Speaker 1: You're listening to Math and Magic, a production of iHeartRadio.
Speaker 2: Welcome to a special bonus episode of Math and Magic.
Speaker 2: I'm Bob Pittman. Remarkable careers, unyielding passion, and strong instincts
Speaker 2: are traits all of our guests have in common, but
Speaker 2: they've each navigated different paths to establish their legacies. I
Speaker 2: believe in anyone's success story, there's one improbable jump, whether
Speaker 2: a promotion or a pivot, or a lesson or stroke
Speaker 2: of luck, there's usually a key moment that unlocks new possibilities.
Speaker 2: In today's bonus episode, we're examining those career jumps. I
Speaker 2: think there's a lot to learn and be inspired by
Speaker 2: along the way. Ryan Seacrest is known by many as
Speaker 2: the hardest working person in showbiz. He's the long running
Speaker 2: host of American Idol. Of course, he was also on
Speaker 2: screen for six years of Live with Kelly and Ryan
Speaker 2: and has recently taken over Pat Sajack's iconic role as
Speaker 2: the host of Wheel of Fortune. But he's behind the
Speaker 2: scenes too, creating shows like Keeping You Up with the Kardashians.
Speaker 2: On top of everything, he's on the air every morning
Speaker 2: with iHeart broadcasting on over one hundred radio stations nationwide.
Speaker 2: I wanted to know about his most important steps along
Speaker 2: the way. Did you intend to do all those things
Speaker 2: or did it just sneak up on you. I never
Speaker 2: intended to do all of those things. I wanted to
Speaker 2: move to Los Angeles when I was growing up in Atlanta.
Speaker 2: I had a dream to do that when I was
Speaker 2: a teenager. I made that dream come true when I
Speaker 2: was nineteen, Still a teenager, I studied the work of
Speaker 2: Merv Griffin Dick Clark, both guys who had a radio
Speaker 2: and TV career, and both entrepreneurs and both asset owners,
Speaker 2: and both very very smart but also very good presenters
Speaker 2: on air. And I watched how they maneuvered the skills
Speaker 2: of business and the skills of performance and what that
Speaker 2: intersection was for them, And in my head, I felt, Okay,
Speaker 2: if I could take baby steps towards those paths, maybe
Speaker 2: it would be the career that I'm looking for and
Speaker 2: be fulfilling to me. But I didn't know how it
Speaker 2: would all come together. Almost every career is enabled by
Speaker 2: one unlikely or improbable stroke of luck somewhere in the process.
Speaker 2: For me, it was to jump from minimum wage part
Speaker 2: time radio announce from Brookhava, Mississippi, to programming the station
Speaker 2: and being on the air at the big NBC owned
Speaker 2: radio station in Chicago just five years later. What was
Speaker 2: yours and how did it happen? One that I think
Speaker 2: about now and hone in on is the big break
Speaker 2: of being the host of American Idol. This came at
Speaker 2: a time when I was twenty six seven years old.
Speaker 2: I was on the radio in Los Angeles doing afternoon drive.
Speaker 2: It had been on television a little bit and gotten
Speaker 2: some good experience, but nothing at the level with the
Speaker 2: impact of what was about to come. And initially I
Speaker 2: met with the producers and I was considered as a
Speaker 2: judge for American Idol. And during the meeting with those
Speaker 2: executive producers, I started asking about the host and they said, well,
Speaker 2: you could audition for the host if you want. So
Speaker 2: I auditioned to be the host of American Idol. After
Speaker 2: the audition that night, they told me that I got
Speaker 2: the job and we start shooting the next day. Literally
Speaker 2: the next morning we started shooting. We were doing audition
Speaker 2: Simon Randy Paula. We were meeting in Hollywood to do
Speaker 2: the auditions for the first season of the show that
Speaker 2: had never been on the air. This was at the time, Bob,
Speaker 2: you probably remember this when people were saying music does
Speaker 2: not work on TV, right, remember that, Well, I remember
Speaker 2: those stories. I know those people, we know those people. Well,
Speaker 2: it did work on TV. It started to become this massive,
Speaker 2: massive event on television. And that was a moment that
Speaker 2: I thought to myself, Wow, I'm lucky here right like
Speaker 2: I got into this, I'm lucky.
