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April 30, 2025 41 mins

This week, S.E. sits down with one of the best communicators, maybe, on the planet — it's Donny Deutsch! The TV host and master marketer talks about growing up in Queens and how being a New Yorker is such an embedded part of his identity. They talk about the evolution of branding and what makes a great brand — and what definitely doesn't. Donny also shares his meandering path to ambition — his first TV appearance on a game show with Betty White — and what it took for him to lock in and get to work. S.E. and Donny also dig into the wild world of the 1980s advertising (very different vibe than Mad Men). There's a lot to learn from this episode and, make no mistake, Donny will tell it to you straight!

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
I've always believed that I'd like to think of myself
as strong and straightforward, the direct. But I don't think
you ever win by goading people or tarry people down.

Speaker 2 (00:12):
Hey, everybody, welcome to off the Cup, my personal anti
anxiety antidote.

Speaker 3 (00:18):
Today we're talking to someone who is.

Speaker 2 (00:20):
So good at talking about anything. Seriously, He's one of
the best communicators, I think on the planet. He's a
master marketer, a TV host, host of On Brand with
Donnie Deutsch. I guess that gives it away, and just
someone I love talking to. Donnie Deutsch, Welcome, thanks for
having me.

Speaker 1 (00:35):
I see, I appreciate it. I'm such a big fan.
I love the work you do, and so it's an
honor to be here. Oh I love that.

Speaker 2 (00:41):
Right back at jam, let's start at the top with
you have done something amazing. You have made branding your brand,
and I can't really think of anyone else who's done that.
I feel like you're in a category of your own.
Do you feel like you created a category?

Speaker 1 (00:56):
Interesting?

Speaker 3 (00:57):
You know?

Speaker 1 (00:57):
I think, yeah, it's interesting because branding is such a
prevalent term. I mean, we're all brands. Yeah, I mean,
if you have a Facebook page, you're a brand. A
brand is a set of values, what you stand for,
what you believe. So we're all yes every day. You know,
we always think traditionally off a brand is you know,
Kellogg Cereal, But everything is a brand. Every person, every athlete,
every movement, every political party, every politician. We're all brands.

(01:18):
And so I have created this unique space as the
guy who kind of you know, talks about it and
has a lot of experience. Obviously, I spent twenty five
years building an agency. So I love that I'm able
to bring that and talk about that through lensing it
through politics and pop culture and other things like that,
because that's what I bring to the table, and I
think other people don't.

Speaker 2 (01:38):
You're right, Like when I was coming up, even me,
you know, twenty years in, was aware of like creating
a brand when I was coming up as a writer
and then started doing TV, and I was aware of it.

Speaker 3 (01:51):
I didn't know how to do it, but I was
aware that I.

Speaker 2 (01:53):
Should probably be a thing with a well thought out plan.
But it just feels like maybe you know this intuitively
branding because you speak off the kuff about it a lot.

Speaker 1 (02:05):
Yeah, I kind of do. It's in my blood. I
don't you know, I don't know why, I don't know how.
You know, the key to understand, the key to what
make great brands is authenticity, honesty, consistency, staying true to
core values. You know, the great brands over time don't deviate.
And so you know, a challenge for politician if you
want to have a strong brand is you can't be
flip flopping too often. You know. The one thing about

(02:27):
Trump and we know you and I both feel the
same way about him, and that's not very well. He
is very authentic to his brand, who he is, what
he's about, and that's one of the things that resonates.
And I think I find most of what his brand
stands for is reprehensible. But I do give him major
points for being a master brander, starting with starting with himself.

Speaker 2 (02:47):
You know, I have I'm asked about this a lot
because sometimes it's in my shot. I have a giant
picture in my office. It's like five by five of
it's Al Gore playing flag football with his kids on
his front lawn.

Speaker 3 (03:02):
And the story of this picture is twofold.

Speaker 2 (03:05):
I'm working at the New York Times many years ago,
and we're in the old building and these Pulitzer Prize
winning pictures are all over the place.

Speaker 3 (03:14):
Right, there's one of like Champion Yankees and da da dah.

Speaker 2 (03:17):
This one happens to be over my workspace for the
entirety of my time there. And when we moved to
the new building, they said, you can have one of these,
like you can take one of these homes.

Speaker 3 (03:28):
So I took this one home.

Speaker 2 (03:29):
The story of this photo is this is about two
days after the two thousand election, and you know this,
we didn't have a president yet.

Speaker 3 (03:36):
We had to do a recall.

Speaker 2 (03:38):
But his people told him go outside on your front lawn,
play football with your kids. It'll look like you're confident.
And of course all it did was look like a
photo op. It looked packaged, and that's all the press
talked about, which was this like photo op and how
inauthentic it looked. And it was sort of a punctuation

(03:59):
on a campaign that was not very authentical.

Speaker 1 (04:02):
Was that a lot of people felt, yeah, a lot
of people. Yeah, that's right.

Speaker 3 (04:05):
It was his thing.

Speaker 2 (04:06):
That was the criticism of al Gore that he just
didn't feel authentic. He was likable enough, he was smart,
he had just been a vice president, he was good looking,
like there were reasons he should have worked.

Speaker 1 (04:17):
It's interesting a lot of politicians post their main political
time find it. He found it afterwards through the Internet
and through environmentalism, And yeah, that was always Hillary's problem,
and she post running for president. Now she has this
kind of I don't give a shit and I'll tell
it like it is and becomes incredibly more likable, more powerful,

(04:38):
and more credible. So I think that's just such a
key thing. And the ones, the politicians that like Bill
Clinton had it, Barack Obama had it, Ron Reagan had it.
The great ones have that.

