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Speaker 1: You're listening to Math and Magic, a production of iHeartRadio.

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Speaker 2: Welcome to a special bonus episode of Math and Magic.

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Speaker 2: I'm Bob Pittman. Remarkable careers, unyielding passion, and strong instincts

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Speaker 2: are traits all of our guests have in common, but

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Speaker 2: they've each navigated different paths to establish their legacies. I

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Speaker 2: believe in anyone's success story, there's one improbable jump, whether

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Speaker 2: a promotion or a pivot, or a lesson or stroke

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Speaker 2: of luck, there's usually a key moment that unlocks new possibilities.

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Speaker 2: In today's bonus episode, we're examining those career jumps. I

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Speaker 2: think there's a lot to learn and be inspired by

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Speaker 2: along the way. Ryan Seacrest is known by many as

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Speaker 2: the hardest working person in showbiz. He's the long running

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Speaker 2: host of American Idol. Of course, he was also on

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Speaker 2: screen for six years of Live with Kelly and Ryan

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Speaker 2: and has recently taken over Pat Sajack's iconic role as

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Speaker 2: the host of Wheel of Fortune. But he's behind the

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Speaker 2: scenes too, creating shows like Keeping You Up with the Kardashians.

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Speaker 2: On top of everything, he's on the air every morning

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Speaker 2: with iHeart broadcasting on over one hundred radio stations nationwide.

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Speaker 2: I wanted to know about his most important steps along

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Speaker 2: the way. Did you intend to do all those things

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Speaker 2: or did it just sneak up on you. I never

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Speaker 2: intended to do all of those things. I wanted to

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Speaker 2: move to Los Angeles when I was growing up in Atlanta.

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Speaker 2: I had a dream to do that when I was

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Speaker 2: a teenager. I made that dream come true when I

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Speaker 2: was nineteen, Still a teenager, I studied the work of

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Speaker 2: Merv Griffin Dick Clark, both guys who had a radio

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Speaker 2: and TV career, and both entrepreneurs and both asset owners,

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Speaker 2: and both very very smart but also very good presenters

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Speaker 2: on air. And I watched how they maneuvered the skills

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Speaker 2: of business and the skills of performance and what that

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Speaker 2: intersection was for them, And in my head, I felt, Okay,

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Speaker 2: if I could take baby steps towards those paths, maybe

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Speaker 2: it would be the career that I'm looking for and

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Speaker 2: be fulfilling to me. But I didn't know how it

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Speaker 2: would all come together. Almost every career is enabled by

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Speaker 2: one unlikely or improbable stroke of luck somewhere in the process.

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Speaker 2: For me, it was to jump from minimum wage part

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Speaker 2: time radio announce from Brookhava, Mississippi, to programming the station

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Speaker 2: and being on the air at the big NBC owned

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Speaker 2: radio station in Chicago just five years later. What was

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Speaker 2: yours and how did it happen? One that I think

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Speaker 2: about now and hone in on is the big break

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Speaker 2: of being the host of American Idol. This came at

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Speaker 2: a time when I was twenty six seven years old.

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Speaker 2: I was on the radio in Los Angeles doing afternoon drive.

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Speaker 2: It had been on television a little bit and gotten

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Speaker 2: some good experience, but nothing at the level with the

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Speaker 2: impact of what was about to come. And initially I

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Speaker 2: met with the producers and I was considered as a

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Speaker 2: judge for American Idol. And during the meeting with those

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Speaker 2: executive producers, I started asking about the host and they said, well,

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Speaker 2: you could audition for the host if you want. So

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Speaker 2: I auditioned to be the host of American Idol. After

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Speaker 2: the audition that night, they told me that I got

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Speaker 2: the job and we start shooting the next day. Literally

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Speaker 2: the next morning we started shooting. We were doing audition

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Speaker 2: Simon Randy Paula. We were meeting in Hollywood to do

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Speaker 2: the auditions for the first season of the show that

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Speaker 2: had never been on the air. This was at the time, Bob,

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Speaker 2: you probably remember this when people were saying music does

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Speaker 2: not work on TV, right, remember that, Well, I remember

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Speaker 2: those stories. I know those people, we know those people. Well,

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Speaker 2: it did work on TV. It started to become this massive,

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Speaker 2: massive event on television. And that was a moment that

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Speaker 2: I thought to myself, Wow, I'm lucky here right like

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Speaker 2: I got into this, I'm lucky.

