Jay Leno on the Future of Late Night & Car Collecting

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0:40on the edge of what we think we know. Wherever you get your podcasts. Bloomberg Audio Studios. Podcasts, radio, news. This is Masters in Business with Barry Ritholtz on Bloomberg Radio. 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 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.

1:47Jay, thank you so much for joining us. Thanks for having me. So let's start out with a little bit talking about your background. Born in New Rochelle, you grew up in Andover, Massachusetts. Which interest came first, cars or comedy? well when you grew up in a little rural town you don't think of comedy as a as a job you know it was the neighbors you know kathy's boy wants to be comedian he'll grow out of that he'll say don't worry kathy you know that that kind of you know that kind of people just it didn't seem like a viable but you know you go to hollywood and you meet kids want to be lighting directors or costumers or because they know people that did that right But when you're an Andor, it's like, what?

2:31So what sparked your interest in comedy? How did you find that path? You know, I had very good teachers. When I was in high school, I had a 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 so do you ever think of writing comedy? I said, well, I never thought it would be a job. Oh, you should think? Oh, yeah. I said, I'll tell you, why don't you, maybe you could, instead of writing a paper, for the final, you give a talk. I said, okay. I tried to put some kid-style jokes in. It was the first time in my life I actually enjoyed doing homework.

3:08Maybe I can make a living doing this. It's a kid. I think people as comedians, you tend to remember things that are funny, things that get a reaction. 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. Just stop that. 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.

3:51Leno, come here. What did you say about Friar Tuck? I went, oh, she told my joke in the teacher's lounge. And I said, oh, I said, it was a French. Oh, that's a very funny thing. I went, oh, that's pretty good. And I thought, oh. And when you're a kid, you know, people, you tend to remember things that get a laugh. You just sort of. A little bit of attention. 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. Who were your comedic influences when you were growing up?

4:27Oh, Robert Klein, George Carlin, Richard Pryor. Primarily Klein, because Klein was like me, middle class white kid. You know, most comedians at that time tend to be, grew up during the Depression. Henny Youngman, all those kind of guys. You know, kids today with the long hair, you know, all that kind of stuff. Right. And then 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 were my influences so since we're at the audrey concourse and motor week let's talk a little bit about cars good transition right your first your first car was a 34 ford stock what'd you do to it i i saw it my dad and i were driving past the tip-top miniature golf in north redding massachusetts it was parked at the shell station with a sale sign i went and i bought it um what'd you pay for that 350 which was a lot of money in 1965.

5:26But I had been working at McDonald's and I'd saved some money. So we dragged it back to my house and I took a couple of years to get it running and then I got my license and I drove it every day to school. Self-taught mechanic? What do you mean you took a couple of years to get it? 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 it. Yeah, I guess self-taught would be the fair way to say it. So 34 Ford is the gateway drug. At what point did you realize this is more than a hobby?

5:57This became something of a passion. Well, when I had a garage full of cars, perhaps this is more than, yeah. Well, how many cars is too many? At what point do you need help just maintaining? Well, I have 214 on the road now. Plus the motorcycles. 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. But that's old newspapers. You have motorcycles and cars, something a little more reasonable. When your parents did the same thing. Right. So how do you decide of the 214 cars, which one are you going to take that day? Okay, that's a first world problem.

6:34That's not really. Very much so. People don't want to hear a rich guy go, how do I decide? I just can't decide which car. Oh, have Jeeves do it. No, I mean, whatever I'm working on. If I do one oil change a day, it takes 18 months. Right. You have to look at it that way. Right. So whatever we just worked on, we said, oh, let me drive it home to see if it's okay. So that's what I enjoy. So you're a little bi-coastal. You're in L.A., but you also have a place here in Newport. I do have a place, and I also have a house in Andover, Massachusetts, where I grew up in. Do you keep any cars out here as well?

7:07No, I don't because of the weather and, you know. So what do you drive when you're out here? I'm one of these people. Really? It's such my car. You know, so if my car was on another coast, oh, that would be horrible. Like when we go out to eat, if I can't see the restaurant from my table, we're not eating here, honey. That's it. Yeah, yeah. So I'm curious how Leno's Garage came about. I have this fantasy that your accountant 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?

