All Episodes

December 26, 2025 35 mins

Barry sits down with Jay Leno at the Audrain Newport Concours & Motor Week. They discuss the future of late night comedy after The Late Show with Stephen Colbert was canceled. They also discuss Jay's classic car collection, watches, and his approach to wealth.

See omnystudio.com/listener for privacy information.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:02):
Bloomberg Audio Studios, Podcasts, radio news. This is Masters in
Business with Barry Ritholts on Bloomberg Radio.

Speaker 2 (00:17):
Happy Holidays and we have an extra special holiday podcast
at the Newport Ordering Concourse to Elegance, I sit down
with Jay Leno talking about cars, comedy, watches, and pretty
much everything else. Jay's a fascinating guy who's created really

(00:38):
an amazing career. I thought this conversation was super interesting,
and I think you will also with no further ado,
my conversation with the former host of the Tonight Show,
Jay Leno. Jake, thank you so much for joining us,

(01:04):
for having me. So let's start out a little bit
talking about your background. Born in New Rochelle, you grow
up in andover Massachusetts. Which interest came first? Cars or comedy?

Speaker 3 (01:19):
Well, when you grew up in a little rural town,
you don't think of comedy as a as a job.

Speaker 4 (01:24):
You know it was then they was you know, Kathy's
boy wants to be comedian. He'll grow out of that,
don't worry, Kathy.

Speaker 3 (01:32):
You know that that kind of you know, people just
it didn't seem like a viable but you know, you
go to Hollywood, you'd be kids want to be lighting
directors or costumers or because they know people that did
that right now.

Speaker 4 (01:44):
But when you're an andro, it's like what commune?

Speaker 2 (01:46):
So what sparked your interest in comedy? How did you
find that past?

Speaker 3 (01:50):
You know, I had very good teachers when I was
in high school. I had a HNGLIS chief, Missus Hawks,
and being dyslexik, I was not the best student.

Speaker 4 (01:59):
And you know, she said, I always see making jokes
in classes. So do you ever think of writing comedy?
I said, well, I never thought would be a job.
Oh you should say, oh yeah, I said, I'll tell you.

Speaker 3 (02:10):
Why don't you Maybe you could instead of writing a
paper for the final, you give a talk, you know.
And I said, okay, And I tried to put some
kids style jokes in and it was the first time
in my life I actually enjoyed doing homework.

Speaker 4 (02:23):
And oh, maybe I can make a living doing this.
But it's a kid you know. I think people in
the community. Do you tend to remember things that are funny,
things that get a reaction? You know.

Speaker 3 (02:34):
I was in the fourth grade and Missus Allen was
my teacher, and I always remember this.

Speaker 4 (02:39):
She was telling us.

Speaker 3 (02:39):
About Robin Hood and how cruel. The Sheriff of Nottingham
was and he would boil Robin's men in oil. And
I put my hand up and I said, you know
why he did that's to Tuck And she said, no,
why because he was a friar.

Speaker 4 (02:53):
Okay, okay, And then she does one of these it's
not funny, just stop that, like, oh, she's kind of laughing,
you know.

Speaker 3 (03:01):
But the real kicker was later in the day, I'm
walking past the teacher's lounge. Give me, what did you
say about falk I said, I went, oh, she told
my joke in the teacher's lounge and I said, oh,
I said he was a fresh Oh that's oh, that's
very funny thing.

Speaker 4 (03:18):
And I went, oh, that's that's pretty good. And I thought,
And when you were a kid, you know people that
you tend to remember things that get a laugh.

Speaker 2 (03:26):
You just sat a little bit of attention.

Speaker 4 (03:28):
Yeah, you put them in your mind.

Speaker 3 (03:30):
It makes a little indentation, you know. So that was
always something I enjoyed doing at ours. Remembered it, but again,
I never thought I could make a living doing.

Speaker 2 (03:39):
Who were your comedic influences when you were growing up?

Speaker 3 (03:42):
Oh, Robert Klin, George Carlin, Richard Pryor, primarily Client because
Client was like me, middle class white kid.

Speaker 4 (03:49):
You know, most comedians that.

Speaker 3 (03:50):
Time tend to be uh, grew up during the depression,
Anny Youngman, all those kind of guys, you know, kids
today with the long hair, you know, all that kind
of stuff.

Speaker 4 (03:59):
Right, Yeah, and then it all along comes Rubber.

Speaker 3 (04:01):
Klein and once again George Carlin, Richard pryor Bill Cosby
before the recent turn of events, you.

Speaker 4 (04:09):
Know, so it was, yeah, those were my influences.

Speaker 2 (04:12):
So since we're at the ordering concourse and MotorWeek, let's
talk a little bit about cars. Good transition, right, Your
first Your first car was a thirty four to for
at stock. What'd you do to it?

Speaker 3 (04:23):
I saw my dad and I were driving past the
Tip Top Miniature Golf in North Reading, Massachusetts. It was
parked at the shell station with a sale sign. I
went and I bought it.

Speaker 2 (04:35):
What'd you pay for that?

Speaker 4 (04:36):
Through fifty?

Speaker 3 (04:37):
Which was a lot of money, yes, in nineteen sixty five,
But I had been working McDonald's and I'd saved some money,
and you know, so then we dragged you back to
my house, and I took a couple of years to
get it running, and I got my license and I
drove it every day to school.

Speaker 2 (04:52):
Self taught mechanic. What do you mean you took a
couple of years to get self.