Speaker 2 (04:48):
Yeah, it's a really interesting way to look at it.
And I always think about it when when I look
at that photo.

Speaker 3 (04:53):
Just be authentic.

Speaker 2 (04:54):
Even in my business, I find even when people are
disagreeing with me, they know I'm speaking authentically as myself.
And I think that's important connecting with people. Let's go back,
Let's go back. What kind of kid were you? I
always like asking what kind of kid someone was.

Speaker 1 (05:12):
I was a good kid. I had a really lucky,
happy upbringing. I had two great parents, you know, who
were married, stayed together. I grew up in Queen's kind
of middle to upper middle class. I mean, I went
to a big high school, four thousand kids. You know,
it's kind of a tough Queen's high school. So it
kind of made me a little bit of who I was.
But yet had everything at home, every privilege I could want.

(05:32):
So I had the best of all worlds I was.
I was a very popular kid. I was president of
my senior class. I had a really fortunate, happy, productive childhood.
I give it, and I have to, you know, give
the credit to my parents because they set the table
and so. But I was a funny kid. I was
getting in trouble, but not horrible trouble, just mischievous kind

(05:52):
of thing. What you would think, what you would think
I was like as a kid. I was a kid,
Okay were you?

Speaker 3 (05:58):
Were you ambitious?

Speaker 1 (05:59):
Yeah? You know. I didn't love studying in school. My parents,
particularly my mother, would push me, and I give her
credit for that. I found ambition after I went to college.
I went to Penn, I went to Wharton. I was
kind of the village idiot them. Yeah, I was the
village idiot. I don't know how I got into this day,
but somehow I snuck in the back door and I
found ambition. Kind of coming out of college. A lot

(06:20):
of my friends got fast starts. They went to Wall Street.
They were doing great. I was working for an ad agency,
ladge agency, and then I was working for my father
who had an agency at the time, and I was
kind of fucking up and my father fired me. And
after that I came back and I found ambition. Now,
I kind of I was at twenty four to twenty five.
I was like, shit, this is passing me by. And
I kind of went from there.

Speaker 2 (06:40):
You grew up in Queens, As you said, how important
is New York to your identity?

Speaker 3 (06:44):
Like, would you be Donnie if you grew up in Phoenix?

Speaker 1 (06:47):
No? Right, No, I am in New Yorker, full through
all the good and all the gather comes with that,
and I own it proudly. I owed my Queen's heritage proudly.
You know. I remember getting in college the first day
and meeting all these kids is that, you know, kind
of had their own BMW's and I didn't. I was like,
what that's your How how is that your car? I
don't even know understand that. But they were soft because

(07:09):
they grew up in very homogeneous, you know, either all
preppy communities, or all. You know, I don't want to
use the word Bosston. All Jewish communities are all very white,
brick communities. And I grew up in a very integrated,
on the street school, and I just remember I couldn't
wait to play cars with them and take their money,
you know. And because they didn't have what the one
thing they didn't have, they didn't have both the street smarts,

(07:31):
and they didn't have the same hunger I had. And yeah,
the challenge we all have, of course, our kids are
all growing up comfortably, is you don't want to rob
your kids in the luxury of being hungry. Wow.

Speaker 2 (07:39):
Yeah, I mean the places you're describing is for sure.
The town my kid is growing up in. Where is
it Connecticut?

Speaker 1 (07:46):
Okay, Okay, my kids growing up on the Upper East
Side of New York. So yeah, not not going to
be exposed to the same thing, you.

Speaker 3 (07:52):
Know, they're not. Yeah, he's just not.

Speaker 2 (07:54):
And I think about it a lot because I grew
up middle class, nothing handed to me. My parents both
worked really hard, and I think he just won't know
a lot of the things that I knew, and I
don't know that I can recreate it for him.

Speaker 1 (08:08):
Can't do it doesn't mask that you could teach them
great values. It's just different. They're not exposed to the
breadth of things. They they're not growing up hungry. I
know kids from incredibly affluent or very prominent families who
are incredible hard workers and achievers, and then I know
the quintessential trust run idiots. You know. So it's not

(08:28):
in absolutely the way, but it makes it more challenging clearly. Yeah.

Speaker 2 (08:32):
And I always found growing up, I moved a lot,
and I went to a lot of different schools, private, public, Catholic,
all girls, you know, all kinds of schools. And I
found ambition was contagious. When I was in a school
where everyone wanted to be great, worked hard, had big goals,
were competitive, I took that on as well. And when
I was in schools where like being cool was more

(08:54):
cool than being smart, it was harder to be ambitious.

Speaker 3 (08:57):
And so maybe it's just like environment all too.

Speaker 1 (09:00):
They've done a lot of studies on this, and that's
they say the most important thing about getting into a
good college is not the rigorous studying, is that you'll
be with a group of kids that will will become
self fulfilling prophecy of how much you strive that they've
done all kinds of psychological studies, not about college, but
about exactly what you're saying. Your peer set defines so much. Galloway,

(09:21):
who I like a lot of talks a lot of
professor Scott Gallery talks, a lot of STU. You know.

Speaker 3 (09:24):
Oh okay, all right, I'm onto something. Okay.

Speaker 2 (09:28):
So in the eighties you join your father's firm. Was
that a choice of yours or his?

Speaker 1 (09:34):
My I went first worked at a large agency ogil
Va May the left after a year went with my
dad as a small agency and look, we were able
to kind of scale it and turn it into a
big agency. But I kind of stand on his shoulders
every day. He did the hard part to build something
from nothing. I don't care how much you scale. You
can build a one hundred x times. That's the I
have tremendous respect and I owe so much of my

(09:56):
success to him, because that's why I always I always
get angry at people in family businesses can't understand that
that doesn't mean you haven't also achieved, but you're still
standing on the found the shoulders and don't.

