Stephen Kellogg on midlife crises, admitting you're wrong, and pizza

This week, S.E. sits down with a friend! The singer-songwriter Stephen Kellogg joins S.E. in the iHeart studio to talk about why he's searching for a pivot, the toll of being a touring musician, and the moments of failure he's learned from. As a father to four, he also shares his best parenting hacks and how he and his longtime partner make it work. S.E. and Stephen also get into some controversial opinions about the best pizza (is it *really* in New Haven?!) AND who he thinks is America's best singer-songwriter of all time (his answers may surprise you). Stephen Kellogg's latest album,"To you, old friend.", is out now. 

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Episode Transcript

Speaker 1 (00:00):
Hey, listeners, you're about to listen to a great interview
with my good friend Stephen Kellogg. We had such a
good conversation, but I think the mediast part is something
really relatable. We talk about being this age. For me
it's forty six, for him it's just a couple of
years older and figuring out where we are in our careers.
What is it about this age that makes us ask

(00:23):
so many questions about what have I accomplished? Have I
done the things I want to do? What's next? Can
I do something different? Why does it feel so existential
at this age to be thinking about your career. I
want to hear from you. Please write us at off
the Cup at gmail dot com. That's cup with two p's,
just like the podcast. Listen for that in my conversation
with Stephen and tell me what you're thinking to.

Speaker 2 (00:47):
So I'm a little bit over some of the things
you know? Are you just being the touring singer songwriter guy.

Speaker 1 (00:56):
Welcome to Off the Cup my personal anti anxiety and
no politics, no polarization, just good convos with interesting people.
It's a special Off the Cup for a few reasons. First,
I'm in studio with my guests, which is always fun. Second,
today's guest is an actual friend. Does anybody have actual

(01:17):
friends or a lot of people in my business have
like industry friends and then they call them friends. This
is an actual friend, and he's one of my favorite
people on the planet. And that's not because he's massively talented,
which he is. It's not because he was my husband
in my first date, which he was. We'll get to that.
It's not because he is so wise and so funny,
which he is. It's because he's one of the most genuine, thoughtful,

(01:42):
kind and caring people I know, and I'm so lucky
to call him and his wonderful family friends. You may
know him as the frontman of the Sixers. You may
know his viral ted talk on job satisfaction or his
book Objects in the Mirror. He's a prolific singer songwriter
who's toured with everyone from Counting Crows to Oar, Josh

(02:03):
Ritter to the Spin Doctors and so many more. You
can catch him now on the Old Friend's Tour, and
he's got a new stand up special in the works.
It's my friend Stephen Kellogg.

Speaker 3 (02:14):
Welcome, Hey, how you doing good? I was love, Thank you.

Speaker 1 (02:21):
It's rare. You get to hear a friend sum up
your importance to them and who they think you are.
It's such a gift. I really like to make it.

Speaker 2 (02:31):
You know. Yeah, first all, that would be like a
cool thing to do for each other. I mean that
because that was that really was lovely. I was like,
it made me feel like someone I don't always feel like.

Speaker 1 (02:41):
That was very we get it, I get it. But
that's the beauty of interviewing a friend. I know you
and I want to, you know, give your flowers.

Speaker 2 (02:49):
Thank you.

Speaker 1 (02:50):
Uh, this is fun and weird. Like I was saying,
we're not industry friends. We might have started sort of
as industry friends because we had adjacent interests, although that's
not how we came to know each other. But we
hang out. Our family is our friends. We have a
diners club, right, what do we regularly do?

Speaker 3 (03:10):
Yeah? I love I love our dinners.

Speaker 2 (03:12):
I like when we I like when we go hard,
go to fancy places sometimes steak.

Speaker 3 (03:16):
Steak is kind of the thing.

Speaker 1 (03:18):
Steak is the thing that ties and binds us.

Speaker 3 (03:20):
Yeah, yeah, it is. It is steak.

Speaker 2 (03:23):
And yes, yes, you know, how did we meet? Well,
so I'm gonna it was Twitter. It was it was
like one of the good things that I really liked
about Twitter. I felt like Twitter was a great way
to stay in touch with people, you know where you're like,
I don't know what this is. It's not you're not

(03:43):
necessarily cell phone level yet, but uh. And I think
that there was a tweet that you where you mentioned
myself and John McLaughlin because we were at the nine
thirty Club, right, So.

Speaker 1 (03:55):
In twenty twelve, Yes, my husband and I my now husband.
Let me just say, we had been dating a little
on the down low, okay, because you know, we were
both in DC and on the hill and people knew us.
We weren't like an out and about public couple yet.
So our first public date was your show at nine

(04:18):
thirty Club with John McLaughlin because my husband was a
big fan. Yeah, he was a fan of yours. And
I didn't know you were John at the time, huh,
but I knew John listened to you a lot, so
i'd heard your songs. We went, We had the best time.
It was such a good show, and I remember it
viscerally like all of you, you, your band, John mcgaughlin's
man all around the mic. Yeah, oh, all these crazy

(04:40):
times yeah, oh it was.

Speaker 2 (04:41):
Such a great show, right yeah, yeah, we sang that,
and John and I had gotten to the habit of
taking each other to make it crack each other up.
During each other's set, we would go through each other's
suitcases and pull out I would put John's clothes on
and go on stage. So there was always this funny
moment of recognition when you'd see what item of clothing one.

Speaker 3 (05:01):
Of us had on its horrible it was that was like.

Speaker 2 (05:04):
That was a great moment of touring and and back.
It was like pretty heavy social media, so I'm sure
we wouldn't have It wasn't like you didn't go to
concerts and posts that you were there, so we never
knew when there was a notable people at concerts, right right, right, Well.

Speaker 1 (05:19):
And then we yeah, so then I started following you
maybe on Twitter, and yeah, we noticed each other's tweets,
I think is what happened. And then maybe DMed about
some things we had in common.

Speaker 2 (05:33):
Yeah, just friendly. Yeah, well we were we were talking
about that, Yeah we should do something.

Speaker 3 (05:38):
What more?

Speaker 2 (05:39):
You know, you do feel at some at some point
I think it goes from you feel like you have
to be you two to make an impact in the world,
and I was like, okay, I might never be you too,
I better get to it. And I think we were
talking about that and we ended up, you know, doing.

Speaker 1 (05:55):
We did, and because my husband liked you. This is
like sanctioned conversation people, well, don't go crazy, well you know,
completely above board, profession but friendly. And then I was
going to do an event in the city for Innaro,
one of the charities I work for, and it was
a performance event, and so we asked if you'd come

(06:15):
and sing as part of this event, and you did
and you were wonderful, and that's when we met met.

Speaker 2 (06:20):
It was awesome and I love obviously I love John,
your husband as well too.

Speaker 3 (06:25):
It was very instantaneous.

Speaker 2 (06:27):
I do feel like, if we're going to talk about this,
we should mention that Anthony Ramos of Hamilton and Beyond fame. Yeah.
I didn't really I then and now don't always do
all my research.

Speaker 3 (06:40):
So he came back stage and.

Speaker 1 (06:42):
He was there for this event as well.

Speaker 3 (06:43):
Yeah, he was there.

Speaker 2 (06:44):
His ex partner was performing, and so I was unaware
of who he was. I think I might have known
that he had been in the cast of Hamilton, but
he came back and he paid me a very nice compliment.
He said, you know, guys like you who are very
specific with your lyrics really paved the.

Speaker 3 (07:00):
Way for guys like me. It was such a nice
thing to say.

Speaker 2 (07:04):
And I immediately go into like wise old owl mode.
And I hear that that he's gonna got an album
coming out, and I mean, I just short of calling
him son. Yeah, I'm like, and I said, you know,
you guys want to make sure you call each other
at least every twelve days. If not that you've got
to really see each other every twelve days, and you
should call each other every day, spend ten minutes.

Speaker 3 (07:26):
I was so giving out the advice.

Speaker 2 (07:28):
Like it's nothing. And a month later, I think we
saw him at the Grammys and then my daughters saw
him on a Calvin Klient billboard and we're.

Speaker 3 (07:37):
Like, I was like, that's the guy I was giving
advice to. And they're like, oh my god, Dad, you're
kidding me.

Speaker 1 (07:43):
I remember that. Yeah, because no, Hamilton was big, but
it wasn't the it hadn't exploded quite yet.

Speaker 2 (07:50):
Maybe well also he was he's like the guy in Hamilton.

Speaker 3 (07:53):
I mean, it would have been neat to meet anybody.

Speaker 2 (07:55):
But he is one idea. Yeah he was, he's he
is a big deal.