Speaker 3: This is going to be a ride.
Speaker 2: How do I take this momentum and turn it into
Speaker 2: something bigger at the same time, and that's when we
Speaker 2: started having conversations with the management for American Top forty
Speaker 2: and Kiss FM, and where I went and hosted E
Speaker 2: News and the red carpet shows and produced series for them.
Speaker 2: So I would say being the host of that singing
Speaker 2: competition show opened the door for all the things that
Speaker 2: came to fruition. Brian embraced an opportunity on a show
Speaker 2: that many didn't think would work, and when it was
Speaker 2: a success, he didn't stop there. Rob Riley has always
Speaker 2: had ambitious goals too, and at points he made curious
Speaker 2: decisions about how to reach them. Rob is the chief
Speaker 2: creative officer of WPP, one of the major advertising groups.
Speaker 2: Rob built his stunning reputational work that is memorable and buzzy,
Speaker 2: from campaigns for companies like American Express and Burger King
Speaker 2: to the Fearless Girl statue in Manhattan's Financial District. His
Speaker 2: improbable career jump was different than Ryan's. Rather than talking
Speaker 2: about how he built his career from the beginning, share
Speaker 2: a story about an unexpected choice at the precipice of
Speaker 2: a huge promotion, he took what seemed like a step
Speaker 2: backwards at the dawn of the century. You were the
Speaker 2: acting chief creative officer at Hill Holiday and you took
Speaker 2: up sixty percent pay cut to change jobs and become
Speaker 2: just a copywriter at Crispin Porter. Clearly it all worked out.
Speaker 2: Why did you take that risk and what lesson did
Speaker 2: you learn?
Speaker 3: Well?
Speaker 4: I had worked for this amazing boss named David Weekle,
Speaker 4: and he was the chief creative officer and they parted ways,
Speaker 4: and I was one of the more senior people there,
Speaker 4: but not very senior at all, and they said, well,
Speaker 4: maybe you can step in temporarily while we search for
Speaker 4: a new CCO. Might have been some discussion if you
Speaker 4: want to throw your hat in the ring, to be
Speaker 4: that person, and I kind of realized that I had
Speaker 4: all the skills of a great creative director without maybe
Speaker 4: the work of a great creative director. And I didn't
Speaker 4: want to end up being a New York creative at
Speaker 4: a certain age that kind of giant salary but didn't
Speaker 4: have the work where people would follow you.
Speaker 3: So I ended up going down.
Speaker 4: To Crispin Porter and Buguski at the time, probably one
Speaker 4: hundred and twenty people, sort of getting known for doing
Speaker 4: some really interesting national work for smaller clients, and I
Speaker 4: pitched Alex Buguski, now my current wife, my only wife,
Speaker 4: but she was my girlfriend the time she was working there,
Speaker 4: so I had a connection. But Alex wasn't going to
Speaker 4: hire me just because I was the boyfriend. Maybe in fact,
Speaker 4: didn't necessarily want some guy from New York who had
Speaker 4: all the wrong sort of closed and was a big
Speaker 4: creative director from New York City come down to his
Speaker 4: agency in Miami that.
Speaker 3: Was really small, tight culture.
Speaker 4: But I knew that's the kind of work I needed
Speaker 4: to be part of, because in the end, you don't
Speaker 4: necessarily just follow people. You follow people because of the
Speaker 4: work they've done. And I had all the skills of
Speaker 4: being able to present and good with clients and maybe
Speaker 4: good with teams. But I didn't have enough creative work
Speaker 4: that I thought was like culture changing that was going
Speaker 4: to get me in to a long term career. So
Speaker 4: I took a few steps back. But it wasn't the
Speaker 4: easiest ride. When I got there, I was the guy
Speaker 4: from New York. Everybody's in flip flops and shorts. I'm
Speaker 4: here in the product boots in black. I stood out
Speaker 4: like a sore thumb. And about thirty days into it,
Speaker 4: Alex calls me in his office said, listen, man, I
Speaker 4: love the work you're doing. I think you're fantastic. Here's
Speaker 4: the problem. No one else likes you. So I thought
Speaker 4: he would say, it doesn't matter as long as I
Speaker 4: like you. He said, that's the opposite. I can't have
Speaker 4: one guy who ruined the culture. So you got to
Speaker 4: figure out how to get people to like you. And
Speaker 4: long story short, I ended up going back and deciding, like,
Speaker 4: you know what, I'm just going to shut my mouth
Speaker 4: and sit in the corner and crank out work. And
Speaker 4: that's what I did. And then once you start making work,
Speaker 4: people respect. That was the beginning of building a body
Speaker 4: of work that I'm really proud of at every level. Copywriter,
Speaker 4: creative director, CCO, creative chairman, to down with WPP.
