February 20, 2025 • 20 mins
Whether it’s a promotion or a pivot, a great pitch or a stroke of luck, behind most successful careers is an improbable jump that unlocks new possibilities. Ryan Seacrest went from small-time broadcast host to breaking big with American Idol. On the other hand, Rob Reilly, the Chief Creative Officer of WPP, shocked his colleagues when he stepped backwards just as his career was about to peak, and IPG’s Jacki Kelley made some moves that surprised even herself. Plus, radio and podcast personality Angela Yee and advertising executive Tim Castree have amazing tales to tell about climbing the ladder and making a name for yourself.
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Speaker 1 (00:01):
You're listening to Math and Magic, a production of iHeartRadio.
Speaker 2 (00:11):
Welcome to a special bonus episode of Math and Magic.
I'm Bob Pittman. Remarkable careers, unyielding passion, and strong instincts
are traits all of our guests have in common, but
they've each navigated different paths to establish their legacies. I
believe in anyone's success story, there's one improbable jump, whether
a promotion or a pivot, or a lesson or stroke
(00:32):
of luck, there's usually a key moment that unlocks new possibilities.
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
(00:54):
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
(01:15):
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
(01:36):
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
(01:59):
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
(02:19):
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
(02:40):
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
(03:03):
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
(03:23):
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
(03:47):
I thought to myself, Wow, I'm lucky here right like
I got into this, I'm lucky.
Speaker 3 (03:52):
This is going to be a ride.
Speaker 2 (03:53):
How do I take this momentum and turn it into
something bigger at the same time, and that's when we
started having conversations with the management for American Top forty
and Kiss FM, and where I went and hosted E
News and the red carpet shows and produced series for them.
So I would say being the host of that singing
(04:15):
competition show opened the door for all the things that
came to fruition. Brian embraced an opportunity on a show
that many didn't think would work, and when it was
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
(04:37):
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
(05:00):
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.
(05:21):
Why did you take that risk and what lesson did
you learn?
Speaker 3 (05:24):
Well?
Speaker 4 (05:25):
I had worked for this amazing boss named David Weekle,
and he was the chief creative officer and they parted ways,
and I was one of the more senior people there,
but not very senior at all, and they said, well,
maybe you can step in temporarily while we search for
a new CCO. Might have been some discussion if you
want to throw your hat in the ring, to be
that person, and I kind of realized that I had
(05:45):
all the skills of a great creative director without maybe
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.
Speaker 3 (06:00):
So I ended up going down.
Speaker 4 (06:02):
To Crispin Porter and Buguski at the time, probably one
hundred and twenty people, sort of getting known for doing
some really interesting national work for smaller clients, and I
pitched Alex Buguski, now my current wife, my only wife,
but she was my girlfriend the time she was working there,
so I had a connection. But Alex wasn't going to
hire me just because I was the boyfriend. Maybe in fact,
(06:23):
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.
Speaker 3 (06:33):
Was really small, tight culture.
Speaker 4 (06:35):
But I knew that's the kind of work I needed
to be part of, because in the end, you don't
necessarily just follow people. You follow people because of the
work they've done. And I had all the skills of
being able to present and good with clients and maybe
good with teams. But I didn't have enough creative work
that I thought was like culture changing that was going
(06:55):
to get me in to a long term career. So
I took a few steps back. But it wasn't the
easiest ride. When I got there, I was the guy
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
(07:16):
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
(07:38):
of work that I'm really proud of at every level. Copywriter,
creative director, CCO, creative chairman, to down with WPP.
Speaker 3 (07:46):
Head of a holding company.
Speaker 2 (07:48):
Well, you know, let's go back in time for a second.
Why didn't they like you? What were you doing?
Speaker 3 (07:54):
Why didn't they like me? Well? I probably had the
wrong clothes.
Speaker 4 (07:57):
I had an incredibly intelligent, smart, beautiful girlfriend who's now
my wife and doing all the amazing work.
Speaker 3 (08:05):
And I was the boyfriend from New York.
Speaker 4 (08:08):
I came from a big New York ad agency and
it wasn't quite fitting in the culture.
Speaker 3 (08:12):
And I think growing up in New Jersey like we're loud.
Speaker 4 (08:15):
And when I went and told my wife that Alex
said that people didn't like me, her response was, why
don't you just try shutting up and doing the work.
