Keep Paddling with Conan O’Brien

you and I are going to be hang out a lot any time you want to hang. I don't think that's true.

Yeah. I think I'm going to start any cold calling him. It's true for you.

Yeah. So here's the thing. When I come to L.A.

Reagan's coded when I let's have it shoot some hoops.

That's right. I'm going to drain some threes from 80 yards away. They don't go anywhere near

the bucket. No, we're near. I tell you, that's the thing. You can, and then I'll go to

the back alley comedy club with you. I think you would do better.

You would do better comedy than I would at basketball.

This episode is brought to you by Chase Home Lending.

Hey, little girl, you look so dapper today. So I was telling Julia one of our producers that

this is one of my favorite jackets. Yeah, I like that.

So I only wear it once a year on the show. I should wear it more often.

Or get another one. Do that. It only comes in gray.

No, they come in different colors, but I like this color.

Oh, you like the gray? I like this gray.

Well, I think it would look good in other colors too.

Off camera. Okay. So it gets a lot of wear.

Okay, that's good. It's good to know. It's good to know.

But it's not as hot as your leather outfit. You got good.

Actually, this isn't leather. It's sort of like a faux faux leather.

So they're actually more juicy. They just have a finish.

They have a, it's a jean finish. It's a sort of a wash that's over right.

So this is really just a jean that gives the leather effect.

Got it. Got it. So just so you know, and they're very comfortable.

So you don't get the squishiness of the stiffness of a leather.

But thank you. Thank you for noticing. You're always put together.

So we, we've hit a milestone. It is just, it's amazing because it went by like that.

Yeah, it's been a year since we launched IMO.

I know. So we finished our first year.

And we want to thank all our listeners, all the people on YouTube who have tuned in.

It's so fun hearing your everybody's comments and feedback.

And you know, my friends are always texting me with,

I can't believe you said X, YRZ.

And you run into people all the time.

I do because I'm out here in the street. So I run into people all the time who are like,

it is a fantastic show. You and your sister are so cute together.

We love the guests. And I also want to thank our staff.

Everybody here who helped produce this thing.

It is, it's been a really neat ride.

And I've said this many times on this show, being six years old and being able to learn

something completely new around a young group of people where it is,

it's changed my aging. I feel like I'm aging backwards now.

Well, it's the beauty of continued evolution in this phase of life.

I say it all the time. It's like, you know, 60 doesn't mean what it used to.

When I start counting back to what 60 was. And I think about the fact that

Dandy grandma or grandparents were this age when we thought they were old.

That's kind of a trip. But they kind of stopped.

I mean, it's sort of like they pushed the, yeah, they pushed the pause button on life once they

retired. And I just think, you know, the recreation of self and trying some new things

I do think keeps you young. Yeah, yeah. And obviously we miss mom and she's not here to see this.

But we're doing exactly what she did, right? She retires at the retirement age,

waits about six months, and then goes back to work.

Yeah, right. It's like, what are you doing? And she went right back to work right in the same

office. And I think I think that put some years on, but added some years to her life.

So, and she would be proud of of this project. She would get such a big kick out of listening

to us. Go back and forth. She'd be sitting in the back over there. Yeah. Yeah. That would,

that would have been good, having her here in the studio. But, you know, this show is a tribute

to her because of the parenting that mom and dad gave us because of the people that they were

and I think our relationship has always been strong, has remained strong. And it's

and a lot of the IMOs, the opinions we have come from the wisdom they pass down to us, you know,

I mean, it's a trip. People, I hear their voices so clearly in my head every day, guiding me

and, you know, giving me the reassurance that I'm living life in a way that would make them proud.

So it's fun to be able to share some of that advice with the listeners. And hopefully, I mean,

that's what we hope is that when you list, when people listen to the show, they hear some of what

we got to hear, you know, and that it's helping some people along the way because that's really

the goal here is, you know, to entertain, but to also, you know, share some wisdom along the way.

It really is. So this is when I'm in the airport or, you know, wherever I am, people stop me and

they just say, boy, your parents must have been really great. And so that's the real,

that's the real tribute for me. And I also want to make sure to thank all of our sponsors

this year. Too many to name right now. We don't want to take, but, and of course, the show would be

nothing without great guest. And we have another great one for this episode. Yeah. Yeah.

Conan O'Brien. I know. I know. I'm at a little disadvantage because you have a terrific

relationship with him. And I'm just getting to know him. And I feel, I feel very special.

You know, Conan is my friend. Yeah. That's so sweet. He's giggling over there. You are my friend.

I'm a, I'm a, I'm a, I'm a little jealous of Conan because you, the way you talk about him,

being such a nice guy and doing things for you, it just sounds like, sounds like me.

Are you jealous? And so that's probably why I like Conan because he's a tall, friendly guy,

just like my big brother. He's saying right now, but I think he's probably done a little

more for me over the years than you have. I know. I've been busy. I've been busy. I've been busy.

Well, let me give just a couple of flowers here for Conan. As everyone knows, he's a television

host, comedian writer, producer. He hosted three late night talk shows, a late night with Conan

O'Brien, the tonight show and Conan. And it's currently the host of the podcast. Conan O'Brien

needs a friend, which he has one in me, which I have recently learned was the first podcast

that you ever did. So he was one of the ones I felt safe with in that early stage. Yeah.

And he will be hosting the 98th Academy Awards. So Conan, come on down. Hey, it's my friend.

When you come, came in like, yeah, work to do. Yeah. Yeah. I just had a lot of sugar this morning.

So I think you probably have a lot of sugar every morning. I mean, it's not like you, you know, you

know, it's funny. This is a true story, but I have always had a lot of manic energy. And about,

almost about 10, 15 years ago, my doctor retired. So I went to see a brand new doctor for the first

time. And he's running me through the checklist, you know, of this, this, this just wants to get to

know me. And he said, he finally got to this one part of the checklist. And he said, now let's talk

about drug use. And I said, which is true, I'm never done drugs in my life. Never try to drug.

Never wanted to get into that. So I said, I've never done any drugs. And he said, let me ask you again

about your drug use. And I said, I've never done any drugs. And he said, what about cocaine? And I

said, this is true. I said, no, no, no, this is 100% true. And I said, I've never done cocaine.

And then he put his clipboard down and he said, this questionnaire doesn't work if you're not

being honest with me. And I said, I'm being honest with you with you. And he said, I've seen your

work. And he just assumed that I'm all coped up. And I'm saying this comes naturally for better

or worse. I was born this way. Yeah, this is the way I mentioned this a bunch, but my dad was a,

you know, a doctor and a scientist. And maybe after 15, 20 years of being on television,

he looked at me and he wasn't trying to be funny. He just said, I think I understand you

are making your living off of something that should probably be treated.

I said, I love you too, dad. How, how were you when he gave you that observation?

Well, I was a, I mean, I think he had seen me do the late night show. I mean, I might have been

in my late 40s when he said that. Oh my God. Yes, this was not something he said to a, you know,

this was him looking at the arc of my life and seeing that all of this nonsense that comes

out of my head and the crazy energy in another era, they would have treated me. You know,

they would have put me in a special, admitted, admitted me. Yes. That's the nicest thing you've

said to me in a while, put me in a facility of some kind. But now we live in this weird,

I mean, it's all when you're born, it's such luck. But in another era, my people in Ireland,

yeah, you know, standing around and we're supposed to build a stone wall, I wouldn't have been

helping with the stone wall. I'd have been off to the side doing bits and going, yeah, I'm

done this guy and then that. And they'd be saying, this idiot doesn't do anything. Are you unique

in your family? Because you have a big fan. I'm one of six. I will say, my siblings are really

nice. They're really smart. They're sweet. They do. They do drugs. No. They do not. I think we all

should. But no, they don't. It is, I see a lot of similarities with my siblings. We all have

sort of the same stuff and it comes in different versions. They're very creative. They're all

really funny. And then I just happen to match this particular time in history when we have

television and podcasts and places where people like me can actually do this and put a roof over

our head doing it, which I don't think existed. It took just in the last 100 years for this to come

along. Well, you said they're all funny. Where does that come from? Were your parents funny?

