Jay Leno on the Future of Late Night & Car Collecting

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 https://omnystudio.com/listener for privacy information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  At Brookfield, we believe you can own wealth that's measured in generations. Because true ownership looks beyond today and beyond cycles. For 125 years, we've built long-term wealth through expertise, discipline, and a clear vision for the future. Providing investors access to alternative strategies built for what's next. Brookfield. Own what's next. Learn more at Brookfield.com/own. This is not an offer to sell or investment advice. Investing involves risks, including loss of capital. Past performance is not indicative nor a guarantee of future results. Please review performance and offering materials before investing.

• 0:38Speaker 01

  This is the Bloomberg Tech Minute brought to you by ChatGPT. I'm Carol Muster. Getting hired at SpaceX requires exceptional ability and may include having Elon Musk review a candidate's resume. So writes Bloomberg Business Week's Lauren Grush. She reports that the company culture is defined by Musk and job candidates must understand that a commitment to SpaceX means adhering to this culture and exhibiting loyalty to Elon Musk. To get hired, candidates must demonstrate their achievements from past jobs and hands-on experience matters more to recruiters than advanced degrees, with the company looking for people with raw innate intelligence. A spokesperson for SpaceX didn't respond to a request for comment on its recruiting and hiring practices.

• 1:21Speaker 01

  But according to recruiters, advisors, and those who've interviewed for jobs there, it's the space exploration dream that draws people to the company and Musk invokes that dream regularly to remind workers why they're there. Prospective hires are told that the job will require stamina, including in job ads that candidates, quote, "must be willing to work extended hours and weekends as needed." One major perk for all that hard work? Employees' access to equity, either the right to buy shares or payment in the form of restricted stock units that vest over time. That's the Bloomberg Tech Minute brought to you by ChatGPT. Get started at ChatGPT.com.

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  This is Masters in Business with Barry Ritholtz on Bloomberg Radio.

• 2:49Barry Ritholtz?

  Happy holidays, and we have an extra-special holiday podcast at the Newport Order 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.

• 3:34Barry Ritholtz?

  Jay, thank you so much for joining us.

• 3:35Speaker 05

  Thanks for having me.

• 3:36Barry Ritholtz?

  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?

• 3:50Speaker 05

  Well, when you grow up in a little rural town, you don't think of comedy as a... As a job, you know, and always 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 bit. You know, you go to Hollywood and you meet kids who want to be lighting directors or costumers or cause they know people that did that.

• 4:15Barry Ritholtz?

  Right.

• 4:16Speaker 05

  You know, but when you're an andor, it's like, what?

• 4:18Barry Ritholtz?

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

• 4:22Speaker 05

  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, oh, I see you're making jokes in class and stuff. Do you ever think of writing comedy? I said, well, I never, I never thought it'd be a job. Oh, you should think, oh, yeah, it's a job. 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, 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 all. Well, maybe I can make a living doing this. But it's a kid, you know, I think people that are comedians, you tend to remember things that are funny,

• 5:03Speaker 05

  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, you know why he did that? It's to tuck. And she said, no, why? Cause he was a friar. Okay. Okay. And then she does one of these. I, I, that's not funny. Just stop that. I, oh, oh, oh, I see. 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. I went, Leno, come here. What did you say about Friar Tuck? I said, I went, oh, she told my joke in the teacher's lounge.

• 5:46Speaker 05

  And I said, oh, I said, he's a Friar. Oh, that's a, oh, that's very funny thing. I went, oh, that's, that's pretty good. And I thought, oh, and when you're a kid, you, you know, people that, you tend to remember things that get a laugh. You just sort of...

• 5:59Barry Ritholtz?

  A little bit of attention?

• 6:00Speaker 05

  Yeah, you put them in your mind. You try, 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.

• 6:11Barry Ritholtz?

  Who were your comedic influences when you were growing up?

• 6:14Speaker 05

  Oh, 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.

• 6:31Barry Ritholtz?

  Right.

• 6:31Speaker 05

  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.

• 6:44Barry Ritholtz?

  So, since we're at the ordering 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?

• 6:55Speaker 05

  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.

• 7:07Barry Ritholtz?

  What'd you pay for that?

• 7:08Speaker 05

  $3.50, which was a lot of money in 1965. But I had been working at McDonald's and I'd saved some money and, you know. So, and 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.

• 7:24Barry Ritholtz?

  Self-taught mechanic? What do you mean, you took a couple of years to get it?