Speaker 3 (08:21):
You know you're the problem.
Speaker 4 (08:24):
So I was taught a lesson early on to shut
my mouth and do the work. And when you have
the work, you get the respect.
Speaker 2 (08:32):
Well that's a great lesson. And ten years later you
were the chief creative officer of Crispin Porter.
Speaker 3 (08:37):
So it all worked out. Yeah, it all worked out.
Speaker 2 (08:42):
Rob knew he wouldn't be able to achieve his goals
in the long term. If he moved up too quickly,
he took a pay cut and acclimated to a new
team so he could build the right foundation for future growth. Likewise,
Jackie Kelly has taken some unexpected turns in her career.
Today she is the Chief Client Officer at IPG and
was at DENSU as CEO of the Americas. Before that,
(09:04):
her career evolved around media and advertising, with leadership roles
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
(09:25):
to the agency side running media brands. What made you
jump the fence?
Speaker 5 (09:31):
This is kind of a fun story, and I give
credit to people that can identify talent and then encourage
us to do something that would not be obvious to us.
So in my case, I had left USA, I had
gone to Yahoo and worked for Wyndham Millard. Wyndham Millard
is an incredible mentor for me and convinced me to
come to Yahoo. But It wasn't that hard to convince
(09:52):
me because I knew newspapers were changing. I knew I
needed to get a much better digital education. I wanted
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
(10:13):
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,
(10:37):
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
(11:00):
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
(11:24):
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.
Speaker 2 (11:48):
Jackie decided to keep an open mind and try experiencing
a part of the industry she had serious doubts about.
Instead of writing it off, she jumped in head first
and brought her career to the next level.
Speaker 3 (11:59):
We'll be right.
Speaker 2 (11:59):
Back after a quick break. Welcome back to Math and Magic.
Angel le Yee has been on the airwaves for over
a decade as founding member of the Breakfast Club, host
of her midday show Way Up, and now the podcast
(12:21):
Lip Service. She's also an entrepreneur who loves to get
back to communities in need. During a live recording at
the National Association of Broadcasters in Las Vegas, I learned
how she made her career jump from intern to assistant
to manager and eventually host. Even as an assistant, she
did right by some pretty important people and carved out
(12:42):
a name for herself early on.
Speaker 6 (12:44):
So the first internship I had was at a label
called tvt Records right and they also licensed like all
the TV tunes, the cartoon music that you hear. And
so when I did that internship, it was in the
legal department. I did not care about the legal department
at all, but I knew that in order for me
to get my foot in the door, that was just
a way for me to get in. And so one
(13:04):
thing I learned was just get your foot in the door.
And so I started doing these internships. I had an
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
(13:26):
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
(13:46):
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.
Speaker 2 (13:58):
That job, seaking of learning things. There's a story that
you went on the road as a manager and you
turned out to be a roaring success because you were
good with money. Can you talk a little bit about that,
because there's a lesson in there somewhere.
Speaker 6 (14:14):
So I ended up going on the road with Jizza
from Wu Tang. He had to go to Europe at
the last minute his manager couldn't go, and so I
went on the road and when we came back, had
like a whole ledger down to the penny of what
everybody got paid and what money we had left, and
he had never gotten that before, and I just thought,
that's how I have to do things. And so he
(14:35):
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.
Speaker 3 (14:46):
Wow, that's pretty good.
Speaker 6 (14:47):
I think that at the foundation of things, that hard
work is the fundamental thing. I feel like a lot
of times people see other people who are successful and
they think it just happens, or they think it's just relationships.
You can get your foot in the door, but then
what happens after that? And so for me, I've always
been like the first person in the office the last
(15:08):
person to leave. That's what I was doing. And also
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.
Speaker 2 (15:26):
By making yourself trustworthy, Angela became indispensable very early in
her career. Tim Castri has a similar story about catching
the attention of potential mentors at a young age. Today
Tim is the VP of Global Content and Media at Amazon,
but he used to be a kid in Melbourne groofing
off at his grocery store job until he got a
(15:47):
lucky break. So you started as the advertising cadet. What
is an advertising cadet?
Speaker 7 (15:55):
I think I was the first and only ever advertising cadet.
