10 Questions with ... Shawn Pennington

BRIEF CAREER SYNOPSIS:

Originally from Pittsburgh, Pennsylvania, Shawn spent the early 90's touring the world as a professional musician before moving to Nashville in early 1997 to become the bandleader and tour manager for the then up and coming RCA recording artist Sara Evans. The next five years of hard work brought great success as Sara's career blossomed, selling more than 2 million records and touring with some of the greatest legends in our format - namely Kenny Chesney, George Strait, Alan Jackson and Reba McIntire.

At the end of 2001, industry relationships built during his tenure with Sara, led to an opportunity that could not be passed up, a position within the powerhouse management firm Dale Morris & Associates, who at the time were already accredited with the development and management of some of country music's most iconic artists including Alabama, Kenny Chesney, Louise Mandrell, and many others.

Over the next eight years, and with absolute best mentors you could ever ask for (Dale Morris, Clint Higham, & Marc Oswald) Shawn's talents as a musician/producer, tour and production manager and eventually artist management would play an important role in the careers of Big & Rich, John Rich, Gretchen Wilson, Cowboy Troy, the Muzik Mafia, Kellie Coffey and Alabama frontman Randy Owen. Shawn was also fortunate enough to sit on the board of the Academy of Country Music from 2007-2009

In May of 2009, Shawn resigned from Dale Morris to launch his own company, Matchless Management. Matchless is a full service artist management, production, and consulting firm.

1) Congratulations on starting Matchless Music Group. What can we expect to see from Matchless in 2010?

Thanks! I've got my hands in a number different things right now, and I'm really excited about the three incredible new acts I have on my roster: Ash Bowers, David St. Romain and Thompson Square. All three have completely different strategies for the rollout, which is going to keep us very busy in 2010.

2) You started your career in music as a traveling musician and then continued touring as tour manager for Sara Evans. Do you ever miss being on the road?

I actually still travel with my artists quite a bit for shows, radio visits, etc. It's important to be in the trenches with your artists and remain hands on at all times! For the better part of the group Alabama's iconic career, Dale Morris was at nearly every show maximizing opportunities and making sure the machine ran flawlessly. Obviously it paid great dividends!

3) What made you decide to move from pursuing being a musician to getting into the artist management side of things?

I had some musician friends that were in the band of a very high profile artist in our format through the 90s. They had been with this artist for 13 years had great salaries, benefits, the whole deal. The artist's career had run its course and one day they all got a phone call saying it was over. So here are these guys that were in their mid to late-40s out of a job wondering what they were gonna do with their lives. I didn't want to end up in that position and I recognized that I probably wasn't musically talented enough to take it to the next level. I was able to say to myself that I had done most everything that I ever wanted to do as a musician by the time I was 26. I decided it was best to be thankful for that and head down another road. Interestingly enough, it wasn't until many years after I quit working as a musician for a living that I was able to accomplish one of two unfilled desires, and that was playing on a major album release.

4) You worked with artist management firm Dale Morris and Associates for eight years before launching Matchless. You listed them (Dale Morris, Clint Higham & Marc Oswald) as mentors in your bio. What are the greatest lessons they taught you?

There are way too many to list, and all three have completely different approaches to artist management - and they all work! But the single most important thing I've learned from them is to NEVER EVER EVER be afraid to walk away from a deal, no matter how sweet the deal is or how bad you need it. Otherwise the person on the other end of the table has you by the balls and no one can be effective from a position of fear. There is always another deal right around the corner.

5) You have managed a wide range of Country artists. What artists stick out to you that you have been particularly proud of?

I'm really proud of all of them, but I have to say the things we were able to accomplish with Big & Rich were pretty special, and it took an army of us to make it happen! For a little while there we were looked at like the anti-Christ of Country music. Understandably, it was somewhat difficult for radio to embrace them initially, but the business of B&R rivaled some of our formats biggest stars. At the end of the day though, it all started with the fact that when John and Kenny get onstage together it is pure magic, and their, how do I say it, "Eccentric" personalities help to bring forth some amazing opportunities that we would have probably not had otherwise.