Speaker 3 (04:55):
Well, yeah, I mean just you know your kid, you're
playing with it after school, you know that kind of thing.

Speaker 4 (05:00):
Yeah, it took me a couple of years to learn. Yeah,
I guess self taught would be a fair way to say.

Speaker 2 (05:05):
So thirty four Ford is the gateway drug. At what
point did you realize this is more than a hobby,
This became something of a passion.

Speaker 4 (05:14):
We have a ride full of cars. Perhaps this is
more than a yeah.

Speaker 2 (05:19):
Yeah, well how many cars is too many? At what
point do you need help?

Speaker 3 (05:23):
And fourteen on the road now, plus the motorcycles you
see I.

Speaker 4 (05:26):
Watch the show Hoarders and go the guy's fine, it's
a problem, man. You can still get to the bathroom.

Speaker 2 (05:34):
Look, but that's old newspapers. You have motorcycles and cars
something a little.

Speaker 4 (05:38):
More reason when your parents did the same.

Speaker 2 (05:40):
Thing, right, So how do you decide of the two
hundred and fourteen cars which one you're going to take?

Speaker 4 (05:47):
That say, that's the first world problem?

Speaker 2 (05:50):
Not very much so.

Speaker 4 (05:51):
People don't want to hear a rich guy, go how
do I just I just can't decide. Oh have jeeves
do it?

Speaker 2 (05:58):
No?

Speaker 3 (05:59):
I mean whatever working on? If I do one, I'll
change a day. It takes eighteen months. You have to
look at it that way. So whatever you've just worked
on is, oh, let me let me drive it home
to see if it's okay.

Speaker 4 (06:10):
So that's what I enjoy.

Speaker 2 (06:11):
So you're a little bi cooastal. You're in LA, but
you also have a place here in Newport?

Speaker 4 (06:16):
Do you have a place And I also have a
house and Ander and Massachusetts where I grew up.

Speaker 2 (06:19):
Do you do you keep any cars out here as well?

Speaker 4 (06:22):
I don't because of the weather. And you know, so what.

Speaker 2 (06:25):
Do you drive on?

Speaker 3 (06:26):
I'm one of these people really touch my car, you know?
So if I if my car was on another coast, Oh,
that would be horrible.

Speaker 4 (06:32):
Like we go out to eat. If if I can't
see the restaurant from my table, we're.

Speaker 2 (06:37):
Not eating here any That's it.

Speaker 4 (06:38):
Yeah.

Speaker 2 (06:39):
Yeah, So I'm curious how Leno's garage came about. I
have this fantasy that your accountant says to you.

Speaker 3 (06:48):
No, no, no, I have a garage. I have friends
with cameras. I'm on TV already. It seems like a
fairly natural transition. So why don't you take the TV
hobby and put it on TV? In this way you
try to, you know, monetize as much as you can.
I did it for nothing for the first I guess

(07:11):
fifteen years. Really, Yeah, you know, just because I enjoyed
doing and it was fun and.

Speaker 4 (07:18):
It just opens up another you know, you should have something.

Speaker 3 (07:21):
I'm not a particularly interesting person, you know, so if
you have other things of interest that other people like,
then you have something in common you can talk about it.
So cars, motorcycles, anything that rolls, explodes, makes no issues
is interesting.

Speaker 2 (07:36):
Do you know what the cars that are top of
the list here are going to be? Have you walked
around seen much so far? Yeah?

Speaker 4 (07:43):
You have some of the best cars in the world here.
This is quite an event. You are and inevitably you
see something you've never seen before or or never even
heard of.

Speaker 3 (07:51):
You know, they're all countries are working on automobiles in
different you know, you had cars and Czechoslovakia the people,
but on the other side of the mountains never heard of,
you know, like a Tatra, a very unusual car. Most
America has never seen one but it's very popular in
Czechoslovakia or what.

Speaker 4 (08:08):
Was then check Withakia did so. Yeah.

Speaker 3 (08:11):
So it's a fascinating hobby and a nice thing about
it is it's no more than really one hundred.

Speaker 4 (08:15):
And fifty years old.

Speaker 3 (08:17):
You know, if you like, if you're like Egyptology, well
now you've got to go back six thousand years and
stand in hot sun and dig in the sand. And
you know that with cars you only have to go
back a few years.

Speaker 2 (08:29):
We took a walk down the boulevard earlier. The two
that kind of leapt out to me, aside from the
goal wing I know you have. One of those was
the Talbot Lagos Spectacular.

Speaker 4 (08:42):
Yeah, very interesting, that very art deco.

Speaker 3 (08:45):
You know, it's only in recent years cars are seen
as kinetic.

Speaker 4 (08:49):
Artwork, right, you know, it used to be just an
old car.

Speaker 3 (08:52):
But now people are looking at them and I mean
it's you know, by painting that this for one hundred
million dollars something that rolls down on the road looks
pretty as a practical.

Speaker 4 (09:02):
Element to it. So and only close to tenth as much, Yeah,
across the tent, or sometimes almost as much.

Speaker 3 (09:08):
I mean Ferraris go for the I think the last
Ferra sold for seventy five million dollars.

Speaker 4 (09:13):
I mean, it's pretty crazy.

Speaker 2 (09:14):
That's a one of one though, right, No, no, that's
one of thirteen thirteen. Wow, I also saw them and
there wasn't a sign on it, So I'm doing this
by sight. But a Mercedes SK five hundred, the giant
front fenders as yeah, spectacular, also, they are there.