Speaker 1 (08:00):
And I bet he's left your advice at heart and
he will always remember the old man.

Speaker 2 (08:08):
I know, the obscure Americana songwriter being like, listen to me,
young man.

Speaker 1 (08:13):
Yeah, that's great, that was a great night. Look, I
want to talk to you about so much because in
so many ways you're the perfect Off the Cup guest
because here we talk about parenting, mental health, career arcs, managing,
getting older, you know, evolving in our lives. There's so
much there for you. But first I always like to ask,

(08:34):
what kind of kid were you?

Speaker 2 (08:35):
I was super serious, super serious. I remember my mom
has told me that in kindergarten they were worried about
They said they almost wanted me to get in more trouble.
And I'm in my forties now, hanging on to my forties,
and I feel like, I mean I was. I am

(08:56):
the most comfortable I've ever been. I was definitely waiting
to be an adult, and I found childhood to be.

Speaker 3 (09:04):
Really stressful because.

Speaker 2 (09:06):
You're surrounded by kids and care freeness, and I just
didn't have I have been serious. I have felt like
death could be right around the corner since I was
a kid, you know, And thinking about this recently, I
did go to sleep to Cat Stevens's tea for the
Tillerman album Every Night, which is really kid as a kid,
which is kind of a sad you know, And I

(09:29):
sometimes think about did it just fit my disposition then?
Or am I slightly melancholy now because I did just
my night I'm having these like sad ass songs pounded
into my brain.

Speaker 3 (09:43):
But I don't know. I was serious.

Speaker 1 (09:45):
Yeah, you know that's interesting. I was too in a way,
not that I couldn't have a laugh, I love, you know.
I could get very hyper and sort of you know, excitable,
but I was anxious and I wasn't worried. Death was
around every corner, but I I was waiting for the
next thing to happen. When are we gonna move again?
My parent's gonna get divorced again? You know, there was

(10:06):
a lot of anxiety. Have you thought back to what
your childhood was like and maybe asked why you were
so serious or worried as a kid.

Speaker 2 (10:16):
Yeah, I mean I think I think about it to
a degree, especially when I was kind of trying to
figure out certain things ways of being as an adult
that I was trying to, you know, have been trying
to sort of sort out, Like, for instance, I've played
a lot of shows, almost three thousand then, right, and

(10:36):
and yet I spent the first fifteen years of shows
going on stages though it were war, you know, as
though it was like Braveheart, and I assuming assuming people
would not like me unless I somehow won them over.

Speaker 1 (10:49):
You had to prove yourself, yeah.

Speaker 3 (10:51):
Big time.

Speaker 2 (10:52):
You know, like I kind of saw everybody as an enemy,
which sounds crazy because my music's sort of affable and I, yeah,
you know, but that's how it felt. And I did,
I did, I don't do. I don't play that way anymore.
I go on and assume people will probably like it,
and if they don't, that's okay. You know, it's not
everybody's thing. And I think that some of that must

(11:13):
have come from childhood, because I didn't always feel and
this would be painful for my parents to hear. It
had nothing to do with them. But I didn't always
feel safe, you know, you know, these are It wasn't
tragedies on a big scale, but I was mugged a
few times.

Speaker 3 (11:28):
I was beat up in high school.

Speaker 2 (11:30):
I I felt like if I made myself too big,
it caused problems for me. And that's that's weird when
you sort of have an artistic disposition where you you
want to stand.

Speaker 3 (11:41):
Out and be special, you know.

Speaker 2 (11:43):
Yeah, and you're like, so this could be a liability,
you know, And I mean that's it's not something I
think or talk about a lot. But you know you're asking,
and it does. It brings up feelings you remember, you remember,
you know what it was like to sort of lay
there and wonder if you're going to get hassled at

(12:05):
school the next day or whatever. You know, those things, Yeah,
I think they drive artistic dispositions into art.

Speaker 3 (12:11):
I mean, it is Christ for the mill too.

Speaker 1 (12:13):
Sure.

Speaker 2 (12:14):
So can I ask were you a did you get
involved in games because you're good at so many things?
Were you like, were you in the mix as a
Did you appear to feel comfortable in your when you
were in school?

Speaker 1 (12:28):
It depended. I moved a thousand times, and so I
was always auditioning for the new group, and like you,
was I being too big for this group? Did they
want me to be a smaller person? Okay? That's who
I am? Is being smart, cool, in this school, then
I'll be smart. Is being smart not cool in this school,
then I won't be smart. I was always adapting for

(12:50):
the new school. And some were wonderful and I had
friends instantly and like never wanted to leave, and then
of course did and some were awful and I was
you know, got harassed, bullied, picked on, you know. So
I had a little of everything, yeah, and very little stability.
And this is not a knock on my parents either.

(13:10):
My my parents were great, are great. I had a
great childhood, but there was a lot of moving, instability
and anxiety for me. Yeah. Yeah, And I'm learning now
how that's manifesting, right, I guess.

Speaker 2 (13:23):
We all that's the age sort of that we're in now.
But then, so this is interesting though, because my folks,
I think there is a tendency to say no, no,
it wasn't like that, and I'm like, what it feels
like it was that way to me, and that is
my prerogative. Just like with my own kids, I have
to accept that they're going to have their own narrative

(13:44):
of all this stuff.

Speaker 3 (13:45):
And that's hard. I do get it.

Speaker 2 (13:47):
And then I went through a yearbook recently and people
wrote really nice things, and I'm like, did I have
I have I constructed this to support my artists and
I don't know, I don't know, but I did feel
I can remember the visceral feeling of Cat Stevens and
a little bit of fear and just it was stressful,

(14:11):
you know, Yeah, I was really. I feel like my
life began when I was eighteen, you know.

Speaker 1 (14:15):
Same I got to college and found myself, found my people.
And sometimes when I think about my son, you know, Jack,
you know, he's an anxious kid and there's a lot
going on in his head at all times, and I
just wonder his childhood going to be the hard part
for him, and adulthood's going to be great, you know.
That's what I hope, And you know, not to make
childhood so big. Maybe he's gonna have an easier time

(14:39):
next year or starting middle school whatever, but he's an
anxious kid and so was I, and I just hope
in adulthood he really finds himself and it gets like
gets easier, yeah for.

Speaker 2 (14:48):
Him, I hope. So yeah, forever, Yeah, that's it would be.
It feels like that's the arc, you know, yeah, if
the child if your childhood was your best days I
don't really understand those people.

Speaker 1 (15:00):
Well that's a whole other thing. Yeah, I don't understand
them either. You grew up in Massachusetts mostly.

Speaker 2 (15:20):
I mostly grew up in Connecticut.

Speaker 3 (15:22):
Actually okay, but but.

Speaker 2 (15:24):
I things started in Massachusetts and I had a I
have like a farmer there. My family was split between
farmers and academics, which explains a lot. Yes, you know,
I mean like that is that's all going on. But
my family, in order to get away from the farmer
side of things, I think, moved to Connecticut and got it.
And so I lived in Bridgeport, Connecticut and Fairfield, Connecticut.

Speaker 1 (15:47):
So unlike me, because I, i'd say, mostly grew up
Masachusetts despite all the moves. Unlike me, I don't think
Duncan Donuts is like your entire personality.

Speaker 2 (15:56):
No, right, right, I see that your I see that
on Yourstagram though you're you're a diehard good.

Speaker 1 (16:01):
Yeah, yes, let's go. Yes, it's a major part of my.

Speaker 3 (16:04):
Yeah, it's a thing. It's a thing, definitely.

Speaker 1 (16:07):
So I know the answer to this. But you met
your wife when.

Speaker 2 (16:11):
We met when we were I was just about to
turn sixteen, first weekend of junior year of high school
at a mixer, and it was if there, if there.

Speaker 3 (16:22):
Were a movie, it felt like dream weaver moment.

Speaker 2 (16:25):
You know, I definitely saw her there, and if you
asked her about how it felt, she would she would
tamp it down a little bit. I mean, people were like,
when did you fall in love with him? She's like,
I think a little after college, which means we'd been
together nine years at that point. I'm like, oh, no, no,
none taken. But it was it was very thunderbolty for me.

Speaker 3 (16:50):
Yeah.

Speaker 1 (16:51):
Well, and you guys have such a great family. You
must have weathered a lot. You've been together so much.
You're a touring musician. That's it's not easy on the
strongest of marriages, and yet you've raised like such down
to earth, grounded girls. You have four daughters. Just looking
back in totality, how do you think, top line, how

(17:13):
do you think you did it and capture family together?

