Jay Leno on the Future of Late Night & Car Collecting

Summary

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Masters in Business – Jay Leno on the Future of Late Night & Car Collecting

Host: Barry Ritholtz (Bloomberg)
Guest: Jay Leno
Date: December 26, 2025

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Episode Overview

In this captivating holiday episode, Barry Ritholtz sits down with legendary comedian and car enthusiast Jay Leno at the Newport Audrain Concours d’Elegance. Their wide-ranging conversation covers Leno’s journey from small-town Massachusetts to comedy stardom, his famous car collection, the evolution and future of late-night television, the parallels between cars and mechanical watches, and Leno’s practical approach to finances and collecting. Blending humor, insight, and personal anecdotes, Jay Leno shares the philosophy and stories behind a remarkable career and an even more remarkable garage.

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Early Life and Finding Comedy

• Growing Up in Andover, MA

  • Leno discusses the humble beginnings in a small rural town where comedy seemed like an unlikely career (“You don’t think of comedy as a job…In Andover, it’s like, what, comedian?” – 03:11, Jay Leno).
  • Encouraged by a high school English teacher, Mrs. Hawks, who suggested he try writing jokes for a class talk instead of a paper because she noticed him making people laugh in class.
    • Quote: “It was the first time in my life I actually enjoyed doing homework. And I thought, maybe I can make a living doing this.” (04:00, Jay Leno)

• Early Signs of a Comedian

  • Shared an early classroom pun about Friar Tuck: “She was telling us how the Sheriff of Nottingham would boil Robin’s men in oil…And I said, you know why he did that to Tuck? Because he was a friar.” (04:38, Jay Leno)
  • The joke eventually made it to the teachers’ lounge, giving him his first taste of the attention, and validation, comedians crave.

• Comedy Influences

  • Leno cites Robert Klein, George Carlin, Richard Pryor, and Bill Cosby (pre-scandal) as his primary influences. He appreciated Klein’s relatability as someone from a similar background (“middle class, white kid” – 05:34, Jay Leno).

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Cars: The Life-long Passion

• First Car and Becoming a Mechanic

  • Jay bought his first car, a 1934 Ford, for $350 after working at McDonald’s (“I took a couple of years to get it running...Self-taught would be the fair way to say it.” – 06:45, Jay Leno).
  • His collection started with this “gateway drug” and grew to over 214 cars and a significant array of motorcycles.

• Car Collection Philosophy

  • “If I do one oil change a day, it takes 18 months.” (07:39, Jay Leno)
  • Leno enjoys working on the cars himself, rarely trusting anyone else to even park them.
  • “I watch the show Hoarders and go, the guy’s fine...You can still get to the bathroom!” (07:18, Jay Leno)

• On Leno’s Garage TV Show

  • Originated from having a garage, cameras, and friends—made sense to film the hobby for TV.
  • “I did it for nothing for the first, I guess, 15 years. Just because I enjoyed doing it. It was fun.” (09:05, Jay Leno)

• What Cars Stand Out at Concours and Why

  • Jay marvels at the rare, often regional cars showcased (e.g., Czech-made Tatras) and sees car collecting as approachable compared to ancient collectibles: “With cars, you only have to go back a few years.” (10:08, Jay Leno)
  • Artistry: “It’s only in recent years cars are seen as kinetic artwork.” (10:34, Jay Leno); mentions that some classic Ferraris now go for astronomical prices (“last Ferrari sold for $75 million...it’s pretty crazy.” – 10:57, Jay Leno)

• Classic Design and Aesthetics

  • On Jaguar XKE: “The best looking cars are both masculine and feminine...I don’t know any women that don’t find Jaguars attractive...” (12:25, Jay Leno)
  • Laments modern car aesthetics, noting computerized designs lack the “flow” of hand-drawn classics.

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Watch Collecting and Mechanical Fascination

• Parallel between Watches & Cars
  • Both are feats of intricate mechanics; most collectors (including Leno) favor mechanical over quartz or digital.
  • “Quartz watches are obviously the most accurate...but don’t appear to have a soul...The watch needs you. If you don’t wind it, it won’t run.” (14:25, Jay Leno)
  • Enjoys the interaction and dependency involved: “I like things that need me. My cars need me because I need to do certain things to make sure they run correctly.” (15:23, Jay Leno)

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The Rise of EVs and Collectibility

• Electric Vehicles (EVs) and the Modern Market
  • Leno drives a Tesla Plaid for utility during the week and brings out classic cars for rallies and social car events on weekends.
  • “Sitting on the freeway in a 1966 Hemi 426 that gets 3 miles per gallon doesn’t really make a lot of sense.” (20:07, Jay Leno)

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Comedy Craft and Career Longevity

• Precision in Stand-Up

  • Jay draws a clear analogy between comedic timing and mechanical precision:
    • “You want a joke every six to nine seconds...It’s a bit like spinning plates on the Sullivan Show.” (20:54, Jay Leno)
    • Critiques comedians who waste time with crowd work instead of jokes (“How y’all doing?...That’s not comedy. You’ve wasted 40 seconds.” – 21:09, Jay Leno)
    • Admires Rodney Dangerfield for “economy of words...getting the funniest words in the shortest amount of time.” (21:13, Jay Leno)