Speaker 3 (09:31):
I try to enjoy some suspicious things happened in Germany,
even the thirty to the middle forties.

Speaker 4 (09:38):
I tend to avoid those for obvious reasons. But the
early ones I love you.

Speaker 2 (09:41):
So let's let let's talk about some of these classic designs.
What do you think has aged especially well? What looks good?
Perhaps that wasn't thought of so well when it first
came out?

Speaker 4 (09:54):
Oh oh what an age Rowler wasn't thought when the
first came up. It's two different.

Speaker 3 (09:58):
I mean, shapes evolve. I mean cars used to change
just for the sake of change. Now they change mostly
because of aerodynamics and efficiency and things of that nature.

Speaker 5 (10:09):
You know.

Speaker 3 (10:10):
I mean, a pres is about an efficient shape as
you can get, but it's not It's attractive enough, but
it's not striking.

Speaker 4 (10:18):
It doesn't take your breath away the way some ferraris
by Piniferen or whatever. You know. Back in the in.

Speaker 3 (10:25):
The twenties, thirties, forties, fifties, things are drawn by hand.

Speaker 4 (10:29):
So there's there's a flow, yeah, flow.

Speaker 5 (10:34):
Yeah.

Speaker 4 (10:35):
Now everything is sort of computer design. You have all
these sort of weird angles and things like that. But
you know.

Speaker 3 (10:41):
The best looking cars are both masculine and feminine, like
an xke. I don't know any women that don't find
Jaguars attractive.

Speaker 4 (10:49):
Even women don't know anything about cars.

Speaker 3 (10:50):
It's something about because it has a feminine element to it,
but then it has the rear haunches and so it
has a masculine so.

Speaker 4 (10:56):
It's a little bit of both to it. You know,
a lot of cars look.

Speaker 3 (10:59):
Too brutal, you know, lambergoody, kuoncash, thse look like guy
cars you drive When of the girls.

Speaker 4 (11:05):
Go how old are you? Your boy took it? You
pull them a jag.

Speaker 2 (11:08):
You're like, oh, well that So sometimes the proportions, the shapes,
the lines, they speak to everybody. They're universal.

Speaker 3 (11:15):
Yeah, I mean the trick is, well, if it speaks
to everybody, then you have a Corolla, you know the best,
cause some people love it.

Speaker 4 (11:24):
Some people hate.

Speaker 3 (11:25):
Anything that gets emotion going is probably going to work
on some level, you know. I remember talking to Bob
Let's about this when the viper came out and said,
a lot of people think it looks like a cartoon car.
It's a bit over exaggerating because we're not trying to
sell it to them.

Speaker 4 (11:39):
We're trying to sell it to the people think it
looks good. And there's enough them out.

Speaker 2 (11:42):
There, you know for sure. So so let's talk about
people have to ask you questions about cars all the time.

Speaker 4 (11:50):
But they don't have to actually, most of them just
people must.

Speaker 2 (11:52):
I assume lots of people do. When someone asks you
for a recommendation, what what What do you recommend as
a good cheap set of wheels for a budding enthusiasts.

Speaker 4 (12:02):
Well, you know there are almost for an enthusiast, or
for transportation.

Speaker 2 (12:06):
Transportation is easy. I mean someone who wants something fun
for the weekly.

Speaker 3 (12:10):
Well, first they tell me what it is they're looking for,
you know, I mean obviously our cars, Mustangs, Camaros, things
in this nature, any.

Speaker 4 (12:18):
Sort of two seated supports car. Yeah, there's plenty of
choices out there. You don't need me for that.

Speaker 2 (12:24):
So this event is sponsored in part by Alanga and Sona.
We're both wearing long watches. What drew you to watches?

Speaker 4 (12:33):
I paid for mine? So did I? You did?

Speaker 2 (12:35):
I paid for mine also, so so, and you probably
have access to more of these than I can get.

Speaker 4 (12:41):
So well, it's interesting.

Speaker 3 (12:42):
You know, watchmaking and automotive things have a lot in
common because they're both extremely mechanical. Most watch people don't
really like electric watches the same way they don't.

Speaker 4 (12:52):
Like quartz watches. Quart watches are obviously the most accurate
you can get, but don't appear to have a soul
to them.

Speaker 3 (13:00):
You know, these kind of things. When you turn to
hear the the you know, it's a sort of the car.
The watch needs you. If you don't wind it, it
won't run.

Speaker 4 (13:10):
So there's a human element that needs to be attached
to watch to get it to the run, you know.

Speaker 2 (13:15):
And if you flip it over you can see the
absolute spectacular mechanicals on you. Yeah, it's a beautiful job, right,
so so very parallel the precision and the intricacy of
a mechanical watch and a classical automobile.

Speaker 4 (13:31):
Yeah, yeah, I seen them as a somewhat similar I mean,
I like the things that need me. You know, my
cars need me because I need to do certain things
to make sure they run correctly. Electric cars kind of run.
The matter who the master is, you know, It's about
like that screen door. After a while you learn it
has to be shut a certain way and normal people
can't do it. But you know that you lift it

(13:51):
and turn it just a quarter of an inch, Oh
it will click.