Speaker 2 (17:18):
Well, thank you for saying that, And I you know,
it feels very much like a work in progress. I'm
still trying to make sure that this turns out inasmuch
as I have any control over it. Well, and you know,
I think there were adjustments. I don't I'm going to
get like choked up saying this, but I feel that

(17:39):
really that was the biggest That was the lynchpin to my.

Speaker 1 (17:43):
Whole life, meeting your wife or her.

Speaker 2 (17:45):
You know, it really was. It was like having that
workout is the thing that has made all the other
things work out, you know. And yeah, I didn't know
it was going to be that way because I'm ambitious
and I wanted to. I wanted to. I thought you
kind of got that squared away, and then you worked
on your music and your profession, and I thought that's

(18:07):
what success was.

Speaker 1 (18:08):
You were like, okay, marriage said it and forget Oh
I got it.

Speaker 3 (18:11):
Good.

Speaker 1 (18:11):
Now I can go off and be ambitious.

Speaker 2 (18:13):
Yeah, and this is like and then I realized, from
working as hard as I know how to work and
doing this that like, you know, your career will kind
of ebb and flow and you'll have wins and you'll
have hits no matter who you are, but the people
that you share the ride with are the whole game. Really. Yeah,
So whether that's your friends or your spouse is such

(18:34):
a big one. And I didn't know that then, but
I did instinctly. I think we just went after it.

Speaker 3 (18:42):
You know.

Speaker 2 (18:42):
In college, there was a very real possibility that I
was going to just be too jealous. It's hard to
turn that corner from high school sweethearts very and Kirsen
is so beautiful that she had a lot of suitors,
you know, I mean.

Speaker 1 (18:58):
People waiting out your relationship fashion.

Speaker 2 (19:00):
There were a lot of guys trying to take my
station here and and uh, you know, you can't shut
each other down. It's no way to live, but you do.
But I am you know, the same thing that lets
all the love in is very I'm in intense personality.
And I felt this, you know, constant. There's no there's

(19:20):
no becoming way to talk about. I was just I
felt jealous all the time. And so you're sort of
like in college, it's thank god there wasn't the Internet
and the things that we have.

Speaker 3 (19:30):
Now, you know.

Speaker 2 (19:31):
So she's just I went to a concert with people
and you just had to.

Speaker 1 (19:34):
And you never know what that looked like.

Speaker 3 (19:36):
No, and thank god, you.

Speaker 2 (19:37):
Know, and so and I didn't lose her because I
did realize like, Okay, I have to be able to adjust,
and and she had to adjust because as I got into.

Speaker 1 (19:47):
Music, yes, and totally very threatening, totally musician for a
woman to be.

Speaker 2 (19:51):
In yeah, she's completely the opposite of me. Though it's
never it seems to never face.

Speaker 3 (19:55):
I almost wish it would. I'm like, you realize I'm.

Speaker 2 (19:58):
Kind of a big deal, Like, yeah, there.

Speaker 3 (20:01):
Are women that like me.

Speaker 2 (20:03):
But she's kind of like, oh, that's nice for you.
I mean she has she's the total. She balances it
well and I think that, but I did at some point,
you know, we had a conversation before we got married
where I said, you know, I don't want to ruin
your life, and losing you would be the hardest thing
in the world. But I I'm gonna be doing this.
I'm gonna be gone a lot. Yeah, I'm really gonna

(20:24):
be gone a lot. Is this should we And we
both kind of went into our marriage like let's try,
because if we don't try, we always wonder, you know.

Speaker 1 (20:33):
I mean that's a really good realization to have beforehand
and acknowledge that. And that's a very selfless thing to say,
like I don't want to ruin your life and this
is but this is.

Speaker 2 (20:43):
What I want to do.

Speaker 3 (20:43):
And what would I have done if she had been like, yeah,
this could be this could be right. And it does
go back. It all comes back to Anthony Ramos, because.

Speaker 2 (20:53):
The advice that it was given to me early on
was you need ten minutes if you if you travel lot,
and so does your special you need ten minutes a
day where you're not just doing laundry lists. You're not
just saying okay, I did this.

Speaker 1 (21:06):
You know, did you get this done?

Speaker 2 (21:07):
You're chatting the way you would in your living room.

Speaker 1 (21:09):
Yeah.

Speaker 2 (21:09):
And his this advice was given to me, and it
said if you missed ten days because you're doing LA
or something like that, you got to make it up
the next day. And there were times I would sit
and look at my watch and I wouldn't want to
talk on the phone. I mean you do like sort
of shut down parts of yourself when you're on the
road for survival mode. I mean you traveled totally. Ti.
I this is but it's dangerous because if you do

(21:30):
it for too long, you do become disconnected. Right. So
I was a big believer in just the metrics of
ten minutes a day of actual communication doesn't have to
be you know, big stuff, And it helped me keep
us advice.

Speaker 1 (21:42):
You know, it's such a grind trying to make a
name for yourself. And I remember in very different ways.
When I look back at my twenties when I was hustling,
I mean I worked twenty hour days, I said yes
to everything, I was on planes every week. I'm exhausted
thinking about how hard it was just to get where
I wanted, like a good enough place that I wanted

(22:06):
to get. What do those early days look like for
you now when you look back at the work, Well.

Speaker 2 (22:11):
What you just described feels like to me like your
life now kind of. I mean, don't even get me startups.

Speaker 1 (22:17):
Even I am pissed. I know that I am forty
six and working as hard as I had to in
my twenties. I am pissed.

Speaker 2 (22:23):
Well, same answer, I am too. I feel so the
you know, I feel indignant about I'm like, why this is?

Speaker 3 (22:31):
I thought we were going.

Speaker 2 (22:32):
To row out and then you would just be coasting
a little bit. And I feel like I'm working like
five times as hard as I was in the beginning.

Speaker 1 (22:39):
So you're having the same experience as me looking back
being like, oh, this is very familiar. Yeah, I'm not pleased,
but it's it's familiar. I've done this before.

Speaker 2 (22:48):
So is that a result of not being where you know?
Where we envision that we would get.

Speaker 3 (22:53):
Is it like I'm not there yet.

Speaker 2 (22:55):
So I need to do that And if that's the case,
you know, I don't know if that's the case. Is
the problem that we just we got to get to
that spot or is it? Is it like an inability
to be content, which is what my friends will tell me, like, hell,
you know your life is great, and I know it is,

(23:16):
but I I with that. I'm like, there is there's
some stuff that has not quite landed in the way
that I wanted to And I don't know any other
way than I've got to just keep trying to hammer
it this.

Speaker 1 (23:28):
You know, I feel the same. Some of the reason
I'm working so hard is just like the economy and
my business right it's changing a lot, and we're all
trying to future proof for what it's going to become, right,
and so part of it is like strategic, But there's
another part, like you, where I haven't done everything I
want to do yet. And it's not that I haven't
gotten as high as I want to get. I've you know,

(23:48):
posted my own show You're.

Speaker 2 (23:50):
You Are, you Are, You've done great. I mean it's
easier for me to look at your life. Why would
you feel like she needs to work all the time.

Speaker 1 (23:59):
I mean, for lots of reasons. It's complicated and it's
not any one thing. And at this age that I'm
at too, I'm stubborn. I want No one's going to
kick me out of this. Yeah, I know lots of
people want to. Yeah, because I'm at a certain age
as a woman. You know, you knew people want to
come in. That's fine, I'm not leaving. Yeah, And so
part of me is like, you're gonna have to like

(24:21):
kick me out the door because I'm not slowing.

Speaker 2 (24:24):
Down well, and I'm the same way. Yeah, okay, because
I have become without meaning to, I've become sort of
this underground thing where people because the reality is most
people don't know who I am, you know, but I have.
It doesn't it doesn't diminish sort of now the life
and the career you've done so much too, where the

(24:45):
people who do know, they're like, it means a lot
that I stay in the game. And so part of
me is like, Okay, for my legacy, I don't mean
to be so grand about it, but for my legacy
to remain intact, I need to never give in.

Speaker 3 (25:01):
I need to just ride.

Speaker 2 (25:03):
This wave and this is going this is who I am. Yeah,
but a kid myself sometimes, and I imagine is as
recently as this week, I was like, Okay, well, so
I'm gonna be fifty in a couple of years and
I might just like want to do something totally different.

Speaker 3 (25:18):
And Kirsen looked.

Speaker 2 (25:19):
At me and she just smiled at me, and she's like, okay, sure, right,
whatever you need to tell yourself. Man, you know you're
you like being Stephen Kellogg and she's not wrong, but
I need to believe that there's an option if just
in case.