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Speaker 3: This is going to be a ride.

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Speaker 2: How do I take this momentum and turn it into

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Speaker 2: something bigger at the same time, and that's when we

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Speaker 2: started having conversations with the management for American Top forty

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Speaker 2: and Kiss FM, and where I went and hosted E

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Speaker 2: News and the red carpet shows and produced series for them.

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Speaker 2: So I would say being the host of that singing

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Speaker 2: competition show opened the door for all the things that

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Speaker 2: came to fruition. Brian embraced an opportunity on a show

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Speaker 2: that many didn't think would work, and when it was

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Speaker 2: a success, he didn't stop there. Rob Riley has always

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Speaker 2: had ambitious goals too, and at points he made curious

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Speaker 2: decisions about how to reach them. Rob is the chief

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Speaker 2: creative officer of WPP, one of the major advertising groups.

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Speaker 2: Rob built his stunning reputational work that is memorable and buzzy,

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Speaker 2: from campaigns for companies like American Express and Burger King

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Speaker 2: to the Fearless Girl statue in Manhattan's Financial District. His

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Speaker 2: improbable career jump was different than Ryan's. Rather than talking

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Speaker 2: about how he built his career from the beginning, share

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Speaker 2: a story about an unexpected choice at the precipice of

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Speaker 2: a huge promotion, he took what seemed like a step

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Speaker 2: backwards at the dawn of the century. You were the

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Speaker 2: acting chief creative officer at Hill Holiday and you took

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Speaker 2: up sixty percent pay cut to change jobs and become

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Speaker 2: just a copywriter at Crispin Porter. Clearly it all worked out.

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Speaker 2: Why did you take that risk and what lesson did

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Speaker 2: you learn?

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Speaker 3: Well?

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Speaker 4: I had worked for this amazing boss named David Weekle,

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Speaker 4: and he was the chief creative officer and they parted ways,

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Speaker 4: and I was one of the more senior people there,

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Speaker 4: but not very senior at all, and they said, well,

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Speaker 4: maybe you can step in temporarily while we search for

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Speaker 4: a new CCO. Might have been some discussion if you

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Speaker 4: want to throw your hat in the ring, to be

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Speaker 4: that person, and I kind of realized that I had

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Speaker 4: all the skills of a great creative director without maybe

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Speaker 4: the work of a great creative director. And I didn't

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Speaker 4: want to end up being a New York creative at

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Speaker 4: a certain age that kind of giant salary but didn't

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Speaker 4: have the work where people would follow you.

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Speaker 3: So I ended up going down.

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Speaker 4: To Crispin Porter and Buguski at the time, probably one

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Speaker 4: hundred and twenty people, sort of getting known for doing

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Speaker 4: some really interesting national work for smaller clients, and I

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Speaker 4: pitched Alex Buguski, now my current wife, my only wife,

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Speaker 4: but she was my girlfriend the time she was working there,

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Speaker 4: so I had a connection. But Alex wasn't going to

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Speaker 4: hire me just because I was the boyfriend. Maybe in fact,

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Speaker 4: didn't necessarily want some guy from New York who had

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Speaker 4: all the wrong sort of closed and was a big

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Speaker 4: creative director from New York City come down to his

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Speaker 4: agency in Miami that.

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Speaker 3: Was really small, tight culture.

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Speaker 4: But I knew that's the kind of work I needed

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Speaker 4: to be part of, because in the end, you don't

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Speaker 4: necessarily just follow people. You follow people because of the

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Speaker 4: work they've done. And I had all the skills of

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Speaker 4: being able to present and good with clients and maybe

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Speaker 4: good with teams. But I didn't have enough creative work

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Speaker 4: that I thought was like culture changing that was going

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Speaker 4: to get me in to a long term career. So

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Speaker 4: I took a few steps back. But it wasn't the

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Speaker 4: easiest ride. When I got there, I was the guy

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Speaker 4: from New York. Everybody's in flip flops and shorts. I'm

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Speaker 4: here in the product boots in black. I stood out

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Speaker 4: like a sore thumb. And about thirty days into it,

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Speaker 4: Alex calls me in his office said, listen, man, I

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Speaker 4: love the work you're doing. I think you're fantastic. Here's

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Speaker 4: the problem. No one else likes you. So I thought