Speaker 3: Head of a holding company.
Speaker 2: Well, you know, let's go back in time for a second.
Speaker 2: Why didn't they like you? What were you doing?
Speaker 3: Why didn't they like me? Well? I probably had the
Speaker 3: wrong clothes.
Speaker 4: I had an incredibly intelligent, smart, beautiful girlfriend who's now
Speaker 4: my wife and doing all the amazing work.
Speaker 3: And I was the boyfriend from New York.
Speaker 4: I came from a big New York ad agency and
Speaker 4: it wasn't quite fitting in the culture.
Speaker 3: And I think growing up in New Jersey like we're loud.
Speaker 4: And when I went and told my wife that Alex
Speaker 4: said that people didn't like me, her response was, why
Speaker 4: don't you just try shutting up and doing the work.
Speaker 3: You know you're the problem.
Speaker 4: So I was taught a lesson early on to shut
Speaker 4: my mouth and do the work. And when you have
Speaker 4: the work, you get the respect.
Speaker 2: Well that's a great lesson. And ten years later you
Speaker 2: were the chief creative officer of Crispin Porter.
Speaker 3: So it all worked out. Yeah, it all worked out.
Speaker 2: Rob knew he wouldn't be able to achieve his goals
Speaker 2: in the long term. If he moved up too quickly,
Speaker 2: he took a pay cut and acclimated to a new
Speaker 2: team so he could build the right foundation for future growth. Likewise,
Speaker 2: Jackie Kelly has taken some unexpected turns in her career.
Speaker 2: Today she is the Chief Client Officer at IPG and
Speaker 2: was at DENSU as CEO of the Americas. Before that,
Speaker 2: her career evolved around media and advertising, with leadership roles
Speaker 2: at USA today, Yahoo, Martha Stewart, Living and Bloomberg. But
Speaker 2: the world of media is always changing, and there have
Speaker 2: been points when Jackie's decision to change with it surprised
Speaker 2: even herself. You went on to Yahoo, you did a
Speaker 2: stint with Martha Stewart, and then you crossed the fence
Speaker 2: to the agency side running media brands. What made you
Speaker 2: jump the fence?
Speaker 5: This is kind of a fun story, and I give
Speaker 5: credit to people that can identify talent and then encourage
Speaker 5: us to do something that would not be obvious to us.
Speaker 5: So in my case, I had left USA, I had
Speaker 5: gone to Yahoo and worked for Wyndham Millard. Wyndham Millard
Speaker 5: is an incredible mentor for me and convinced me to
Speaker 5: come to Yahoo. But It wasn't that hard to convince
Speaker 5: me because I knew newspapers were changing. I knew I
Speaker 5: needed to get a much better digital education. I wanted
Speaker 5: to go to the deep end. At the time, Yahoo
Speaker 5: or Google were your two choices, and Yahoo was teaching
Speaker 5: brands how to build a brand on the web, so
Speaker 5: that was obvious for me. And then followed Wynda to
Speaker 5: Martha Stewart to fully integrate Martha's organization. It was post
Speaker 5: her being in what she calls the clink clink, and
Speaker 5: we were building her brand back and consumers never left
Speaker 5: their advertisers had, so there was a lot of work
Speaker 5: to do around integrating her organization. I'd love that challenge.