Speaker 1 (25:35):
But you know, I feel the same way, and I
think about, you know, maybe I don't want to do
politics anymore, or want I do something else. But I'm
finding maybe, like you, people don't want me to leave politics.

Speaker 2 (25:47):
Yeah, I know, it's all they want.

Speaker 1 (25:48):
And when I try to go to a new space,
they're like, you're not giving us politics. What's going on?
They're disoriented, And so I keep getting roped back into
the thing that people know me for. And that's tough because,
like you, I want to give people what.

Speaker 2 (26:01):
They want, I know, and you're really good at it.

Speaker 3 (26:05):
And that's the kind of thing.

Speaker 2 (26:06):
So I'm a little bit over some of the things,
you know, just being the touring singing singer songwriter guy. Okay,
like the physicality of it, two nine hundred shows right
as this thing, okay. And I'm not doing this always
at that some cities, I am doing this at the

(26:27):
level that I want to do it. But in some cases,
I'm going to cities I've been going to for twenty
five years and I'm doing less business than I was,
and but I feel better at what I'm doing than
I ever did.

Speaker 3 (26:40):
And part of me.

Speaker 2 (26:41):
Goes, well, I don't know how many more of these,
you know, I don't know how many more of these
I have in me because I'm a little bit I
don't want to go on stage with a chip on
my shoulder.

Speaker 3 (26:52):
But part of me is like, well, where is everyone?

Speaker 2 (26:54):
And it's the age that we're at, the demographic that
comes to see me. I get it, We're busy. We
don't like leaving our house at all. You know, you
got kids or you got parents, You've got things you
got to do.

Speaker 3 (27:05):
But I don't know how much more of that I
have in me.

Speaker 2 (27:07):
I'm a little bit over that, and so that has
led me to write that book and do the stand
up special because I am thinking, like what else? I
don't want to just do the same things I've been doing.
And that is probably a good, healthy impulse. I think
it's good to like.

Speaker 3 (27:22):
But most people are like, cool, cool, cool, read your book.

Speaker 2 (27:25):
When are you playing again?

Speaker 1 (27:26):
Right?

Speaker 2 (27:28):
You know, let's do something else here, you know.

Speaker 1 (27:31):
But yeah, I've tried to find a way to keep
doing that thing, that thing that pays the bills, that
thing that people know me for, that thing that I
used to really love. And there are moments I still
love it on the regular, I don't, you know. Just
being honest, it's not fun covering politics today the way
we used to cover it, and my business the media
isn't a fun place to be either. But to give

(27:54):
myself some fun, I get to do things like this, Yeah,
which is what turns me on. This is fulfilling. The
five second hit on TV about tariffs is not. This
is fulfilling, And so I feel like, Okay, I can
take the bad because I'm also getting some of the good.

Speaker 2 (28:11):
Now.

Speaker 1 (28:12):
Is that how you feel about like your stand up?

Speaker 3 (28:14):
And yeah, this is why we're friends.

Speaker 2 (28:16):
I mean we're because we since we've met, there have
been these shared two three moments. And that is so,
whether people realize it or not, or whether I fully
grasp it. Doing stand up writing the book has made
me fall in love with music again, right, And so
this I just put out a record, and this record

(28:37):
feels inspired, which you wish they all felt inspired, but
they don't always.

Speaker 3 (28:43):
And so it's bringing back the love.

Speaker 2 (28:45):
And I'd love a little more room if I was
picking the diet and the balance of my life, I
would love a little more room, Like like, what could
happen if I could get a little more space from
so that you don't start to like the thing, Yeah,
that is your main.

Speaker 1 (29:02):
That became your job. You fought so long and so
hard to make us a job out of this, and
then you made it a job and then you got
actually good and it wasn't just you got big and
you got you know, it's a it can be a
mind fulk to like navigate all of this and then
you feel ungrateful, like I want to take a step back.
That's so ungrateful.

Speaker 2 (29:23):
You know of me even now I'm self conscious of
like do we just do I I'm not knowing about you,
but do I just sound like a like someone who's
complaining about a great job, because that's not This.

Speaker 1 (29:34):
Is honest, and I think it's better to be honest
rather than say, you know, I'm just lucky to be
here and it's been great, and you know, no, it's
taken a huge toll on my mental health. And there
are so many people we talked to on this podcast
and then outside of the podcast who are at an
age we're regardless of what they're doing, they're confronting the

(29:54):
same existential questions and talking about it. Honestly. For people
there who look at someone like you, wow, successful touring
musician like or you know me, someone's on TV doing politics,
to talk this way, I think is way more helpful
than to put a shine on it and pretend like
we're not going through some of these, you know, questions

(30:16):
and challenges in our lives. That's the point of this. Yeah, yeah,
so I don't feel subconscious. This is what this is
what we're meant to do. Your parenting. I've met your kids,

(30:43):
and you can share as much as little as you
want to about your kids. But your kids are incredible.
You have four beautiful daughters. I just want to ask
broadly when you had your first Sophia, think about your
parenting philosophy as you just had your first kid, and
now tell me what your parenting philosophy looks like or
has changed four kids in what is that? What is

(31:04):
that gap? Is it a big difference or is it
very very similar?

Speaker 3 (31:07):
I love the question.

Speaker 2 (31:09):
It feels like something has shifted.

Speaker 3 (31:11):
And you know, when I loved that, I didn't know
what I.

Speaker 2 (31:17):
Was getting into. I think that's sort of an essential
component of parenting, is you need I'm glad we didn't know.
There's something like evolution wise that when you have kids
you don't know as much as you know twenty years.

Speaker 1 (31:32):
Late, because if you did, you wouldn't do it because they'd.

Speaker 2 (31:34):
Be too scary. It's too like you're just the desire
to protect.

Speaker 3 (31:39):
Them is so big that you're like, you know.

Speaker 2 (31:42):
But so when we had Sophia, you know, yeah, we
were twenty eight, we were I just kind of thought
this is.

Speaker 3 (31:48):
All going to work out.

Speaker 2 (31:49):
I mean, that's where the farmer side of things, you know,
that was just like, hey, this is cool. The kid
hangs and they hang already hung around the band and
me playing music till late they fell us. You know,
we would just fall asleep in the practice space, sometimes
just laying there.

Speaker 1 (32:04):
And you're like, this is cool.

Speaker 2 (32:05):
Yeah, And judge your parents right now would be like,
so you're telling me you didn't have earphones on your
kid and you play music while she slept. That can't
be healthy and they're not wrong. But that's also how
we did it, and it had such a good impact,
I think because we didn't, you know, make a big deal.
But this was just our life. We didn't stop traveling.
We didn't say we can't go out, we didn't say

(32:26):
we have to be quiet. We kept living our life,
you know. And at her christening, I can remember it
Heresen saying you should probably not have anything else to
drink because we were like we you know, we're just
but I was really fun and it was and they
saw that. And now that my two oldest are twenty
and seventeen, I went into the recording studio with my

(32:46):
oldest Sofia this week and we made music together. It's
a beautiful thing because we are it's shifting from you know,
caretaker to sort of advisor, you know, and that's really
fun and I'm really grateful for that. But to your question,
how has it shifted this is not the same since
the advent of the smartphone.

Speaker 3 (33:08):
I mean, it's not the same. We're not doing different.

Speaker 2 (33:12):
Skill sets are now required, right and for my younger two,
I'm really feeling somewhat inept and I just have a
much harder time managing it because we're sort of doing
battle with something that hasn't really existed before and that
has such a hold on me. And you talk about anxiety,

(33:35):
I just it's like, you know how they you'd hear
your parents say we didn't know cigarettes were bad. You're like,
of course you knew cigarettes were bad. You maybe didn't
know the ins and outs, but you knew they were bad.
I do feel that our screen situation is the same
thing is the cigarettes of today. And so in some ways,
when I'm just exhausted because I'm more exhausted and Kirsten's

(33:58):
more exhausted, and there's four of us, So in some ways,
right at the moment where we're wanting to be less
stringent as parents with the babies of the family, we
are also sort of like, have these cigarettes if we're
doing the metaphor that are in play all the time, yeah,
and you're like, don't smoke, and you so I don't
mean everyone smoking.

Speaker 1 (34:18):
I know, and you don't have because you know I
have one. You four you would imagine, I bet you imagined.
You've gained all this confidence in wisdom through the first
two at least. Yeah, And so you think, well, the
second two I've got, I've got I'm confident I've got it.
But then this wrench comes in of social media that
completely changes the rules, and now it's like, wait a second,

(34:41):
I didn't sign up to be a parent in this environment.