• Why He Never Stopped Touring

  • Continued stand-up throughout his Tonight Show tenure for creative control and direct feedback:
    • “On the road, you rise or fall strictly on your own ability. You get all the blame but you also get all the glory.” (22:09, Jay Leno)
    • Cites the unpredictability and bureaucracy of TV (“My favorite TV line of all time...We want what’s above number one…What is above number one?” – 22:27, Jay Leno)

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Money, Investing, and Collecting

• Leno’s Financial Philosophy

  • Kept things simple due to dyslexia and lack of comfort with financial risk:
    • “My money relaxes. I don’t want my money out working for me because he’s going to screw up somewhere.” (23:27, Jay Leno)
    • Always banked income from major gigs (e.g., “I never touched a check in 22 years from the Tonight Show. I banked everything—I lived on the money I made as a comedian.” – 24:02, Jay Leno)

• On Starting Out

  • Humbling stories of sleeping in alleys as a struggling comic, highlighting that everything after those days feels like “gravy.” (24:25–25:12, Jay Leno)

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Stories Behind the Cars

• Memorable “Barn Find” Stories

  • 1963 Jaguar XKE found under junk after the owner’s passing (“I paid more than a fair price because I don’t flip cars. I don’t sell cars. This way, nobody goes, ‘Jay Leno ripped me.’” – 26:23, Jay Leno)
  • The touching Hudson Hornet story: buying it from a 94-year-old widow, restoring it, and giving her and her “kids” (ages 74 and 72) a joyful ride (27:17–28:25).

• Collection Motives

  • “I buy the story as much as I buy the car.” (26:38, Jay Leno)
  • “The key to success is low self-esteem—you never assume you’re the smartest person in the room. I assume I’m the dumbest.” (28:49, Jay Leno)
  • Noted the importance of collaborative work culture at Tonight Show—everyone could “pull the cord and stop the train” if something wasn’t working. (28:46–29:47)

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The Future of Late Night and Free Speech

• Interviewing Presidents

  • Barack Obama as first sitting president on Tonight Show. Leno shares a humorous story about Obama giving him his phone number and answering Leno’s prank call:
    • “Hello, Barack here. Mr. President? Yeah, Jay Leno. What can I do for you, Jay? I’m just here with some friends...Lose this number, Jay. Click.” (35:23, Jay Leno)

• Politics and Comedy

  • Known for going “down the middle,” making fun of both sides. (35:39–35:57)
  • Defends free speech for comics: “You either believe in free speech or you don’t...It only becomes annoying when it says something you don’t like.” (36:14, Jay Leno)
  • On Chappelle and the state of the industry: “I don’t like this new thing of comics criticizing other comics...I will defend [free speech] to the end.” (37:13, Jay Leno)

• Late Night in the Streaming Era

  • Streaming is upending the old model: why watch seven minutes with a star on TV when you can find more online (“It changes...just another format you can use.” – 38:14, Jay Leno)
  • Cites overabundant commercials as one of the main problems with late night: “The thing that really kills late night is the incessant number of commercials...Suddenly seeing Jake from State Farm again, okay, enough with this guy.” (39:04, Jay Leno)

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Speed Round — Jay Leno’s Picks and Preferences

(Timestamps approx. 39:31–42:20)

• Favorite car to drive: “Duesenberg.” (39:42)
• Favorite motorcycle: “Brough Superior.” (39:46)
• Best bang for the buck: “Corvette.” (39:53)
• Favorite car overall: “McLaren F1.” (39:59)
• Biggest maintenance annoyance: “1925 Doble steam car.” (40:06)
• Biggest regret passing on: “Oh, yeah.” (40:19 — not specified)
• Annoying modern car feature: “Infotainment system.” (40:28)
• Car driven the most: “Mustang...Actually the Tesla, when I have to go to the airport.” (41:01)
• Rarest car: “Doble steam car.” (41:15)
• Any brand avoided? “No, not with everyone.” (41:24)
• Surprise factor car: “1906 Stanley Steamer...when it’s on fire, people are surprised.” (41:44)
• Most recent addition: “Mustang GTD.” (42:05)
• Best sounding engine: “Porsche GT V10.” (42:12)
• Still hunting for a dream car? “No, I’m quite happy with what I have. Just make sure you have enough.” (42:20, Jay Leno)

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Notable Quotes

• On humility and learning:

  • “The key to success is low self-esteem.” (28:49, Jay Leno)

• On mechanical passions:

  • “I like things that need me…Electric cars kind of run no matter who the master is.” (15:23, Jay Leno)

• On comedy precision:

  • “It was the economy of words…Getting the funniest words in the shortest amount of time.” (21:13, Jay Leno)

• On collecting:

  • “I buy the story as much as I buy the car.” (26:38, Jay Leno)

• On financial discipline:

  • “I never touched a check in 22 years from the Tonight Show…I lived on the money I made as a comedian.” (24:02, Jay Leno)

• On modern entertainment:

  • “When you could turn on streaming and see Harrison Ford talk for half an hour…or watch him do a seven-minute segment on a talk show, what you gonna do?” (38:14, Jay Leno)