Your kitchen table funny? Yes. Dinner time. Everything starts at the kitchen table.

For us, it was Sunday dinners. My mom always insisted that we all eat together. We have a Sunday

meal after church. We come back. We sit around this round table and we would have our meal. And then

people would jockey for who's the funny one at the table and who can really make

mom and dad laugh. And especially my dad, when he would laugh, repressed Irish Catholics.

And you see this thing that every culture has, what's the key where they're allowed to lose their

control a bit? My parents didn't drink. Obviously, there's no drugs. There's no, no one talked about sex.

So there are all these areas that are off limits, but you're allowed to be funny and laugh.

And you're allowed to eat tons of fried ham. And those are the areas where we're allowed to

let our hair down. And so my dad, when he would laugh, my mom had a great laugh, my dad would

like hug himself. And he would kind of clap himself and hug himself and rub his hands together.

And huge fan of you and the president. And I brought him to an event I did once in Washington,

D.C. And he got his picture taken with you guys. And the president was so nice. He said,

yeah, I hate Conan. Dad, dad, get over here. And he made it all about my dad.

And my dad, for the next 15 years of his life, just had the picture with you guys and your

daughters were kids then, but they were in the picture too. And that was something I think,

I think he lived another 10 years because of that. Talked about it nonstop. Oh my gosh.

So but so much of my career was, I think it all began with trying to make the parents laugh.

And that's where things start. And you can then later on, it can become, oh, I'm hosting the

Oscars or I've got a late night show where I'm doing this big deal or that big deal. But it's

really no different. You're still in some way trying to make them laugh. And I think just like the two

of you, you're probably for the rest of your life going to be trying to live up to what your mom

or your dad would want. And that stays with you. And I'm a big believer in, we lose these people,

but we don't lose them. Oh for sure. They're with you. Oh my gosh. And they're why you still,

a lot of people would say, you two are good. You're good. You can let your hair down now. You can,

but you are trying to still live up to that standard. And I think that's what I'm trying to do with my parents.

Hey, Mish, you remember we used to go on road trips and mom used to meticulously pack the

truck a car with plenty of food like fried chicken and it never tasted better than in the back seat

of a car. Man, with coming out of the tin foil, you know, it was really good. And it would pound

cakes, cookies, the whole nine. And I remember it'd be a treat to even get flavored potato chips

because you know, mom would say, let's just get the plain ones. No barbecue, no salt and sour.

Not a lot of extras in the Robinson house. Oh, no. But now, you know, the difference is night

and day when I travel with my family, what do you think? Yeah, I mean, you know, mom would have to pack

for us staying in a place a long time. So it wasn't just snacks for the car because you couldn't just

get anything you wanted. So she had to come on vacation with everything she needed for the week,

which seemed like a hassle. Yeah, it was like we had the whole trunk of a car was a grocery store.

Now, are you particular about your snacks? For example, I like my cheddar cheese, but I want to

cut on blade number one. Really? What about you? Yeah, I like mine thin. I like my cheese cuts

sliced thin. I don't think I'm that particular. I think a snack is a snack.

Well, now when I travel with the family and we book a stay on Airbnb,

I have the convenience of having our fridge stocked with our favorite snacks or anything we might

forget or don't have. We could have used that when we were a little, how about it? As a matter of

fact, Kelly always uses Instacart when we're on vacation. But with this new Airbnb plus Instacart

partnership, I love the convenience this feature within Airbnb services to order our groceries on

Instacart. The partnership allows you to seamlessly book with your Airbnb reservation before

or during your trip. I might do some cooking during my stay this time because our groceries will

already be there when I arrive, making it feel like home from day one.

You're manic, you're silly, but you are wicked, wicked smart. Oh, I mean, yeah.

And so was your family. I mean, I love hearing about the fact that your mom went back to law

school. Can you talk about her? Yes, my mother. She's a badass. So both my parents were the first ones

in their families to go to college. Everybody's got an immigrant story. Everybody comes from

someplace else. Let's say that again. Last night, I was trying some Oscar jokes out in a comedy

club and I took an Uber home and the drivers from Jordan. He recognized me and we started chatting.

We had the greatest chat on the long ride from East LA back to my house and just a wonderful talk

and he put me on the phone. He said, can I call my daughter and I said, sure, she's 25. So he's a

Jordanian immigrant. His daughter is taking her MCAT. She's gone to college and I just was telling him,

this is our story too. We came to this country late 19th century and there's a lot of people

not too thrilled to see the Irish in Boston. So my people moved out to the central Massachusetts

and worked hard and I think had good values. And then my mother grew up in Worcester, Massachusetts.

Her father directed traffic in downtown Worcester. One of the funniest people I've ever met.

I remember my grandfather when they were well, we called him Huffer because he knew some dance moves

and so everyone called him Huffer. And you got none of those jeans. I didn't get those. Look,

if I knew I was getting slammed on the show, she would not have been, okay, you don't have to take

that fact. Apparently I do. Yeah, apparently I do. So my mother worked hard and she got a full

scholarship because they didn't have her father earned $55 a week. So she didn't have that kind of

money. She got a full scholarship to go to Vassar, which is a big deal. And then she went to Vassar

and when she graduates, she gets a full scholarship to go to Yale law school. She goes to Yale law

school. She leaves and she goes to a big law firm in Boston. She clerked for a State Supreme Court

Justice thing. But she also raised, this was after she had kids, right? Well, what was the timing?

It was before she had kids and then she just started a law firm when she started to have kids.

And then she had to take time off because she had a lot of kids. She had a lot of kids come,

kept coming and coming. I mean, I swear to God, I think she had a child every four months.

Medical science is still trying to figure out how the Irish can do that. But yeah, I think my

brother Neil is 61. It was born in 61, Luke and 62, me and 63, Kate and 64. I mean, no one ever

knew my name in that house. And then there's Kate, Jane, Justin, and she went back to work.

Well, she went back to work after. So how was she? She went back to work when I was about,

I want to say nine. I was not happy about that because I love coming home and my mom was there.

But she went back to work. But she had stories of the early days, early, you know, 1960s when

she is a graduate of Yale Law School and she's working at a big firm and she would go to a meeting

with other lawyers. And then they would take a break to go to lunch. And they would all go into

the dining room, but she couldn't go in because it's men only. And so I would ask her,

do that make you angry? And she said, oh, no, it was just the way it was. And they set up, she said,

they set up a card table for me. I sat outside. And two of the lawyers were very nice and sat with me.

And so there was this, I think it gets overlooked sometimes, but there's a thing that happens

with people who are on the front line of change, they sometimes you think they're going to be angry.

Sometimes they're not because they think, I don't have time for this. I've got to win.

I got to get the win. So she got, she worked hard. She became a partner and I think she was,

you know, maybe the second or third woman to ever be a partner in this big law firm.