Speaker 2 (34:44):
Yeah, yeah, it's yeah, totally, And I know that tons
of people are going this way and it's not it's
not meant to you know, I never am the person
who judges the parent who's dragging their kids through target. Like,
I get it. I have been all those things, and
Kirson has been them even more. But I do feel
like we are trying to exercise a level of tough

(35:06):
love now that is so hard for us to do
at this moment. Where're and when we do, the results
are pretty good. When we're like, Okay, here's the deal,
and we've got this wide open aperture too, it's like
we let them be on these things a lot, but
we have some rules about like you have, it has
to be in the basket by this time, and they'll
come down two minutes after that time, and I'm like, well,

(35:29):
you got to give us your phone and they want
to kill me, which I'm not used to either, because
I didn't really that wasn't I wasn't the type of
parent where, you know, my kids, this is a new
thing that they get really mad at me and I
have to like hold the line in.

Speaker 3 (35:45):
A way that I I'm not that good at.

Speaker 2 (35:49):
It's just this is like it's changed, and I feel
I'm starting to feel shittier at the job. I think
I'm like, am I worse as a parent now? And
I hope not.

Speaker 1 (35:59):
You know, well, listen, I don't know a single parent
who feels like I've got this, Not a single one,
you know. I mean, you can look back and think, well,
I was a much better parent at this point or
with this kid or whatever. But no one in the
moment feels like I've got this. You know, you just can't.
It's it's there's too much incoming at once to feel
like I've got ground under my feet and like I've

(36:21):
figured this out.

Speaker 2 (36:23):
Think about our kids, though, they don't you feel that
they are who they I mean, don't you feel like
to some degree they just came out the way that
they are And you're like, I'm not sure how much
good or bad? Yeah, I'm you know, I'm obviously we're
getting you fed and keeping you right alive, but like,
I don't know, I question our impact.

Speaker 1 (36:43):
So so much. The same for me too, because there's
a lot of Jack I don't recognize in me and
Frankly or John, like, you know, he's just his own
and he's lucky that there's you know, that distance. But also, yeah,
I just have to constantly remind my especially since he
was diagnosed on the spectrum, I have to remind myself

(37:04):
like he's his own person and I don't have to
be the greatest mom. I just have to be his
mom and listen to him. Yeah, right, And what does
he need for me?

Speaker 3 (37:16):
You just just you just have to show up. You're
basically modeling.

Speaker 2 (37:19):
Hey, this is how you show up and try? Which
is the most useful thing to model?

Speaker 1 (37:25):
What would you say is your best parenting hack?

Speaker 2 (37:29):
Hmm?

Speaker 3 (37:31):
You know what it is.

Speaker 2 (37:35):
It's okay to apologize, yes, you know, it's okay to
screw things up royally. I have said things to my children,
and I write all these songs that you hear. A
lot of my songs are about I mean people erroneously
just assume I'm a great dad because they hear these
loving songs.

Speaker 3 (37:52):
Yeah, they're like, you love kids.

Speaker 2 (37:54):
I'm like, no, I love my kids. Most of those
My kids are assholes. So don't don't. Let's not put
words in my mouth. But I think the greatest hack
is just that when you screw up, it's okay to go. Hey, hon,
Dad was really frustrated and I didn't mean those things,
and I'm sorry. I'm going to try not to say

(38:15):
those I cannot guarantee I'm never.

Speaker 3 (38:18):
Going to raise my voice again.

Speaker 2 (38:19):
I'm never going to say something awful. And to me,
it makes me feel better to do that, it seems to,
even if they want to hold it over your head
for a minute. You know, I think that that's the
most important thing that we've learned to do. I like
my parents, just like admit when you're wrong. It's not

(38:40):
it's not weakness.

Speaker 1 (38:41):
It's it's it's just strength.

Speaker 3 (38:43):
It's just owning it, you know.

Speaker 2 (38:45):
And one day the girls were fighting and they were
this was during COVID. They were being it was so loud,
and I said, hey, guys, can we what, like what's
going on? And they said, Dad, you know how you
and mom just need a minute sometimes just.

Speaker 3 (38:58):
Let like And I was like, oh yes.

Speaker 1 (39:01):
Right, oh yeah, respect, advocate for yourself. Girls.

Speaker 2 (39:04):
Yeah, yeah, it's like have it. It's okay to this
thing of running around and expecting each other, trying to
hold each other to these perfection standards, which we do
with everybody and in the media, you guys are like,
you take moments out of context. Yeah, completely have to.
This becomes the way that you are. And yeah, what
like if we all had hot mics all the time,
it would not be pretty.

Speaker 3 (39:25):
It would not you know, so we just accept that.

Speaker 2 (39:27):
Yeah, life is like super messy like this, and you
do say shitty things. Yeah for them, you know, I'm not.
I feel sad thinking about some of those moments.

Speaker 3 (39:36):
But also I don't know my.

Speaker 2 (39:39):
Two older ones. I said those same awful things to
them and they're my good friends. Now, Yeah, they turn
out just fine.

Speaker 1 (39:44):
This is okay, you know well, And my therapist always said, like,
don't aim to be a perfect parent and beat yourself
up when you're not, because you're not raising perfect kids,
and they need to see imperfection and know that that's okay.
That Mom's not perfect, Dad's not perfect. Mom doesn't always
have the right answer. Mom doesn't always behave perfectly, and

(40:05):
she'll admit when she when she doesn't. That means I
don't have to be perfect. So it's like lower modeling
it exactly. Yeah, and you would want that for them,
of course.

Speaker 2 (40:14):
You know, the people who.

Speaker 3 (40:15):
Love you, you want to see yourself.

Speaker 2 (40:17):
This is that movie PS, I Love you, but it's
like you want to see yourself through the eyes of
somebody that loves you.

Speaker 3 (40:23):
That's the kindest way you can be to yourself.

Speaker 2 (40:25):
And if you can show your kids, you know, they're
kind of like, well you do it, and you're like, oh,
that's hard, right, right?

Speaker 3 (40:31):
That is a lovely way to exist.

Speaker 1 (40:34):
It is good. You know what I've been trying recently,
and it's really helpful. I've been taking you know, we
all have worries about our kids, existential worries, but also
worries like tomorrow, right, what's going to happen at school?
This thing? But also what's adulthood going to be like? Right?
And I've started taking worries and kind of flipping them

(40:56):
on their head and examining them through their opposites. So
to give you an example, Jack, Jack is ten and
Jack does not ever like to be alone. Okay, Jack
has a great room with toys and books and spends
no time there. Jack is a great playroom downstairs with
a TV and Nintendo's spends no time there. Whatever he's doing,

(41:19):
he wants to be doing it next to my husband
and I. One of us doesn't like to shower without
anyone standing outside the room. Okay, yeah, won't brush his
teeth without someone standing right there. Just doesn't want to
be alone once playdates all the time we're going out,
Can we bring a friend you know very much wants

(41:41):
to interact at all times. And this, you know, worries me.
Oh my god, Like he's ten, When is he too codependent?
You know? When's he going to feel like he can
do stuff on his own? And am I indulging this?
And blah blah blah, And I said, okay, let me take
this problem. Let's now talk about what the opposite of
this would be. A kid who spent all his time
in his room, never wanted to be around his parents,

(42:04):
never wanted to interact with friends, never wanted to do
stuff after school, was completely inside of himself, either escaping
into video games or whatever he was doing alone. Well,
I'd be a lot more freaked out about that kid,
sure than my kid.

Speaker 2 (42:21):
Sure.

Speaker 1 (42:21):
Right. Yeah, And so that doesn't mean I'm dismissing the
thing I was very worried about. But I'm taking I'm
creating a lot of distance between the urgency of this problem,
which is not anywhere near as bad as the opposite
of this problem.

Speaker 2 (42:39):
Yeah.

Speaker 3 (42:39):
Yeah.

Speaker 1 (42:39):
And all it does is it allows me to like
sleep at.

Speaker 2 (42:42):
Night, offer some perspective on the situation.

Speaker 1 (42:44):
Yeah, and takes my temperature down so that I can
parent intentionally, rationally, calmly and not under dress because I'm
just like white knuckling it and like worried all the
time about every single thing.

Speaker 3 (42:58):
Yeah, yeah, totally.

Speaker 2 (42:59):
And everything requires a strategy session. I mean, it's there's
so much and if you if you have the sort
of the luxury of being able to dedicate time to it,
parenting becomes its own art form. It's like, how well
can I do this? How well can I take this?
We're basically taking a test that is impossible to ace, right,

(43:20):
you know, there is no, a scene of this test
and just like, how do we how do we do it?
You know? And so getting perspective sounds like it would
be good, and I'm not sure, you know, I want
to think about how I could apply that in my
own world.