Speaker 2 (13:54):
In coming up, we continue our conversation with Jay Leno
line from the Newport Au Drain Concourse the Elegance, discussing
how a career in comedy and car collecting led to
a fascination with mechanical time pieces. I'm Barry Ritolts. You're

(14:14):
listening to Masters in Business on Bloomberg Radio. I'm Barry Ridolts.
You're listening to Masters in Business on Bloomberg Radio. My

(14:38):
extra special guest this week is Jay Leno, comedian, car
collector time piece enthusiast. Let's return to our conversation live
at the Newport Or Drain Concourse, Delegance. What are your
thoughts on on the new evs and hybrids that are
coming out? What does this do to the collectible market?

(15:00):
I believe you have a Tesla plaid is that it's.

Speaker 4 (15:03):
A great look.

Speaker 3 (15:04):
I use my electric car during the week I mean,
sitting on the freeway in a forty nineteen sixty six
Hemi for twenty six. It gets three miles per gallon.
It doesn't really make a lot of sense. You're not
going fast, You're not You're just annoying people and poisoning
the atmosphere.

Speaker 4 (15:19):
So you take your electric car. Then on the weekends,
if there's a car rally, you drive your Mustang or
whatever car you have to the rally and you sit around.

Speaker 3 (15:27):
You tell lies about it to other people, and they
tell you lies about their car, and you know, it's just.

Speaker 4 (15:32):
Sort of a little bit of interaction, you know.

Speaker 2 (15:34):
So, so I mentioned the precision of automobiles in the
precision of watches. You have famously been touring for forty years,
forty plus years. When you put together a stand up set,
do you put the same sort of precision into structuring
that set?

Speaker 4 (15:50):
You like to think?

Speaker 3 (15:51):
So, I mean you want to have a joke every
six to nine seconds. It's a bit like spinning plates
to the Tullivan showdre and then then you want to
keep it going, you know.

Speaker 4 (15:59):
So you want to make sure that the people. You're
not wasting people's time. I hate people. How are you
all doing? Boom and by from Boston, Boston. Yeah, okay,
that's not comedy. You've wasted forty seconds, you know, get right, Yeah,
keep it moving.

Speaker 3 (16:13):
You know when you watch Rodney Rodney was I was
a big fan of Rodney did Interfield and.

Speaker 4 (16:18):
It was it was the economy of words.

Speaker 3 (16:20):
It's getting the funniest words you can in the shortest
amount of time. You know, Rodney had jokes I love
like I worked practice strip joint and said topless and bottomless.

Speaker 4 (16:29):
I went in there was nobody there. I mean, it's
a funny joke. I mean because I didn't waste your time.
It wasn't a three minute setup. You know, one of
those favorite jokes. It's so stupid.

Speaker 3 (16:40):
My doctor wanted a semen sample, a stool sample, and
a year one sample.

Speaker 4 (16:44):
So I gave my undepands. I mean, okay, but it's
quick boom boom boom. You're not You're not wasting people's time.

Speaker 2 (16:53):
Really interesting, So you've been known as somebody who just
has toured his whole career, even during what was it
twenty two years of the Tonight show, you still were
doing stand up on a regular basis.

Speaker 3 (17:04):
Well, when you're on television, you rely on one hundred
and seventy five other people. They really can't do the
show without all the elements to it. And when you
go out on the road, you're by yourself. You rise
a fall strictly on your own nobility, and I like that.
You get all the blame, but you also got all
the glory and.

Speaker 4 (17:24):
I like that.

Speaker 3 (17:25):
Plus it's piecemeal, right, joke, tell joke, get check boom,
next show.

Speaker 4 (17:29):
Nobody says, you know the jokes you told two months
ago and they're not working out. Come back. You got
to come back and do the show again. You don't
have to do that.

Speaker 3 (17:35):
You know, on TV you get there so many irons
in the fire and what you're dealing with. You know,
my favorite TV line of all time. When NBC was
letting me go, I said, you know, I've been number
one for twenty three years, well for eighteen eighteen of
the twenty three years, and they said, we want what's
above number one?

Speaker 4 (17:56):
I said, okay, what what is above? What is above number?
I mean, it just made me laugh and even they
realize how stupid that sounds. I said, what do you mean,
how can you have? What's the bud? Just tell me,
somebody tell me what. It just made me laugh.

Speaker 2 (18:08):
So since this is Bloomberger Financial Network, let's let's talk
a little bit about money.

Speaker 4 (18:14):
All right.

Speaker 2 (18:15):
You are known as someone who is savvy with your money.
You only spent the money you earned.

Speaker 4 (18:20):
Well, I'm not savvy. I'm dyslexic.

Speaker 3 (18:22):
Yeah, okay, So consequently I don't really understand it.

Speaker 4 (18:26):
All I know is my I work and my money relaxes.
That's my Thay.

Speaker 3 (18:31):
I don't want my money out working for me because
he's going to screw up somewhere.

Speaker 4 (18:35):
I don't want that.

Speaker 3 (18:36):
Whenever I hear and there's minimal risk, and I hear
the word risk and minimals, that means they're going to
lose something right now.

Speaker 4 (18:43):
No, I know, I don't. I always had, even as
a kid.

Speaker 3 (18:47):
I worked at Wilmington Ford, I worked at McDonald's. Whichever
job made the most, I banked and the other money
was my.

Speaker 2 (18:55):
You did the same with it Tonight Show. You banked
to Tonight Show, you have.

Speaker 3 (18:57):
A touch to check In twenty two years of the
Tonight Show, I banked everything I lived on the money
I made as a comedian.