6) What motivated you to make the jump to running your own music company? What surprises were there that you didn't expect?

Well first, I use those words lightly. Let's be honest, anyone with a checkbook, computer and cell phone can start a "company" so I don't pretend to act like I'm running some major operation. But more and more everyday as the industry changes, you're seeing more and more small independent operations being extremely successful, and a lot of times under the radar! If you set things up right, limit your risks and aren't afraid to work really really hard, small wins can turn into really big wins for those involved! I felt like doing this would allow me the best opportunity for me to accomplish the career goals I have set for myself.

The biggest surprise has been how much harder it can be to get people to care when you don't have a superstar on your roster to leverage and you're trying to break three new baby acts from the ground up! But it comes with the territory!

7) You're a self-proclaimed "Jack of all Trades." You have been a musician/producer, a tour and production manager and tackled artist management. Out of all of these things, what have you most enjoyed?

Jack of all, master of none! I absolutely hate routine of any kind. I get very bored and unfocused if things aren't changing all the time! That combined with just enough skills to be dangerous in many different areas has allowed me to try and build a "Shawn can do it" reputation for myself, which I feel has been the key to my growth in this business. So I really love it all!

8) You're a pilot and called yourself an "aviation freak." What got you interested in flying?

When I was 10, my Dad bought me a copy of Flight Simulator for my computer. At that time, it was really more of a game and hadn't developed into the training tool that it has become today, but nonetheless it really hooked me. A few years later, my mother took me out to the airport in Pittsburgh to check into flying lessons. I found out that you couldn't get your license until you turned 17 so it went on the back burner and I got into playing guitar, girls, etc., but I always maintained that passion for it. Fast-forward to three years ago - Allen Jackson, who is Kenny Chesney's personal pilot, knew I shared an interest in flying calls me and invites me out to the airport to hang out. There just happens to be a flight school right next to Chesney's hangar and Allen introduced me to the owner who took me up in a little Cessna for an hour intro flight. When I got back I had 10 new voicemails and 48 new emails waiting on me, and it occurred to me that I completely forgot about my Blackberry for an entire hour! It has become therapy for me. I've had real therapy! Flying is way better! :) Since then I have gotten my pilots license, I'm currently working on my instrument and commercial ratings, last month I took a Boeing 737 introductory course and I have become completely obsessed with all things aviation. I could tell you just about anything that is going on with any airline at any given moment.

I'm actually in the process of putting together another business venture that will allow me to combine some of my industry experience and my obsession with aviation. I hope to roll it out in late first quarter of the New Year.

9) Your wife is a violin teacher and you have a two-year-old daughter. Is she into music already and would you be excited if she wanted to be a singer when she gets older?

Yeah, she is doomed. She always singing, dancing, banging on instruments, etc.!

I went to a tech school after high school for architectural drafting for like three months before I started really thinking about chasing my dreams and trying to play guitar for a living. My entire family and a lot of my friends thought I was out of my mind. The ONLY person who supported me was my mother. She actually convinced me to quit school and go for it. Had she not, I wouldn't be here right now. So the answer is, I will support and be excited about any career path my daughter chooses. Providing its legal of course! :)

10) You have worked with a lot of artists through the years. With all your knowledge, who are the newer artists (any genre) that you feel like could be the next superstars?

To be fair I won't mention my own. He's already a "star," but I think Jason Aldean is going to be the biggest artist in our format in a short time! There is nothing stopping that machine! The entire vibe around him right now is very reminiscent of Chesney circa 2002, right before he took over the world!

1) What is the first concert you ever attended?

Def Leppard - "Adrenalize" Tour - November 7th, 1992

2) What are your favorite Nashville restaurants and some of your favorite dishes?

Brenda's Kitchen in Virginia's Market is my absolute favorite place to eat in town!

I also love Sushi at Tenno on West End Ave.

And I could eat the steak salad at Dan McGuiness every single day of my life!

3) You have toured all over the world. What are your favorite places to visit?

Gstaad, Switzerland is like being in a fairy tale! The countryside is like something you'd only see in a movie! And Venice, Italy is a very close second.