Speaker 5: It was in that moment that Wynda actually had heard
Speaker 5: about an opportunity through a friend of hers that was
Speaker 5: running UM globally, a gentleman named Matt Syler, and she said,
Speaker 5: you should look at this because it would be a
Speaker 5: next phase of your career. And I had never wanted
Speaker 5: to be at the agency side. I'd been on a
Speaker 5: panel at Advertising Week and famously referred to agencies as
Speaker 5: a barrier to my progress as a media owner, which
Speaker 5: did not go overwhelm but I believed that agencies were
Speaker 5: failing clients and media owners because they or not giving
Speaker 5: us the gift of time and transparency. Those were the
Speaker 5: two things that I really wanted from an agency, and
Speaker 5: I just couldn't get anyway. Long story short, Matt saw
Speaker 5: what I saw. Matt saw the opportunity to leverage media
Speaker 5: owners as real content partners in the work that media
Speaker 5: brands and UM specifically was doing for clients. And it
Speaker 5: was the first time that I saw an agency executive
Speaker 5: see what I saw as the opportunity to partner differently
Speaker 5: with media owners. And it was one of those moments
Speaker 5: in life where you can keep complaining and pointing the
Speaker 5: finger and wishing it was different, or you can jump
Speaker 5: to the other side and help make that so. And
Speaker 5: then I got this right. Then I just loved the
Speaker 5: agency side. It's such an incredible place to operate in
Speaker 5: our industry. But that's how I got there. Great people
Speaker 5: that told me I should.
Speaker 2: Jackie decided to keep an open mind and try experiencing
Speaker 2: a part of the industry she had serious doubts about.
Speaker 2: Instead of writing it off, she jumped in head first
Speaker 2: and brought her career to the next level.
Speaker 3: We'll be right.
Speaker 2: Back after a quick break. Welcome back to Math and Magic.
Speaker 2: Angel le Yee has been on the airwaves for over
Speaker 2: a decade as founding member of the Breakfast Club, host
Speaker 2: of her midday show Way Up, and now the podcast
Speaker 2: Lip Service. She's also an entrepreneur who loves to get
Speaker 2: back to communities in need. During a live recording at
Speaker 2: the National Association of Broadcasters in Las Vegas, I learned
Speaker 2: how she made her career jump from intern to assistant
Speaker 2: to manager and eventually host. Even as an assistant, she
Speaker 2: did right by some pretty important people and carved out
Speaker 2: a name for herself early on.
Speaker 6: So the first internship I had was at a label
Speaker 6: called tvt Records right and they also licensed like all
Speaker 6: the TV tunes, the cartoon music that you hear. And
Speaker 6: so when I did that internship, it was in the
Speaker 6: legal department. I did not care about the legal department
Speaker 6: at all, but I knew that in order for me
Speaker 6: to get my foot in the door, that was just
Speaker 6: a way for me to get in. And so one
Speaker 6: thing I learned was just get your foot in the door.
Speaker 6: And so I started doing these internships. I had an
Speaker 6: internship with MTV and the person I interned for. He
Speaker 6: was a music manager, so he would present the videos
Speaker 6: that they would then have to decide what was going
Speaker 6: to air. So everybody wanted to get in with him,
Speaker 6: you know. I remember going to Puffy's studio back then
Speaker 6: when he was playing like Bigis videos for him and
Speaker 6: they gave us champagne and I was just interning and
Speaker 6: I was like, this is amazing. And so for me,
Speaker 6: internships in college were really important, and so when I
Speaker 6: graduated from college, I had an opportunity to work at
Speaker 6: either Columbia Records, but I was actually going to visit Wuting.
Speaker 6: It was the same day that they were doing summer
Speaker 6: jam and I didn't even realize it, and they were
Speaker 6: like coming us a summer jam, and the guy who
Speaker 6: I interned for was like, you know, we've been trying
Speaker 6: to find you. We wanted to hire you, and so
Speaker 6: I was like okay, cool, and I turned down everything
Speaker 6: else because I felt like this was a better opportunity
Speaker 6: and that's why I took.
Speaker 2: That job, seaking of learning things. There's a story that
Speaker 2: you went on the road as a manager and you
Speaker 2: turned out to be a roaring success because you were
Speaker 2: good with money. Can you talk a little bit about that,
Speaker 2: because there's a lesson in there somewhere.