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Timestamps for Key Segments

• 03:11 – Growing up and discovering comedy
• 06:15 – First car, learning to fix cars
• 09:32 – Genesis of Leno’s Garage TV show
• 10:34 – Cars as kinetic art
• 12:25 – Evolution of car design
• 14:25 – Mechanical watches and cars compared
• 20:07 – EVs and how they fit in Jay’s life
• 20:54 – Standup and comedic precision
• 23:27 – Leno’s approach to money and risk
• 24:25 – Sleeping in alleys—humble beginnings
• 27:17 – The Hudson Hornet heartwarming story
• 35:23 – Joking with President Obama
• 36:14 – Free speech and the future of late night
• 38:14 – Streaming vs. late night TV; commercials problem
• 39:31–42:20 – Speed round: best cars, motorcycles, regrets, pet peeves

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Tone and Language:
The episode retains Leno’s easygoing, self-deprecating wit and blend of humor with practical wisdom. Both Leno and Ritholtz keep the conversation light, candid, and full of affable banter, making it accessible and engaging even for listeners outside the car or comedy worlds.

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Transcript

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[Hannah Fry]

Bloomberg Audio Studios podcasts Radio News this is Masters in Business with Barry Ritholtz on Bloomberg Radio.

[Barry Ritholtz]

Happy holidays. And we have an extra special holiday podcast at the Newport Audrain Concourse d'. Elegance. I sit down with Jay Leno talking about cloud, cars, comedy, watches and pretty much everything else. Jay's a fascinating guy who's created really 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. Jay, thank you so much for joining us.

[Jay Leno]

Thanks for having me.

[Barry Ritholtz]

So let's start out with a little bit talking about your background. Born in New Rochelle, you grow up in Andover, Massachusetts. Which interest came first, cars or comedy?

[Jay Leno]

Well, when you grew up in a little rural town, you don't think of comedy as a, as a job. You know, it always the neighbors. You know, Kathy's boy wants to be a Comedian, he'll grow out of that. He'll say, don't worry, Kathy. That kind of, you know, people just, it didn't seem like a viable, you know, you go to Hollywood, you meet kids who want to be lighting directors or costumers or because they know people that did that.

[Barry Ritholtz]

Right.

[Jay Leno]

But when you're an andor, it's like, what comedian?

[Barry Ritholtz]

So what sparked your interest in comedy? How did you find that path?

[Jay Leno]

You know, I had very good teachers when I was in high school. I had an English teacher, Mrs. Hawks, and being dyslexic, I was not the best student. And you know, she said, I always see making jokes in class and stuff. Do you ever think of writing comedy? I said, well, I never thought it'd be a job. Oh, you should think, oh yeah, that's a job. I'll tell you, 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 kid style jokes in and it was the first time in my life I actually enjoyed doing homework. And I thought, well, maybe I can make a living doing this. But as a kid, you know, I think people at comedians, you tend to remember things that are funny, things that get a reaction. You know, I was in the fourth grade and Mrs. Allen was my teacher. I always remember this. She was telling us 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 to Tuck? And she said, no, why? Because he was a friar. Okay, okay. And then she does one of these. That's not funny.

[Odoo Advertiser]

Just stop that.

[Jay Leno]

Oh, she's kind of laughing, you know. But the real kicker was later in the day, I'm walking past the teacher's lounge. Leno, come here. What did you say about Friartuck? I said, I went, oh, she told my joke in the teacher's lounge. And I said, oh. I said it was a friar. Oh, that's a fraud. That's a very funny thing. I went, oh, that's pretty good. And I thought, and when you're a kid, you, you know people that you tend to remember things that get a laugh.

[Barry Ritholtz]

You just sort of a little bit of attention.

[Jay Leno]

Yeah, you put them in your mind, it makes a little indentation, you know. So that was always something I enjoyed doing. I always remembered it. But again, I never thought I could make a living doing it.

[Barry Ritholtz]

Who were your comedic influences when you were growing up?

[Jay Leno]

Oh, Robert Klein, George Carlin, Richard Pryor, primarily Klein, because Klein was like me, middle class, white kid. You know, most comedians that time tend to be grew up during the Depression. Hannah Youngman, all those kind of guys, you know, kids today with the long hair, you know, all that kind of stuff.

[Barry Ritholtz]

Right.

[Jay Leno]

And then all along comes Robert Klein and once again, George Carlin, Richard Pryor, Bill Cosby before the recent turn of events, you know, so it was. Yeah, those are my influences.

[Barry Ritholtz]

So since we're at the Ordring concourse and motor week, let's talk a little bit about cars.

[Jay Leno]

Good transition, right?

[Barry Ritholtz]

Your first, first, your first car was a 34 Ford stock. What'd you do to it?

[Jay Leno]

I saw it. 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.

[Barry Ritholtz]

What'd you pay for that?

[Jay Leno]

350. Which was a lot of money. Yes, in 1965. But I had been working at McDonald's and I'd saved some money and you know, so we dragged it 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.

[Barry Ritholtz]

Self taught mechanic. What do you mean you took a.

[Jay Leno]

Couple of years to get self taught? Well, yeah, I mean just, you know, you're a kid, you're playing with it after school, you know, that kind of thing. Yeah, it took me a couple of years to learn how to do. Yeah, I guess self taught would be the fair way to say it.

[Barry Ritholtz]

So 34 Ford is the gateway drug. At what point did you realize this is more than a hobby? This became something of a passion.

