Bob Pittman: How I Went from Creator of MTV to CEO of iHeartMedia | 20VC #958

Bob, this is such a joy to do. I heard so many good things, especially from our friend Brad Gerstner before. But thank you so much for joining me today.

Oh, I'm delighted to be here. Thank you.

Not at all. But I heard from a little buddy that you started in radio at 15. Can you just talk to me, how did you start in radio at the tender age of 15?

Well, I wa- I grew up in a very small town in Mississippi and, uh, and I needed a job to pay for flying lessons and I tried every place in town. I tried the men's clothing store, they said I was too young. I tried the high-paying job in town which was bagging groceries at Piggly Wiggly.

(laughs)

No jobs. And I walked into this little radio station and, uh, asking a guy named Bill Jones, who owned the station, if I could have a job. And he said, uh, he said, "You know, uh, do you get... You got good grades?" I said, "Yeah, I have pretty good grades." He said, "You get in trouble." I go, "Not really." He goes, "Okay, come in this room." He put on a tape, he gave me some wire copy. Back in the days all the wire came off teletype machines. He tore some off, said, "Read this," and a minute or so, he came back in and said, "That's good enough. Uh, you're hired."

(exhales) .

And that began my career in radio. And back in those days, technology was such that there was no way to bring in signals from outside your market, so in little towns, they hired high school kids to be on the air.

(laughs)

And it's stunning the number of people who got their start doing that. Tom Brokaw, one of the great newscasters on NBC, started in Yankton, South Dakota as a, as an on-air disc jockey, so, so it s- it was a great way to get into the business.

Can I ask, did you love it from the very first minute or was there a moment where you were like, "This is what I really have a passion for"?

No. At first, I loved airplanes, and this was a way to get there. What I did love is that I found all the kids in town would call me on the request line, including girls, which age 15 is very important to you, um, and, uh, but it...

(laughs) .

But I fo- I actually began to fall into radio, and by the time I was sort of 17 or 18, I was just mesmerized by it.

(smacks lips) Can I ask, Bob, I always think careers have inflection points, big break moments where, for some reason, you're given more opportunity, chance than maybe one should at a young age. When you think back over your career, what would you isolate as a big break point in your career where you really scaled trajectory fast?