7:46and this way you try to you know monetize as much as you can um i did it for nothing for the first i guess 15 years really yeah you know just because i enjoyed doing it it was fun um and it just opens up another you know you should have something i'm not a particularly interesting person uh 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 do you know what the cars uh that are top of the list here are going to be have you walked around seen much so far yeah this 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 you know they're 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.

8:48It was a very unusual car. Most Americans have never seen one, but it was 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 like Egyptology, well, now you've got to go back 6 ,000 years and stand in hot sun and dig in the sand. And then, you know, with cars, you only have to go back a few years. 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.

9:25Talbot Lagos, yeah. Spectacular. Yeah, very interesting car. That very Art Deco, you know. Yes. It's only in recent years cars are seen as kinetic artwork. Right. You know, it used to be just an old car. But now people are looking at them and, I mean, by painting this for$100 million, it's something that rolls down the road, looks pretty, has a practical element to it. And only cost a tenth as much. Yeah, only 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. That's a one of one, though, right? No, no, that's one of 13.

10:0213, wow. Now, I also saw them, and there wasn't a sign on it, so I'm doing this by sight, but a Mercedes SK500, the giant front fenders. Yeah. Spectacular also. They are. I try to enjoy them. Some suspicious things happen in Germany in the 30s to the middle 40s. I tend to avoid those for obvious reasons. But the early ones I love, yeah. 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? Oh, what did it age well that wasn't thought of when it first came out? It's two different cars.

10:43I 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. I mean, a Prius is about an efficient shape as you can get, But it's attractive enough, but it's not striking. It doesn't take your breath away the way some Ferraris, Pinoferino, you know, back in the 20s, 30s, 40s, 50s, things were drawn by hand. So there's a flow. 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.

11:31I don't know any women that don't find Jaguars attractive. Even women don't know anything about cars. 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 it's a little bit of both to it, you know. A lot of cars look too brutal. You know, a Lamborghini Countach. Those look like guy cars. You drive one, and the girls go, how old are you? Boy toy. You pull them a Jag, and you're like, ooh, I like that guy. So sometimes the proportions, the shapes, the lines, they speak to everybody. They're universal. Yeah. I mean, the trick is, well, if it speaks to everybody, then you have a Corolla.

12:06The best car is some people love it, some people hate it. Anything that gets emotion going is probably going to work on some level. I remember talking to Bob Letts 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 because we're not trying to sell it to them. We're trying to sell it to the people who think it looks good. And there's enough of them out there. For sure. So let's talk about people have to ask you questions about cars all the time. But they don't have to, actually. People must. I assume lots of people do. When someone asks you for a recommendation, what do you recommend as a good cheap set of wheels for a budding enthusiast?

12:47Well, you know, there are almost for an enthusiast or for transportation. Transportation is easy. I mean, someone who wants something fun for the weekend. 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. So this event is sponsored in part by Alanga and Sona. We're both wearing Alanga watches. What drew you to watches? I paid for mine. So did I. Oh, you did. I paid for mine also. And you probably have access to more of these than I can get.

13:26Well, 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. quart watches are obviously the most accurate you can get but there's don't appear to have a soul to them you know these kind of things when you turn to hear that the you know this is a sort of a the carton 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 and if you flip it over you You can see the absolute spectacular mechanicals on the other side.

14:06Yeah, they do a beautiful job. Right. So very parallel, the precision and intricacy of a mechanical watch and a classic automobile. Yeah, yeah. I see them as somewhat similar. I mean, I like 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 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. Coming up, we continue our conversation with Jay Leno, live from the Newport Audrain Concourse d 'Elegance, discussing how a career in comedy and car collecting led to a fascination with mechanical timepieces.

14:57I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio.

15:27And I sat down with two experts to discover how we can support the massive connectivity needs of AI. Find out what I learned at Bloomberg.com forward slash Nokia.

15:47I'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? I have a Tesla Plaid. It's a great. Look, I use my electric car during the week. I mean, sitting on the freeway in a 1966 Hemi 426 that gets three miles per gallon doesn't really make a lot of sense.

16:30You'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. 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 as you do with a car?