[Jay Leno]

Well, I had a garage full of cars. Perhaps this is more than. Yeah, yeah.

[Barry Ritholtz]

Well, how many cars is too many? At what point do you need help?

[Jay Leno]

Well, I am. Well, I have 214 on the road.

[Barry Ritholtz]

Now, plus the motorcycles.

[Jay Leno]

You see, I watch the show Hoarders and go, the guy's fine. It's a problem, man. You can still get to the bathroom.

[Barry Ritholtz]

Look, but that's old newspapers. You have motorcycles and cars. Something a little more reasonable.

[Jay Leno]

When you're a parent, they're the same thing.

[Odoo Advertiser]

Right.

[Barry Ritholtz]

So. So how do you decide of the 214 cars which one you're going to take that.

[Jay Leno]

Okay, that's a first world problem.

[Barry Ritholtz]

That's not very much.

[Jay Leno]

So people don't want to hear a rich guy go, how do I decide? I just can't decide which car have Jeeves do it. No, I mean, whatever I'm working on, if I do one oil change a day, it takes 18 months.

[Barry Ritholtz]

Right.

[Jay Leno]

You have to look at it that way.

[Barry Ritholtz]

Right.

[Jay Leno]

So whatever you just worked on is, oh, let me. Let me drive it home to see if it's okay. So that's what I enjoy.

[Barry Ritholtz]

So you're a little bicoastal. You're in la, but you also have a place here in Newport.

[Jay Leno]

I do have a place, and I also have a house in Andover, Massachusetts, where I grew up.

[Barry Ritholtz]

Do you. Do you keep any cars out here?

[Jay Leno]

No, I don't because of the weather and, you know.

[Barry Ritholtz]

So what do you drive?

[Jay Leno]

When 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. Like, we go out to eat. If. If I can't see the restaurant from my table, we're not eating here, honey.

[Barry Ritholtz]

That's it.

[Jay Leno]

Yeah. Yeah. Yes.

[Barry Ritholtz]

So I'm curious how Leno's garage came about. I have this fantasy that your accountant.

[Jay Leno]

Says to you, no, no, no, I have a garage. I have friends with cameras. I'm on TV already. This seems like a fairly natural transition. So why don't I take the TV hobby and put it on tv? And this way you try to, you know, monetize as much as you can. I did it for nothing for the first, I guess, 15 years.

[Barry Ritholtz]

Really?

[Jay Leno]

Yeah, you know, just because I enjoyed doing it. It was fun, and it just opens up another. You know, you should have something. 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 noise, is interesting.

[Barry Ritholtz]

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?

[Jay Leno]

Yeah. You have some of the best cars in the world here. This is quite an event. And inevitably you see something you've never seen before or never even heard of. You know, all countries are working on automobiles in different. You know, you had cars from Czechoslovakia that people on the other side of the mountains never heard of. You know, like a Tatra, very unusual car. Most Americans never seen one, but it's very popular in Czechoslovakia or what was then Czechoslovakia at the time. So. Yeah, so it's a fascinating hobby. And the nice thing about it is it's no more than really 150 years old. You know, if you. If you like Egyptology, well, now you got to go back 6,000 years and stay stand in hot sun and dig in the sand and you know, like with cars you only have to go back a few years.

[Barry Ritholtz]

We, we took a walk down the boulevard earlier. The two that kind of leapt out to me, aside from the gull wing I know you have one of those was the Talbot Lagos.

[Jay Leno]

Talbot Lago. Yeah.

[Barry Ritholtz]

Spectacular.

[Jay Leno]

Yeah, Very interesting. They're very art deco. You know, it's only in recent years cars are seen as kinetic artwork.

[Barry Ritholtz]

Right.

[Jay Leno]

You know, it used to be just an old car, but now people are looking at them and I mean it's. You know, you can buy a painting that this for $100 million. Something that rolls down the road. Looks pretty, has a practical element to it, so.

[Barry Ritholtz]

And only cost a tenth as much.

[Jay Leno]

Yeah, it cost a tenth or sometimes almost as much. I mean Ferraris go for. I think the last Ferrari sold for $75 million. I mean it's pretty crazy.

[Barry Ritholtz]

That's a one of one though, right?

[Jay Leno]

No, no, it's one of 13.

[Barry Ritholtz]

13.

[Jay Leno]

Wow.

[Barry Ritholtz]

I also saw him and there wasn't a sign on it. So I'm doing this by sight. But a Mercedes SK500. The giant front fenders.

[Jay Leno]

Yeah.

[Barry Ritholtz]

Spectacular also.

[Jay Leno]

They are, they are. I try to enjoy. Some suspicious things happen in Germany from the 30s to the middle 40s. I tend to avoid those for obvious reasons, but the early ones I love.

[Barry Ritholtz]

So 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.

[Jay Leno]

Oh, what is age? Well, it wasn't thought of when it first came out. Two different cars. 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, you know, I mean a Prius is about an efficient shape as you can get, but it's not, it's attractive enough, but it's not striking. It doesn't take your breath away. The way some Ferraris by Pinnifer, you know, back in the, in the 20s, 30s, 40s, 50s, things were drawn by hand. So there's a.

[Barry Ritholtz]

Flow.