Speaker 3 (10:06):
Right, don't ever forget that you didn't do the hardest part.

Speaker 1 (10:08):
I didn't do that. I don't think I did the hardest. Yeah,
I think I give myself a a. I mean, I
built it to a really big, big, big, big agency.
But I still think he did the hardest part still,
you know, grinding out for nothing.

Speaker 2 (10:21):
The eighties New York advertising man. Yeah, my uncle wasn't it.
My uncle was at BBDA. No, sure, Gary Apollo.

Speaker 1 (10:29):
Will you do that? I know that name somehow, I
don't know.

Speaker 3 (10:31):
I bet you did.

Speaker 2 (10:32):
He was a big He was a big wig. Yeah,
he did v SATs everywhere you want to be.

Speaker 1 (10:36):
He was. He was a creative director, right, yes, I think, yeah, okay,
I remember the name.

Speaker 2 (10:40):
Yeah, he had big account, he had PEPSI, he had big,
big account.

Speaker 1 (10:43):
No, that's BBDO. Yes, yeah, three dos.

Speaker 2 (10:46):
You might have met him, which is so funny. He's
about twenty years older than you.

Speaker 1 (10:50):
But thank you for saying. It.

Speaker 2 (10:51):
Just seems like the eighties Manhattan. Yeah, Midtown advertising was
just like a world.

Speaker 1 (11:00):
It was, you know, it was a different version of
mad Men. You know, we all know mad Men, Sixties
Martinis and you know the whole kind of thing. It,
you know what, didn't have that romanticism and had a
kind of a grittier cocaine flat Wall Street very much.
It was a creative, sexier Wall Street. But it had
all But it was rough, rowdy, and it was crazy

(11:22):
and it was fun. We lived, you know, it was
very interesting. The work environments were very very different. Everybody
was dating each other. It was a very different. It
was a very different world and it was it was
exactly you know, it was interesting. Jay Leno opened up
when he left his show. One of the things he
did at the end, he showed in the curtain and
he showed all the families that met at his workplace,
and he was most proud of that. You would never

(11:43):
do that today. You know. It was very very different,
and you know, obviously we've come to a better place.
But so much of work was the social aspect of it,
particularly in a creative if you were in the TV business,
if you're in the advertising business, if you were you know,
in the journalism business. I mean, you know what newsrooms
were like years ago. Yeah, and obviously they were like
what they were like, you know, and it's hopefully that

(12:03):
is what they were like. You know, it has changed
a lot, and it's changed for the better.

Speaker 2 (12:08):
I don't know, if most people know this about you.
But your first TV appearance was on the game show
Match Game.

Speaker 1 (12:12):
Wow, you did your homework here, Okay, we're gonna find
out about Donnie Deutsch. First, tell us where you're from.
My name is Donny Deutsch. I'm out here visiting from Queens,
New York. I just recently graduated the University of Pensylvania,
and since that time, I've been working for a large
advertising agency in New York. Oh my god, Oh my god,
Oh my god, Big Afro, Huge jew.

Speaker 3 (12:33):
Care is stunning. Here is stunning, Johnny.

Speaker 1 (12:35):
Judefro like this with a beard. Yes, that was my
initial TV appearance nineteen seventy nine, the Match Game with
Gene Rayburn. I matched the Super Match five thousand dollars
with Betty White. Let's see if you would I don't
know if you saw the clip, but see if you
would get the answer the way you would do it.
They would give you a word and you'd have to
fill in the other words. So, okay, situation blank.

Speaker 3 (12:56):
Do they give you letters a number of letters?

Speaker 1 (12:58):
No, no, no, no, you just you have to match
what the person is going to say, you know, they
write it down and then you guess what they.

Speaker 3 (13:02):
Said, situationship.

Speaker 1 (13:05):
That's such a modern situation, situation comedy.

Speaker 3 (13:09):
Situation comedy.

Speaker 2 (13:10):
I wouldn't have even thought of that because we just
say sick on sick.

Speaker 1 (13:13):
Yeah, that to me was the only thing that came
to my head. Yeah, it was the only thing that
came to my heead. But we got so. I won
five thousand dollars in nineteen seventy nine. That was not
that it's not a lot of money today, but it
was a real lot of money back then and allowed
me to stay in California for a period of time
just hang out and it was. It was bizarre, and
it still lives on the internet today. So if you
if you type in dining dos match game, you'll see

(13:34):
a guy with really big afro and a beard who
looks really weird.

Speaker 3 (13:38):
I'll attest it's stunning.

Speaker 1 (13:40):
Thank you, thank you, thank you.

Speaker 3 (13:52):
Did you ever envision a career on camera?

Speaker 1 (13:56):
No? What happened? Was I used to when I was
running my agency, I tended to. I was kind of,
you know, every industry has a couple of faces that
you know, there's always the divorce lawyer that ends up
on TV or this. I was kind of the ad
guy that you know, if you were the Today Show
or you were CNBC, you want to you know, I
kind of a guy before me was Jerry del Fanminao
was that guy. I tended to be that guy. And
every time I would do an interview, two things would happen.