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Speaker 4: he would say, it doesn't matter as long as I

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Speaker 4: like you. He said, that's the opposite. I can't have

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Speaker 4: one guy who ruined the culture. So you got to

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Speaker 4: figure out how to get people to like you. And

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Speaker 4: long story short, I ended up going back and deciding, like,

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Speaker 4: you know what, I'm just going to shut my mouth

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Speaker 4: and sit in the corner and crank out work. And

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Speaker 4: that's what I did. And then once you start making work,

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Speaker 4: people respect. That was the beginning of building a body

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Speaker 4: of work that I'm really proud of at every level. Copywriter,

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Speaker 4: creative director, CCO, creative chairman, to down with WPP.

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Speaker 3: Head of a holding company.

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Speaker 2: Well, you know, let's go back in time for a second.

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Speaker 2: Why didn't they like you? What were you doing?

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Speaker 3: Why didn't they like me? Well? I probably had the

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Speaker 3: wrong clothes.

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Speaker 4: I had an incredibly intelligent, smart, beautiful girlfriend who's now

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Speaker 4: my wife and doing all the amazing work.

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Speaker 3: And I was the boyfriend from New York.

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Speaker 4: I came from a big New York ad agency and

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Speaker 4: it wasn't quite fitting in the culture.

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Speaker 3: And I think growing up in New Jersey like we're loud.

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Speaker 4: And when I went and told my wife that Alex

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Speaker 4: said that people didn't like me, her response was, why

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Speaker 4: don't you just try shutting up and doing the work.

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Speaker 3: You know you're the problem.

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Speaker 4: So I was taught a lesson early on to shut

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Speaker 4: my mouth and do the work. And when you have

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Speaker 4: the work, you get the respect.

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Speaker 2: Well that's a great lesson. And ten years later you

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Speaker 2: were the chief creative officer of Crispin Porter.

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Speaker 3: So it all worked out. Yeah, it all worked out.

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Speaker 2: Rob knew he wouldn't be able to achieve his goals

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Speaker 2: in the long term. If he moved up too quickly,

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Speaker 2: he took a pay cut and acclimated to a new

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Speaker 2: team so he could build the right foundation for future growth. Likewise,

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Speaker 2: Jackie Kelly has taken some unexpected turns in her career.

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Speaker 2: Today she is the Chief Client Officer at IPG and

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Speaker 2: was at DENSU as CEO of the Americas. Before that,

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Speaker 2: her career evolved around media and advertising, with leadership roles

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Speaker 2: at USA today, Yahoo, Martha Stewart, Living and Bloomberg. But

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Speaker 2: the world of media is always changing, and there have

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Speaker 2: been points when Jackie's decision to change with it surprised

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Speaker 2: even herself. You went on to Yahoo, you did a

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Speaker 2: stint with Martha Stewart, and then you crossed the fence

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Speaker 2: to the agency side running media brands. What made you

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Speaker 2: jump the fence?

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Speaker 5: This is kind of a fun story, and I give

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Speaker 5: credit to people that can identify talent and then encourage

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Speaker 5: us to do something that would not be obvious to us.

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Speaker 5: So in my case, I had left USA, I had

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Speaker 5: gone to Yahoo and worked for Wyndham Millard. Wyndham Millard

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Speaker 5: is an incredible mentor for me and convinced me to

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Speaker 5: come to Yahoo. But It wasn't that hard to convince

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Speaker 5: me because I knew newspapers were changing. I knew I

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Speaker 5: needed to get a much better digital education. I wanted

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Speaker 5: to go to the deep end. At the time, Yahoo

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Speaker 5: or Google were your two choices, and Yahoo was teaching

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Speaker 5: brands how to build a brand on the web, so

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Speaker 5: that was obvious for me. And then followed Wynda to

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Speaker 5: Martha Stewart to fully integrate Martha's organization. It was post

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Speaker 5: her being in what she calls the clink clink, and

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Speaker 5: we were building her brand back and consumers never left

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Speaker 5: their advertisers had, so there was a lot of work

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Speaker 5: to do around integrating her organization. I'd love that challenge.