This wasn't a long line of but it was basically
a way to give a break to a high school
kid who was in a family situation where I couldn't
afford to go to college. Moment said, look, you need
to go to work for a few years. That's what
the family needs. So I was working in a supermarket
after school. I thought the girl who worked in the
Dali was kind of cute, and I was showing off
to her juggling watermelons in the supermarket. Two watermelons, not three,
(16:19):
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
(16:39):
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
(17:00):
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?
Speaker 3 (17:19):
Yes?
Speaker 2 (17:19):
I do. I do want to hear that.
Speaker 7 (17:20):
So I was in this cadet ship and they were
waiting to give the contract to Leo Burnette. A bunch
of folks they took into the agency. A bunch they
let go and moved into other departments, and I was
the last person they hadn't resolved. My story is basically
a long litany of people who gave me breaks. And
there was a guy who ran advertising. His name was
John Simon, and John was saying to the CEO of
Leo Benett, you've got to take this guy, Tim. He's fantastic,
(17:42):
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,
(18:04):
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
(18:24):
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.
Speaker 2 (18:43):
Well, you did really well, so you must have impressed somebody.
What did you do in that advertising cadet job that
so impressed them that you began to move up in
the world.
Speaker 7 (18:52):
Now, I had a real work ethic. When you grow
up in a working poor family. I mean a lot
of people who have that experience, they burn, you know,
they really burn with the ambition and a drive. And
I had that as well. You know, a lot of
fuel from my childhood circumstances really pushed me forward. So
I'd say it was a real combination of work ethic.
God gifted me with a good brain the gray matters
always worked pretty well, and also real willingness to take
(19:13):
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.
Speaker 2 (19:25):
When luck struck and doors opened for him, Tim ran
through and proved himself worthy of the chances he got.
Tim ended up being CEO of Leo Burnette Australia and
One Australia's Agency of the Year Award. That's a career
jump you can't forget. That's all for today, I'm Bob Bittman.
Thanks for listening, and stay tuned for a brand new
season of Math and Magic coming up.
Speaker 1 (19:52):
That's it for today's episode. Thanks so much for listening
to Math and Magic, a production of iHeart Podcasts. The
show is hosted by Bob Pittman. Special thanks to Sydney
Rosenbloom for booking and wrangling our wonderful talent, which is
no small feat. The Matho and Magic team is Jessica
crimechicch Bahid Fraser, and Julia Weaver. Our executive producers are
Ali Perry and Nikki Etour. Until next time.
You're listening to Math and Magic, a production of iHeartRadio.
Speaker 2 (00:11):
Welcome to a special bonus episode of Math and Magic.
I'm Bob Pittman. Remarkable careers, unyielding passion, and strong instincts
are traits all of our guests have in common, but
they've each navigated different paths to establish their legacies. I
believe in anyone's success story, there's one improbable jump, whether
a promotion or a pivot, or a lesson or stroke
(00:32):
of luck, there's usually a key moment that unlocks new possibilities.
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
(00:54):
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
(01:15):
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
(01:36):
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
(01:59):
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
(02:19):
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
(02:40):
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
(03:03):
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
(03:23):
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
(03:47):
I thought to myself, Wow, I'm lucky here right like
I got into this, I'm lucky.
Speaker 3 (03:52):
This is going to be a ride.
Speaker 2 (03:53):
How do I take this momentum and turn it into
something bigger at the same time, and that's when we
started having conversations with the management for American Top forty
and Kiss FM, and where I went and hosted E
News and the red carpet shows and produced series for them.
So I would say being the host of that singing
(04:15):
competition show opened the door for all the things that
came to fruition. Brian embraced an opportunity on a show
that many didn't think would work, and when it was
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
(04:37):
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
(05:00):
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.
(05:21):
Why did you take that risk and what lesson did
you learn?
Speaker 3 (05:24):
Well?
Speaker 4 (05:25):
I had worked for this amazing boss named David Weekle,
and he was the chief creative officer and they parted ways,
and I was one of the more senior people there,
but not very senior at all, and they said, well,
maybe you can step in temporarily while we search for
a new CCO. Might have been some discussion if you
want to throw your hat in the ring, to be
that person, and I kind of realized that I had
(05:45):
all the skills of a great creative director without maybe
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.
Speaker 3 (06:00):
So I ended up going down.