(14:18):
I would love it, I'll get a rush, and the
producer or the interview would say, you're really good at this.
You should do this one day, you know. So I
sold my agency and I was looking for something to do,
and I met with an agent and hooked me up
with the NBC and we kind of went from there.
But it was like something just that I always loved doing.
I love performing. I was never in theater or anything
like that, but I think back now, my favorite class

(14:39):
in school was speech, you know, so, and part of
what I did in advertising was perform and present, you know.
I mean, it's a fair you know. We used to
see the Don Draper standing up in front of the
clients and it's theater. You're doing theater. Obviously there's a
lot underneath it, and there's a lot that goes into it,
and that's just the kind of the cherry on the top.
But I was always good at the theater and the
presentation that the pitch, so to speak, And that's what
you're doing on TV. You know, if I'm with a

(15:01):
client and I'm pitching, I'm with you know, I ke it.
I'm you know, pitching them the best way to do
their furniture advertising. I have to sell my vision. I
have to sell it to them. I have to understand
my audience put it to them in a way that
they can accept it. That that get my point across. Well,
what are you doing on the air? What are you doing?
You're making a point and the best way how do
I present it? How do I do it in the

(15:21):
most cohesive, you know, succinct, compelling human way? How do
I do it that my audience is gonna be able
to take it in in the way I want them
to take it in. So the kind of the I
don't call them art forms, but the muscles are kind
of the same. Yeah.

Speaker 2 (15:36):
I think that's really interesting because you say, you know,
you loved being on TV.

Speaker 3 (15:40):
You got a rush from it, And I always I'm.

Speaker 2 (15:41):
Fascinated by that because I get nothing from TV physiologically.
I don't get nervous. It doesn't it doesn't make me excited.

Speaker 1 (15:49):
I don't get nervous, but I get pupped. I walk
into morning jokes every day. Take I love it. I
get a rush from it. It's not that I'm being
on now, not that I'm thinking to myself, Oh, you're
on TV and people are watching.

Speaker 2 (15:59):
It's just, yeah, I'm in.

Speaker 1 (16:02):
A conversation that matters, you know. That's that somehow is
going to connect, you know, I what I love. You know,
I used to have a show on CBC. I'm sure
the big idea. I love when somebody stops me on
the street and say, you know, I used to watch
a show and I started my business because of it,
Or somebody stops me on the street and says, you know,
you really convinced me about this. You said about women voting,
and I think that's really important. Whatever it is that

(16:23):
at the end of the day, what are we here for?
What do we want to leave our children? We want
to make a difference. I don't even mean change the war.
So if you can inform, I don't mean literally inform,
but you know, affect somebody one way and somehow add
something to their life to something you said or thought,
what a wonderful gift and that's what I get excited about,
you know.

Speaker 3 (16:40):
It is that part is gratifying.

Speaker 2 (16:43):
It comes with so many awful other things, but yeah,
that part is for sure gratifying.

Speaker 3 (16:50):
You said recently when you had me on your pod.

Speaker 1 (16:53):
Which was great, which the great numbers, by the way,
who knew? Right?

Speaker 2 (16:58):
Okay, you said to me, you said, you wear your
insides on your outside, and no one's ever said that
in that way. I love the way you said that,
And I wouldn't know how to do it differently because
I don't think about how I'm doing it.

Speaker 1 (17:16):
That's what that's That's what authenticity is. That's what I mean.
That's kind of an it's kind of like a grimier
way to say authenticity. You know, it's just what you
see is what you get. People can smell it, they
know it. That's what it was interesting. Before I had
my show on CBC, I got friendly with Michael J. Fox.
I'm on his board. What a privilege to be a
dear friend of his. And I asked them for advice.

(17:36):
What do I do because for yourself, they'll know the
difference if you're not, you know what I mean. So
like that, they're either gonna buy it they're not gonna buy,
but they'll know if you're not. So just you know,
be who you are. And that's why when everybody says
to me, you know, I'm gonna take media trading or
this and that, I'm saying, just be who you are,
don't don't worry about cadences, don't worry about this. Just
just let it. And I think that works for an actor.

(17:57):
I think that works for that works works for a politician.
We talked about that. So the one kudo I'm gonna
give Trump is he's authentic, authentically repulsive, but he means it.
So it's yeah, you know, you can't argue with that.
I mean, you know, take the line out, but you know,
he is what he is and really and a lot

(18:19):
of people. That scores with a lot of people. Yeah,
a lot of people will say when you watch people
being interviewed wife runner A Trump, well, I know, first
of all, they say, he talks like me. You know,
he sounds like me because he's not talking perfectly. He's
talking about you know, and you know, and I believe him.
He believes what you know. I don't agree with him,
but I believe him, you know, And yeah, that scores

(18:40):
a lot of points.

Speaker 2 (18:41):
I had this conversation with a producer, my producer the
other day. I had written in a script maybe like
a fores syllable word, and he was like, you got
to take that out. It's too big. No one knows
what you're talking about. I'm like, I this is me, Yeah,
like this is me. I'm a writer, Like this is
how I talk. And he's like, I don't care. You
can't be you if you're.

Speaker 1 (19:01):
Going to be like that for this show.

Speaker 2 (19:03):
Yes, yes, So offline we talked about this. I loved
the show Donnie. It was so fun to watch the.

Speaker 1 (19:13):
Short lived comedy on USA. Now would tell me.

Speaker 2 (19:16):
How it happened, because I just like developing other things too.
How did this happen?