Well, you may make a good point that, and I want young people to understand this because sometimes

when change has happened and the younger generation doesn't know what it takes, they can be

a bit judgmental about what it took for those to the kind of mentality, the kind of, because

there's some young women who say, well, why didn't you speak up and why didn't you use your voice

or look at the older generation and say that, you know, you're allowing something to happen without

understanding the context of the growth. Yes. And I think that's why sometimes we get in the way

of change because the younger people want it, think it should look different. They think the

attitude should be different. And you just, your mom knew what she knew, being the first woman,

the only woman to ever practice law. And then to make partner, you know, what kind of compromises

your mom had to make to get there. And she needed the job too. She had six. How many of you all?

I don't even know. I've tried to count my siblings and there's just two more, too many. I can't

do it. But the, yeah, it reminds me a little bit of that, there's that Jackie Robinson ethos where

because he was the first, he felt he had to be completely above reproach. I know a little bit

about that. Yes. Well, that's what I'm saying is the, you know, I think I could tell when you and

I took a trip once to visit a big giant military base in the Middle East. And I, it was an amazing

trip. It was an amazing trip. I could tell that you and your team were being so careful that

everything is done by the book that there's no, you know, that if, if, you know, there's no perks,

there's no, I was really impressed with that. And I, it occurred to me then, oh, I see, everyone

feels we need to be so, so, so far beyond. It wasn't even a feeling it was the truth.

It's the truth. Yeah. I mean, there's absolutely no way that the behavior in this current

administration would have been accepted by the first black family in the White House.

So fortunately, it wasn't difficult to do because we are those people. It wasn't difficult to

follow rules. It wasn't difficult to have high standards. It wasn't very difficult because in

order to get where we are, as you're, you've seen in your mother, you don't get here without being

damn near perfect. Yeah. We don't, we don't get to fail. Right. Two, three, five, seven times.

We don't get to file bankruptcy over and over again and still be considered a successful business

person. Right. You know, we don't, we don't get to not be at the top of the class.

You know, every, every, I has to be dotted. Every T has to be crossed. And your mom was among the first

to begin to pioneer that, that firstness. Yeah. And I think because they, you know, the big game

changer for Irish Catholics in my parents' generation was John F. Kennedy. And you've got this very

glamorous first family and their Catholic and Irish. I think that made a huge difference

for people in my parents' generation and made a big difference for me because it's, they made it

cool. Yeah. They made it cool to be Irish. And then I made it uncool.

Speaking of John Kennedy gave us, I took away. Were you a cool kid growing up? God knows.

How can you ask that? You know, you know, why would you ask that with a straight face? Here's why,

here's why when I first met you, you were surprised how tall I was as I of you. Yep.

In the first thing, I thought, I'm sure he was an athlete in high school and one of the cool kids

and funny in the locker room that kind of thing. So I want to give that. Tell me what happened.

Let me explain what happened. Let me explain to you what happened, sir.

I was, my, my height came late. So I was one of those guys who had a growth spurt kind of later in the

game. Okay. So I recently saw someone found footage of me in, when I'm 22, I'm just at a college,

and I think I look like a 14 year old, yes, of undetermined gender. And I, I look at that person

and I think you're 22. So you weren't, you didn't get your height then? No, no, I had my height

by then, but I was six four. When I moved out to LA to start my career, I was six feet four inches

tall. I think 155 pounds. Okay. Now I ask any engineer who's listening, do the math on that structure?

It will collapse. It's gonna break. It's gonna go down. And if a moth lands on it, it will collapse.

So there was no, you know, people sometimes say, because I make fun of myself a lot,

and they say, well, that's kind of an act. And I go, no, no, that comes from, I think obviously

they know now your core personality is formed fairly early on. And then you, you do a little finishing

touches to it. But by the time you're 15, 16, 17, it's there. And those were years for me where I

didn't feel, I was not cool. I was not a good athlete. My brother Luke, who's a year old,

than me, is much smarter than me. My brother, Neil, was much stronger. And I just thought,

I don't have anything to offer. I really thought that for a long time. And it took me a while.

It took me a long time to kind of put it all together, which is why when I say I find myself

kind of ridiculous, it comes from a place of honesty. Like that, that was my personality growing up.

And so I did not, I was not, I was funny with my friends, but it was not the class clown.

The class clown, I maintain, you know, usually ends up in like a motel shootout, you know,

the class clown, the guy who gets up and changes the clock forward and is, you know, throwing stuff

out the window, they're in prison soon after high school. I was not that guy. I was joking around

with my friends. And then when the teacher came in, I was really quiet and a nerd. So that's my

story. But it got you to Harvard, which is where a lot of funny nerds go. Yeah, I didn't even,

you know, the irony is a kid I dreamed about being in show business. And I loved comedy. And that's

how my dad and I really bonded, you know, you're always trying to like, yeah, I think a lot of

boys look at their dad and think, what's the, how do I key into this person? How do I,

you know, he can be formidable. I'm not sure how I can really connect with this person. And then

we would watch comedians together. We would watch comedic movies. And I would see him laugh. And

that was where my interest started. And I started doing things and loving the idea of getting to

do comedy. And then I thought, I'm in Boston, Massachusetts for a client. Nobody within a thousand

miles is in show business. I've never seen anyone in show business. That's not a real thing.

I got to find another way. So I decided I want to go to a good college and make something

myself. So I'll just become a grind. It's not a glamorous story, but I was a grind. And I was grinding

it out in my little room, memorizing things. And I, uh, what did you think you wanted to be?

I thought, well, I'll be, I will be a serious person. I'll be a, you know, editor of a newspaper

or I'll be an academic. What would you make? I was, I was loved English. I was a history and literature

major. And I thought, that's what I'll do. So I get to, I achieve that goal. I get into Harvard,

didn't think I was going to. I did. I think now it's time to become the serious man of letters.

And someone said, I'm going to go to this meeting of something called the lampoon. And I said,

I've heard of that. That's pretty famous. Yeah. And I said, maybe I'll tag along. Was this first

year? This was first semester freshman year. I was at Harvard for two, maybe weeks. And so I went

and there's this kooky little building there. And I sat on the floor and they come in and we're

all sitting on the floor. And they talked to us. And they said, it's very competitive. But you

all have to submit funny stuff. And we'll see what happens. And I said, I'll give it a try.

And made it through the first cut, made it past the second cut, made it through some other

things. And then the next thing you know, I'm a first semester freshman and I'm on the lampoon.

And that's I was hooked. Let me just explain to the listeners. I equate the lampoon to like the

Harvard Law Review of comedy. I mean, it is considered very flattering. But it was a it was a

huge deal. And so many famous funny people and great, right, John Updike,

you know, Robert Benchley and the guys that created national lampoon and did animal house. And

I mean, it all came, all this great stuff came out of the lampoon. And it was unusual to

be selected as a freshman. Yeah, I was it was it was a little bit unusual. And then I gave my whole

life to it. You know, it was one of those things where I I felt like I had a calling. Up until

that point in my life, I thought anything that I achieved, this is very Catholic, but I'm sure it's

not just Catholic. It's tons of religions and cultures. I thought anything good has to come

through suffering. Yeah. So I really suffered to do well on the test. I really suffered. I

really suffered. I was had a lot of anxiety. And then I would do well on the test because I suffered

this was the first time I live that I would say, Hey, what about this? And people would say,

that's great. And I'd say really that was easy. That was easy. I had fun. Wait a minute. I had

fun. Yeah. Didn't take a lot of time. Yeah. And now people are reading it and laughing. And I'm

getting that same dopamine hit. I get when I make my dad or my mom laugh, what's this all about?

And then I was hooked. I mean, I said I don't do drugs, but this is to me the most powerful drug.

