Gary Hailes

VP/General Sales Manager and Partner, Union Broadcasting

IMG_3998It was awesome sitting down and now sharing the career path of my friend Gary Hailes. He easily clears the bar for having a “cool” job because he has spent the last 17 years as VP/General Sales Manager & Partner of the largest all sports talk radio station in America. At his core he is a sales guy, but he has been an integral part of the growth of Union Broadcasting where he splits time between Kansas City and Louisville running national sales for all of the sports talk radio stations. It is quite the journey after starting out as a 19-year old R&B DJ on a college radio station.

Have you always had a passion for sports? Yes, I always had a passion for sports. I was never great at any one sport, but passionate about basketball, so yea I loved playing and watching all sports.

What did you think were cool jobs during your formative years? I wanted to be a TV news anchor.

Share a brief history about your career path? I received a degree in Speech and Communication with a minor in Radio Broadcasting from Ottawa University. My career kind of got its start while I was in college. I was a DJ on the campus radio station and had a Thursday evening show. It was cool and that was fun for three years. I was like “Venus Flytrap” and remember talking in a low voice and playing a lot of R&B. It was a great experience and I learned so much but I realized before graduating that being a DJ wasn’t for me as a career. I realized it was very limiting and so I knew I would pursue a different path.

My first few months out of college were rough and I had several jobs. I had one evening job at the Lawrence Community Center along with a day job at the local newspaper, The Lawrence Journal-World. I actually worked in the mail room for my first job. As a matter of fact, I also worked on the weekends dragging ball diamonds and chalking fields for the parks and rec. Eventually, I moved into the sales department within the Journal-World and that was my start in the world of sales. An interesting story about the job was that I had to fake that I could type, but it was a prerequisite for doing some of the ad copy and I made it work until I learned how to type. Sometimes you have to do what it takes to get that first break and me attending an adult education class at night at the local high school to learn how to type is what it took. All said, it was a great way to break into the sales world and even included being part of a Dale Carnegie sales class that was impactful. In total I was at the newspaper for 8 years.

At that point, I was ready for a move and my path got very interesting. I am originally from Charlottesville, Virginia, and there was a very influential man, John Kluge and his wife Patricia that were involved in some philanthropic things that my Father was involved in. JW Kluge was a pretty successful entrepreneur, with interests in TV, Radio, Cellular Communications and the motion picture industry. In fact, they had recently sold all of their TV and Radio properties to the Hearst Corporation. At the recommendation of my dad, I went home and met with Mrs. Kluge who in turn was generous enough to write a recommendation for me to a television station in Kansas City that got my foot in the door. I have been especially grateful to Mrs. Kluge for that letter and helping me take the next step in my career.

I was able to land a job in television with Channel 41 in KC in their sales department. It gave me a chance to learn the business of TV sales, but I only worked there for one year. After that one year of learning the business, I moved to the ABC affiliate Channel 9, at the time the biggest station in KC. With a raise and promotion, I moved to Channel 9 and stayed there for nine years which was a great ride. After I went as far as I could with the station, I decided to move on and see what was next in my career.

My next stop ended up being with one of my previous clients at the station, Vanguard Airlines. Over the years, I had worked so closely with them and helped them grow the business so much that it was a natural step to go work for them. They needed help in marketing and growing their business, so I took a chance and temporarily left the media industry. Even though it was new for me, I took a marketing role in a startup airline that was very entrepreneurial.   It was exciting and invigorating and I did that for 18 months. During that time, I made some great relationships while involved in the media in Kansas City that turned out to set the table for where I am today. One of the radio stations I created a partnership with was 1510 Sport Talk Radio. We did some great “flyaway” promotions around the KC Chiefs and Vanguard that really raised my level of interest with sports talk radio.

I decided to take a job with Sports Talk Radio 1510, which became known as Union Broadcasting. The station quickly turned into WHB AM 810 and I was the National Sales Manager and a partner. The ride has been great and 17 years later we are the largest all sports talk radio station in America. I have had the good fortune to be a part of an unbelievable group of ownership partners that are still at the core together to this day. As part of the ride, we also picked up several stations in Louisville that are part of Union Broadcasting today. It really is a lifelong dream to combine a love for sports with radio and sales. The funny summary is that it all started with a passion for radio and getting a minor in radio broadcasting.

Who was helpful or a mentor along the journey? Obviously my wife, but beyond her, my best friend and college roommate was Marvin Harvey. Marvin has always been the guy that I have bounced things off of throughout my life. Whether it was career moves or helpful advice with kids, we have always used each other as a sounding board.

Career highlight or accomplishment you are most proud of? Longevity, it sounds crazy but in this business I am very proud that I have always been able to control my own destiny. Maybe it has been because I always heeded my dad’s advice of “You will know when to leave a job, when the passion is gone.”

Who would you trade jobs with tomorrow if given the chance? Dream job? Well I kind of have the dream job because I am in sports and sales, but sure –  I always thought it would be cool to work for the NFL because it is just the pinnacle of sports. I heard a guy talk, who worked for the “League” or the “Shield” and always thought that would be awesome.

If you took a different career path what would it have been? I would have pursued a career as an Athletic Director or in college athletics. I have lived in college communities like Charlottesville, VA and Lawrence, KS so college athletics would have been appealing.

Advice for a kid going to college today who wants to get into sports and media? I would first tell people to learn how to sell yourself, express yourself and listen. I also think networking is critically important and should be something young folks start doing early and while still in college. People like talking about their jobs and themselves, so try and talk to as many people as possible to connect with those people in a genuine way. Once you have connected with people, stay in touch and keep the relationships active. So many people drop the ball after an initial conversation or meeting and that is the easy part, so stay in touch.

Advice for making it in the sports industry? Just pay attention to details, stay away from controversy and also figure out a way to give back. It sounds trite, but figure out a way to get involved in a variety of ways to give back and be a part of the community. Make yourself invaluable inside and outside the walls of your company or business. Companies want to hire and keep people that are making an impact in a variety of ways.

Advice for a good work/life balance and dealing with the grind of sports industry? Take them to as many events that you can. We are fortunate to be in the sports world where there is an opportunity to include your family. I have created a bucket list and am so lucky to have brought my family to so many of those events over the years. I think including your family and having them be a part of the ride helps create a balance.


Now for some fun quick hitters to get to know Gary better……..

Name your Favorite Golf or Dinner outing? For dinner, it would be my Dad with his five brothers. Golf would be with Charles Barkley, Michael Jordan, Magic Johnson and Shaq

What is your favorite movie of all time? I have two – The Count of Monte Cristo and Wall Street

Favorite book? The Power of Positive Thinking by Dr. Norman Vincent Peale

Top 3 favorite athletes of all time? Michael Jordan, Walter Payton, and Bo Jackson

What was your favorite TV show as a kid? Leave it to Beaver

Three items you would take to a deserted island? Boots, generator and solar powered cell phone.

Favorite game to play as a kid? Inside, I played a lot of Uno, but outside just a ton of basketball

Hobby that would surprise people? Cooking and I love the Food Network

Do you have a favorite charity you volunteer with or support? Cancer awareness can never get enough attention. My wife is a survivor and so it is important and close to me. We started a Cancer Support group, when she needed answers and information.

Childhood idol? My dad, I always watched what he did. I learned so much from my dad and how he handled people and situations. He was my idol.


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