Speaker 6: So I ended up going on the road with Jizza
Speaker 6: from Wu Tang. He had to go to Europe at
Speaker 6: the last minute his manager couldn't go, and so I
Speaker 6: went on the road and when we came back, had
Speaker 6: like a whole ledger down to the penny of what
Speaker 6: everybody got paid and what money we had left, and
Speaker 6: he had never gotten that before, and I just thought,
Speaker 6: that's how I have to do things. And so he
Speaker 6: was so impressed by the fact that he got all
Speaker 6: his money that he was supposed to get, everybody was
Speaker 6: paid what they were supposed to get paid, and everything
Speaker 6: was correct to the penny. That after that I just
Speaker 6: was his manager.
Speaker 3: Wow, that's pretty good.
Speaker 6: I think that at the foundation of things, that hard
Speaker 6: work is the fundamental thing. I feel like a lot
Speaker 6: of times people see other people who are successful and
Speaker 6: they think it just happens, or they think it's just relationships.
Speaker 6: You can get your foot in the door, but then
Speaker 6: what happens after that? And so for me, I've always
Speaker 6: been like the first person in the office the last
Speaker 6: person to leave. That's what I was doing. And also
Speaker 6: honesty is important. I feel like money can get people
Speaker 6: to act very different when that gets involved, and so
Speaker 6: they're always surprised when you can be really transparent, but
Speaker 6: people appreciate that it's rare.
Speaker 2: By making yourself trustworthy, Angela became indispensable very early in
Speaker 2: her career. Tim Castri has a similar story about catching
Speaker 2: the attention of potential mentors at a young age. Today
Speaker 2: Tim is the VP of Global Content and Media at Amazon,
Speaker 2: but he used to be a kid in Melbourne groofing
Speaker 2: off at his grocery store job until he got a
Speaker 2: lucky break. So you started as the advertising cadet. What
Speaker 2: is an advertising cadet?
Speaker 7: I think I was the first and only ever advertising cadet.
Speaker 7: This wasn't a long line of but it was basically
Speaker 7: a way to give a break to a high school
Speaker 7: kid who was in a family situation where I couldn't
Speaker 7: afford to go to college. Moment said, look, you need
Speaker 7: to go to work for a few years. That's what
Speaker 7: the family needs. So I was working in a supermarket
Speaker 7: after school. I thought the girl who worked in the
Speaker 7: Dali was kind of cute, and I was showing off
Speaker 7: to her juggling watermelons in the supermarket. Two watermelons, not three,
Speaker 7: and this area manager came around and she said, what
Speaker 7: the hell are you doing? And get back to work.
Speaker 7: And then about an hour later, I was on my
Speaker 7: lunch break and she came and talked to me and
Speaker 7: she said, oh, sorry, I'm so hard on you. I said, no,
Speaker 7: no problem. I shouldn't have been juggling watermelons. And we
Speaker 7: got talking and we hit it off. Her name was
Speaker 7: Margaret Kem and she said, well, you're about to graduate
Speaker 7: high school. What are you doing? I said I don't know,
Speaker 7: and I explained my situation how I needed to go
Speaker 7: out and work, and she said, what do you want
Speaker 7: to do? I said, I really want to work in
Speaker 7: marketing and advertising, and she said, well, you know, we
Speaker 7: have an advertising department here at Safeway. Why don't I
Speaker 7: make some phone calls and see if there's anything they
Speaker 7: could do for you? Lo and behold. She called me
Speaker 7: back three days later and said, you know what, They've
Speaker 7: just decided to launch this first ever cadetship program, and
Speaker 7: why don't you apply for that and I'll see if
Speaker 7: I can help you. And sure enough, I applied and
Speaker 7: I was given this cadetship, which was basically working in
Speaker 7: the internal advertising department of Safeway Supermarkets and loved it.
Speaker 7: About a year into it, the internal advertising department got
Speaker 7: absorbed into Leo Burnett. So I moved from Safeway into
Speaker 7: Leo Burnette about a year after I'd started, which is
Speaker 7: a whole other story. Do you want to hear that?
Speaker 3: Yes?
Speaker 2: I do. I do want to hear that.