Speaker 4 (19:03):
Then when I when I uh, when the show ended, Oh,
opened this little past book. Oh look this, it's quite
a bit of money here. You know this is good.

Speaker 1 (19:12):
Yeah.

Speaker 2 (19:13):
So when you started collecting cars, did you ever envision
this collection would get this large or this valuable.

Speaker 4 (19:20):
No? I never thought that.

Speaker 5 (19:22):
No.

Speaker 3 (19:22):
When I I remember, I would sleep in the alleys
in New York and it was the most depressing. I
remember sleeping in an alley. It's one of those alleys.
Were guys who would come with hookers and I'd be
in the back, just hideing behind some trash cans and
they were doing up.

Speaker 1 (19:36):
Again.

Speaker 4 (19:36):
Really, this is my life now, I mean it was
like the most horrible.

Speaker 2 (19:40):
Really on the road you were that.

Speaker 4 (19:42):
I'm hard travel I'm forty fourth and ninth. There was Dike's.

Speaker 3 (19:46):
Lumberyard right across the way from from the alley where
I slept a couple of nights.

Speaker 4 (19:50):
I could see Dyke's lumber yard.

Speaker 3 (19:52):
I always had that in my mind, and hookers would commanded,
it's just.

Speaker 4 (19:56):
Horrible, it's terrible. They just hear terrible sounds. It's horrible.
I said, really, this is my life, this is what
it is. Now you know, so everything better than that
was gravy.

Speaker 2 (20:08):
Yeah, well it's been a little bit of gravy. You
recently had a going you found in a barn. You
had a number of No, No, I didn't.

Speaker 4 (20:16):
I didn't buy that. I didn't buy that car was found.

Speaker 3 (20:19):
They were sold for ten million dollars and we had
the own We had it on the show, We had
it on the show.

Speaker 4 (20:24):
Yes, I did not. I would like to have owned
that car, but no, I didn't buy it.

Speaker 2 (20:28):
Didn't You find a number of barn finds cars? What
are some of the more memorable ones?

Speaker 3 (20:36):
Well, the most recent rob was in nineteen sixty three
Jaguar XK. The guy bought it in sixty two, started
drinking about sixty six sixty seven, became a hoarder, just
had trash piled on top of it.

Speaker 4 (20:54):
When he died, the family called me. They said, Cris
right across the street, my uncle's had some kind of car.
We don't know what it was. And it was a Jaguar.
And I said, and this is really the best write.
I said, look google it. Find out what's their worth. Okay,
find out what they're worth and let me know and

(21:15):
I'll pay you that, and that's what it seems fair.

Speaker 3 (21:18):
Yeah, I mean I paid more than a fair price
because I don't flip cars.

Speaker 4 (21:22):
I don't sell cars. So to me, this way, nobody
goes rip me. You don't want any of that.

Speaker 2 (21:27):
Any cars on your list that you're still hunting for anything.

Speaker 3 (21:33):
I buy the story as much as I buy the car. Really, yeah,
I mean to me, the fun you know. I had
a lady called me ninety four years old, and she
and Hudson. Her and her husband bought a fifty one
Hudson Hornet in New Jersey.

Speaker 4 (21:46):
They drove it to California with the two kids.

Speaker 3 (21:49):
He bought a gas station. He ran that for the
next thirty years. He died sometime in the early nineties.

Speaker 4 (21:57):
She calls me about two thousand. I guess three four. Oh,
my husband died like twenty years ago. We got this car,
I say, I already have a fifty three onund Well,
you come look at it, okay. So I got to
look at it. She's ninety four, no hearing her, no
glasses right, show said would you give me five thousand
dollars for it? Okay? So I bought it and take

(22:20):
it back in my garage. It takes about a year
and a half. We get it all of fin Let
me see if she's still alive. I called her up, Hello, Oh,
what's Jalen off? The car's all finished? You want to
go for er okay? Now she's ninety six, and she says,
can I bring the kids? I said, yeah, bring the kids.

Speaker 3 (22:35):
So I get there and the kids have got a
blind fold and the kids are seventy four and seventy
two and they're blindfolded dirt right, and she's like touching
the car.

Speaker 4 (22:44):
Oh, the paint feels so smooth, always used to be.
So we'll take them link. Oh, she starts crying her
we want to go for let's go for RJE. So
the kids get in the back right. So we're driving
along and we're talking and the two kids start doing
this to each other, poking each other. Huh, and she
turned drop.

Speaker 5 (23:00):
I've told you kids, and she's whacking the crap out
of him. Mister Linnell's nice enough to take us right
in his car, and you kids can't be here.

Speaker 4 (23:07):
And the three of them are just laughing. I mean
they're just.

Speaker 5 (23:10):
Falling down that she and she's not holding back, I
mean she's really hitting them but she's laughing while.

Speaker 4 (23:15):
She's you know, and it was just so funny. It
was just so funny. She lived through me one hundred
and six. Wow.

Speaker 3 (23:21):
And every time I get in the car it makes
me laugh because it was just so fun to see
these two old men and they all look the same age.
You know, she's ninety six, it's seventy four, and she
just whacking the.

Speaker 4 (23:33):
Crap out of the hilarious.

Speaker 2 (23:35):
So more stories than there's a hole in your collection,
or you're enamored.

Speaker 4 (23:40):
With this, because I know I have a namor with this.

Speaker 2 (23:42):
Now, it's just about the stories.