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Speaker 5: It was in that moment that Wynda actually had heard

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Speaker 5: about an opportunity through a friend of hers that was

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Speaker 5: running UM globally, a gentleman named Matt Syler, and she said,

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Speaker 5: you should look at this because it would be a

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Speaker 5: next phase of your career. And I had never wanted

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Speaker 5: to be at the agency side. I'd been on a

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Speaker 5: panel at Advertising Week and famously referred to agencies as

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Speaker 5: a barrier to my progress as a media owner, which

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Speaker 5: did not go overwhelm but I believed that agencies were

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Speaker 5: failing clients and media owners because they or not giving

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Speaker 5: us the gift of time and transparency. Those were the

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Speaker 5: two things that I really wanted from an agency, and

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Speaker 5: I just couldn't get anyway. Long story short, Matt saw

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Speaker 5: what I saw. Matt saw the opportunity to leverage media

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Speaker 5: owners as real content partners in the work that media

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Speaker 5: brands and UM specifically was doing for clients. And it

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Speaker 5: was the first time that I saw an agency executive

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Speaker 5: see what I saw as the opportunity to partner differently

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Speaker 5: with media owners. And it was one of those moments

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Speaker 5: in life where you can keep complaining and pointing the

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Speaker 5: finger and wishing it was different, or you can jump

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Speaker 5: to the other side and help make that so. And

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Speaker 5: then I got this right. Then I just loved the

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Speaker 5: agency side. It's such an incredible place to operate in

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Speaker 5: our industry. But that's how I got there. Great people

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Speaker 5: that told me I should.

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Speaker 2: Jackie decided to keep an open mind and try experiencing

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Speaker 2: a part of the industry she had serious doubts about.

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Speaker 2: Instead of writing it off, she jumped in head first

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Speaker 2: and brought her career to the next level.

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Speaker 3: We'll be right.

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Speaker 2: Back after a quick break. Welcome back to Math and Magic.

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Speaker 2: Angel le Yee has been on the airwaves for over

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Speaker 2: a decade as founding member of the Breakfast Club, host

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Speaker 2: of her midday show Way Up, and now the podcast

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Speaker 2: Lip Service. She's also an entrepreneur who loves to get

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Speaker 2: back to communities in need. During a live recording at

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Speaker 2: the National Association of Broadcasters in Las Vegas, I learned

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Speaker 2: how she made her career jump from intern to assistant

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Speaker 2: to manager and eventually host. Even as an assistant, she

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Speaker 2: did right by some pretty important people and carved out

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Speaker 2: a name for herself early on.

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Speaker 6: So the first internship I had was at a label

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Speaker 6: called tvt Records right and they also licensed like all

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Speaker 6: the TV tunes, the cartoon music that you hear. And

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Speaker 6: so when I did that internship, it was in the

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Speaker 6: legal department. I did not care about the legal department

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Speaker 6: at all, but I knew that in order for me

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Speaker 6: to get my foot in the door, that was just

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Speaker 6: a way for me to get in. And so one

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Speaker 6: thing I learned was just get your foot in the door.

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Speaker 6: And so I started doing these internships. I had an

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Speaker 6: internship with MTV and the person I interned for. He

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Speaker 6: was a music manager, so he would present the videos

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Speaker 6: that they would then have to decide what was going

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Speaker 6: to air. So everybody wanted to get in with him,

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Speaker 6: you know. I remember going to Puffy's studio back then

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Speaker 6: when he was playing like Bigis videos for him and

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Speaker 6: they gave us champagne and I was just interning and

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Speaker 6: I was like, this is amazing. And so for me,

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Speaker 6: internships in college were really important, and so when I

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Speaker 6: graduated from college, I had an opportunity to work at

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Speaker 6: either Columbia Records, but I was actually going to visit Wuting.

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Speaker 6: It was the same day that they were doing summer

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Speaker 6: jam and I didn't even realize it, and they were

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Speaker 6: like coming us a summer jam, and the guy who

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Speaker 6: I interned for was like, you know, we've been trying

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Speaker 6: to find you. We wanted to hire you, and so

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Speaker 6: I was like okay, cool, and I turned down everything

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Speaker 6: else because I felt like this was a better opportunity

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Speaker 6: and that's why I took.

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Speaker 2: That job, seaking of learning things. There's a story that

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Speaker 2: you went on the road as a manager and you

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Speaker 2: turned out to be a roaring success because you were

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Speaker 2: good with money. Can you talk a little bit about that,

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Speaker 2: because there's a lesson in there somewhere.