And it goes for all of us. When you find that thing that gives you joy and then you realize

that in whatever hundreds and hundreds of years ago, people thought the greatest thing would be

able to turn lead into gold. I think the closest thing I've seen to that in life is when you can

do something that gives you joy, but it gives other people joy too. And then someone hands you

$20 afterwards a check. I hope it's more than $20. But maybe that's just a little bit more than

you'll make for the Oscars. Yeah, probably haven't even looked into that yet. But I'm sure I'll lose money.

But that is to me, that is magic in our time is when you can do something that and you both

experienced this where wait a minute, I'm having fun. I'm doing what I think I was put here to do

and other people are thanking me. That's insane. So that to me was when I got that first hit. And

everything has just been an extension of that. When I called my parents senior year and I said,

I have to give this comedy thing a try. And I talked to them as if I was becoming a monk. I said,

look, there's probably no money in it. No one will marry me. Yeah, no one will marry me. And that was

true for a long time. And then, you know, it's really just all that happened then. And then

everything else has just been moving the little chest piece a little further forward. And now

I'm here talking to the two of you. So that's the miracle of it all.

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After Harvard, did you immediately? Yeah, I had a good friend in school. I knew that the

thing I had to do was go out to LA, that we had to go that I needed to go out to LA,

but not New York. It wasn't a lot of work in New York. There really wasn't a lot of work in New

York and a lot of the work was in LA and so I said to a really good friend of mine in college,

Greg Daniels, who went on to create, I mean, most of the great TV shows was 25 years, the office,

Parks and Recreation, King of the Hill, I mean co-create that. He's just had this huge career,

but at the time we're two pretty nerdy guys and we're newly 22 years old and I said,

you want to do this with me. One of the things that was really key was Greg's a really funny guy,

but he was also like an ethical good person and I thought, I don't want to go out there without

a friend who's with me who I know to be a really high quality person and yeah, rule number one

is gotta be funny and he's clearly hilariously funny, but also really good work ethic and a good

person. So we went out together and you know, we started, we got some work on a show called

Not Necessarily the News, which was on HBO and this is HBO back when if you wanted to watch the show,

I think in those days, I'd have to tell my parents, you need to go check into a motel.

Hey, check out my show. What's it on? Is it on NBC? Yeah, you need to go to a motel.

Yeah, and yeah, it was like I was working in Pornow or something. We'll just clean that up. Anyway,

it was, but it was a start. We got started and then the first and earning a salary, earning a

salary right away because the comedians we have on and the performers, they all go out. Yeah,

we do the same thing, but they're struggling for a period of time. We were lucky. We got that gig

right away. I knew I wanted to perform. So I started going to do improv at night. Wow. And so I

would work in the day and write and then I would go to these little places where you put a $10 bill

in a jar and then you get up and you do improvisational scenes with other people and my first time that I

went to an improv class. I noticed like I was looking at everyone else because it's the same thing if

you're an athlete, whatever you're doing, you look around and you try an eye size up,

size up people. And who's the one who's like, okay, they're good. Yeah, they're good. I walk into

this place that's on La Siena Ga, the Coronet Theater and it's this tiny little room and

there's a teacher there, Cynthia Sighetti and you put your money in the jar and then you get up

and she had us doing different exercises and I'm looking around the room and I'm going, no, no,

who is that? She's good. She's really funny. Her name was Lisa Kudrow going on to be in

France and I didn't know this but at the time she's looking around the room doing the same thing.

Yeah. And she's like, okay, that guy, the guy that's 155 pounds. I was like, how was it going to ask?

Now I weighed 156 pounds. I had a bagel. And so then I started working with her and we became

really good friends and I started meeting other people. Then we lost the job that we had because

they headed down scale the staff. So I think Greg taught SAT prep and I went to work for Wilson's

House of Swade and Leather. Really? Yeah. And it wasn't even. No, no, I'm telling you.

Of all the shops, you picked Wilson's House of Swade and Leather.

You know, I want to give them a plug. I think I went to a temp agency and they assigned me there

and they didn't put me on the floor because I did not look like a guy who could pull off any kind

of leather. So they put me like in an office situation. And I wasn't too happy during that period

of my life. But then we got another gig and then we ended up on Saturday Night Live. So we

moved back to New York. And then I go to this. So you end up writing for it? I'm writing. And then

and then I'm on the Simpsons and then I was always the writer who would get up on a table and

act things out and make the other writers laugh. And so when it came time to find someone to

replace David Letterman on his late night show, my I worked for Lauren Michaels and I give him

all the credit. He told NBC. You thought about this guy Conan. They said the writer. Yeah. And

with the hair and the weird name. And then he said, you know, I'm just and they said, well,

Lauren, if you'll vouch for him, he can audition. And so I auditioned and I had a really good audition

because I didn't think I had a chance. Yeah. That's always the way. And so I thought I'm never

getting this. This is the biggest star on television. Next, you know, I'm going to replace him and

I'm just this guy who's 29 years old. I'm still, you know, like, oh, my skin broke out again.

It's still happening. And then I just went into that audition and had a blast.

What do you think prepared you? I mean, I think late night talk show hosting is one of the hardest

things. I mean, it's just hard being on the show. I think what helped me the most

is at the time people said you need to be a standup comic, which I had never done. I'd done a lot

of improv. They said you have to be a standup comic to be a late night host. And I found that the

improv training is all about looking at people and listening and looking for what's funny organically.

So I found that to be hugely helpful. Yeah. I've heard you talk about

being able to take advantage of all the great luck that you had. And that warms my heart because

as a coach and as a player, as an athlete, you're always taught that the most prepared person

is also the luckiest. Yeah. Yeah. It's that old saying you make your luck. I think, first of all,

I got just the time in which I was born. I am a poster child for incredible luck. I've been

very, very lucky. And I give it up for that. I also know that I work really hard and I prepare

and I try to treat people the right way. But I get very angry when people don't give it up for luck.

And I'm also really aware that, you know, as a, you know, what was my path like as a white male coming

up in the 1980s, 90s, a lot easier than a lot of other people in comedy and probably in any

profession. So take a second, give it up for that. Yeah. Don't have an attitude about it. Be

grateful. And then, um, and then don't shut the door on everybody else. Oh, no, shut the door.

Shut. I disagree completely shut that door and nail a shot.

Once you get in, don't let anybody else in. That's the message of this episode. Yeah. No,

exactly. Yeah. And that's one of the things. I mean, I noticed it today. I show up and you've

got all these great young people. There's great music playing. Everyone's, it's, yeah, everyone

looks like they're, you know, 20, 21, 22. Uh, and I, I get, except for Dan, except for Dan.

Yeah. Dan and listen, you served your country in the Korean War and we appreciate it. 110

years old. But I, but I feel, I get so much energy from young people. And whenever,

when I, when I see young people that are really funny, I choose not to be threatened. I choose

to be excited. This is this person, this guy, this girl, this person is great. They're terrific.

They really make me laugh. Um, I want to enjoy them. I want to try and help if I can.

And, uh, and just, just anything, you know, people, I know your, uh, your husband feels the same way,

but I'm always preaching optimism to my people. And I, and cautious optimism. I always say I'm

like a 51, 52% optimism. But I do say the world has always been filled with corbalness. There's

always been trouble. Um, and this, when young people preach to me, it's all over or say it's all,

it's, it's the end of the world. And I'd say you have to understand this is the way it's always

been. Yes. And this is how it feels. It kind of reminds me of this great scene in the movie,

The African Queen, Humphrey Bogart, Catherine Hepburn, they're in his boat, they're lost in the weeds.

It's a great metaphor for life. They're trying to get out. They're trying to get out. He's

pulling the boat with a rope. It's covered in leeches. He gets back in the boat. And finally,

he gives up. And she gives up. And he says, we're never getting out of these weeds with this boat.

