Kevin Sheehan: Talking His Way To the Top

Kevin Sheehan is living his dream.

His distinctive voice and encyclopedic knowledge of the local sports landscape have made him a staple of Washington, DC sports talk radio for the past 15 years.  Redskins. Caps. Nats. Wizards.  He always has an opinion and is not afraid to share it with his audience, his co-hosts or his guests.

But Kevin’s path to the microphone has been anything but conventional.

“My journey to sports talk radio has certainly been unique.”

That would be an understatement.  He never served in a small market.  He never pursued a traditional internship. Kevin Sheehan reached the pinnacle of a completely different career before leaving to pursue his original dream in sports talk radio.  And once he talked his way into his first broadcasting job, there was no looking back!

The story of Kevin Sheehan is a story of resiliency and hustle.  And there are lessons for all of us in his unconventional journey.

The Foundation

Kevin Sheehan grew up in Bethesda, MD as the oldest child in a middle class family.  He attended Walt Whitman High School and went on to major in commuications at the University of Maryland.  Upon graduation, Kevin landed a job at local Fox affiliate WTTG, working in television for sports anchor Steve Buckhantz and director and producer Ernie Baur.

“I couldn’t have had a better experience with those guys.  They were so encouraging, and really served as trusted mentors.  What a blessing.”

And Sheehan wasn’t alone.  Future sportscaster and good friend Scott Van Pelt worked under Buckhantz and Baur as well as Gus Johnson and Chick Hernandez.  It was a training ground for future Washington, DC on-air talent.  But Kevin Sheehan’s career path would take several turns before veering back into the media world.

A Different Path

After two years at WTTG, Kevin became restless and decided to leave the media world.  He had always had an affinity for entrepreneurship and decided to try his hand in business.  After a few startup ventures, Kevin helped found internet grocer Streamline.com.

The business started slowly.  The concept was ahead of its time and resilience was the key to success in those early years.   But as online purchasing became more prevalent, sales increased exponentially.

Kevin Sheehan found himself at the epicenter of the dot-com boom!  In 1999, he helped take Streamline.com public.   And two years later, Streamline.com was purchased by Dutch global conglomerate Ahold, the parent company of Giant Foods.  Streamline would get folded into the popular Peapod delivery service.

By 2003, Kevin Sheehan’s time in the startup world was winding down.   At this point, he had options.  But none as attractive as pursuing his lifelong passion.

A Dream Emerges

During his time with Streamline.com, Kevin frequently travelled up and down the East Coast from Boston to Washington, DC.  And in every city, he would always tune in to the local sports radio channel.

“There is something magical about local sports talk radio.  I’ve always loved it.  The fans are much more passionate and the experience much more intimate than the national shows.”

Kevin had always been around sports.  He played, he coached, he soaked it in on the radio every chance he got.  And one day, while listening to the original sports talk radio station, WFAN in New York, it hit him:

“I want to do this for a living!”

This is where Kevin’s story differes from so many others.  Many of us talk about our dream jobs.  Many of us fantasize about pursing our passion.  But few of us follow through.

“After 15 years of being on the road and living the ups and downs of start-up companies, I was ready for something new.”

Kevin Sheehan’s chapter in the dot-com business had closed.  But a glorious new chapter was just beginning.

Starting From Scratch

It had been years since Kevin had left WTTG.  He had virtually no experience in radio or in announcing games.  But that didn’t stop him from answering an ad for a play-by-play commentator for Catholic University of America (CUA) football games.  Why not?

Kevin pieced together an audition tape from homemade recordings and approached CUA Athletic Director Bob Talbott with confidence.

Talbott listened to his pitch: He was local.  He knew the market.  He had worked with Buckhantz and Scott Van Pelt. He had a deep knowledge of DC sports and an affinity for CUA.  Most importantly, he had been doing this for years (It was mostly true.  He had been doing play-by-play in his head for years!)

Kevin was relentless.

“Okay, Okay!” Talbott finally tapped out. “The job is yours.”

“How much does it pay?”

“Zero!”, exclaimed Talbott.

“Deal!”

It was a start.

After three games, Sheehan now had a legitimate resume tape. But he wasn’t done scratching and clawing for his dream.

He walked in off the street to local Cable TV Station Channel 21, uninvited and unannounced, to inquire about an on-air sportscaster role.

“The manager thought I was crazy. But as fate would have it, they needed someone to start the next day. Might as well be me.”

If you never ask for the order, you never get the order.  

In addition to passion and a deep knowledge for sports, Kevin Sheehan now had experience. The sky was the limit.