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Speaker 6: So I ended up going on the road with Jizza

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Speaker 6: from Wu Tang. He had to go to Europe at

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Speaker 6: the last minute his manager couldn't go, and so I

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Speaker 6: went on the road and when we came back, had

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Speaker 6: like a whole ledger down to the penny of what

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Speaker 6: everybody got paid and what money we had left, and

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Speaker 6: he had never gotten that before, and I just thought,

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Speaker 6: that's how I have to do things. And so he

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Speaker 6: was so impressed by the fact that he got all

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Speaker 6: his money that he was supposed to get, everybody was

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Speaker 6: paid what they were supposed to get paid, and everything

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Speaker 6: was correct to the penny. That after that I just

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Speaker 6: was his manager.

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Speaker 3: Wow, that's pretty good.

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Speaker 6: I think that at the foundation of things, that hard

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Speaker 6: work is the fundamental thing. I feel like a lot

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Speaker 6: of times people see other people who are successful and

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Speaker 6: they think it just happens, or they think it's just relationships.

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Speaker 6: You can get your foot in the door, but then

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Speaker 6: what happens after that? And so for me, I've always

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Speaker 6: been like the first person in the office the last

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Speaker 6: person to leave. That's what I was doing. And also

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Speaker 6: honesty is important. I feel like money can get people

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Speaker 6: to act very different when that gets involved, and so

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Speaker 6: they're always surprised when you can be really transparent, but

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Speaker 6: people appreciate that it's rare.

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Speaker 2: By making yourself trustworthy, Angela became indispensable very early in

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Speaker 2: her career. Tim Castri has a similar story about catching

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Speaker 2: the attention of potential mentors at a young age. Today

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Speaker 2: Tim is the VP of Global Content and Media at Amazon,

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Speaker 2: but he used to be a kid in Melbourne groofing

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Speaker 2: off at his grocery store job until he got a

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Speaker 2: lucky break. So you started as the advertising cadet. What

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Speaker 2: is an advertising cadet?

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Speaker 7: I think I was the first and only ever advertising cadet.

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Speaker 7: This wasn't a long line of but it was basically

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Speaker 7: a way to give a break to a high school

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Speaker 7: kid who was in a family situation where I couldn't

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Speaker 7: afford to go to college. Moment said, look, you need

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Speaker 7: to go to work for a few years. That's what

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Speaker 7: the family needs. So I was working in a supermarket

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Speaker 7: after school. I thought the girl who worked in the

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Speaker 7: Dali was kind of cute, and I was showing off

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Speaker 7: to her juggling watermelons in the supermarket. Two watermelons, not three,

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Speaker 7: and this area manager came around and she said, what

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Speaker 7: the hell are you doing? And get back to work.

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Speaker 7: And then about an hour later, I was on my

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Speaker 7: lunch break and she came and talked to me and

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Speaker 7: she said, oh, sorry, I'm so hard on you. I said, no,

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Speaker 7: no problem. I shouldn't have been juggling watermelons. And we

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Speaker 7: got talking and we hit it off. Her name was

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Speaker 7: Margaret Kem and she said, well, you're about to graduate

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Speaker 7: high school. What are you doing? I said I don't know,

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Speaker 7: and I explained my situation how I needed to go

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Speaker 7: out and work, and she said, what do you want

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Speaker 7: to do? I said, I really want to work in

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Speaker 7: marketing and advertising, and she said, well, you know, we

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Speaker 7: have an advertising department here at Safeway. Why don't I

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Speaker 7: make some phone calls and see if there's anything they

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Speaker 7: could do for you? Lo and behold. She called me

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Speaker 7: back three days later and said, you know what, They've

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Speaker 7: just decided to launch this first ever cadetship program, and

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Speaker 7: why don't you apply for that and I'll see if

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Speaker 7: I can help you. And sure enough, I applied and

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Speaker 7: I was given this cadetship, which was basically working in

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Speaker 7: the internal advertising department of Safeway Supermarkets and loved it.

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Speaker 7: About a year into it, the internal advertising department got

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Speaker 7: absorbed into Leo Burnett. So I moved from Safeway into

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Speaker 7: Leo Burnette about a year after I'd started, which is

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Speaker 7: a whole other story. Do you want to hear that?

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Speaker 3: Yes?

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Speaker 2: I do. I do want to hear that.