We're never getting out of here. And they give up. And they say, we're just going to die now. And

the camera starts just, they kind of pass out. And the camera slowly pulls up. And you see,

it starts to rain. And you see that their boat is about 15 feet from a massive river. They just

don't know it. And then the water rises. And when they wake up in the morning, they're on the river

and they're safe. And I always think about that. I think there've been probably 35 times in my

life when I thought dead on the boat. I thought I was on the boat and I'm dead on the boat. I am

not going to make it through. I'm not going to get to the college. I want to go to

it's over. Now I'm in the college, but I'm not going to, I made that, but I'm not going to

get the career. Then you get part of it. Oh, no. I've got this late night show. But critics hate

me. Uh-huh. And everyone says this was a mistake. This kid who gave him this job.

There's no way I'm going to make it. Everyone's saying, you'll make it a few months, but then you're

out. And then I make it past that. But then later on, I get the tonight show. And I think,

now I'm in good shape. Nope. That blows up. And I thought, now it's really over. No, it's not.

It keeps happening over and over and over again. And then it's just learning

to roll with it, to roll with it and say, okay, what's my next opportunity? Reset,

recommit and look for the next opportunity. And that is something I try to impart to my kids.

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My mom really like meeting you. Oh, that's nice. She really like meeting you. So we,

you know, and I used to, I live a train ride away from her. So I visit her all the time and we

talked, well, yeah, it was really fun getting together and seeing, but that Conan, he was just

such a nice nice. So you should, you should know that. Oh, well, that's huge for me.

That must have helped you land a beautiful wife. I don't know what I did there. I just got,

yeah, my wife lies is pretty incredible. How'd you guys meet? We met. I was, I was out doing a

field piece and those, how those work is, there's silly idea. I say, okay, I'll do it. And then I show

up some place and we, we shoot cameras out. Was it, were you in it? I was in it. It was a bit where

it's a long story, but there was a really, we decided to be very funny if I went to a top

advertising agency and pitched a terrible idea. I just love that I was, that I was, and, and,

you know, my favorite spot is me being very confident about something that's really stupid.

Okay. And so I went, and so it was my idea was, most of my idea was someone else's idea,

but my job was to go in there and go, let me tell you something. And these are the, these are the

people that do like, you know, air Jordan ads, the best of the best in room. And I'm supposed to

go in and pitch them the worst idea and have total confidence in it and almost treat them with

contempt if they don't get what I'm saying. So I go into this room and I start doing my thing I do

and I do one person, one person and then I start talking to this woman and I immediately stop

being funny. And I just start saying, oh, so, oh, okay. So you, and then did you write a,

so, oh, I see. So you got your degree and, huh? And then she went, yeah, and I was like, no, no,

we'll see. Yeah. But what I did was I, I studied this, but then I did that. And we were just talking

about the most mundane stuff. It wasn't comedy. I wasn't even trying to be funny. And my producers

or they got the headsets on. What is happening? What's he doing? This is death. What's he doing?

And then we chatted for a long time. And then I finally, I finished up the segment. And then

I, my head writer, Mike Sweeney, who's still my head writer and working with me on the Oscars

and does an amazing job. But she was like, what was that all about? And then I said, I don't know,

but maybe we should get everyone's contact information. And he said, why would we need their

contact information? And I said, I don't know, editing. He's like, that doesn't make any sense.

Editing. What are you talking about? But the next thing you know, we just start,

it's, we just start talking on the phone. Yeah. So we didn't even have a set, we didn't,

well, that's not even a date. We were just mad. And then I just, we just talked on the phone.

Were you? I was, I'd be 35. I was no spring. So you completely ruined the bit because

they sell them. They sell it to fit. But you know, it's great. You can look it up. You can say

Conan meets his wife. Conan meets Liza. And you can see me. I look still like a, you know, now I,

I'm 35. So I looked like a 20 year old girl. And, and I'm there going, oh, hey, how are you? And

you can see us talking to each other. And it's online. And I never watched it. Because I know

what the real experience was. I don't want to see it. But we ended up, you know, dating. And then

we got married and kids. And it's been, I think we got married in 2002. So I didn't go to a good

school. I can't do the math. Yeah. I'm not even trying. That neat story. It's a great,

yeah. And it was really nice. And, you know, it's crazy. Liza's mom watched it at home.

She stayed up and watched it at home. Her dad was like, I'm going to bed. I don't need to see.

And she was like, our daughter is going to be on national television. The bit's airing tonight.

He didn't know anything about us. You know, we hadn't even shattered yet. We had, we had met,

but that was it. We hadn't even talked on the phone yet. But Pam, my wife's mom,

she stayed up and she watched it. And in the morning, she said to Jake,

unless that guy's an ax murderer, he's going to be our son-in-law. No way. And they said,

she said that to more than one person. And they said, what are you talking about? Yeah. That

that TV show host who had a brief exchange with your daughter is going to be your son-in-law.

And she went, I just think that's what's going to happen. Wow. And happened.

She knew. She knew. And I know that Liza just lost her mom. Yeah, she lost her mom. I'm sorry.

But, well, you guys have been through it too. It's just one of those, it's too profound to even

contemplate. But I think that is some consolation is we, uh,

these people are with us. They're in us. That's right. Like we didn't lose them.

They're, and I really believe that. And you don't even have to be spiritual to believe that.

They imprinted on us and they're with us. So you're always going to have your mom.

I'm always going to have my parents. Liza's always going to have her mom. They live on through us.

We just lost Catherine O'Hara, who is one of the, you know, maybe possibly one of the,

I mean, not possibly, but one of the great, great, great, great comedic actresses of all time.

And at the same time, one of the best people, just a lovely, lovely person and talk about walking

the walk. She really showed up for everybody. And Martin Shorten's gave the eulogy and he just said,

she's with us. We didn't lose her. She's, she's with all of us. She imprinted and her work is with

all of us. And so that's what I take away from. Yeah. And sometimes I, I literally,

my mom comes out of my mouth, you know, and I'm noticing it more and more when I say something.

And I was like, that was mom. Yeah. Yeah. Yeah. It's like I even, I've, I hear it. I was like,

oh my God. She just, yeah. Yeah. Yeah. Yeah. So, so, um, well, I want to talk about the Oscars

because you said something right when you came out that you went to do, you went to a comedy club

to try something out. Yeah. Yeah. Can you talk about that whole process to somebody like me who's

sort of not in the, and, and, and probably are listeners who don't get a chance to talk to someone?

If you explain to me how to be an athlete, then I can do that. You would work with me for a five

year period. Listen, I'm, I love developing talents. Okay. Well, I have no talent in that area.

So good luck to you. Perfect. But, um, I have you making shots in. Oh, really? Two weeks. Yeah.

Two weeks. Yeah. Yeah. Yeah. Really. I like to be that guy that's way, way outside,

taking up crazy three point shots that don't go near, but with total confidence.

I love to shout style stuff out when I'm doing it. And a freeze. And yeah. And then freeze and do

that look of like deal with it. And it doesn't even hit the rim. It misses the back door. Okay.

That's the next bit. That's the next bit. Yeah. That's it. Where you have a coach who's working

with you for weeks. And you have all that added to that. That's all you have. I did this. I did a

thing with, um, Magic Johnson. We shot a thing where I think we played a game of horse together.

And I'm just being such a clown. Um, and, but he was so funny, making fun of me. The way I shot,

the way I moved, he starts to imitate me at some point. It was, that was a dream come true.

