Interview With The Agent: Matthew Kingsley

Matthew Kingsley
Matthew Kingsley

Matthew Kingsley is the President and CEO of 3 Kings Entertainment, LLC, an agency focused on representing a diverse group of media personalities in broadcasting news, sports and entertainment.  Over his almost 20 years in the agent business, Kingsley has represented hundreds of clients and has negotiated thousands of contracts for talent on ESPN, ABC, CNN, NFL Network, MLB Network, Big Ten Network, Golf Channel and beyond.  Some of his current sports clients include: ESPN’s Doug Kezirian, Zubin Mehenti and Cary Chow; NFL Network’s Desmond Purnell and Kyle Montgomery; NESN’s Elle Duncan and Gary Striewski; CSN Chicago’s Aiyana Cristal; CSN Boston’s Jessica Moran; FOX Sports Minnesota Timberwolves play-by-play voice Dave Benz; CNN Sports’ Andy Scholes; BTN’s Rick Pizzo and 120Sports’ Chelsea Gates.  Follow Kingsley on Twitter here.

1) When did you decide you wanted to become a broadcasting agent?  Why did you decide to pursue that career path?

It’s actually a great lesson of how being open to opportunity in life can ultimately take you to places you never thought or imagined.

I grew up playing sports and studied sports management and business in college and quickly realized I wasn’t going to be a professional athlete but was extremely interested in who was behind these athletes in negotiating their contracts on the field and brokering lucrative endorsement deals for them off the field and how this ultimately was building and enhancing their overall brand.

In the early to mid 1990s, there were what everyone called “the big three” sports agencies: IMG, ProServe and Advantage International (now Octagon).  All three had offices in Washington, DC where I grew up so I was able to interview with all of them and was offered an internship with Advantage International in athlete marketing right out of college and soon after that, I worked with Rick Schaeffer who was a very successful sports agent and attorney out of Baltimore who represented many NFL players, coaches and front office executives.  This is where the willingness to be open and to move comes into play.  I was then contacted by Jules Young who runs Hollywood’s top staffing agency and search firm with an opportunity to work for Ken Lindner & Associates, which is one of the premier broadcasting talent agencies in the country.

This was when my true passion was born and where I found my calling as a broadcasting agent.

2) What internships early on in your career/college prepared you well?  Any key lessons/learnings from those?

While still in college, I was able to set-up a credited internship as the assistant athletic director and was hired as a junior varsity football coach at my old high school.  Also, as I previously mentioned above, I did an internship at Advantage International (now Octagon) in Athlete Marketing.  I quickly learned that I didn’t want to be an athletic director or a high school football coach.

3) You worked for Ken Lindner and Associates (KLA) in the early 2000s before starting your own practice.  Why did you think in 2003 that you were ready to take the leap and become your own boss?

Growing up, my dad would always tell me to find my passion and to work for myself someday.  So, it was always part of my plan.  I felt that after my many experiences in the sports agent business and then with the platform KLA had given me to build a business within a business.  I was well prepared as an agent who had an established client base of 75 clients and built great relationships and contacts in the industry.  The time was right, and I haven’t looked back since.  It’s proved to be the best decision I’ve ever made in my career.

4) Take us maybe through your first negotiation as an agent — what client was it for, which network were you talking to, how did it go down, any learnings from it that you took from your career with you to this day, etc.  As much detail as you can provide. 

Shortly after I started at KLA in 1999, I signed Ray D’Alessio who at the time was the Sports Director at WXIN-TV, the local FOX station in Indianapolis.  Unfortunately, his contract wasn’t picked up and he was unemployed for the first time in his career and things became very difficult for him as he was forced to sell cars and paint houses to take care of his family.  During this transitional period, I was able to get Ray many interviews throughout the country in a few local markets, at a CSN sports regional network and at CNN.  At that time, nothing had panned out and almost 18 months had gone by.  It was then that I received a call from one of my closest friends in the industry, Bill Galvin, Vice President & Executive Producer of CNN Sports who I’ve been doing deals with for 15 years and said that Ray’s luck was about to change because CNN was launching CNN Headline News (HLN) and needed to hire a sports anchor for Robin Meade’s morning show.  I immediately called Ray with the good news, and he was in tears.  It was an easy negotiation because both sides wanted to be in business with one another and my relationship with Bill, CNN and HLN has been a very fruitful one.  What I’ve learned over the years is in any negotiation everybody has the same goal in making a good deal where it’s a win-win for all parties.  In this case, and almost any deal I do with any network, it all comes down to having an honest, respectful and trusted relationship.

5) What is the hardest part about being an agent?

I think the hardest part is that you can never fully turn it off.  You are always working.  It’s literally a 24/7 job.  I’m constantly speaking on the phone, sending emails and texting my clients.  You will work on weekends and even when on vacation.  That’s what being an agent and a successful business owner requires.

6) How has social media, especially Facebook, Twitter and Instagram, helped in your role as an agent representing clients across numerous network? 

Social media has made all news and information in the media space become instantaneous in how we connect on so many platforms.  I use it as a means to promote my business and share the different ways I’m able to move, market, position and place my clients at the various media outlets.

7) What trend/development in the agency business are you going to be watching and closely following in 2015?

Change is constant and in order to be successful, you have to embrace change, especially within the technology age.  You have to learn to go digital to survive today’s medium.  Also, local news is doing less in covering sports, but this has opened a huge need for the launch of sports regional networks, leagues and conference specific owned outlets.  Sports is a multi-billion dollar business and the media right’s deals are its driving force.

8) In 100 words or less, what advice would you give aspiring sports business professionals looking to work as an agent representing athletes or sports broadcasters? 

The sports agent and media representation business is a tough industry and a highly competitive field to break into.  The “people business,” as I like to call it, is built on trusted relationships, who you know and what clients you represent and how you can help someone else be successful by creating value where no one else can —“your network is your net worth.”

Everyone takes a different path in their journey.  There’s never one way to live your dream, but there is a mindset.  So, live your passion, work your craft, have purpose, stay hungry, be focused, don’t take no for an answer, never settle because playing it safe is risky, be fearless!

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