Speaker 1 (19:20):
So it basically what it was when people don't know
I did this is in twenty fifteen, I think, so
you know about eight years ago, nine years ago, whatever
it is. It was a kind of a soft scripted
covered like a Larry David prebutres not to compare myself
to him or that, but it was a the Jaques
Jean jer It was a comedy where I played myself
a more ridiculous version of myself in the show. I

(19:40):
had a sleazy daytime talk show and it wasn't really scripted,
and we would do it loosely like they do Curb.
We would just know, here's the scene, and go and in.
And I had two kids, and we shot it actually
in my real home here. I live in townhouse in
New York. And it was I'm so proud of it.
It was funny you it was on the wrong place.
It went on you. It needed to me. It was
before streaming really hit, Like if you had put Curb

(20:03):
on ten thirty on a Tuesday night in USA network.
People consume shows like that, not appointment TV, you know.
So it didn't do well in the ratings that I
thought it was. It was hysterical. I made fun of myself.
I was a very I kind of whatever you would
think of me as stereotypical. I played to the nth
degree and I just had the idea and I just

(20:24):
kind of wanted to use another It's interesting. I was
talking to a very well known news person the other
day who was asking me about it and thinking about
doing the same, not that same thing, but a more
entertainment scripted thing. I said, using a different muscle is
so exciting. And I loved it. It's the thing I
don't say I'm most proud of, but it's the thing
I most surprised myself that I was able to do,
you know, writing it, I created it, acting in it,

(20:47):
you know, just building it from ground zero. I loved
it only the last one season, but I love it.
And by the way, and I loved it too. If
anybody just go on I guess iTunes or Apple however
you find these things. Just it's called Donnie exclamation point. Yeah,
six episodes. Will you will left? I promise you will,
leaf you will?

Speaker 2 (21:04):
I loved it, Thank you. I wrote a sitcom set
in a newsroom. It's comedy, and this was born out
of a frustration I had been asked to consult on
two shows about the news. Aaron Sorkins The Newsroom, which
I loved, which was wonderful writing, I mean wonderful.

Speaker 1 (21:23):
And Jeff Daniels I mean Off the Chick.

Speaker 2 (21:25):
Oh so good. And I love Aaron, and so that
was great. I'd be on set at MSNBC where I
used to have a show, and I'd get a call
from Aaron. Okay, I just saw you arguing with your
co host. What did you guys talk about in the
break that was talked about getting sushi. But so I
did that one, and then I got asked to consult
on the morning show for Apple. And when I heard

(21:48):
the morning show was going to have Reese and Jennifer
Aniston and Steve Carrell, I thought, oh, good, a comedy
because the newsroom was very much a drama.

Speaker 3 (21:55):
It took the news.

Speaker 2 (21:56):
Very serious, very seriously, very and I thought, you know,
I really just want to be funny. And then I
got in the writer's room and we started talking and
I realized, this is not going to be a comedy.

Speaker 3 (22:07):
It's going to be a drama.

Speaker 1 (22:09):
How does it work. I've never consulted on this. So
they bring you into take me through that. What does
that look like?

Speaker 2 (22:15):
Well, for the morning show, they brought me into a
literal writer's room, and this is so typical and funny.
They needed to know what a conservative sounded like because
I don't think they'd ever met one.

Speaker 3 (22:26):
Yeah, this is like so typical Hollywood.

Speaker 2 (22:28):
So I came in to say, well, here's what I
would say in this situation, or here's what a conservative
girl like that's character might do in this situation. So
that was particular like that was I was brought in
to inform that particular part of it, and I just
remember afterwards being like, well, I can't wait for someone
to call me to consult on a comedy about a newsroom.

Speaker 3 (22:51):
And I thought, why am I waiting? Like, maybe I'll
just write one.

Speaker 1 (22:53):
Sure, So I did.

Speaker 3 (22:55):
I wrote a pilot. It seems like no one wants
to watch a newsroom sitcom.

Speaker 1 (23:01):
But sitcoms are tough to sell because streaming doesn't do
half hour comedies. They don't work exactly. I mean, Curve worked.
I think ted Lasso is a half hour, but they're
few and far between. They can't make money on them,
they cancel them internationally, so you're basically stuck with the
broadcast networks that are dying. And that's that's a problem,
you know exactly. But SA, when was the last when

(23:22):
was the lass good really good sitcom? Well?

Speaker 3 (23:25):
I feel it was Weepes.

Speaker 1 (23:27):
Beep was actually I don't remember, but that was on
streaming obviously, But it's very hard to do a I
minded it is, you know, high minded sitcom today?

Speaker 2 (23:38):
Yeah, just all right, Well then I don't feel so bad,
don't feel sure. It's great, It is great, I heard like.
I sent it to Aaron. He was like, this is great.
HBO liked it, but they had just done veep and
it's kind of deep in a newsroom, right, and so
they wanted to give it some time. But I don't know,
maybe i'll shop it around again. I want to go
back to twenty ten. You're host at MSNBC and you

(23:58):
got in a little trouble.

Speaker 1 (24:00):
Oh god, you remember this, yes, yes, it was so insane.
Phil Phil Griffin, the head of the MS, who I
love and who was great it was. He was such
an amazing TV executive. He said to me, we'll try
out it's kind of weird. We'll try out three in
the afternoon, right for a week, you know, see if
that goes, then maybe we'll give you a show. And
the first wasn't I think it was? The first was
the second day I did? I think now it's It

(24:22):
was so naive. It was so dumb on my part.
We did an old segment on anger and TV and
news and the producer. I don't want to blame the producer,
but I had nothing to do with this. In the
upfront piece and the setup piece showed, you know, all
the angry Conservatives and then showed Keith Olberman, you know network, Yeah,
my network, you can't. You can't do that.

Speaker 3 (24:41):
No.

Speaker 1 (24:42):
Now, Keith, who was a major asshole, instead of kind
of taking it in shride, went didn't show up for
work next day and said if he's on the air,
I'm not on the air. I meane, what a douche,
you know. And so by the way, it was a mistake.
It was a mistake by the producer because I didn't
even know. I certainly never talked about it, and I
was doing going after the Conservatives. I didn't know what
was going to be in the in the in the

(25:02):
in the piece up up top. So I understand why
he was upset. You can't like make me part of
your piece that's hitting people. But like just he just
went went on a like insane rate.