[Jay Leno]

Yeah, flow, yeah. Now everything is sort of computer design. You have all these sort of weird angles and things like that. But you know, the best looking cars are both masculine and feminine, like an xke. I don't know any women that don't find Jaguars attractive. Even women don't know anything about cars. There'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 it's a little bit of both to it. You know, a lot of cars look too brutal. You know, Lamborghini, Countach, those look like guy cars, right? You drive one of the girls go.

[Superhuman Advertiser]

How old are you?

[Jay Leno]

Yeah, boy toy. You pull them in a Jag, you're like, oh, I like that guy.

[Barry Ritholtz]

So sometimes the proportions, the shapes, the lines, they speak to everybody. They're universal.

[Jay Leno]

Yeah. I mean, it's tricky. Well, if it speaks to everybody, then you have a Corolla, the best. Cause some people love it, some people hate it. Anything that gets emotion going is probably going to work on some level. You know, I remember talking to Bob Lutz 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 exaggerated. He goes, we're not trying to sell it to them, we're trying to sell it to the people think it looks good. And there's enough of them out there.

[Barry Ritholtz]

You know, for sure. So. So let's talk about. People have to ask you questions about cars all the time, but they don't have to, actually.

[Jay Leno]

Most of them, just people.

[Barry Ritholtz]

Must I assume lots of people do.

[Jay Leno]

Yeah.

[Barry Ritholtz]

When someone asks you for a recommendation, what, what, what do you recommend as a good, cheap set of wheels for a budding enthusiast?

[Jay Leno]

Well, you know, they're almost for an enthusiast or for transportation.

[Barry Ritholtz]

Transportation is easy. I mean, someone who wants something fun for the weekend.

[Jay Leno]

Well, first they tell me what it is they're looking for. You know, I mean, obviously you have cars, Mustangs, Camaros, things of this nature. Any sort of two seater sports car. Yeah, there's plenty of choices out there. You don't need me for that, you know.

[Odoo Advertiser]

Mm.

[Barry Ritholtz]

So this event is sponsored in part by a. Lange and Sona. We're both wearing Lange watches. What drew you to watch this?

[Jay Leno]

I paid for mine.

[Barry Ritholtz]

So did I. Oh, you did. I paid for mine also. So. So. And you probably have access to more of these than I can get, so.

[Jay Leno]

Well, it's interesting, 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 like quartz watches. Quartz watches are obviously the most accurate you can get, but don't appear to have a soul to them. You know, these kind of things. When you turn, you hear the. You know, it's a sort of a.

[Barry Ritholtz]

The car.

[Jay Leno]

The watch needs you. If you don't wind it, it won't run. So there's a human element that needs to be attached to the watch to get it to the run, you know.

[Barry Ritholtz]

And if you flip it over, you can see the absolute spectacular mechanicals on the other side.

[Jay Leno]

Beautiful job, right?

[Barry Ritholtz]

So, so very parallel. The, the precision and intricacy of a mechanical watch and a classic automobile.

[Jay Leno]

Yeah, yeah, I, I seen them as somewhat similar. I mean, I like things that need me. You know, my, my cars need me because I need to do certain things to make sure they run correctly. Electric cars kind of run no 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 if you lift it and turn it just a quarter of an inch, oh, it'll click in.

[Barry Ritholtz]

Coming up, we continue our conversation with Jay Leno live from the Newport Audrey Concourse d', Elegance, discussing how a career in comedy and car collecting led to a fascination with mechanical timepieces. I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio.

[Hannah Fry]

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[Barry Ritholtz]

I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio. My extra special guest this week is Jay Leno. Comedian, car collector, timepiece enthusiast. Let's return to our conversation live at the Newport Ordrain Concourse d'. Elegance. What are your thoughts on the new EVs and hybrids that are coming out? What does this do to the collectible market? I believe you have a Tesla plaid. Is that right?

[Jay Leno]

Tesla plaids are great. Look, I use my electric car during the week. I mean sitting on the freeway in 1966 hemi 426 that gets 3 miles per gallon doesn't really make a lot of sense. You're not going fast, you're just annoying people and poisoning the atmosphere. 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, you sit around, you tell lies about it to other people and they tell you lies about their car. And you know, it's a sort of a little bit of interaction.

[Barry Ritholtz]

So. So I mentioned the precision of automobiles and the precision of watches you have famously been touring for 40 years. 40 plus years when you put together a stand up set, do you put the same sort of precision into structuring that set?

[Jay Leno]

I think, I like to think so. I mean, you want to have a joke every six to nine seconds. It's a bit like spinning plates in the Sullivan show. And then you want to keep it going, you know, so you want to make sure that the people. You're not wasting people's time. I hate when people. How y' all doing?

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[Jay Leno]

Anybody from Boston. Woo Boston.

[Odoo Advertiser]

Yeah.

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Okay.

[Jay Leno]

That's not comedy. You've wasted 40 seconds. You know, get right. Yeah, keep it moving. You know, when you watch Rodney, Rodney was. I was a big fan of Rodney Dangerfield and it was, it was the economy of words. It's getting the funniest words you can in the shortest amount of time. You know, Rodney had jokes I loved. Like I practiced strip joint. It said topless and bottomless. 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 his favorite jokes, it's so stupid. My doctor wanted a semen sample, a stool sample and a urine sample. So I gave him my underpants. I mean, okay, but it's quick. Boom, boom, boom. You're not, you're not wasting people's time.