Speaker 1 (43:34):
Something will come up.

Speaker 3 (43:36):
Exhaust It's exhausting.

Speaker 2 (43:37):
I'm a little exhausted right now. Summer feels exhausting too,
because there's certainly home and I know I'm going to
miss this, but I'm also like, I don't have the
summer off. I know, right, exactly right, nobody's nothing changed
for me except that you're home all the time now.
And I'm like, well, they got to work here sin
It's like she's twelve though she can't even get there's

(43:58):
not really a job for her to and I'm like, well,
there has to be something.

Speaker 1 (44:02):
She can do.

Speaker 3 (44:03):
It doesn't acquire coming.

Speaker 2 (44:05):
To me and saying, yeah, it's hard.

Speaker 1 (44:08):
We talk a lot about mental health on this podcast,
and you and I have talked a lot about mental health,
and kids today are talking a lot more about mental
health than we did, for sure, For example, how do
you model mental health with your kids and how do
you interpret mental health as a dad?

Speaker 2 (44:29):
This is interesting I I am, I'm not sure. You know.
There's there have been moments where Kirsten said, you should,
you really need to talk to somebody, and my response
has kind of been like, I don't have the time
or the money to do that right now. I'm putting
it all into our things. I do also feel that

(44:50):
I have some people in my life who probably take
the brunt of what a therapist would take.

Speaker 3 (44:58):
And I write intensively in my journal.

Speaker 2 (45:01):
My journals are so filled with crazy, you know, and
it helps so much, and then it does keep the
head sort of straight. I mean, it's I think that
it's let me answer this more succinctly than I am.
It's so hard to be to do the human experience

(45:24):
for anyone, whatever your income strata is, whatever your lot
in life is. Everybody is finding this to be a challenge.
So it's great that we're talking more about it, because
that should be considered a baseline.

Speaker 3 (45:38):
You know.

Speaker 2 (45:39):
It's silly to think that money makes all the problems
go away, or success or fame or living here or
living there.

Speaker 3 (45:46):
These things.

Speaker 2 (45:46):
It's like, it's hard to be a person, you know.
So that sort of helps me and I go, all right,
I need to I'm just gonna I have my journal,
and I have my people that I talk to, and
if I'm leaning too heavily on them, I have people
I can talk you know. Then I'll bring in a
therapist and go, hey, I'm not going to see you

(46:07):
every week, but here's what's going on. Yeah, talk to
give me some strategies. And they do. And that's a
beautiful thing that there's no.

Speaker 3 (46:14):
Stigma on that.

Speaker 1 (46:15):
Yeah.

Speaker 2 (46:16):
I would guess that some of the people closest to
me would probably question parts of my mental health, you know,
because I am an intense person and I'm wound tightly
and I carry a lot of weight, and I think
that that is it's unfortunate that the people around me
have to feel that sometimes. I also would say, you know,

(46:37):
for my friends who have been like, are you okay?
They worry about me because they see me cry on
a daily basis that you know, just and I'm like,
you don't because I am actually quite well. I sort
of swim around in a melancolia that I enjoy when
it's raining outside. I'm like, at last, whether that reflects
my general demeanor. You know, I hate Southern California. I

(47:01):
go there, don't you love the sunshine. I'm like, this
just makes me feel like I'm supposed to be exercising.
Hell no, I don't like this. It feels so at
odds with you know, the blue. I just have the blues.

Speaker 3 (47:12):
But it's not.

Speaker 2 (47:13):
Depression, right, Yeah, and depression is a monster and you
have to watch that. Yeah, but that's not been my lot.
My mental health is actually good. I'm a little too intense.
I'm definitely melodramatic. There are things, but that's also the
things that lets me write songs. It lets me feel
what's happening in the room for others. I mean, it's
I try to embrace that, you know, Yes, this is

(47:34):
who I am and I have to you know, sometimes
it goes too far. But show me one person who
doesn't go too far in the direction of their personality
right on occasion, you know, do you feel emotionally more

(47:58):
connected to your music or your lyrics just to.

Speaker 3 (48:03):
The lyrics the music.

Speaker 2 (48:04):
I have to bring in producers with better taste, Yeah,
and I haven't always picked the right producers, so sometimes
you end your music sounds like but I don't really care.
All I care about is what's being said, and.

Speaker 3 (48:16):
That's how I listen to music.

Speaker 2 (48:17):
So I love listening to eminem even though that's not
like my genre I love.

Speaker 3 (48:22):
I just love the lyrics.

Speaker 2 (48:24):
You know, the lyrics move me. And I can listen
to the cheesiest of country music and have no problem
with the deep accent or whatever's going on the put
on the lift kind of production. If the words are moving. Yeah,
you know, Yeah, that's what I love. I love.

Speaker 3 (48:40):
Yeah, I'm a lyric guy for sure.

Speaker 1 (48:41):
Well I can tell, and I'm sure your fans can
tell as well. Not that your music isn't great. Your
music is also great, but you can tell you pour
so much into your music's.

Speaker 2 (48:50):
Fine, but the music I also bring people into the Hey,
how do we make this cool so that people actually hear?
Like Billy Joel is an artist I love whose lyrics
are so good, but you almost don't realize it because
his melodies.

Speaker 3 (49:01):
Are so good.

Speaker 2 (49:02):
Yes, and I know he's actually polarizing to some people.

Speaker 3 (49:05):
He's not cool or whatever.

Speaker 1 (49:06):
He's fantastic.

Speaker 3 (49:07):
He's amazing.

Speaker 1 (49:08):
That's one of my all time favorites.

Speaker 2 (49:09):
Yeah, he's great, and you don't realize his lyrics are
actually just crushingly good.

Speaker 3 (49:14):
Yes, I sent.

Speaker 2 (49:15):
Josh Ritter uh, because Josh was kind of not on
the Billy Joel train, and so I sent him The
Stranger and I'm like, I want a full report on
what is not amazing about this and he's he's sort
of conceded it since then, probably I think I think
I'm working. I'm bringing around because Billy Joel needs my
help bringing around.

Speaker 1 (49:33):
Yeah right right, yeah, yeah, thanks, thank thank you, Steven.

Speaker 2 (49:37):
Yeah.

Speaker 1 (49:38):
Oh, I love Billy Joel so much. I don't like
people who like hate on him, yeah, or call him
pedestrian or like he doesn't have a great voice. I
think give me Billy over Dylan any day, as like
America's songwriter. That's just for me.

Speaker 2 (49:51):
Okay, yeah, well Dylan, I mean Dylan, that's you might
have picked the one guy that I got to kind
of maybe defens down on it. But we just watched
the Dylan movie, me and the girls, Yeah, and they
were like Dylan was hot, and I'm like, well, well,
Timothy Shalla May's hot, you might. That's your takeaway, guys.

Speaker 1 (50:14):
Okay, before we go to a lightning round, I want
to talk to you about failure because you know, perception
isn't reality. As you know, I get a lot of
like the perception of my career, and I think the
perception of anyone's career is you know the highlights. You know,
people know what I've done. They don't know what I
haven't done. They don't know the thing that almost happened

(50:36):
but didn't. They don't know the thing that I tried
and failed at. And those were so much more instrumental
in my education and learning how to be better at
what I do. But nobody knows them because you don't
talk about them, either because they're painful or the it's
not relevant. It didn't happen, I didn't get to do it,
or I did it and it didn't work. You can

(50:59):
be specific abroad, but like what if you failed at
or what's something a failure you've really learned from.

Speaker 2 (51:05):
Oh, there's so many, and you're so you're so right
about you know, we don't necessarily publicize these things, but
they're so important and you learn so much from them, right.
And one of the things about recently getting into stand
up that I love is the stand up ethos is
so willing to fail. There's no way to be funny

(51:27):
without occasionally going past it, realizing you're not being clear
and So the lovely thing about the stand up community
that I've encountered is you can I've watched comics go
up there in absolutely tank, maybe because they're not even
very good at it, but you get your points just
for putting your hat in the ring. Yeah, I think

(51:48):
that's kind of a beautiful thing, and I think it's
something we don't necessarily value enough as as a culture.
You know, is like putting your hat in the ring.
There's a lot to be said for that, for showing up.

Speaker 3 (51:59):
It's like the parent thing.

Speaker 2 (52:00):
So personally, I have failed at so many things, and
one of the and the brand for me is almost
being the guy that shares it. You know, I'm trying
to lean into it because if I'm not going to
be out there in the in the you know, if
I'm not going to be a household name and this,
all these things, it's like, well, let me mean a

(52:21):
lot to a more focused group of people. Let me,
let me share my life with them to the degree
that they can look at this and go, Okay, this
guy is just like me. Okay, And maybe he's giving
me by sharing his insights about what these failures.

