My guest today, Bob Pittman, has had one of the most interesting careers I’ve ever come across. Today, he’s the CEO of iHeartMedia, the country’s largest operator of radio stations and podcasts. Bob also created MTV, was the CEO of Six Flags and 21 Century Real Estate, and the COO of AOL and AOL Time Warner. He’s the Dos Equis man of business. In our conversation we discuss why convenience is king for consumers, his lessons from building MTV into one of the most iconic brands and media properties in the world, the rise of user-generated content platforms, and the future of media. We also discuss what qualities make for a great host, a topic that given my current position, is always fascinating. Please enjoy my great conversation with Bob Pittman.

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Show Notes

(2:56) – (First question) – His personal interest that unites all of his business ventures

(4:09) – His philosophy on the consumer

(7:43) – Biggest quality mistakes business leaders make

(9:31) – Respecting convenience in consumer preferences

(11:08) – Founding insight to build MTV

(16:23) – Fred Seibert on Math in Magic Podcast

(17:14) – How the music video concept evolved with MTV

(22:37) – Role of hosts vs guests in the media world

(25:13) – Quality that increases the odds a host works

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