it online. I acquired a space in Berry Hill and we made a soundstage out of it, and had our first show with Martina McBride with Gladys Knight. We were off to the races.

We got burned there and we had to shut the label down.

The Lesson:

Out of the ashes of a really bad idea on my part, Skyville Records, came Skyville Live.

Don't try this at home unless you're a billionaire and don't mind losing every dime you've got. It's really impossible to do an independent label if you're aiming for mainstream terrestrial country radio without the help of a major label. We just thought because we had a great act and a great record that we could break in. A lot of people think that.

If you want to be an Americana artist and are willing to get in a van and travel all across America and build an audience, that's very doable. That's what Sturgill Simpson and Jason Isbell did. Playing the terrestrial radio game has always been hard – but the more corporate it becomes, the more difficult it gets. It's just never been easy to fight the major labels.

I absolutely don't regret making this mistake. Even if Skyville Live had not come out of it, I learned a great deal about other facets of the business. The only thing I regret is losing a lot of money personally and for my friend Glen Morgan. I got to know a lot of people around the country who are in the radio business. All in all, it was a good life lesson – but it was not something that I would recommend anybody do.

Follow Skyville Live on Twitter at: @SkyvilleNashville

Photo courtesy of Maureen O'Connor. 

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