Speaker 3 (52:36):
Meant to him.

Speaker 2 (52:37):
Maybe it helps them a little, or at least makes
them feel less alone in their things. So as a parent,
I have not done things the way that I wish
I had. Sometimes, you know, I have said things like
I know that I that I smote regret as a
band leader and a business guy, you know, I mean,
a band is a business, and I look at those

(52:59):
early days and you go, damn, I I maybe didn't
need to be the way that I was, and and
there was broke some of the relationships. You know, This
new album I have is a lot about friendships that broke.
It's very hard. I really don't want I want it.
I want to clean up everything. You can't clean up everything.

(53:21):
People don't want to accept. They want to hold on
to that thing and that I have my own thoughts
on that too, But that's there, right, you know, they
don't owe. You can't control each other. And so you know,
I have failed in music a lot. My first and
really biggest national TV appearance, I we ran the song

(53:44):
eight times flawlessly, and then we were doing it and
the camera operator was waving her hands and I couldn't
really see, and I ended the song inexplicably had a
train wreck on TV. And my manager's watching. It was
kind of like, if you get this, we'll probably get Letterman.
This is and Letterman was still going and I saw

(54:05):
this path forward for myself if I could just stick
this one landing. And she's waving her hands and I
just stopped playing. I don't know why that was. And
then she came up and yelled at me and said,
I was telling you to extend it. And I was like,
we weren't even near the end of the song. Why
were you just you know, why were you? But none
of that matters, Like we can't. I couldn't rewind that clock.

Speaker 3 (54:26):
We didn't.

Speaker 2 (54:27):
It shut down a bunch of things for me.

Speaker 3 (54:29):
You know, I wound up. I'll leave I'll leave you
with this.

Speaker 2 (54:34):
This is probably my most profound failure, and it led
to a lot of good things. I'd been writing songs
for years. I had been on Universal Atlantic, I was
on Vanguard Records, and we'd had a minor hit. And
they said, Steven, we like you and we want you
to win, but you need to give us a hit.
So I'm feeling this very real pressure, and they insisted
I work with a producer who had produced a bunch

(54:55):
of hits, but whose methods were dubious. Okay, he worked
backwards off of other people's hits. This was very uncomfortable
to me. Some people do it with reasonable success. It's
much more accepted now than it was even when I
was doing this in twenty eleven. So we did a
couple songs that we wrote together, and we kind of
worked and I'm like, Okay, I guess I guess this

(55:19):
is unique enough now, but it felt weird. And when
we put the song out, the radio starts playing it
and our fans start going, this sounds like this Paul
Simon song, which I hadn't gone and listened to because
I didn't want. I was like, I kind of stuck
my head in the sands.

Speaker 1 (55:35):
Yep, yep.

Speaker 3 (55:35):
It's embarrassing to.

Speaker 2 (55:36):
Even be telling you, but I want to give you
something meaty, and this is meaty. So we did this,
and I had a Jerry Maguire moment because I was like,
I can't stand behind this. I then went back and
listened to the song and was like, this feels way
too close. It was already on the radio and I'm
listening back and Sophia, who's little at the time, she's

(55:57):
like five, came in and said, Daddy, who song is this?
And I said, this is Paul Simon's song and she
said it sounds.

Speaker 3 (56:03):
Like your song.

Speaker 2 (56:06):
And that was like so embarrassing. It was so embarrassing
and so not what I'm about. And I have these
hundreds of songs I've written, and suddenly my integrity is
called into question, and I pulled a full on Jerry Maguire.
I wrote a letter to the record label, my management.
I said, look, we know this was meant to be
a tip of the hat. It's come to my attention

(56:28):
that it's far too close. I'm rewriting the song. I'll
pay for the rewrites, and I want you to withdraw
this from the radio. And I was told, in very
clear terms, radio is very fickle, and you've got a
great thing going. They like you, but if you insist
on this, they're not going to play you anymore. And

(56:48):
I said, I hear you, but pull it. And they
were right, Like I lost so much career momentum that
I've never really gained back. And a year later I
did a Ted talk and I talked about this, yeah,
and it was like I could sleep again.

Speaker 3 (57:07):
The next night. I just knew who I was. I
was like, Okay, well, whatever.

Speaker 2 (57:10):
Happens happens now. That was a huge lesson, probably the
most profound failure.

Speaker 1 (57:15):
I don't think that's a failure.

Speaker 2 (57:17):
And not in the end, it's not, you know, but
it's it's it was ugly going through it, and you know,
there are some people who were impacted by that who
probably think, you know, why did he have to be
the way he was? But it wasn't an option. It
wasn't and I don't regret it, and it's not a
big deal to talk about it now because I didn't

(57:37):
keep it, it would have turned into shame.

Speaker 1 (57:39):
Right, and then it would have eaten you away, it.

Speaker 2 (57:41):
Would have yeah, yeah, no, So it was very liberating. Yeah,
but it is a little embarrassing because it's like it
doesn't come up in daily conversation and when you know,
as you can tell, it took me like five modest
failures to get to that. I'm like, oh, and there's
just one other thing that's kind of the biggest by
a mile, But that was a big one.

Speaker 1 (58:01):
Like those are career crossroads and they're really tough to navigate,
especially when integrity is involved. And I've been there too.
I have been there. Too in those moments. Thank you
for sharing that. I appreciate it. Let's do a lightning round.

Speaker 3 (58:13):
Okay.

Speaker 1 (58:19):
Career highlight.

Speaker 3 (58:22):
Career highlight.

Speaker 2 (58:23):
Last September playing the Ocean's Calling Festival on my sets
earlier in the day, Counting Crow said, Hey, why don't
we do your song? Almost woke you up in our set.
So there are forty five thousand people there. I happen
to have my daughters with me.

Speaker 3 (58:38):
They said they got to sing too.

Speaker 2 (58:41):
So I rolled out on stage front of forty five
thousand people singing my song between my favorite band and
Adam Durrett's on my left, and my two oldest daughters
on my right, and my family and the wings. And
that is as close to heaven as I've known.

Speaker 1 (58:57):
It get better, it doesn't get better.

Speaker 3 (58:59):
Yeah, good special.

Speaker 1 (59:01):
Who's the greatest singer songwriter of all time? Is it Dylan?
Did I shoot on your greatest writer?

Speaker 2 (59:07):
Yeah? I don't see, because Dylan has a changed.

Speaker 3 (59:11):
But you know who i'd put in there?

Speaker 2 (59:12):
I'm gonna put I'm gonna, I'm gonna you're supposed to
answer one. I'm gonna put Tom Petty and Taylor Swift
in there. Excuse me for sure, Tom Petty and Taylor Swift.

Speaker 3 (59:22):
They're my true Norths. But but if you're but I
kind of feel like i'd answer with Dylan.

Speaker 2 (59:25):
But my true Norths are Tom and Taylor because they
have they have changed their gears, genres, they brought their
people along with them, right there are Their catalogs are
just massively filled with moving music that that that just
doesn't that defies genre.

Speaker 3 (59:43):
I think those are my people.

Speaker 2 (59:45):
I love that.

Speaker 1 (59:45):
Yeah, we can talk about Taylor Swift later, but I
love that. Yeah for you, Yeah, what's the best concert
you ever attended? Not playing at Uh?

Speaker 3 (59:55):
That's between Petty.

Speaker 2 (59:58):
Petty used to say, you have to get the audience
ready to take what you want to give them, which
I thought was such a nice balance between like you know,
Ryan Adams like I'm gonna do whatever I want it right,
and you know bands that I don't want to name
who are so people pleasy that they just kind of
just the hits.

Speaker 3 (01:00:15):
And it's like, No, I thought that was so between
Petty and.

Speaker 2 (01:00:20):
You can be mean, I'm not gonna do it. Yeah, no,
I I it'd be between Petty and def Leppard for me.

Speaker 1 (01:00:27):
Yeah, that's gonna make John so happy.

Speaker 3 (01:00:29):
Yeah, def Leppard.

Speaker 2 (01:00:30):
I mean, that is a great concert. And Kirsen, my
wife was all She's like, I don't know if I'm
gonna be into this like eighties metal, And I was like,
you wait, and I swear she was.

Speaker 1 (01:00:40):
She was.

Speaker 3 (01:00:40):
She would have gone home with Joe Elliott.

Speaker 2 (01:00:42):
It was definitely like I had to pull her out
of there by.