Speaker 4 (23:44):
My key to success is low self esteem. I've heard
you say that before, Yes, because if you have low
self esteem, you never assume you're.

Speaker 3 (23:53):
The smartest person in the room. I assume one of
the dumbest person in the room. Let me look around
and see what the other people are.

Speaker 4 (23:58):
Doing here, and that's what you do.

Speaker 2 (24:01):
You know.

Speaker 3 (24:01):
I have so many friends that do TV shows and
they really think, I don't like I want to change
these lights, and the lighting director who's been in the
business forty years, I don't think why I want to change?

Speaker 4 (24:11):
Well, no, I don't want to just let the lighting
director his job.

Speaker 3 (24:16):
You know, the fun thing about the Tonight Show was
when I did it, anybody could pull a cord and
stop the train because I don't like this, I don't
think this is funny. Did it get to be annoying sometimes?
But everybody felt they had a say in what was
going on. They felt like they were part of the
whole system. This idea that you know, do not make
contact with the star and just all that kind of nonsense,

(24:37):
you know.

Speaker 4 (24:38):
So to me, that was always the key to being successful.

Speaker 2 (24:43):
Coming up, we continue our conversation with Jay Leno live
from the Newport Audrain Concourse, The Elegance. I'm Barry Ritholts.
You're listening to Masters in Business.

Speaker 6 (24:55):
On Bloomberg Radio. I'm Barry Ridolts.

Speaker 2 (25:14):
You're listening to Masters in Business on Bloomberg Radio. My
extra special guest this week is Jay Leno, comedian, car collector,
time piece enthusiast. Let's return to our conversation live at
the Newport or Drain Concourse Delegance. So let's stay with

(25:36):
the tonight show and comedy. You've interviewed a few presidents, right,
you interviewed Barack Obama. What other presidents did you interview.
Barack Obama was Reagan before you started on.

Speaker 4 (25:52):
No I'd interviewed Reagan.

Speaker 3 (25:54):
They had dinner with Reagan the White House a couple
of times, but he wasn't ever on the show. Barack
Obama was the first sitting president ever to do the show.
Barack Obama. Hillary had the nomination locked up, and then
he announced he was running for president. So I called
him up and said, why come on the show.

Speaker 4 (26:13):
Oh, thank you so much, Joe.

Speaker 3 (26:16):
He rented a car, drove himself to the show, you know,
walks out and going, hey, my name is Barrock was
saying Obama, I'm really President of the States. I said, okay,
black guy from Chicago named Hussein.

Speaker 4 (26:27):
I said, you know, you shouldn't even have the campaign.
I just think you're chewing with that. And you know,
he got the joke and he laughed.

Speaker 3 (26:34):
He was very funny and we got to be friends.
And so next time he came on the show, I
asked him. It was the first time.

Speaker 4 (26:40):
A sitting president and the whole parking lot was tented
so the satellite could not see where he came in. Kime,
I got to tell you, and I.

Speaker 3 (26:51):
Mean I've told this story, but this is. I have
the same idiot friends I had in eighth grade. So
I'm telling him how Barack.

Speaker 4 (27:00):
Obama on the show, and he gave me his phone number.
Now you get it. You said, now, all right, let's
call him up. Go it's the President United States. I'm
not going to call him up. No, you don't have it.
So I take up my phone book and I covered
the phone and they go, see what it says there,
Barack Obama, President United States. His phone was ready here. Yeah,
I said, all right, all right, I'll call him. You

(27:21):
want me to call him?

Speaker 1 (27:22):
I call.

Speaker 4 (27:22):
It's like three o'clock. I figure, okay, we can go
rock Hello Brock here mis president. Yeah, jay Len, we're
going to aj I'm just here with some of my friends.
Lose this number. J click.

Speaker 2 (27:37):
So your reputation has never been a very political comedian.
You play it straight down the middle.

Speaker 3 (27:45):
Well, I used to get We usually get quoted every
day in the New York Times. We try to make
fun of both sides.

Speaker 4 (27:50):
Yeah, but yeah, that's the way we did it. That's
not the way everybody else does it. But that's okay.

Speaker 2 (27:55):
So, so recently, Jimmy Kimmel mentioned on the air that
you call to check in on him when when he
was temporarily suspended. Is what do you think the future
of Late Night looks like? And what does that say
about the comedians have to watch what they say?

Speaker 4 (28:12):
Well, apparently they don't have to watch what they say
because he's back on TV. Okay, I mean, you either
believe in free speech or you don't. You know, free
speech it only becomes annoying when it says something you
don't like. Other than that, it's fine. That's really the
only problem. And there's always something somebody doesn't like, whether

(28:34):
it's banning books or huck Finn or whatever it might be.

Speaker 3 (28:37):
So to me, I always support three. I mean, I
support Jimmy as a comedian, but also just the whole premise.
You don't have to agree with him to realize. I mean,
I had people that taught me apart every day, but
they had the right to do it. I didn't like
what they said, but I agree with their.

Speaker 4 (28:57):
Right to say it if they chose you.

Speaker 2 (28:59):
You have Day Chappelle speaking at the Comedy Festival in
Saudi Arabia, saying he feels like a free speech is
under assault in the US, not that Saudi Arabia is
a hotbed of free speech.

Speaker 4 (29:11):
Well, yeah, yeah, again.

Speaker 3 (29:13):
I don't like this new thing of comics criticizing other comedy.

Speaker 4 (29:17):
It's just we're comedians, okay, just you know, I believe
in free speech.

