John Dickey

How to Build a Communications Empire

I was excited to interview John Dickey, one of the brothers behind the media giant Cumulus Media. The Dickeys bought one radio station and continued to scale to become the nation’s second largest radio company. I sat down with Dickey to learn how he navigated the ups and downs of a changing landscape and ended up on top. 

For more information on John's latest pursuit, visit Ora.TV.

In this episode, you'll learn:

  • What small business owners today are doing wrong with their marketing (7:10)
  • How to work with family members (10:11)
  • How to scale your business for growth (11:45)
  • What it means to be authentic, especially when weaving branded content into your own content (32:14)


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Why did you choose to have John as a guest?

John was an add-on to the Larry interview in order to talk about Ora and the future of digital TV, but I find John fascinating because he and his brother grew Cumulus Radio from 2 radio stations to the 2nd largest radio network in the US! How’d you get the interview? Larry’s publicist suggested him in an interview alongside Larry (which you can see at the end of John’s interview.)

What was he like?

Nice but reserved, somewhat quiet and very business-like.

What went wrong?

I love John’s story but the Ora people were hoping for a piece more about Ora and Larry than about John’s past building Cumulus. I have to write what I believe is the right story, however. To compromise I’m writing a second piece on John to focus on his advice for media entrepreneurs and the future of digital media, which is important, but had to stand alone as its own separate piece.

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