Speaker 2 (25:12):
And then the network said, you were taking time off
to deal with the personal issue.

Speaker 3 (25:16):
That's how fucked up our business is.

Speaker 1 (25:18):
Yeah, yeah, you know, I don't remember what the personal
action I had the personal issue, and you know it
was Yeah, it was just one of those great TV
moments that you just go, this is some business, you know.
But I remember even learned that they put the producer
on leave. Thank god they didn't fire the producer, yeah,
or the or It wasn't the main it wasn't the showrunner.
I mean, it wasn't the EP. It was just somebody
who was putting a piece together, you know, and it

(25:40):
was not to put Keith in that group was not
a smart thing to do.

Speaker 3 (25:44):
Well, he's such a douche.

Speaker 2 (25:45):
He once said that my parents should have availed themselves
of Planned Parenthood's services.

Speaker 1 (25:51):
Are you serious? Just not a good guy? You know,
eventually the really bad guys get found out. You know,
I didn't business was getting hired where you don't really
he I mean, he was a he was a major presence.
He had he had a big platform, and he was
kind of what Rachel is today at MS. He was
then he was kind of the main anchor or not
actually jo I want to say what Joe was. I

(26:13):
have to stick to my home team, you know, but
you know that's that what he had a big platform.
He doesn't have that anymore.

Speaker 2 (26:21):
That's true, that that moment aside, like do you stop
yourself from getting personal or nasty or like ad Hominem
when you're on the air.

Speaker 1 (26:33):
Yeah, I I've always believed that I'd like to think
of myself as strong and straightforward the direct, But I
don't think you win. I go after a bully. I'll
go after Trump very very hard. But I don't think
you ever win by goating people or tarry people down,
or I'd like to think that who I am shows
on the air. Uh you know that that? How would

(26:56):
I describe just just me and just trying to do
the right I'm trying to do the right thing at
this stage of my life. You know, I'm not a
kid anymore. I'm sixty seven. I'm going to be sixty seven,
and you kind of want to be on the right
side of things. Yeah, in my this is my father
fatherly instincts coming out. I really worry about us, not
in the abstract sense. I worry about we will no

(27:18):
longer be everything that we take for granted or truly
free society. I feel like that people will continue to
be pitted against each other. I just my good side
comes out. Yeah, that's that's not always My always issue
with people voting for Trump and I'm not. It's like,
how do you vote for bad? How do you vote
for me? And how do you vote for evil? How
do you vote for pugnacious? How do you vote for

(27:39):
you know, devisive? It like it's just the very thing
like truth. What is the first thing we teach our kids?
What is the one thing you can will always get
past it, But you have to tell me the truth. Yes,
the simplest common denominate we put for our children. I
would like to keep the leader of our country accountable
for you know.

Speaker 2 (27:56):
But what you do, it's really specific and I'm sure
it's authentic, But you don't do this condescending like where
you're looking down on Trump voters.

Speaker 1 (28:09):
No, No, first of all, I don't don't do that.
I don't. First of all, the people I get angry at,
not that look down, but get angry at. By the way,
if you're a mega guy, you think he's gonna you're
gonna put more food on your table or whatever reason
you're it's the people that only care about another three
percent of their taxes, that have a lot of money,
that know right from wrong and no better, they don't

(28:30):
get it. Yeah, that's the people I don't know that
I look down and I get angry at them, and
I know a lot some of them are my friends. Yeah,
where like maybe it's not perfect for you. Maybe it
might cost you an extra dollar here there, But don't
you care about right and worship and the very things
that people that our grandfather's fought for in World War Two?
Like we'reout gonna do heavy. Don't you have that perspective

(28:50):
that goes beyond narrowly what's better for you. You're in
the point in life where you can make decisions not
just what it's a better right and isn't that what
it's Those are the people I get very firsh tregure with.

Speaker 2 (29:00):
Well, I get angry at the people on my side,
the conservatives who I know no better of course, that
he's not conservative, that he doesn't care about the values
that we used to care about that I still.

Speaker 3 (29:13):
Do and know better and sell out and just go
where the power is. Those are the people that bother me.

Speaker 1 (29:19):
I as a man, not to sound sexist, I wonder
how they look at their wives and their children and
they're doing it. I think the same thing, and like
their friend, like, are you that much of a fucking
weenie as a human being? You know? I had am
kinsinggram I show a couple of weeks ago, and I said,
the guys used to come up to you off the record,
go we wish he goes. You would not believe the names.
I could name thirty well known people that what I

(29:42):
was doing. When I was doing, I wish I could
do what you were doing. I know you're right. How
do you look at yourself? Yes? How do you you know?
Like it? Just and I know it's their jobs. But
if you said to me, you know you could have
the best prime time show in the world. All you
have to do is back Trump, I would have no way,
not like, how do you look at yourself? You lose,
you miss your self leveling.

Speaker 3 (30:02):
You know, I've had to make those decisions.

Speaker 2 (30:05):
I've had to sort of navigate right wing media and
that world through Trump. I've had to make those decisions.
They were not hard decisions for me. They were super
easy because I have to sleep at night.