Speaker 3 (29:22):
I shouldn't have to say any more than that, and
I will defend it to the end. But you know,
and how about when he said this again, whatever, I
don't have to agree with it.

Speaker 4 (29:32):
You know, it's like the Nazis watching in Skokie. Okay,
they have the right to do that. I don't agree
with it. Well, is he liked to see someone punched
them in the face. Yes, but I don't want that
to be police doing it. If some angry Jewish guy
was about it, well, okay finding me. You know, I
might even cheer him on. But no, I again, I
think you it's America.

Speaker 2 (29:53):
And what about the in the era of streaming. What
about the future of Late Night? We heard Colbert is
supposedly not profitable. I don't know how true that is.
We heard similar threats about Jimmy's show. How do you
look at you were steward of the Tonight Show for
twenty two years. What do you think the future of
this looks like?

Speaker 3 (30:12):
Well, I mean when you can turn on streaming and
see Harrison Ford talk for half.

Speaker 4 (30:20):
An hour saying whatever you want unscripted, or.

Speaker 3 (30:22):
You can watch them do a seven minute segment on
a talk show which.

Speaker 2 (30:28):
You can, or Jay Leno for forty five minutes.

Speaker 4 (30:30):
Maybe yeah, but yeah, I mean, to me, I think
it's just the nature of television.

Speaker 3 (30:34):
It changes, it goes from one thing to another. I mean,
it's like going from CD players.

Speaker 4 (30:39):
To cassettes to CDs. So it's just another it's another
format that you can you can use. So the thing
that really kills late night is the incessant number of commercials.
After eleven thirty, you can run like nine minutes at
twelve o'clock where it looks some yeah, it's great wild

(31:02):
So and when you realize you've just watched all three
Godfather movies in a row without one commercial, suddenly seeing
Jake from State Farm again, you know, okay enough with
this guy.

Speaker 6 (31:12):
You know.

Speaker 3 (31:12):
To me, that's the thing that's really hurt late night.
It's not necessarily people say, it's the fact that people are,
oh god.

Speaker 4 (31:18):
Another commercial. You just you know, just weeding through.

Speaker 2 (31:21):
All right, So we don't want to keep you all
day because we know you have a lot of places
to go, cars to see. I want to I want
to do a speed round. A speed round. Right, A
dozen questions and under a minute. I'm just going to
throw these at you and give me your answers, starting with,
what's your favorite car to drive? I do some what's

(31:42):
your favorite motorcycle in your garage? Brough supperor what car
offers the best bang for the buck.

Speaker 4 (31:51):
Corvette?

Speaker 2 (31:52):
What's your favorite car in your collection? Not necessarily a driver,
but just a favorite car, Mclarinet one. That's that's stuff
I want to argue with. What's been the biggest maintenance
annoyance in your collection?

Speaker 4 (32:05):
My nineteen twenty five Doble steam car, the.

Speaker 2 (32:07):
One that kind of blew up?

Speaker 4 (32:09):
Is that the one we're talking about that blew up?
But that wasn't the one that actually blew up in
my face?

Speaker 2 (32:13):
Now, any cars you have any regrets passing on?

Speaker 4 (32:17):
Oh? Yeah?

Speaker 2 (32:18):
What? So? What modern car features do you find most annoying?

Speaker 4 (32:26):
Probably the infortainment system?

Speaker 3 (32:29):
You know, I have my fifty one Hutson, I reach
out my press a button, I get a station.

Speaker 4 (32:34):
I don't have to stop and look at it. Are
you happy to say yes. Would you make this suction again? Yes,
others have made this selection. Would you continue, yes, I will,
you know. Would you pick your language? English? Is good?
Thank you? You know it's annoying.

Speaker 2 (32:47):
What car do you drive the most often from your collection?

Speaker 4 (32:51):
Oh? I don't know. Well, I drive a lot of them. Incredible,
that's what they were made for, Model TS, kind of fun,
and I guess I don't drive it that much.

Speaker 3 (33:02):
Probably the Mustang that's pretty good. Well, actually, the Tesla
won't have to go to the airport and all those
kind of things.

Speaker 2 (33:07):
What's the rarest car in your collection? Not necessarily the
most valuable, but one of very few.

Speaker 4 (33:13):
What that would be the double steam car?

Speaker 2 (33:18):
Is there any one brand you would never buy that
you stay away from?

Speaker 4 (33:22):
No, no, not everyone.

Speaker 2 (33:23):
Bro, you don't have a lot of ferraris right.

Speaker 3 (33:25):
No, I don't have any Fries, But I'm not to
do with the cars. The cars are excellent.

Speaker 2 (33:29):
You know.

Speaker 4 (33:30):
For the longest time, you had.

Speaker 3 (33:31):
To buy two mandy Els before you're allowed to buy
the car, you know, So I just never took part
in that.

Speaker 2 (33:37):
What car surprises people the most, whether driving it or
just the way it's put together.

Speaker 4 (33:42):
Well, I have the kind of cars.

Speaker 3 (33:43):
People about surprised that I got there earlier late, the
surprise I got there at all. When you show up
on a nineteen oh six Stanley Steamer and it's on fire,
people like, oh my god, your car's on fire.

Speaker 4 (33:56):
I know it's supposed to be if you carry open flame.

Speaker 2 (34:00):
What's the most recent addition to the collection?

Speaker 4 (34:03):
I Mustang GTD.