Speaker 4 (06:02):
To Crispin Porter and Buguski at the time, probably one
hundred and twenty people, sort of getting known for doing
some really interesting national work for smaller clients, and I
pitched Alex Buguski, now my current wife, my only wife,
but she was my girlfriend the time she was working there,
so I had a connection. But Alex wasn't going to
hire me just because I was the boyfriend. Maybe in fact,
(06:23):
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.
Speaker 3 (06:33):
Was really small, tight culture.
Speaker 4 (06:35):
But I knew that's the kind of work I needed
to be part of, because in the end, you don't
necessarily just follow people. You follow people because of the
work they've done. And I had all the skills of
being able to present and good with clients and maybe
good with teams. But I didn't have enough creative work
that I thought was like culture changing that was going
(06:55):
to get me in to a long term career. So
I took a few steps back. But it wasn't the
easiest ride. When I got there, I was the guy
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
(07:16):
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
(07:38):
of work that I'm really proud of at every level. Copywriter,
creative director, CCO, creative chairman, to down with WPP.
Speaker 3 (07:46):
Head of a holding company.
Speaker 2 (07:48):
Well, you know, let's go back in time for a second.
Why didn't they like you? What were you doing?
Speaker 3 (07:54):
Why didn't they like me? Well? I probably had the
wrong clothes.
Speaker 4 (07:57):
I had an incredibly intelligent, smart, beautiful girlfriend who's now
my wife and doing all the amazing work.
Speaker 3 (08:05):
And I was the boyfriend from New York.
Speaker 4 (08:08):
I came from a big New York ad agency and
it wasn't quite fitting in the culture.
Speaker 3 (08:12):
And I think growing up in New Jersey like we're loud.
Speaker 4 (08:15):
And when I went and told my wife that Alex
said that people didn't like me, her response was, why
don't you just try shutting up and doing the work.
Speaker 3 (08:21):
You know you're the problem.
Speaker 4 (08:24):
So I was taught a lesson early on to shut
my mouth and do the work. And when you have
the work, you get the respect.
Speaker 2 (08:32):
Well that's a great lesson. And ten years later you
were the chief creative officer of Crispin Porter.
Speaker 3 (08:37):
So it all worked out. Yeah, it all worked out.
Speaker 2 (08:42):
Rob knew he wouldn't be able to achieve his goals
in the long term. If he moved up too quickly,
he took a pay cut and acclimated to a new
team so he could build the right foundation for future growth. Likewise,
Jackie Kelly has taken some unexpected turns in her career.
Today she is the Chief Client Officer at IPG and
was at DENSU as CEO of the Americas. Before that,
(09:04):
her career evolved around media and advertising, with leadership roles
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
(09:25):
to the agency side running media brands. What made you
jump the fence?
Speaker 5 (09:31):
This is kind of a fun story, and I give
credit to people that can identify talent and then encourage
us to do something that would not be obvious to us.
So in my case, I had left USA, I had
gone to Yahoo and worked for Wyndham Millard. Wyndham Millard
is an incredible mentor for me and convinced me to
come to Yahoo. But It wasn't that hard to convince
(09:52):
me because I knew newspapers were changing. I knew I
needed to get a much better digital education. I wanted
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
(10:13):
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,
(10:37):
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
(11:00):
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
(11:24):
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.
Speaker 2 (11:48):
Jackie decided to keep an open mind and try experiencing
a part of the industry she had serious doubts about.
Instead of writing it off, she jumped in head first
and brought her career to the next level.
Speaker 3 (11:59):
We'll be right.
Speaker 2 (11:59):
Back after a quick break. Welcome back to Math and Magic.
Angel le Yee has been on the airwaves for over
a decade as founding member of the Breakfast Club, host
of her midday show Way Up, and now the podcast
(12:21):
Lip Service. She's also an entrepreneur who loves to get
back to communities in need. During a live recording at
the National Association of Broadcasters in Las Vegas, I learned
how she made her career jump from intern to assistant
to manager and eventually host. Even as an assistant, she
did right by some pretty important people and carved out
(12:42):
a name for herself early on.