[Barry Ritholtz]

Really interesting. So you've been known as somebody who just has toured his whole career. Even during, what was it, 22 years of the Tonight show, you still were doing stand up on a regular basis.

[Jay Leno]

Well, when you're on television, you rely on 175 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 or fall strictly on your own ability. And I like that. You get all the blame, but you also get all the glory. And I like that. Plus, it's piecemeal, right? Joke, tell joke, get check, boom. Next show, nobody says, you know those jokes you told two months ago, they're not working out. Come back, you got to come back and do the show again. You don't have to do that. You know, on TV you get, there's so many irons in the fire and whatnot. And 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 23 years. Well, for 18, 18 of the 23 years. And they said, we want what's above number one. I said, okay, what. What is above? What is above number. I mean, just made me laugh. And even they realized how stupid that sounded. I said, what do you mean?

[Barry Ritholtz]

How can you have.

[Jay Leno]

What's the. But just tell me. Somebody tell me what. Yeah, it just made me laugh.

[Barry Ritholtz]

So since this is Bloomberg, a financial network, let's. Let's talk a little bit about money. All right? You are known as someone who is savvy with your money. You only spent the money you earned.

[Jay Leno]

Well, I'm not savvy. I'm dyslexic.

[Barry Ritholtz]

Yeah.

[Jay Leno]

Okay. So consequently, I don't really understand it. All I know is money. My. I work and my money relaxes. That's my. I don't want my money out working for me because he's going to screw up somewhere. I don't want that. Whenever. Here. And there's minimal risk. And I hear the word risk and minimal. So that means I'm going to lose something, right? No, no, I. No, I don't. I always had. Even as a kid, I worked at Wilmington Ford. I worked at McDonald's. Whichever job made the most, I banked. And the other money was my.

[Barry Ritholtz]

You did the same with the Tonight Show. You banked the Tonight Show?

[Jay Leno]

I never touched a check. And 22 years from the Tonight.

[Barry Ritholtz]

That's amazing.

[Jay Leno]

I banked everything I lived on the money I made as a comedian. Then when I. When I. When the show ended, I opened this little passbook. Oh, look this. It's quite a bit of money here. This is good. Yeah.

[Barry Ritholtz]

So when you started collecting cars, did you ever envision this collection would get this large or this valuable?

[Jay Leno]

No, I never thought that. No. When I. I remember, I would sleep in the alleys and New York, and it was the most depressing. I remember sleeping on the alley. It's one of those alleys where guys would come with hookers and I'd be in the back just hiding behind some trash cans and they were doing whatever. Really, this is my life now. I mean, it was like the most.

[Barry Ritholtz]

Horrible that really on the road, you.

[Jay Leno]

Were that hard travel on 44th and 9th. It was Dykes Lumberyard, right across the way from the alley where I slept a couple of nights, I could see Dykes Lumberyard. I always had that in my mind. And hookers would come in and it's just horrible. So terrible. They just hear terrible sounds horrible. I said, really? This is my life. This is what it is now, you know? So everything better than that was gravy.

[Barry Ritholtz]

Yeah, well, it's been a little bit of gravy. You recently had a gullwing you found in a barn. You had a number of.

[Jay Leno]

No, I know. I didn't. I didn't buy that. I didn't buy that car was found. It was sold for $10 million, and we had the owner.

[Barry Ritholtz]

You had it on the show?

[Jay Leno]

We had it on the show, Yes. I did not. I would like to have owned that car, but no, I didn't buy it.

[Barry Ritholtz]

Didn't you find a number of barn finds cars? What are some of the more memorable ones?

[Jay Leno]

Well, the most recent one was a 1963 Jaguar XKE. The guy bought it in 62, started drinking about 66, 67, became a hoarder. Just had trash piled on top of it. When he died, family called me. They said, guys, right across the street, my uncles had some kind of car. We didn't know what it was, and it was a Jaguar. And I said, and this is really the best way. I said, look, Google it. Find out what's it worth. Okay. Find out what they're worth and let me know and I'll pay you that. And that's what I.

[Barry Ritholtz]

Seems fair.

[Jay Leno]

Yeah. I mean, I paid more than a fair price because I don't flip cars. I don't sell cars. So to me, this way, nobody goes, jay, let it rip me. I don't. You don't want any of that.

[Barry Ritholtz]

Any cars on your list that you're still hunting for anything you'd like.

[Jay Leno]

I buy the story. As much much does that buy the car, really? Yeah. I mean, to me, the fun, you know, I had a lady call me 94 years old, and she and her husband bought a 51 Hudson Hornet in New Jersey. They drove it to California with their two kids. He bought a gas station. He ran that for the next 30 years. He died sometime in the early 90s. She calls me about 2,000, I guess, three, four. Oh, my husband died like 20 years ago. We got this car. I say, I already have a 5300. Will you come look at it? Okay. So I got to look at it. She's 94, no hearing and no glasses.

[Barry Ritholtz]

Right.

