Bonus Episode: Improbable Career Jumps

In today's bonus episode, we're examining those career jumps. I think there's a lot to learn and be inspired by along the way. Ryan Seacrest is known by many as the hardest working person in showbiz. He's the long running host of American Idol. Of course, he was also on screen for six years of Live with Kelly and Ryan and has recently taken over Pat Sajack's iconic role as the host of Wheel of Fortune. But he's behind the scenes too, creating shows like Keeping You Up with the Kardashians.

On top of everything, he's on the air every morning with iHeart broadcasting on over one hundred radio stations nationwide. I wanted to know about his most important steps along the way. Did you intend to do all those things or did it just sneak up on you. I never intended to do all of those things. I wanted to move to Los Angeles when I was growing up in Atlanta. I had a dream to do that when I was

a teenager. I made that dream come true when I was nineteen, Still a teenager, I studied the work of Merv Griffin Dick Clark, both guys who had a radio and TV career, and both entrepreneurs and both asset owners, and both very very smart but also very good presenters

on air. And I watched how they maneuvered the skills of business and the skills of performance and what that intersection was for them, And in my head, I felt, Okay, if I could take baby steps towards those paths, maybe it would be the career that I'm looking for and be fulfilling to me. But I didn't know how it would all come together. Almost every career is enabled by one unlikely or improbable stroke of luck somewhere in the process.

For me, it was to jump from minimum wage part time radio announce from Brookhava, Mississippi, to programming the station and being on the air at the big NBC owned radio station in Chicago just five years later. What was yours and how did it happen? One that I think about now and hone in on is the big break of being the host of American Idol. This came at a time when I was twenty six seven years old. I was on the radio in Los Angeles doing afternoon drive.

It had been on television a little bit and gotten some good experience, but nothing at the level with the impact of what was about to come. And initially I met with the producers and I was considered as a judge for American Idol. And during the meeting with those executive producers, I started asking about the host and they said, well, you could audition for the host if you want. So I auditioned to be the host of American Idol. After the audition that night, they told me that I got

the job and we start shooting the next day. Literally the next morning we started shooting. We were doing audition Simon Randy Paula. We were meeting in Hollywood to do the auditions for the first season of the show that had never been on the air. This was at the time, Bob, you probably remember this when people were saying music does not work on TV, right, remember that, Well, I remember those stories. I know those people, we know those people. Well,

it did work on TV. It started to become this massive, massive event on television. And that was a moment that I thought to myself, Wow, I'm lucky here right like I got into this, I'm lucky.

a success, he didn't stop there. Rob Riley has always had ambitious goals too, and at points he made curious decisions about how to reach them. Rob is the chief creative officer of WPP, one of the major advertising groups. Rob built his stunning reputational work that is memorable and buzzy, from campaigns for companies like American Express and Burger King to the Fearless Girl statue in Manhattan's Financial District. His

improbable career jump was different than Ryan's. Rather than talking about how he built his career from the beginning, share a story about an unexpected choice at the precipice of a huge promotion, he took what seemed like a step backwards at the dawn of the century. You were the acting chief creative officer at Hill Holiday and you took up sixty percent pay cut to change jobs and become just a copywriter at Crispin Porter. Clearly it all worked out.

Why did you take that risk and what lesson did you learn?

the work of a great creative director. And I didn't want to end up being a New York creative at a certain age that kind of giant salary but didn't have the work where people would follow you.

hire me just because I was the boyfriend. Maybe in fact, didn't necessarily want some guy from New York who had all the wrong sort of closed and was a big creative director from New York City come down to his agency in Miami that.

from New York. Everybody's in flip flops and shorts. I'm here in the product boots in black. I stood out like a sore thumb. And about thirty days into it, Alex calls me in his office said, listen, man, I love the work you're doing. I think you're fantastic. Here's the problem. No one else likes you. So I thought he would say, it doesn't matter as long as I like you. He said, that's the opposite. I can't have one guy who ruined the culture. So you got to

figure out how to get people to like you. And long story short, I ended up going back and deciding, like, you know what, I'm just going to shut my mouth and sit in the corner and crank out work. And that's what I did. And then once you start making work, people respect. That was the beginning of building a body of work that I'm really proud of at every level. Copywriter, creative director, CCO, creative chairman, to down with WPP.

at USA today, Yahoo, Martha Stewart, Living and Bloomberg. But the world of media is always changing, and there have been points when Jackie's decision to change with it surprised even herself. You went on to Yahoo, you did a stint with Martha Stewart, and then you crossed the fence to the agency side running media brands. What made you jump the fence?

to go to the deep end. At the time, Yahoo or Google were your two choices, and Yahoo was teaching brands how to build a brand on the web, so that was obvious for me. And then followed Wynda to Martha Stewart to fully integrate Martha's organization. It was post her being in what she calls the clink clink, and we were building her brand back and consumers never left their advertisers had, so there was a lot of work to do around integrating her organization. I'd love that challenge.