Speaker 2 (34:05):
What's the best sounding engine you own?

Speaker 4 (34:10):
Porshcur GTV ten?

Speaker 2 (34:13):
And final question, is there one dream car you're still
hunting for?

Speaker 4 (34:18):
No? No, I'm quite happy when I have. O'd be
happy with you have. Just make sure you have enough.

Speaker 2 (34:25):
There you go. Thank you Jay for me, Thank you,
thank you, thank you. That was my live interview with
Jay Leno at the Newport or Dream Concourse to Elegance.
If you enjoyed that conversation, check out any of the
five hundred and ninety two we've done over the past
twelve years. You can find those at iTunes, Spotify, Bloomberg YouTube,

(34:51):
wherever you get your favorite podcasts. And be sure and
check out my new book, How Not to Invest, The
idea's numbers and behavior that destroys wealth and how to
avoid them at your favorite bookstore or bookseller. I would
be remiss if I do not thank the crack team
that puts these conversations together each week. My videographer at

(35:12):
the live event was Sebastian Escobar. Alexis Noriega is my
video producer. Anna Luke is my podcast producer. Sean Russo
is my researcher. Sage Bauman is the head of podcasts
here at Bloomberg.

Speaker 6 (35:27):
I'm Barry Ridults.

Speaker 2 (35:28):
You've been listening to Masters in Business

Speaker 6 (35:31):
On Bloomberg Radio
Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

The Burden

The Burden

The Burden is a documentary series that takes listeners into the hidden places where justice is done (and undone). It dives deep into the lives of heroes and villains. And it focuses a spotlight on those who triumph even when the odds are against them. Season 5 - The Burden: Death & Deceit in Alliance On April Fools Day 1999, 26-year-old Yvonne Layne was found murdered in her Alliance, Ohio home. David Thorne, her ex-boyfriend and father of one of her children, was instantly a suspect. Another young man admitted to the murder, and David breathed a sigh of relief, until the confessed murderer fingered David; “He paid me to do it.” David was sentenced to life without parole. Two decades later, Pulitzer winner and podcast host, Maggie Freleng (Bone Valley Season 3: Graves County, Wrongful Conviction, Suave) launched a “live” investigation into David's conviction alongside Jason Baldwin (himself wrongfully convicted as a member of the West Memphis Three). Maggie had come to believe that the entire investigation of David was botched by the tiny local police department, or worse, covered up the real killer. Was Maggie correct? Was David’s claim of innocence credible? In Death and Deceit in Alliance, Maggie recounts the case that launched her career, and ultimately, “broke” her.” The results will shock the listener and reduce Maggie to tears and self-doubt. This is not your typical wrongful conviction story. In fact, it turns the genre on its head. It asks the question: What if our champions are foolish? Season 4 - The Burden: Get the Money and Run “Trying to murder my father, this was the thing that put me on the path.” That’s Joe Loya and that path was bank robbery. Bank, bank, bank, bank, bank. In season 4 of The Burden: Get the Money and Run, we hear from Joe who was once the most prolific bank robber in Southern California, and beyond. He used disguises, body doubles, proxies. He leaped over counters, grabbed the money and ran. Even as the FBI was closing in. It was a showdown between a daring bank robber, and a patient FBI agent. Joe was no ordinary bank robber. He was bright, articulate, charismatic, and driven by a dark rage that he summoned up at will. In seven episodes, Joe tells all: the what, the how… and the why. Including why he tried to murder his father. Season 3 - The Burden: Avenger Miriam Lewin is one of Argentina’s leading journalists today. At 19 years old, she was kidnapped off the streets of Buenos Aires for her political activism and thrown into a concentration camp. Thousands of her fellow inmates were executed, tossed alive from a cargo plane into the ocean. Miriam, along with a handful of others, will survive the camp. Then as a journalist, she will wage a decades long campaign to bring her tormentors to justice. Avenger is about one woman’s triumphant battle against unbelievable odds to survive torture, claim justice for the crimes done against her and others like her, and change the future of her country. Season 2 - The Burden: Empire on Blood Empire on Blood is set in the Bronx, NY, in the early 90s, when two young drug dealers ruled an intersection known as “The Corner on Blood.” The boss, Calvin Buari, lived large. He and a protege swore they would build an empire on blood. Then the relationship frayed and the protege accused Calvin of a double homicide which he claimed he didn’t do. But did he? Award-winning journalist Steve Fishman spent seven years to answer that question. This is the story of one man’s last chance to overturn his life sentence. He may prevail, but someone’s gotta pay. The Burden: Empire on Blood is the director’s cut of the true crime classic which reached #1 on the charts when it was first released half a dozen years ago. Season 1 - The Burden In the 1990s, Detective Louis N. Scarcella was legendary. In a city overrun by violent crime, he cracked the toughest cases and put away the worst criminals. “The Hulk” was his nickname. Then the story changed. Scarcella ran into a group of convicted murderers who all say they are innocent. They turned themselves into jailhouse-lawyers and in prison founded a lway firm. When they realized Scarcella helped put many of them away, they set their sights on taking him down. And with the help of a NY Times reporter they have a chance. For years, Scarcella insisted he did nothing wrong. But that’s all he’d say. Until we tracked Scarcella to a sauna in a Russian bathhouse, where he started to talk..and talk and talk. “The guilty have gone free,” he whispered. And then agreed to take us into the belly of the beast. Welcome to The Burden.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.