Speaker 1 (30:15):
What I love about what I love about you and
why I feel we have a great connection is and
you start out right of center. I start out left
of center. Yeah, but we comfort what we think is
right and fair, and we're able to get out of
our lane. We're not in a lane. We start with
what's right, at least what we think is right and wrong.
They were able to drift into certain places and there

(30:36):
aren't tons of people in the media could do that.
You know, I like that a lot about the show
that I do Joe and make. I really feel Joe
really is driven by his I'm not just saying this
Christmas is Shoe, that's what. You know. He comes out
what he thinks is right. And yes, he started as
a conservative, but if you really listen to him, he's
going by what he thinks is right as a father,
you know. Yeah, And I see that with you, and

(30:56):
I've always respected that about you.

Speaker 4 (30:57):
Thank you.

Speaker 2 (31:13):
You and I have talked a little bit about mental health, yes,
and I've talked about my challenges. You've talked a little
about your challenges. Can you talk a little bit about
what you had to confront what you had to deal with?

Speaker 1 (31:25):
Sure? You know, Look, I've had some depression issues and
I've dealt with that, and you know, you find out
people like the Rock and other people. I mean, it's
just it's part of who we are. It's part of
our chemistry. I find sometimes the more unique you are,
the more challenges you can have. And so many people
have issues with anxiety and depression, and you know, you've

(31:47):
written about it, you've talked about it, and you know
it's one thing is nothing to be embarrassed about. Is
any issue, It's no different if you have issues with
something like with anxiety or depression, it's no different than
having high blood pressure or high cholesterol. It's something chemical
in your system that we now have medication that solves.
And so my only suggestion to anybody out there who's

(32:07):
having any kind of struggles, whether it's anxiety or depression
or anything in there, just we've got a lot of
help to get today, that there's no reason to suffer
in the way that people had to suffer decades ago.

Speaker 2 (32:18):
How did you get to a place as a man
of a generation, How did you get to a place
where you were just comfortable getting help and then talking
about it?

Speaker 1 (32:28):
You know, it wasn't I don't really talk about it
a lot. Somebody asked me about it. I'll talk about it.
I'm not, you know, an advocate for it. I think
you get secure as a person and you realize it.
It doesn't make you less strong. It actually makes you
stronger to talk about it because maybe you help somebody
else and seeing other people of tremendous stature who would
talk about it, you know, you know people like Churchill,

(32:48):
and you know it goes on and on and on.
Abe Lincoln suffered from the great So I don't it's
not a scorecard for how strong you are, how good
you are, As I said, it's like, no different than
if you had diabetes.

Speaker 2 (33:00):
Yeah, what really bothers me because I do talk about
it a lot for all the reasons. What really bothers
me are people who go on TV or on their show,
on their podcast and criticize someone who's talking openly about
their mental health. And this happened a lot with like
Naomi Osaka and Simone Biles and Megan Markle.

Speaker 1 (33:22):
I know that that was just like, it's incomprehensible.

Speaker 2 (33:25):
You know, it's incomprehensible how you use a platform. I'm
talking about Megan Kelly. I don't know why I don't
have to like use other hide her name. She really
went after these people. And so you're lazy and entitled
and rat and grow up And.

Speaker 1 (33:39):
That's hate and ignorance. It's all wrapped into one's hate.

Speaker 3 (33:42):
What is the purpose of that purpose?

Speaker 1 (33:44):
Is the purpose is for somebody like that is a
few things? Is a what can I do? That's contrarian.
It's gonna get clicks and bites, and you know, oh,
everybody's celebrating her. I'm gonna detegrate her ignorance and just
mean spiritedness, just not a decent human being. It's like,
you can't hear this person who publicly obviously went through

(34:05):
traumatic situations both of these people, and had to step
aside and did so and bravely talked about it. That
surely helped other young women.

Speaker 3 (34:14):
Definitely is it?

Speaker 1 (34:16):
Yes?

Speaker 2 (34:17):
And I don't this isn't your beat either, Like you
don't have to weigh in on this. Your beat is
not mental health or sports or whatever. You don't have
to say anything about what Naomi Osaka is going through.
You choose to, which I just don't understand. There is
zero good coming out of denigrating someone for being honest

(34:39):
about their struggles.

Speaker 1 (34:40):
No. I wonder if somebody, you know, take somebody like
Tucker Carlson, and I wonder I'll put them in the
same YEP category. Do they know? Is it performance art?
Are they playing to?

Speaker 3 (34:53):
For him?

Speaker 1 (34:54):
It is? I know him, I've never met him, and
I go nobody. He's a father, he's got four kids.
I think he's got four kus, very smart. You can't
believe this stuff, and then you go with make it
worse or better? Yeah, you know, yeah, I mean I
think it's worse. It's transactional, you know. And it's just like,
how do you the ship that comes out of you
about how do you sit there with a guy who's
saying the real devil in World War Two was not Hitler,

(35:17):
was Churchill? And you're sitting there going, how do you
give that personal platform not Chuck? And then go home
and face your children. You know, there are certain things
that there are not two sides to certain things, you know,
and and the news sometimes makes that mistake. Sometimes there
is not there's no equivalency there is, there's no two
sides to that argument, you know. So I don't know,
I you know, I always wandered that about a lot

(35:39):
of these guys. You know, I've met Hannity. Seems like
a really good guy. You know, I don't know him personally,
he is, he's a nice guy. You know. You get
the feeling he's in on the joke a little bit.
You know.

Speaker 2 (35:51):
Listen, Tucker's smart. I worked for Tucker. Tucker is a
student of history.

Speaker 1 (35:55):
Oh, no, of these guys are dumb. I mean, let's
not make any mistake about it, right, you know.

Speaker 2 (36:00):
Yeah, so it's I think it's a little worse. Yeah, Okay,
I want to do a lightning round.

Speaker 1 (36:05):
Okay, okay.