Um, the Oscars, uh, one of the, there's a lot of different parts of it. And you start thinking

about different bits and what could we do for pre tapes? What could we do? What kind of production

number could we have? But you're always thinking about jokes. What could the jokes be? And you really

want to test them. And one of the ways to do that is to go out to clubs. And what I like to do

is go way, way, way, start way far out. So we went to Covina, which is way out there. I mean,

I think I was driving for almost an hour, got to Covina and you go into a club and you're a surprise.

And then you read a bunch of Oscar jokes. And it's fun because you make them part of it. You say,

look, if you guys laugh at a joke that isn't good, that might convince me to do it. And then I

die on the Oscars. So don't do that to me. And they're laughing at the part where you're not even

reading the joke. I love that. And I've gone to a couple of clubs like that. I did one last night.

And you just go way out there. All of them are the same. They're the same in that you're in some

back room or an alley standing around with other comics. And you, this is less than I've learned

again and again and again, which I actually find kind of filled with hope, which is you think you've

gotten to this other level. What's I'm hosting the Oscars. And I'm going to walk out at the top and

have a tuxedo. But I'm in Covina in an alley. And I'm hanging out and someone's got a ventriloquist

dummy. And I'm waiting for my, you know, I'm waiting for my turn to go out there. Did you?

You did that. No, I didn't. You did that. I did not. Food told them. What? I don't know what I

got. Craig loves control. I honestly, I swear to you. I swear to you. I don't trust you. You're

too funny. We've been talking about this episode after episode. You don't. I do not. He is, I think

the last person who believes that ventriloquism is a lost art is an underlying to bring it back.

Vehicle. When you see a good ventriloquist, it is really funny. How about it? I'm going to

sigh. When you see a really good one, it's really funny. It's so funny. See? Okay. Did you put

them up to this? I don't know. I don't know anything about this. You're linked to ventriloquism.

I swear to you. I swear to you. I would tell you. No one said. Yeah. I did not do that. I

just mentioned like that's how kooky it is when you're in the alley. And I love that. I love that

it's this constant dance between put on the tuxedo and you're in an alley in a t-shirt and jeans.

Does your nerves get, I mean, I mean, I watch you walk on stage to this audience of every famous

person on earth. And you know, they're not a regular audience. They're not a regular. They're

nervous. They're looking at themselves. They're very self-involved and self-conscious. And you're

out there to be funny. I mean, does that change the nature of it? It's very different. Yeah.

It's a very different audience. Like when we would do the White House Correspondent Stinner and I

did that once under your administration. And I remembered I got to sit with you and it was really fun

because you know, you were so nice to me that night. We're sitting up on the day. But that is not

a normal crowd. Yeah. That is a crowd of people that think they're the coolest people in the world.

And they're there. They're thinking a lot about their own world. And you need to be funny.

But you can't act like you know too much because then they'll resent you for that or think you

don't belong. And so everything is this incredible long period of preparation to gauge what's

going to work in that room that doesn't go too far this way. It doesn't go too far that way. And

and I've talked your husband about this. They make you follow the leader of the free world. He

goes first. Right. Really? And kills it. Right. And then before there's usually they don't. Yeah.

Yeah. Well, I know. The format. Yeah. Yeah. Yeah. It usually works well in the best

interest of the host. The president we're discussing. Unusually good at that. And then he would

finish like drop the mic, crowd going crazy. And a voice would go, well, I said, I'm a Colonel Brian.

And you're like, well, that's it. And you're walking up. And you see people like, what?

Who would go now? And so you got to wade through that a little bit. But it's all calculating

for what's the assignment and the assignment is with the Oscars like the White House correspondents

dinner is think about that room and calculate it's not you're not at a club where they are there

to get a drink. And then suddenly you pop up and they're really thrilled. Yeah. They're not,

you know, if you go to a high school and they're just losing their mind that you show up,

that's a very different crowd than now I'm going to speak to a bunch of, you know,

a list people who don't really like to give it up for anybody. But it's all just a calculation.

You got to calculate and then have fun. Do you like that risk? Does it feel like, you know,

I know how to be, I know, like, this is you on some high wire. Do you feel, does it?

I like, I like, I think I must like that to some degree because I keep signing up for things like that.

And so that's a problem. And when it's three o'clock in the morning and I can't sleep,

um, lies as like, maybe we don't do another one of these. But, um, but I do like, uh,

I think the trick is to figure out a long time ago with I'm having a good time.

It thinks tend to go well. Yeah. It's almost unheard of for me to have a really good time

up in front of people. And people after would say, well, that was awful. Yeah. If I'm enjoying myself,

so I just keep trying to think of things. I want to tell a joke. I really like. Yeah.

Now they may not like it, but if I really like it, you'll crack yourself up. I will crack myself up.

And then I'm like, okay, well, you know, this job didn't pay much anyway. So I had a good time.

And that's kind of my mission is I want to think of things and do things that I enjoy.

And I think instinctively we like to watch people having fun. We like to watch athletes

who are having fun. Yeah. Right. You know, they're really like

when they're playing well, they're enjoying themselves. It's fun to play at that level. It's fun

to give a great speech. It's fun to, um, be up in front of people doing what you feel you were

put here to do. So that, that part I really like. And it's just doubling down on that. How do I

figure out? And if something starts to develop, and I think I don't really like doing this kind of

don't do it. Do you feel like comedy is more fraught these days? I mean, it just, you know,

yeah, I think it's talk show host or not. Yeah. I mean, I obviously, I, I friends with the other,

the host. I'm not a one of a late night host anymore, but I'm friends with them. And I think

they're all very talented. They're really good people. Um, and they're in a tough situation

because of your job is to go out and talk about the news every day. And I was never, um, you know,

strictly a comedian that live off the news or did, you know, I usually try to find things that

were silly and funny outside of the news. But we also had to do the news. And

and things are so divisive right now. And I think it's got to be just a really tough task. Yeah.

And, um, I do have empathy for people who are trying to figure out what's funny in this because

I know just as a citizen, I get up in the morning and I look at what happened in the news. My first

instinct, I like to be funny, but my first instinct when I read the news is nothing here gives me

joy or is making me laugh that hard. And that makes me think of ideas outside of the news about

everyday life or something. I've, there's a weird ad on TV that cracks me up. Those are the things

that I probably look for. But, um, if you're doing one of those shows, um, how do you not talk about

it? And then, uh, how do you not wear your heart on your sleeve and maybe get mad or, you know,

so it's, it's, it's difficult. It's difficult. On our show, we have an audience

question, a listener question. But before we get to the listener question, I need some development.

You've been in the podcast business for a long time. It feels, well, actually, no, not that long,

but yeah, I guess kind of longer than IMO. Yes. Okay. Yes. Any tips, any best practices?

What is it about the podcast that you like doing that might be helpful to, uh, I won't say

young, but fledgling podcast or like yourself, you are younger than me. No, I'm older than you.

Yeah. He's my older brother. Yeah. He said older than you. He's an old man. I was probably on

campus when you were on camp. I was probably over in, uh, the gym that played in your basketball team

when you were a freshman. Yeah. Yeah. Um, so I'm older than you are. So you were in the gym playing

real sports. When I was in a, you were at the lampoon. I was in a, a weird castle.

On my normal street, thinking of something weird and giggling. Yeah. Um, and I probably would have

preferred to be over there. He asked me, yeah. You know, uh, who's the cool one really? Um,

yeah. Wow. That's incredible. I, I thought you were maybe 32 years old. Oh, incredible. Yeah.

Thanks. Uh, and a ventriloquist. Uh, but I'm, butting ventriloquist. Uh, I'm with you on that.