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Speaker 7: So I was in this cadet ship and they were

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Speaker 7: waiting to give the contract to Leo Burnette. A bunch

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Speaker 7: of folks they took into the agency. A bunch they

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Speaker 7: let go and moved into other departments, and I was

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Speaker 7: the last person they hadn't resolved. My story is basically

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Speaker 7: a long litany of people who gave me breaks. And

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Speaker 7: there was a guy who ran advertising. His name was

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Speaker 7: John Simon, and John was saying to the CEO of

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Speaker 7: Leo Benett, you've got to take this guy, Tim. He's fantastic,

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Speaker 7: he's a young guy. And they said, look, we just

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Speaker 7: we don't know what to do with advertising cadet, and

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Speaker 7: so we don't need him. John was adamant about it,

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Speaker 7: and they went back and forth on this for weeks

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Speaker 7: while they were negotiating the contract. They got to the

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Speaker 7: final day where John was about to sign the contract

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Speaker 7: to give them the account. It was still unresolved, and

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Speaker 7: he said, look, I'm not signed until you give him

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Speaker 7: a job. And he held then and he sat and waited.

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Speaker 7: Took him about ninety seconds after that, I said, fine, fine,

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Speaker 7: we'll give the kid a job. And then he signed

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Speaker 7: the contract. And that's how I was. What was their job, Well,

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Speaker 7: they basically brought me in a similar capacity in Lea Burnette.

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Speaker 7: So they said, we'll take him on for two years

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Speaker 7: and we'll move him around to all the various departments

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Speaker 7: from production to creative to account management and media. They

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Speaker 7: didn't have programs like that at the time. But my

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Speaker 7: boss there was still one of my best friends to

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Speaker 7: this day, a woman named Melinda Gertz. She went to

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Speaker 7: Northwestern and they've transferred to the Melbourne office of LEO

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Speaker 7: Burnett from the Chicago office. Melinda just said, well, I'll

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Speaker 7: take him and I'll redesign what we used to do

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Speaker 7: at Leabnett in Chicago. I'll just make a little training

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Speaker 7: program for one and so that was where they designed

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Speaker 7: this kind of program to put me around in each

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Speaker 7: of the departments and learn the ropes of advertising.

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Speaker 2: Well, you did really well, so you must have impressed somebody.

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Speaker 2: What did you do in that advertising cadet job that

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Speaker 2: so impressed them that you began to move up in

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Speaker 2: the world.

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Speaker 7: Now, I had a real work ethic. When you grow

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Speaker 7: up in a working poor family. I mean a lot

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Speaker 7: of people who have that experience, they burn, you know,

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Speaker 7: they really burn with the ambition and a drive. And

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Speaker 7: I had that as well. You know, a lot of

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Speaker 7: fuel from my childhood circumstances really pushed me forward. So

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Speaker 7: I'd say it was a real combination of work ethic.

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Speaker 7: God gifted me with a good brain the gray matters

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Speaker 7: always worked pretty well, and also real willingness to take

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Speaker 7: risks and put myself out there. I'd be constantly making

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Speaker 7: proposals and recommendations that were far beyond my pay grades,

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Speaker 7: far beyond what I knew. But I really tried hard

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Speaker 7: to make a difference and to have an impact. And

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Speaker 7: I think they noticed that.

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Speaker 2: When luck struck and doors opened for him, Tim ran

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Speaker 2: through and proved himself worthy of the chances he got.

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Speaker 2: Tim ended up being CEO of Leo Burnette Australia and

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Speaker 2: One Australia's Agency of the Year Award. That's a career

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Speaker 2: jump you can't forget. That's all for today, I'm Bob Bittman.

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Speaker 2: Thanks for listening, and stay tuned for a brand new

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Speaker 2: season of Math and Magic coming up.

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Speaker 1: That's it for today's episode. Thanks so much for listening

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Speaker 1: to Math and Magic, a production of iHeart Podcasts. The

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Speaker 1: show is hosted by Bob Pittman. Special thanks to Sydney

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Speaker 1: Rosenbloom for booking and wrangling our wonderful talent, which is

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Speaker 1: no small feat. The Matho and Magic team is Jessica

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Speaker 1: crimechicch Bahid Fraser, and Julia Weaver. Our executive producers are

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Speaker 1: Ali Perry and Nikki Etour. Until next time.