17:05Well, 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 a celibate and show. And then you want to keep it going, you know. So you want to make sure that you're not wasting people's time. I hate when people are like, how you all doing? Woo! Anybody from Boston? Woo! Boston, yeah! Okay, that's not comedy. You've wasted 40 seconds. You know, get right into it. Yeah, keep it moving. You know, when you watch Rodney, Rodney was a big fan of Rodney Dangerfield. And it was the economy of words. It's getting the funniest words you can in the shortest amount of time.

17:39You know, Rodney had jokes I loved, like I worked back to 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 wasting people's time. 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.

18:20Well, 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. Write joke, tell joke, get checked. Boom. Next show. Nobody says, you know those jokes you told two months ago? They're not working out. Come back. You've got to come back and do the show again. You don't have to do that. On TV, you get there's so many irons in the fire and whatnot you're dealing with.

18:56My 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 is a buff number? I mean, it just made me laugh. And even they realized how stupid that's sound. I said, what do you mean? How can you have, what's a buff? Just tell me, somebody tell me. Yeah, it just made me laugh. So since this is Bloomberg, a financial network, 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.

19:35Well, I'm not savvy, I'm dyslexic. Yeah. Okay, so consequently, I don't really understand it. All I know is I work and my money relaxes. That's my thing. I don't want my money out working for me because he's going to screw up somewhere. I don't want that. Whenever I hear, and there's minimal risk. And I hear the word risk and minimal, so that means I'm going to lose something. Right. 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... You did the same with The Tonight Show. You banked The Tonight Show.

20:12I never touched a check in 22 years from The Tonight Show. That's amazing. I banked everything, and I lived on the money I made as a comedian. Then when the show ended, I opened this little passbook. Oh, look at this. There's quite a bit of money here. This is good. So when you started collecting cars, did you ever envision this collection would get this large? No. Or this valuable? No, I never thought that. No. I remember I would sleep in the alleys in New York, and it was the most depressing. I remember sleeping in alleys. 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.

20:51Really, this is my life now. I mean, it was like the most horrible. Really, on the road, you were that hard to travel. On 44th and 9th, it was Dykesley Lumberyard right across the way. And 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 just, that's 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. Yeah. Well, it's been a little bit of gravy. You recently had a gullwing you found in a barn.

21:28You found a number of barns. No, no, I didn't buy that. I didn't buy that car was found. It was sold for$10 million. And we had the owner. You had it on the show. 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. Didn't you find a number of barn finds? Yeah, sure, sure. What are some of the more memorable ones? 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, the family called me. They said, guys are across the street. My uncle's had some kind of car.

22:16We don'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 they're worth, okay? Find out what they're worth and let me know. And I'll pay you that. and that's what i seems fair yeah i mean i paid more than a fair price because i i don't flip cars i don't sell cars so to me this way nobody goes get a little bit i don't you don't want any of that any cars on your list that you're still uh hunting for anything you know 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 call me 94 years old and she and her hudson her 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 2000 i guess three four uh oh my husband died like 20 years ago we got this car i said i already have a 53 300.

23:22Will you come look at it? Okay, so I got to look at it. She's 94. No hearing aid, no glasses. I 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 up. Hello. Oh, it's Jaylen. The car's all finished. You want to go for a ride? She said, 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.

23:59Oh, the pain feels so smooth. Oh, it used to be so rough. We'll take the blindfold. Oh, and she starts crying. We want to go for it? 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.

24:30And it was just so funny. It was just so funny. She lived to be 106. Wow. 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. She's 96. They're 74. and she's just whacking the crap out of her. Hilarious. So more stories than there's a hole in your collection or you're enamored with this. No, I don't have a hole in my collection. No, I don't have a hole in my collection. It's just about the stories. My key to success is low self-esteem. I've heard you say that before. Yes, yes, because if you have low self-esteem, you never assume you're the smartest person in the room.

25:09I 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 to change. 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?

25:40Sometimes. 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 nonsense, you know. So to me, that was always the key to being successful. 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.

26:28I'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. So 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? Was Barack Obama. Was Reagan before you started on? No, I interviewed Reagan. I had dinner with Reagan at 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.