[Jay Leno]

She said, would you give me $5,000 for it? Okay, So I bought it. I take it back to my garage. It takes about a year and a half. We get it all finished. Let me see if she's still alive. I called her a pillow. Oh, it's Jaylin off. The car's all finished. You want to go for a ride? She goes, okay, now she's 96. And she says, can I bring the kids I said, yeah, bring the kids. So I get there and the kids have got a blindfold. And the kids are 74 and 72. And they're blindfolded, right? And she's like touching the car. Oh, the paint feels so smooth. Oh, it used to be so rough. We'll take the blindfold. Oh, she starts crying. You want to go for. Let's go for a ride. 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. And she turns around, I told you kids. And she's whacking the crap out of me. Mr. Lund was nice enough to take us a ride in his car. And you kids can't be here. And the three of them are just laughing. I mean, they're just falling down. And she's not holding back. I mean, she's really hitting them, but she's laughing while she's hitting them, you know? And it was just so funny. It was just so funny. She lived to be 106.

[Barry Ritholtz]

Wow.

[Jay Leno]

And every time I get in that 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 96, they're 74, and she just whacking the crap out of. Hilarious.

[Barry Ritholtz]

So more stories than there's a hole in your collection or you're enamored with this.

[Jay Leno]

I know I have enamored with this.

[Barry Ritholtz]

Now it's just about the stories.

[Jay Leno]

My key to success is low self esteem.

[Barry Ritholtz]

I've heard you say that before.

[Jay Leno]

Yes, because if you have low self esteem, you never assume you're the smartest person in the room. I assume I'm the dumbest person in the room. Let me look around and see what the other people are doing here. And that's what you do. You know, 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 40 years, I don't think. No, I want it changed. Well, no, I don't want to just let the lighting director do his job. 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 eye contact with the star and just all that kind of night, you know. So to me, that was always the key to being successful.

[Barry Ritholtz]

Coming up, we continue our conversation with Jay Leno live from the Newport Audrain Concourse d'. Elegance. I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio.

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[Barry Ritholtz]

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[Barry Ritholtz]

I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio. My extra special guest this week is Jay Leno, comedian, car collector, timepiece enthusiast. Let's return to our conversation live at the Newport Audrain Concourse d'.

[Odoo Advertiser]

Elegance.

[Barry Ritholtz]

So let's stay with 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?

[Jay Leno]

No, I interviewed Reagan, had dinner with Reagan in 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, wanna come on the show? Thank you so much. You know, he rented a car, drove himself to the show. You know, walks out, he goes, jay, my name's Barack Hussein Obama. I'm running president of the United States. I said, okay, black guy from Chicago named who? I said, you know, you shouldn't even have to campaign. I just think you're shooing with that. And, you know, he got the joke and he laughed and 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 a sitting president. And the whole parking lot was tented so the satellite could not see where when he came in, where he came in. And I mean, I've told this story, but this is. I have the same idiot friends I had in eighth grade. So I'm telling them I had Barack Obama on the show and he gave me his phone number. Nuh. Huh? Nuh. You didn't get it. You said, you all right, let's call him up. I go, it's the president of the United States. I'm not going to call him up. No, you don't have it. Nuh. Nuh. So I take out my phone book and I cover the phone and they go, see what it says there. Barack Obama, president of the United States. His phone number is right here. I Said, all right, all right, I'll call him. You want me to call him, I call him. It's like three o'. Clock. I figure, okay, what can go wrong? Hello, Barack here. Mr. President. Yeah, Jay Leno. What can I do, Vijay? I'm just here with some of my friends. Lose this number, Jay. Click.

[Barry Ritholtz]

So your reputation has never been a very political comedian. You play it straight down the middle.

[Jay Leno]

Well, I used to get. We used to get quoted every day in the New York Times. We tried to make fun of both sides.

[Barry Ritholtz]

Yeah.

[Jay Leno]

But. Yeah, that's the way we did it. That's not the way everybody else does it, but that's okay.

[Barry Ritholtz]

So. So recently, Jimmy Kimmel mentioned on the air that you called to check in on him when. When he was temporarily suspended. Is. What do you think the future of late night looks like? And. And what does that say about the comedians? Have to watch what they say?

[Jay Leno]

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. The only problem. And there's always something somebody doesn't like, whether it's banning books or Huck Finn or whatever it might be. So to me, I always support. 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 tore me apart every day, but they had the right to do it. I didn't like what they said, but I agree with their right to say it if they chose.

[Barry Ritholtz]

You have Dave Chappelle speaking at the comedy festival in sleep, Saudi Arabia, saying he feels like free speech is under assault in the U.S. not that Saudi Arabia is a hotbed of free speech.

[Jay Leno]

Well, yeah, yeah. Again, I don't like this new thing of comics criticizing other comics. It's just we're comedians, okay? Just, you know, I believe in free speech. 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, I don't have to agree with it. You know, it's like the Nazis marching in Skokie. Okay. They have the right to do that. I don't agree with it. What, does he like to see someone punch them in the face? Yes, but I don't want that to be police doing it. If some Angry Jewish guy wants to go, well, okay, it's fine with me. You know, I might even cheer him on. But no, again, I think you. It's America.

[Barry Ritholtz]

And what about the. In the era of streaming, what about the future of late night? We hope. 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 a steward of the tonight show for 22 years. What do you think the future of this looks like?

[Jay Leno]

Well, I mean, when you could turn on streaming and see Harrison Ford talk for half an hour saying whatever you want, unscripted, or you could watch him do a seven minute segment on a talk show, what you got to do.