I'm going to help you. I'm going to find you the right dummy. I'm going to get you a good one.

We need to teach you two because I want to see you do it. Um, I think, uh, oh, I mean,

I don't know the answer. I know it works for me. Okay. Which is, uh, and you're doing it. Great

snacks out there. Ever. It starts with the snacks. It ends with the snacks. Okay. Don't let this

one too many kale chips. You know, you got to have some good, and then some of them have to be

bad for you. I mean, that's no kale chip. No kale chips. No high fruit toast. This or that.

Yeah. I know. And you want to have, um, you've got that. You've got good snacks.

Is a really good vibe here. Like it's fun to come here. And I think if that's a big thing,

you want people to come into the store and want to walk around and check stuff out.

And so that is all working. And you two know each other so well. You can finish each other's

sentences and there's a good bond here. So that's all good. And to me, it's like, I don't, I mean,

I think I'd be a fool to give you guys any advice on what to do that you're not doing.

I mean, um, it'd be nice if I got an expensive gift on the way out. I'm just putting it out there.

Okay. You know, okay. I mean, like a watch. Okay. Good watch.

All right. Like a Patek Philippe watch here. You can have those. That watch weighs more than I do.

I could drive that watch home. It looks like a car. Um, no, I, I, I think, uh, I mean, it's,

it's all about, uh, enjoying yourself. Again, I'll go back to that same thing I said about

the word show or doing a nightly show or anything else, which is talk about the things you

want to talk about your passion about. I think passion and authenticity works better than anything

in this format. And you're doing it. So I don't, you know, uh, other than stop lying about your age.

Come clean. You are a 32 year old man. I am. You were born in 2005. I am 63. We're soon to be

64 in April. April. Wow. He's my way. What's your brother's April 21st? I'm the 18th. I'll be 63

on the 18th. Yeah. I like an April birth day. So do I. I like it. You get what's so good

about it? What's so good about it? You get far enough away from the holidays where when you

get gifts, it feels good to get. Yeah. Also, I grew up on the East Coast. Okay. You guys, I know

Midwest, it's turning to get nice. Yes. And so I always associated my birthday with the Sunday

Sunday. The sun is out for the first time in nine months. And, um, there's a little bit of joy.

And some birds are chirping. I like that. The smell of grass. Are you into horoscope stuff? Do you

do? I don't know. I'm not. I'm not at all. I'm not. I thought you were going to say I'm not.

Well, all these young people are. So I probably know more than it because it's all about,

oh, you're a Leo rising in a. I know to sleep. And I'm like, what? No. And then I ask them,

they'll say things like, oh, that's so aries. And I'll say why? And they'll say, oh, because,

you know, aries is, you know, loves a challenge and loves to push themselves and is a ray of light.

And then I'll read, well, what's a tourist loves to really challenge themselves full of goodness

and light? You know, like, it's all. And then if you say something else and they said,

oh, you must be a cancer moon. Yeah. And it's like, okay. So now there's something for every aspect,

you know, because there's moons and there's your sleeping song. What are these? There's only 12.

It can't be that everybody can't, right? But we just only needed your entire staff. I know that

we're listening right now. And they also like manifesting everything. Well, that's Oprah's fault.

We blame Oprah for that. You can manifest it. I can manifest all day and all night that I want

to be an amazing basketball player. It's not happening. Or I like to be a male model. I'm going to

manifest it. Not happening. There's so many things that I cannot manifest. Right.

Well, let's get through our listener question. Okay. Yes. Get some advice.

My name is Jake. And I'm from Indiana. And my question is, how do I overcome feeling lost

in my career? I achieved my childhood dream job at 21. I had worked for it since fifth grade. But

then I decided I just didn't like it enough to do it forever. At 25, I switched to a new job with

good opportunity, but it's far from home where I'm originally from. And I don't want to be here forever.

I'm not 26. And I don't know what I want to do. I don't love the idea of going back to school,

because I'm not sure there's anything I'd love to study full time. I have ideas, but nothing

concrete. And with this constantly evolving world, I feel stuck lonely and depressed as a result.

Help. 23. This is what we were talking about. I know. Yeah. I mean, this has been a big theme of

this podcast, not through design, but it just happened. But you know, in the brief description,

you listen to what Jake's achieved already. And it's really good. And this is just one of the

things that takes a long time to figure out. I do think that we're in a world now where you take

constant snapshots of your life. And if the latest snapshot doesn't please you, you think things

are really dire. And this is called being 26. I mean, it sounds to me like Jake is kind of ahead

of the game, has already had a lot of success, has options. And now is wondering what to do.

Um, this is a feeling you're going to have now. And then it's going to go away and you're going to

have, uh, you're going to have a period where you think you're back on track. And then it's going

to come up again. And this feeling will revisit you. And that doesn't mean there's anything wrong

with you. It means you're a person. And we all have that. And it's anyone who looks at, at you and

thinks, well, she doesn't have any problems. She's a former first lady. And she's just, she's got

the world by the tail. And it's just, you know, doesn't understand that you can have a really bad

Thursday. You can have a really bad, uh, October. You can have a bad year. You can have a bad

two years. You can, I mean, that, that is called being here. That's what, and no one escapes it.

No one gets out of it. And I think, um, young people like Jake put so much pressure on themselves.

And they forget that sometimes treading water is just fine. That's, you know, not every day has to

be a sprints to the finish line. You can have periods of your life. I've had many of them

where I think I'm not really getting anywhere. I'm treading water, but

I'm not drowning. So I, I, I think, um, try not to be too self-critical. Try not to be too, too

tough on yourself and appreciate what you have and what you've already achieved and know that

also 26. You're a baby. Yeah. That's my answer. That's a, it's a, it's a, it's a great answer. It's,

it's spot on. Um, and Jake, it's like, um,

26 is, yeah, and it's, if you're lucky and luck has a lot to do with it,

you, with this generation, they're going to live until they're 90s, you know, assuming that we

continue to have good health care, which this generation should care about. That's going to play a

role, but science is definitely on their side. We've learned a lot, you know, people are healthier,

they're living longer. So let's just say if Jake is lucky, he's going to be here until he's 90.

Yeah. Now that's like, I can do that. That's 70 more years, 70 more years to live a life and to

figure it out. So the 20s and the 30s, and I would even say now the 40s are the period where you

aren't going to know. I mean, they're a handful of people and they're rare that pick a thing at 18

or 22 and they get it right. It's their passion. They're good at it. And then there's a job.

Yeah. Right. Yeah. That's not the norm. You know, that's the exception. And again, with social

media, he's probably seeing some of those people post, look at me, living my best life at 26,

already a millionaire. And I've done this and I have a boat and a dead, you know, that's not the norm.

You know, it wasn't also for me. Also, people don't always tell the truth. That's right.

Social media. Absolutely right. That may be someone else's boat.

Exactly. I've done that. I've often taken photos of boats and said, check out my boat.

That's right. I don't have a boat. That's right. You've often done that. No, I'm going to start doing

it because I just, I'm getting in the idea that that's, that'd be cool. But no, I think that's,

that's people. There are going to be many lives, many except if, you know, and that's what you

want out of life. Yeah. You know, you want to keep evolving. You want to keep trying on new things.

And, you know, I certainly did that. I thought I wanted to be a lawyer, went to law school,

wrong about that, didn't like that. That felt a little shocking. All that debt. And I was like,

damn, I should have checked to see if I liked law before I did it. But I didn't.

And so I left the law. And thank God I did because it wasn't the profession for me. Thank God I had

parents who didn't care about that. And they encouraged me and my brother, we went down a whole

should have been a certain career path. Yeah. And entered into it and said, whoa, this isn't me.