Speaker 3 (01:00:45):
The time we left. Yeah.

Speaker 1 (01:00:47):
Yeah, what's the song you wish you'd written?

Speaker 2 (01:00:50):
Cats in the Cradle. That's the one I've been chasing
my whole life, you know, that's the one I've been
chasing forever.

Speaker 1 (01:00:56):
Well, you've written a lot of great songs about your
daughters and your family. I know.

Speaker 2 (01:01:00):
I keep thinking, well, I've got them all now, And
I keep telling my manager too. I'm like, I'll, uh,
I'm gonna you know, I'll pivot away and write about
the things other than family. But it's just there's more,
there's more juice in the in the lemons, good stuff.

Speaker 1 (01:01:15):
This is controversial. Okay, we both live in Connecticut. Yeah, pizza,
New Haven Pizza? I new, of course you did. Are
you fan or not?

Speaker 2 (01:01:24):
Hell? Yeah, Okay, you don't like New Haven pizza. That's
what we're talking about. Peppe's.

Speaker 1 (01:01:28):
Is it's mad, it's mad, it's fine. I feel like
it's a marketing scam, Like I don't understand why. What
the difference.

Speaker 2 (01:01:34):
Is the white clam pizza at Peppi's whole clams on
a pizza, Okay, it's like.

Speaker 3 (01:01:39):
The greatest of all foods.

Speaker 1 (01:01:41):
So do you think it's the best pizza New Haven
style pizza?

Speaker 2 (01:01:45):
I don't. I mean, I really like pizza posts in Greenwich,
you know, I like just the cheese. Did they do
pizza so well in Connecticut?

Speaker 1 (01:01:55):
Okay?

Speaker 3 (01:01:55):
In the Tri state area, giving.

Speaker 1 (01:01:57):
New York a nod, a nod, A little New York
New York's okay too.

Speaker 2 (01:02:01):
I think my favorite pizza places are in Connecticut. But
that's maybe that's just not meg Pride right.

Speaker 1 (01:02:06):
Well, listen, I like I like a lot of Connecticut
pizza too. I like Rico's and Colony Grill. I like
that hot oil fin pizza.

Speaker 2 (01:02:12):
That's all really good.

Speaker 3 (01:02:13):
That's really good.

Speaker 2 (01:02:14):
That's unique too.

Speaker 1 (01:02:15):
There's really no and it's and it's family pleasing. The
whole family loves it.

Speaker 3 (01:02:19):
But is that the best? Is that?

Speaker 1 (01:02:20):
No? The best is New York style pizza? Steven, I
don't know.

Speaker 2 (01:02:23):
Why we're wearing New York's in my favorite.

Speaker 1 (01:02:27):
It's sixteenth and seventh. It's not like the big ones,
but it was.

Speaker 2 (01:02:31):
You know that I adore food, and I feel like
you should have told me this earlier, that there were pizza, Like, yeah,
we go for oysters and steak.

Speaker 1 (01:02:39):
I know, but listen, No, I don't dislike New Haven's
style pizzas. Just so much marketing. When you come into Connecticut,
the sign says like home of like famous for the
pizza or something. This is insane, but even.

Speaker 2 (01:02:53):
The best places are really great.

Speaker 3 (01:02:56):
No, I think you.

Speaker 2 (01:02:57):
I think you're being a little I think you need
to reconsider.

Speaker 3 (01:03:02):
Let me just ask you to be clear.

Speaker 2 (01:03:03):
You've had the white I knew it. This is it.
You're like someone that's watched the movie and it's like
I didn't think that was a good book.

Speaker 3 (01:03:11):
You've got it.

Speaker 2 (01:03:12):
I think, let's have it and then you can pass judgment.

Speaker 1 (01:03:15):
So what I need to judge New even steal pizza
on is the white clam pizza at Pepees at.

Speaker 2 (01:03:19):
Peppe's and not from sales because they do a different
white clam.

Speaker 3 (01:03:22):
Okay, so it has me.

Speaker 2 (01:03:24):
Peppees just try it and then see if you feel
the same way. Again, I wouldn't say it's the best
because it's such so unique. It's like colony grills, hot oil.
It's that's like its own things. That is a wonderful,
wonderful pizza. Yes, I feel like to judge pizza, you
kind of have to just judge.

Speaker 3 (01:03:39):
The cheese pizza and see what it's right, you know.

Speaker 2 (01:03:42):
But this white clam pizza is one of the greatest
things ever.

Speaker 3 (01:03:44):
And once you've done this, let's revisit it.

Speaker 1 (01:03:47):
And I trust your food.

Speaker 3 (01:03:48):
An addend him to this PODCASTA.

Speaker 1 (01:03:50):
That's fine, that is fair. Yeah, favorite movie about a
musician or a band. It doesn't have to be a biopic.

Speaker 3 (01:03:58):
Oh gosh.

Speaker 2 (01:04:00):
Uh well, I loved the Glenn Hansford one, The Commitments.
That was really fun. That was really good. Yeah. Yeah,
that made me want to be a soul singer. And
you know, in Glenn's school and that's that's good stuff.

Speaker 1 (01:04:14):
Yeah about the Commitment, Yeah, it's a great one. I know.

Speaker 2 (01:04:16):
I gotta watch out with the kids too, that'll be cool.

Speaker 1 (01:04:18):
Did you ever see Satisfaction?

Speaker 3 (01:04:20):
No, what's that?

Speaker 1 (01:04:22):
It's I think like Justine Bateman, maybe Julia Roberts too.
They're in a band.

Speaker 2 (01:04:29):
Okay, eighties nineties.

Speaker 1 (01:04:31):
My producers are looking at me like, yeah.

Speaker 3 (01:04:35):
I don't think I've heard of this? Is that definitely
the title?

Speaker 1 (01:04:38):
Oh yeah, Justine Batman, Julia Roberts, Liam Neeson. Liam Neeson
has a special set of skills.

Speaker 2 (01:04:44):
Before the thriller genre became his go to, he was
making music movies with Julia Roberts.

Speaker 1 (01:04:52):
Maybe it's a cult cult classic. It's a fun one,
I think.

Speaker 2 (01:04:55):
No, I'll check it out. I'm a say I like
all those. I often feel that the or not. I
thought Crazy Heart was a very authentic look, you know, yeah, yeah,
you know in a way that and I'm not I'm
not like a hater, but in a way that a
star is born.

Speaker 3 (01:05:14):
Just did that, just didn't miss free You. That did
not fly for me.

Speaker 2 (01:05:18):
And the music was great and I had friends that road.
I mean, everybody did a good job to me. That's like,
sure you can watch that and imagine that that's how
this business is. But I would put on Crazy Heart
and you know, before you make a comment about white
clam pizza, that's all I'm saying. You know, it's like perfect.

Speaker 1 (01:05:35):
Yeah, final question, it's the most important to me. When
is it iced coffee season.

Speaker 2 (01:05:42):
This is going to be like your Dylan thing. I've
never had coffee, so I don't know. I'm sorry. Thank
you for having me on your podcast.

Speaker 1 (01:05:54):
Yeah, Lauren, is that the first time someone said I've
never had coffee?

Speaker 3 (01:05:57):
Yeah? Yeah.

Speaker 2 (01:05:58):
History is not a just think. I just I just
it's just one of I have plenty of vices, and
I'm English and I kind of got into tea and
I don't know, never had coffee.

Speaker 1 (01:06:07):
You don't have to apologize for that, but I can't.
You definitely can't answer the question right right because the
answer is year round. Okay, Okay, there's no season. It's
year round.

Speaker 2 (01:06:15):
And then you're like, and dunk it brought to you
by Duncan don'huts.

Speaker 1 (01:06:18):
I wish it brought to you by Duncan don'nuts. I
diver for them to sponsor us. No, that's okay, it's okay.
It's just very important to me iced coffee. But I
love getting We have had so many different answers on
this podcast. From the correct one, we've got the correct answer,
but we've also had well I think it's June to
July or you know whatever, great answers. So It's a

(01:06:41):
great question and you learn a lot about a person
by asking it.

Speaker 3 (01:06:44):
I guess so. I guess so, Stephen Kellogu.

Speaker 1 (01:06:47):
I adore you, and thank you so much for coming
on Off the Cup. I loved this conversation, and you
know I could talk to you forever. Luckily I get
to I get to you, guys, all right, thanks, thank you.
Off the Cup is a production of iHeart Podcasts as
part of the Reason Choice Network. If you want more,
check out the other Reason Choice podcasts Spolitics with Jamel

(01:07:09):
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. Rate and review wherever you get your podcasts,
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