Speaker 2 (36:12):
Elon Musk calls you and asks you to help him
save Twitter and his reputation.

Speaker 3 (36:16):
What is your crisis? Camm's advice.

Speaker 1 (36:18):
I wouldn't help him because I think he's a bad guy.
I would never take a cigarette advertising when I was
doing advertising, so I could never use my skills to
help somebody or a cause that I thought was bad
or destructive. I think he's like a Bond villain. I
think he's a really dangerous guy. Yes, so you would
say no, no, I'd say I can't unless it was

(36:39):
I met him, and I genuinely think he had this
cathartic moment he wanted to do good and it wasn't
just completely a convertive. It was, you know, like, I've
really made a mistake and I've learned and I realized
as a result of some of the things that put
on Twitter, this happened, it's not good. And if it
was something that but if it was just like I'm
in trouble. I need to polish my image and go
find someone else.

Speaker 2 (36:59):
Amazing madmen or scandal madmen, not even clothes.

Speaker 3 (37:05):
Favorite adult beverage.

Speaker 1 (37:08):
Favorite adult beverage tequila, to drink tequila with Blanco tequila
with a splash of soda wedge of orange. Wait to
say that again, Uh Blanco tequila? Blanco?

Speaker 3 (37:19):
Okay, I think Vanka tequila. And I was like those
those don't.

Speaker 1 (37:21):
Go down with a splash of soda wedge of orange.
Always pretty much you'll find that we having a couple
of those most nights. I love that.

Speaker 3 (37:28):
What's your favorite band?

Speaker 1 (37:30):
Probably Springsteen? Uh? I put spring I put the Stones
and put Springsteen. Bon Jovi's a friend of mine, so
I always put them up there.

Speaker 2 (37:39):
He did a thing he did, Oh my god, that
was incredible.

Speaker 1 (37:43):
But I mean, for those of you that don't know,
there was somebody that caught Saval's finish. He was taking
a video on a bridge I think in Nashville. There
was a woman who sadly was gonna jump. She was
on there was a ledger of bridge and he was
happy to be there, and he walked over. He talked
her off and he got her. I mean like he
was a real life here. He's a really good guy, Joe,
He's a really good guy.

Speaker 3 (38:00):
That's nice to hear. What's your favorite movie?

Speaker 1 (38:04):
Graduate, I'll give you my top. I have a group.
I have a Graduate. Yes, I have Godfather One, Godfather Too, Goodfellas, Scarface,
Field of Dreams, Swept Away, the Original, Swept Away? What
else would I put in there? Love? Actually? What else

(38:24):
was popp? Midnight Cowboy? I love a lot of the
late seventies. Yeah, it sounds pretty the gritty movies Godfather, Midnight, Cowboy, Graduate.

Speaker 3 (38:34):
Well like French Connection, French Connection.

Speaker 1 (38:36):
I think that period of time, you know, Easy Rider,
that late seventies, I mean Godfather's early seventies, mid seventies.
I think it was the top of filmmak.

Speaker 2 (38:46):
I just saw one for the first time. Robert Redford
plays a journalist. Not all the presidents man, No, no, no.

Speaker 1 (38:55):
Not common door. Yes, yes, it sounds like that.

Speaker 2 (39:01):
There's something days of the Condor, Days are the condor?

Speaker 1 (39:04):
Not common to it?

Speaker 3 (39:05):
Condor or something like yes, yes, yes, yes, it was great.

Speaker 2 (39:07):
I should remember the name, right. I like that era too,
That's a really good era for film. Yeah, okay, this
is the last question. It's really important to me and
my culture. Okay, when is ice coffee season?

Speaker 1 (39:21):
Oh, I can't believe I actually don't have one next
to me. I drink four ice coffee's day, every day
of the year. Yeah, every day of the year is
the correct answer. Every day of the year. I drink
like everybody knows, you know. I start out pumping two
two before I start anything. I'm surprised. I don't know
what time is it now. I usually stopped by the afternoon,
you know, but all morning long, I'm juicing on ice coffee.

(39:41):
You know.

Speaker 3 (39:41):
I don't understand people who are like, that's only for summer.
What would you only eat ice cream in the summer.
Now you have it when you want it, because you.

Speaker 1 (39:49):
Walked right into my wheelhouse, so that we are we're
separated at birth that way totally.

Speaker 3 (39:55):
Well, Donnie, thanks so much. This was really fine.

Speaker 1 (39:58):
This was fun. Really enjoyed it. They keep doing what
you're doing. You're doing good stuff.

Speaker 3 (40:02):
Thanks. That means a lot. I appreciate it.

Speaker 1 (40:04):
Thanks Assie.

Speaker 2 (40:09):
Coming up next week on Off the Cup, I talk
to my friend and fellow podcaster Work in Progress host
Sophia Bush.

Speaker 5 (40:16):
I love interesting and interested women, having conversations with people.
I really do think it's such a special place for empathy, curiosity,
catharsis in our society.

Speaker 2 (40:33):
Off the Cup is a production of iHeart Podcasts as
part of the Reason Choice Network.

Speaker 3 (40:37):
If you want more, check out the other.

Speaker 2 (40:38):
Reason Choice podcasts, Politics with Jamel Hill, and Native Land Pod.
For Off the Cup, I am your host, Si Cup.
Editing and sound design by Derek Clements. Our executive producers
are me Si Cup, Lauren Hanson, and Lindsay Hoffman.

Speaker 3 (40:53):
Rate and review wherever you get your podcasts.

Speaker 2 (40:55):
Follow or subscribe for new episodes every Wednesday.
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Host

S.E. Cupp

S.E. Cupp

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