Speaker 7: So I was in this cadet ship and they were
Speaker 7: waiting to give the contract to Leo Burnette. A bunch
Speaker 7: of folks they took into the agency. A bunch they
Speaker 7: let go and moved into other departments, and I was
Speaker 7: the last person they hadn't resolved. My story is basically
Speaker 7: a long litany of people who gave me breaks. And
Speaker 7: there was a guy who ran advertising. His name was
Speaker 7: John Simon, and John was saying to the CEO of
Speaker 7: Leo Benett, you've got to take this guy, Tim. He's fantastic,
Speaker 7: he's a young guy. And they said, look, we just
Speaker 7: we don't know what to do with advertising cadet, and
Speaker 7: so we don't need him. John was adamant about it,
Speaker 7: and they went back and forth on this for weeks
Speaker 7: while they were negotiating the contract. They got to the
Speaker 7: final day where John was about to sign the contract
Speaker 7: to give them the account. It was still unresolved, and
Speaker 7: he said, look, I'm not signed until you give him
Speaker 7: a job. And he held then and he sat and waited.
Speaker 7: Took him about ninety seconds after that, I said, fine, fine,
Speaker 7: we'll give the kid a job. And then he signed
Speaker 7: the contract. And that's how I was. What was their job, Well,
Speaker 7: they basically brought me in a similar capacity in Lea Burnette.
Speaker 7: So they said, we'll take him on for two years
Speaker 7: and we'll move him around to all the various departments
Speaker 7: from production to creative to account management and media. They
Speaker 7: didn't have programs like that at the time. But my
Speaker 7: boss there was still one of my best friends to
Speaker 7: this day, a woman named Melinda Gertz. She went to
Speaker 7: Northwestern and they've transferred to the Melbourne office of LEO
Speaker 7: Burnett from the Chicago office. Melinda just said, well, I'll
Speaker 7: take him and I'll redesign what we used to do
Speaker 7: at Leabnett in Chicago. I'll just make a little training
Speaker 7: program for one and so that was where they designed
Speaker 7: this kind of program to put me around in each
Speaker 7: of the departments and learn the ropes of advertising.
Speaker 2: Well, you did really well, so you must have impressed somebody.
Speaker 2: What did you do in that advertising cadet job that
Speaker 2: so impressed them that you began to move up in
Speaker 2: the world.
Speaker 7: Now, I had a real work ethic. When you grow
Speaker 7: up in a working poor family. I mean a lot
Speaker 7: of people who have that experience, they burn, you know,
Speaker 7: they really burn with the ambition and a drive. And
Speaker 7: I had that as well. You know, a lot of
Speaker 7: fuel from my childhood circumstances really pushed me forward. So
Speaker 7: I'd say it was a real combination of work ethic.
Speaker 7: God gifted me with a good brain the gray matters
Speaker 7: always worked pretty well, and also real willingness to take
Speaker 7: risks and put myself out there. I'd be constantly making
Speaker 7: proposals and recommendations that were far beyond my pay grades,
Speaker 7: far beyond what I knew. But I really tried hard
Speaker 7: to make a difference and to have an impact. And
Speaker 7: I think they noticed that.
Speaker 2: When luck struck and doors opened for him, Tim ran
Speaker 2: through and proved himself worthy of the chances he got.
Speaker 2: Tim ended up being CEO of Leo Burnette Australia and
Speaker 2: One Australia's Agency of the Year Award. That's a career
Speaker 2: jump you can't forget. That's all for today, I'm Bob Bittman.
Speaker 2: Thanks for listening, and stay tuned for a brand new
Speaker 2: season of Math and Magic coming up.
Speaker 1: That's it for today's episode. Thanks so much for listening
Speaker 1: to Math and Magic, a production of iHeart Podcasts. The
Speaker 1: show is hosted by Bob Pittman. Special thanks to Sydney
Speaker 1: Rosenbloom for booking and wrangling our wonderful talent, which is
Speaker 1: no small feat. The Matho and Magic team is Jessica
Speaker 1: crimechicch Bahid Fraser, and Julia Weaver. Our executive producers are
Speaker 1: Ali Perry and Nikki Etour. Until next time.