Speaker 6 (12:44):
So the first internship I had was at a label
called tvt Records right and they also licensed like all
the TV tunes, the cartoon music that you hear. And
so when I did that internship, it was in the
legal department. I did not care about the legal department
at all, but I knew that in order for me
to get my foot in the door, that was just
a way for me to get in. And so one
(13:04):
thing I learned was just get your foot in the door.
And so I started doing these internships. I had an
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
(13:26):
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
(13:46):
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.
Speaker 2 (13:58):
That job, seaking of learning things. There's a story that
you went on the road as a manager and you
turned out to be a roaring success because you were
good with money. Can you talk a little bit about that,
because there's a lesson in there somewhere.
Speaker 6 (14:14):
So I ended up going on the road with Jizza
from Wu Tang. He had to go to Europe at
the last minute his manager couldn't go, and so I
went on the road and when we came back, had
like a whole ledger down to the penny of what
everybody got paid and what money we had left, and
he had never gotten that before, and I just thought,
that's how I have to do things. And so he
(14:35):
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.
Speaker 3 (14:46):
Wow, that's pretty good.
Speaker 6 (14:47):
I think that at the foundation of things, that hard
work is the fundamental thing. I feel like a lot
of times people see other people who are successful and
they think it just happens, or they think it's just relationships.
You can get your foot in the door, but then
what happens after that? And so for me, I've always
been like the first person in the office the last
(15:08):
person to leave. That's what I was doing. And also
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.
Speaker 2 (15:26):
By making yourself trustworthy, Angela became indispensable very early in
her career. Tim Castri has a similar story about catching
the attention of potential mentors at a young age. Today
Tim is the VP of Global Content and Media at Amazon,
but he used to be a kid in Melbourne groofing
off at his grocery store job until he got a
(15:47):
lucky break. So you started as the advertising cadet. What
is an advertising cadet?
Speaker 7 (15:55):
I think I was the first and only ever advertising cadet.
This wasn't a long line of but it was basically
a way to give a break to a high school
kid who was in a family situation where I couldn't
afford to go to college. Moment said, look, you need
to go to work for a few years. That's what
the family needs. So I was working in a supermarket
after school. I thought the girl who worked in the
Dali was kind of cute, and I was showing off
to her juggling watermelons in the supermarket. Two watermelons, not three,
(16:19):
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
(16:39):
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
(17:00):
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?
Speaker 3 (17:19):
Yes?
Speaker 2 (17:19):
I do. I do want to hear that.
Speaker 7 (17:20):
So I was in this cadet ship and they were
waiting to give the contract to Leo Burnette. A bunch
of folks they took into the agency. A bunch they
let go and moved into other departments, and I was
the last person they hadn't resolved. My story is basically
a long litany of people who gave me breaks. And
there was a guy who ran advertising. His name was
John Simon, and John was saying to the CEO of
Leo Benett, you've got to take this guy, Tim. He's fantastic,
(17:42):
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,
(18:04):
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
(18:24):
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.
Speaker 2 (18:43):
Well, you did really well, so you must have impressed somebody.
What did you do in that advertising cadet job that
so impressed them that you began to move up in
the world.
Speaker 7 (18:52):
Now, I had a real work ethic. When you grow
up in a working poor family. I mean a lot
of people who have that experience, they burn, you know,
they really burn with the ambition and a drive. And
I had that as well. You know, a lot of
fuel from my childhood circumstances really pushed me forward. So
I'd say it was a real combination of work ethic.
God gifted me with a good brain the gray matters
always worked pretty well, and also real willingness to take
(19:13):
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.
Speaker 2 (19:25):
When luck struck and doors opened for him, Tim ran
through and proved himself worthy of the chances he got.
Tim ended up being CEO of Leo Burnette Australia and
One Australia's Agency of the Year Award. That's a career
jump you can't forget. That's all for today, I'm Bob Bittman.
Thanks for listening, and stay tuned for a brand new
season of Math and Magic coming up.
Speaker 1 (19:52):
That's it for today's episode. Thanks so much for listening
to Math and Magic, a production of iHeart Podcasts. The
show is hosted by Bob Pittman. Special thanks to Sydney
Rosenbloom for booking and wrangling our wonderful talent, which is
no small feat. The Matho and Magic team is Jessica
crimechicch Bahid Fraser, and Julia Weaver. Our executive producers are
Ali Perry and Nikki Etour. Until next time.
Host
Bob Pittman
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