And so I had to redefine it. I had to, I had to start looking around asking questions,

exploring, trying on new things. And that's when I learned that I love service. And I actually

like working with people. I don't like reading documents and just writing memos. I like sort of

living in life. I learned that about myself. And if I had stayed in the law firm and become

partner, I wouldn't have, I would probably figure that out because ultimately you do have to wake up.

Even if you pick a thing, I've met people who have been in a profession their entire lives,

just, just putting up with it because it paid the bills. And then at 60 or 70, they find the

thing that they care about. You know, the work is gone is waiting for you. That work of figuring

yourself out. It's waiting for you. And so he's probably in it right now. He's in it right now.

Like a guy like Jake. It's, it's, you know, you're not even aware. Some people think

sometimes I'll talk to one of my kids and they'll say, Oh, I, you know, I wasted time today.

I've got this thing to, but I, I didn't really, I didn't make a lot of progress on it today. And I'll

say, I have found that often you're working and you're figuring things out when you don't even

think you are. Because we have, you know, front part of our brain. And then you have a part of your

brain that's chewing on things while you don't even know it. So Jake might be figuring a lot of

stuff out right now. It's crucial where he realizes, I want to be an astronomer. Yeah, you know,

and then, but that's, that's still a year from now when he has that revelation, but it is working

on him on some level. It's funny. You should, you, you say that, Conan, because I was just watching

something and I can't remember if it was PBS or it could have been on social media. But Neil

DeGrasse Tyson, the renowned scientist who is very entertaining, but I really enjoy him when he

talks, I listen, and he said something that I had never heard before that procrastinators are

usually highly intelligent. Yeah. For the reason you said that they procrastinate because they

want to give their brain enough time to come up with the solution. And like you said, this could

be happening with Jake right now. Oh, yeah. Yeah. Yeah. I think that's true. So hang in there, Jake,

and you know, my sister and I talk about this all the time, you try stuff, try stuff to find,

find your passion. And sometimes you don't find your passion, but you'll find something that's

pretty interesting. Yeah. And there's no, I think a lot of young people don't realize that

they have more room for error than they think they can. You can try something and wipe out,

or it just doesn't go anywhere. No one's paying that much attention. And no one later on is going

to present you with, hey, wait a minute, I know you're a big success now. But remember when you

tried to open that dry cleaning business and it didn't work 35 years ago, whatever.

No, that happened. I got out of it. I paid my debts. And then I tried this. Yeah.

Once you figure out what it is, you're not penalized. No one, there's not a referee there watching

blowing the whistle saying, nope, you're out. You just made a mistake. Yeah. Life's over. It feels

that way, but it's not happening. Yeah. That's a great point. Well, speaking of evolving and hopefully

that helps Jake, you're still evolving. I mean, did you just have your acting debut?

I watched if I had legs, I'd kick you. It's intense. It's intense, but so good. She's, I mean,

Rose Byrne is phenomenal. She is amazing. Yeah. She's absolutely spectacular. And so, yeah,

how was that for you? I mean, was that your first time in your series? Yeah. It was a

serious role. Yeah. They sent me the script. And I said, well, this is a great script, but

this isn't really what I do. This guy's the complete opposite of me. The director

met with me, Mary Bronstein, who wrote it, directed it. And she said, I really want you to do

this. And I said, I don't think you should want me. You should get someone who really knows

what to do with this. And she said, I think it, I really do think it's you. And I said, okay,

I'm going to try, but I give you permission to fire me at any point and we'll still be friends.

And I said, if I'm not, because I love Rose Byrne, I don't want to let her down. I don't want to

get in the way of this amazing movie. Fire me, fire me, fire me. And even if you shoot with me and

you want to cut me out, cut me out. Yeah. No hard feelings. So, but again, I did, I worked on it.

I thought about it a lot. I worked on it. You were good. You were incredibly believable.

There was no sign of regular calling. Well, here's the disturbing part. The guy I play has no

empathy. Everyone hates him and wants to kick him. And people were just so mad at my character.

And it's worrying me that that's inside. I may have let out the real me. Yeah. And it's in there.

And so, but it was, it was a real challenge. And it was scary. But again, going back to,

you know, the, the question we just got, I've gotten to a point in my life where I think, give

it a shot. There are things I know I shouldn't be doing. If someone said, hey, fly this F-16 fighter,

gee, I've never done it before. But, you know, no one's going to penalize me if it doesn't work out.

Yeah, you'll be killed. You might kill other people. I know there were a lot of things I shouldn't

just give a try to. But this one, I really went off the belief of the director. And it was a lot

of fun. And I'm really proud of Rose because she's nominated for Best Actress. And I'm, you've got

Greg is not a pop culture ready. I told him you have to be better in this job where pop culture.

That is not true. You know, you've got to watch movies. What do you, what do you, what do you watch?

Turner Classic movies. Oh, okay. All right. I watch Turner Classic movies. See, listen.

I like watching movies. It's hard to watch these new series that have part after part after part.

I just, you can't keep up. And I have a, you know, I've got a job. I work for the Coaches

Association. I'm coaching my kids teams. And I'm doing this podcast. I don't have time for just,

you know, real housewives on real housewives of Brooklyn. I don't have time. Is there a Brooklyn

housewife? No, there is. There is not. It's New York. It's not Brooklyn. Oh, well,

that's what I'm dealing with. I bet they all. No, they don't.

Does that real housewives that in Ireland? You should check that out. Is it really? No,

I just made it up. Do you have to recuse yourself when the, no, because I really have no power in

this thing. I'm just, I'm like the cruise director on the boat. I'm not the captain. Okay.

Steer it. Okay. My job is to get everyone to play a little shuffleboard. Yeah. Get them drunk.

And then, you know, hope that we don't hit anything. But that is my job. So, no, I don't have to

refuse myself. I'm allowed to be really excited. Should things work out for Rose. But if not,

you know, she's still to give an amazing performance. Yeah. Well, it's been great having you.

This has been lovely. Yeah. Again, these things are what a joy, honor to talk to you both.

And, um, like what? And it's always a joy. Really, really good time. It's great to get to know

you more. And thank you for doing it. So you and I are going to be hanging out a lot.

Anytime you want to hang, I don't think that's true. Yeah. I think I'm going to start any cold calling

hands. It's true for you. So here's the thing. When I come to L.A.

It's going in when I let's shoot some hoops. That's right. I'm going to drain some trees from

80 yards away. They don't go anywhere near the bucket. No where near. I tell you that's the

thing that you can, and then you, and then I'll go to the back alley comedy club with you.

I think you would do better. You would do better at comedy than I would at basketball. That I

know way. Would you would you teach him how to do venture? I'm going to, I don't do ventriloquism,

but I will get, I will get a person to teach you ventriloquism, but we have to get you the right

dummy too. It's got to be a good dummy. No way. Surprise. Why don't you do the honors? Do the

honors. Look at this. Oh my goodness, you guys are too much. Can I just say this is a beautiful

and horrifying at the same time. This dummy has had very bad work done. Look at his hands.

His hands are huge. Yeah. This is the nightmare they will never end for me.

I'm probably, I'm going to be trying to do the Oscars, and I'll stop because this face

will be looking at me. Did you see if we were there in the, in the front row, put them in the front

row. We'll put them right next to Timothy Schalemann. Yeah. Hey, go ahead and get fun up there.

Get some federal material. He's going to steal the show with the Oscars. Yeah. This is a really

tiny dummy. It is. Well, it should go on your lap. It's on my lap. Oh, okay.

Well, he's a basketball player. He's a basketball player. This is perfect.