Making His Own Luck

Armed with play-by-play and on-air experience, and buoyed by his recent success in the hyper-local market, Kevin Sheehan set his sights on the biggest player in the Washington, DC market at the time, Clear Channel Communications.

Bennett Zier was the VP and General Manager of Clear Channel in the local Washington, DC market, and one of the most powerful men in radio. Kevin was introduced to Zier by a good friend. Sheehan launched in and wouldn’t take no for an answer.

Surely, they needed someone to fill in on Sports Talk 980 for the weekend updates.

It was not a particularly attractive job at the time.

“You don’t want to do this,” Zier warned.

“Give me a chance, I can do it”. Sheehan pleaded.

What choice did Zier have?

Zier liked what he heard but ultimately left the decision up to Program Director Tod Castleberry.

Castleberry listened intently and decided to take a chance on Sheehan. That decision was a turning point in Sheehan’s (second) career.

After two weeks of delivering the weekend updates for Sports Talk 980, Sheehan received another huge break. Talented morning weekday update host Meredith Josef announced she was departing on maternity leave. Sheehan now had an opportunity to move into her position, a major promotion after such a short time on the air.

“I know most people say they were lucky in their career. But I REALLY was lucky!”

And that “luck” was only going to continue.

The Sky is the Limit

Just three weeks after Sheehan’s on-air debut as the weekday update guy, legendary local personality Tony Kornheiser returned to the DC-area from his stint on Monday Night Football. Kornheiser secured his own show at the same station Sheehan delivered his updates. It was another enormous break for Sheehan.

Tony would invite Kevin onto the show and ask his opinion about anything from sports to movies to restaurants. He essentially made Sheehan part of his show.

“Tony and I had a great relationship. He didn’t have to let me hang around. But being a small part of Tony’s show gave me more exposure than anything else I was doing. It was important for me.”

Kevin Sheehan was now emerging as a local radio personality. It was around this time that Red Zebra Broadcasting established a competing Washington, DC sports station. Bennett Zier was hired as CEO and he wanted Sheehan to come with him. Sheehan said yes. It was a risk but turned out to be yet another fortuitous move in his burgeoning broadcasting career.

Once at Red Zebra, Sheehan started his remarkable streak of employment in an all-too finicky business. . He co-hosted “The John Riggins Show” with the legendary Hall of Fame running back for a few years. He also handled pre-game and post-game shows for the Washington Redskins with Redskins’ great Joe Jacoby.  He was honing his craft through practice and sheer volume of air time.

“It took me a while, but eventually I felt comfortable being in front of a microphone.  The only way to get there was through repetition.”

Amen, Kevin. It takes hard work and reps to master any worthy pursuit in this life.

Eventually, Red Zebra bought Sports Talk 980 and Kevin was once again back on the station that launched his career.

He worked middays with Redskins great-turned-broadcaster Doc Walker for a year and a half. Then he landed a show with his good friend and columnist Thom Lovero, which lasted for nearly 8 years.

Kevin Sheehan transformed from a start-up executive to established local sports talk radio personality through hard work, hustle, and grit.

And he wasn’t done yet.

Still Making It Happen

Kevin Sheehan currently hosts the “Cooley and Kevin Show” weekday mornings from 7am to 11am with former Redskin great Chris Cooley. And what has he learned from his last 15 years of experience on the air?

“You are only as good as your last show.”

He still has to prepare. He still has to grind. He still has to make every day feel new and fresh. That doesn’t always come easy.

“September through the Super Bowl is a busy time for local sports talk radio. This is still a Redskins town. But we still have to make it interesting Tuesday through Thursday in mid-June.”

And to Kevin, that is the beauty of sports talk radio. Every day is a challenge. Every day is creative and different. Every day is interesting.

After 15 years on the radio, Kevin Sheehan is still making it happen. And that is a dream come true.

What Does This Mean for Us?

Kevin Sheehan carved a unique path to a broadcasting career. But there is something universal in his journey that we can all carry with us.

How many of us appreciate the impact of our mentors?

How many of us follow our dreams with tenacity and passion?

How many of us have the confidence to “fake it until we make it”?

How many of us have the temerity to ask for the order?

How many of us have the perseverance to keep taking reps until we master our craft?

How many of us recognize how lucky we are to be in our position?

Kevin Sheehan had a simple dream. And he worked as hard as possible to make that dream a reality.

His journey is unique.  But he is not alone.

We all have a resilient journey inside us. 

Until next week, keep smiling.