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

(30:15) – Why everyone needs to know how to tell a good story

(31:53) – Peak of his time at MTV

(37:51) – Lessons for new media from his experience

(43:46 – The largest uncertainty in the media landscape amid the rise of user generated content platforms

(49:27) – Where he finds inspiration outside of business

            (55:40) – What Other People Say May Change What You See

(56:16) – Different ownership structures and how they changed his behavior

(59:09) – Finding and respecting your audience

(1:02:11) – Lessons from time at Six Flags

(1:02:24) – Most interesting thing about podcasting

(102:52) – Kindest thing anyone has done for him

Learn More

For more episodes go to InvestorFieldGuide.com/podcast.

Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub.

Follow Patrick on Twitter at @patrick_oshag