[Barry Ritholtz]

Or jay Leno for 45 minutes.

[Jay Leno]

But yeah, I mean, to me, I think it's just the nature of television.

[Barry Ritholtz]

It.

[Jay Leno]

It changes. It goes from one thing to another. I mean, it's like going from CD players to cassettes to CDs. It's just another. It's another format that you can. You can use. So I. The thing that really kills late night is the incessant number of commercials. After 11:30, you can run like nine minutes at 12:00'. Clock. Some crazy.

[Barry Ritholtz]

Yeah, it's wild.

[Jay Leno]

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. You know, to me, that's the thing that's really hurt. Late night. It's not necessarily what people say. It's the fact that people. Oh, God, another commercial. You just, you know, we through.

[Barry Ritholtz]

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.

[Jay Leno]

A speed round.

[Barry Ritholtz]

Right. Dozen questions in under a minute. I'm just gonna throw these at you and give me your answers. Starting with, what's your favorite car to drive?

[Jay Leno]

Duesenberg.

[Barry Ritholtz]

What's your favorite motorcycle in your garage?

[Jay Leno]

Brought. Superior.

[Barry Ritholtz]

What car offers the best bang for the buck?

[Jay Leno]

Corvette.

[Barry Ritholtz]

What's your favorite car in your collection? Not necessarily a driver, but just a favorite car.

[Jay Leno]

McLaren F1.

[Barry Ritholtz]

That's a tough one to argue with. What's been the biggest maintenance annoyance in your collection?

[Jay Leno]

My 1925 Doble Steep car.

[Barry Ritholtz]

The one that kind of blew up.

[Jay Leno]

Is that what we're talking about? That blew up, but that wasn't the one that actually blew up in my face.

[Barry Ritholtz]

Any cars you have any regrets passing on?

[Jay Leno]

Oh, yeah.

[Barry Ritholtz]

What modern car features do you find most annoying?

[Jay Leno]

Probably the infotainment system. You know, I have my 51 Hudson. I reach over, I press a button, I get a station. I don't have to stop and look at it. Are you happy? Yes. Would you make this lecture again? Yes. Others have made this election. Would you continue? Yes, I would. You know, would you pick your language? English is good. Thank you. You know, annoying.

[Barry Ritholtz]

What car do you drive the most often from your collection?

[Jay Leno]

Oh, I don't know. Well, I drive a lot of them quite often.

[Barry Ritholtz]

That's what they were made for.

[Jay Leno]

Model T is kind of fun. I guess I don't drive that much. Probably the Mustang. That's pretty good. Well, actually, the Tesla, when I have to go to the airport.

[Barry Ritholtz]

What's the rarest car in your collection? Not necessarily the most valuable, but one of very few.

[Jay Leno]

Well, that would be the double steam car.

[Barry Ritholtz]

Is there any one brand you would never buy that you stay away from?

[Jay Leno]

No, no, not with everyone.

[Barry Ritholtz]

You don't have a lot of Ferraris, right?

[Jay Leno]

No, I don't have any Ferraris, but I have nothing to do with the cars. The cars are excellent. You know, for the longest time, you had to buy two Mondials before you're allowed to buy the car. You know, so I just never took part in that.

[Barry Ritholtz]

What car surprises people the most, whether driving it or just the way it's put together?

[Jay Leno]

Well, I have the kind of cars people not surprised that I got there early or late. They're surprised I got there at all. When you show up in the 1906 Stanley Steamer and it's on fire, people like, oh, my God, your car's on fire. Yeah, I know.

[Barry Ritholtz]

It's supposed to be.

[Jay Leno]

You carry open flame.

[Barry Ritholtz]

What's the most recent addition to the Collection?

[Jay Leno]

A Mustang GTD.

[Barry Ritholtz]

What's the best sounding engine you own?

[Jay Leno]

Porsche GT V10.

[Barry Ritholtz]

And final question. Is there one dream car you're still hunting for?

[Superhuman Advertiser]

No.

[Jay Leno]

No, I'm quite happy with what I have. Like I said, be happy with you have. Just make sure you have enough.

[Barry Ritholtz]

There you go. Thank you, Jay, for being so.

[Jay Leno]

Thank you, thank you, thank you.

[Barry Ritholtz]

That was my live interview with Jay Leno at the Newport Audrey, Concourse d'. Elegance. If you enjoyed that conversation, check out any of the 592 we've done over the past 12 years. You can find those at iTunes, Spotify, Bloomberg, YouTube, wherever you get your favorite podcasts. And be sure and check out my new book, how not to Invest the Ideas, Numbers, and Behavior that Destroys Wealth. And how to avoid them at your favorite bookstore or bookseller. I would be remiss if I did not thank the crack team that puts these conversations together each week. My videographer at 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, I'm Barry Ritholtz. You've been listening to Masters in Business on Bloomberg Radio.

[Hannah Fry]

It's the season to come together over.

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Your holiday favorites at Starbucks.

[Barry Ritholtz]

Warm up with a creamy caramel brulee.

[Hannah Fry]

Latte, get festive with an iced gingerbread.

[Odoo Advertiser]

Chai or share a velvety peppermint mocha Together is the best place to be at Starbucks.

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So don't wait. Find out how to get your real.

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