It was in that moment that Wynda actually had heard about an opportunity through a friend of hers that was running UM globally, a gentleman named Matt Syler, and she said, you should look at this because it would be a next phase of your career. And I had never wanted

to be at the agency side. I'd been on a panel at Advertising Week and famously referred to agencies as a barrier to my progress as a media owner, which did not go overwhelm but I believed that agencies were failing clients and media owners because they or not giving us the gift of time and transparency. Those were the two things that I really wanted from an agency, and I just couldn't get anyway. Long story short, Matt saw

what I saw. Matt saw the opportunity to leverage media owners as real content partners in the work that media brands and UM specifically was doing for clients. And it was the first time that I saw an agency executive see what I saw as the opportunity to partner differently with media owners. And it was one of those moments in life where you can keep complaining and pointing the finger and wishing it was different, or you can jump to the other side and help make that so. And

then I got this right. Then I just loved the agency side. It's such an incredible place to operate in our industry. But that's how I got there. Great people that told me I should.

to manager and eventually host. Even as an assistant, she did right by some pretty important people and carved out a name for herself early on.

internship with MTV and the person I interned for. He was a music manager, so he would present the videos that they would then have to decide what was going to air. So everybody wanted to get in with him, you know. I remember going to Puffy's studio back then when he was playing like Bigis videos for him and they gave us champagne and I was just interning and

I was like, this is amazing. And so for me, internships in college were really important, and so when I graduated from college, I had an opportunity to work at either Columbia Records, but I was actually going to visit Wuting. It was the same day that they were doing summer jam and I didn't even realize it, and they were like coming us a summer jam, and the guy who I interned for was like, you know, we've been trying

to find you. We wanted to hire you, and so I was like okay, cool, and I turned down everything else because I felt like this was a better opportunity and that's why I took.

that's how I have to do things. And so he was so impressed by the fact that he got all his money that he was supposed to get, everybody was paid what they were supposed to get paid, and everything was correct to the penny. That after that I just was his manager.

honesty is important. I feel like money can get people to act very different when that gets involved, and so they're always surprised when you can be really transparent, but people appreciate that it's rare.

to her juggling watermelons in the supermarket. Two watermelons, not three, and this area manager came around and she said, what the hell are you doing? And get back to work. And then about an hour later, I was on my lunch break and she came and talked to me and she said, oh, sorry, I'm so hard on you. I said, no, no problem. I shouldn't have been juggling watermelons. And we got talking and we hit it off. Her name was Margaret Kem and she said, well, you're about to graduate

high school. What are you doing? I said I don't know, and I explained my situation how I needed to go out and work, and she said, what do you want to do? I said, I really want to work in marketing and advertising, and she said, well, you know, we have an advertising department here at Safeway. Why don't I make some phone calls and see if there's anything they

could do for you? Lo and behold. She called me back three days later and said, you know what, They've just decided to launch this first ever cadetship program, and why don't you apply for that and I'll see if I can help you. And sure enough, I applied and I was given this cadetship, which was basically working in the internal advertising department of Safeway Supermarkets and loved it. About a year into it, the internal advertising department got

absorbed into Leo Burnett. So I moved from Safeway into Leo Burnette about a year after I'd started, which is a whole other story. Do you want to hear that?

he's a young guy. And they said, look, we just we don't know what to do with advertising cadet, and so we don't need him. John was adamant about it, and they went back and forth on this for weeks while they were negotiating the contract. They got to the final day where John was about to sign the contract to give them the account. It was still unresolved, and he said, look, I'm not signed until you give him a job. And he held then and he sat and waited.

Took him about ninety seconds after that, I said, fine, fine, we'll give the kid a job. And then he signed the contract. And that's how I was. What was their job, Well, they basically brought me in a similar capacity in Lea Burnette. So they said, we'll take him on for two years and we'll move him around to all the various departments from production to creative to account management and media. They didn't have programs like that at the time. But my boss there was still one of my best friends to

this day, a woman named Melinda Gertz. She went to Northwestern and they've transferred to the Melbourne office of LEO Burnett from the Chicago office. Melinda just said, well, I'll take him and I'll redesign what we used to do at Leabnett in Chicago. I'll just make a little training program for one and so that was where they designed this kind of program to put me around in each of the departments and learn the ropes of advertising.

risks and put myself out there. I'd be constantly making proposals and recommendations that were far beyond my pay grades, far beyond what I knew. But I really tried hard to make a difference and to have an impact. And I think they noticed that.