• 7:26Speaker 05

  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.

• 7:37Barry 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?

• 7:46Speaker 05

  Well, when I had a garage full of cars, perhaps this is more than, yeah, yeah.

• 7:51Barry Ritholtz?

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

• 7:54Speaker 05

  Well, I have 214 on the road now.

• 7:56Barry Ritholtz?

  Plus the motorcycles.

• 7:58Speaker 05

  You see, I watch the show Hoarders and go, "The guy's fine. What's the problem, man? You can still get to the bathroom, look."

• 8:06Barry Ritholtz?

  But that's old newspapers. You have motorcycles and cars, something a little more reasonable.

• 8:10Speaker 05

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

• 8:12Barry Ritholtz?

  Right. So, so, um... How do you decide of the 214 cars which one you're gonna take that day?

• 8:19Speaker 05

  Okay, that's a first world problem.

• 8:21Barry Ritholtz?

  Mm-hmm, very much so.

• 8:23Speaker 05

  People don't wanna 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 want an oil change a day, it takes 18 months.

• 8:35Barry Ritholtz?

  Right.

• 8:36Speaker 05

  You have to look at it that way.

• 8:37Barry Ritholtz?

  Right.

• 8:37Speaker 05

  So whatever you just worked on, you say, "Oh, let me, let me drive it home to see if it's okay." So that's what I enjoy.

• 8:43Barry Ritholtz?

  So you're a little bi-coastal, you're in LA, but you also have a place here in Newport.

• 8:48Speaker 05

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

• 8:51Barry Ritholtz?

  Do you, do you keep any cars out here as well?

• 8:53Speaker 05

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

• 8:57Barry Ritholtz?

  So what do you drive when you're out here?

• 8:58Speaker 05

  I'm one of these people.

• 8:59Barry Ritholtz?

  Really?

• 9:00Speaker 05

  Except for 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.

• 9:10Barry Ritholtz?

  That's it?

• 9:10Speaker 05

  Yeah, yeah, yeah, see, yeah.

• 9:12Barry Ritholtz?

  So I'm curious how Leno's Garage came about. I have this fantasy that your accountant says to you.

• 9:20Speaker 05

  No, no, no, I have a garage.

• 9:22Barry Ritholtz?

  Uh-huh.

• 9:22Speaker 05

  I have friends with cameras.

• 9:24Barry Ritholtz?

  Uh-huh.

• 9:25Speaker 05

  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.

• 9:44Barry Ritholtz?

  Really?

• 9:45Speaker 05

  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.

• 10:08Barry Ritholtz?

  Do you know what the cars that are top of the list here are gonna be? Have you walked around, seen much so far?

• 10:14Speaker 05

  Yeah, 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 never even heard of, you know. They're, all countries are working on automobiles.

• 10:29Speaker 05

  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. They're a very unusual car. Most Americans have 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're like, if you're like Egyptology, well, now you gotta go back 6,000 years and stand in hot sun and dig in the sand and, you know, with cars, you only have to go back a few years.

• 11:01Barry Ritholtz?

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

• 11:11Speaker 05

  Talbot Lagos, yeah.

• 11:13Barry Ritholtz?

  Spectacular.

• 11:14Speaker 05

  Yeah, very interesting car. They're very art deco, you know? It's only in recent years cars are seen as kinetic artwork.

• 11:21Barry Ritholtz?

  Right.

• 11:21Speaker 05

  You know, it used to be, it's just an old car. But now people are looking at them and, I mean, it's, you know, if I'm painting this for a hundred million dollars, it's something that rolls down the road, looks pretty, has a practical element to it, so.

• 11:35Barry Ritholtz?

  And only close to 10th as much.

• 11:37Speaker 05

  Yeah, only close to 10th, or sometimes almost as much. I mean, Ferraris go for the, I think the last Ferrari sold for 75 million dollars. I mean, it's pretty crazy.

• 11:46Barry Ritholtz?

  That's a one of one, though, right?

• 11:47Speaker 05

  No, no, it's one of 13.

• 11:49Barry Ritholtz?

  13, wow. I also saw, and there wasn't a sign on it, so I'm doing this by sight, but a Mercedes SK500, the giant front fenders.

• 12:00Speaker 05

  Yeah.

• 12:01Barry Ritholtz?

  Spectacular also.

• 12:02Speaker 05

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

• 12:13Barry Ritholtz?

  So, 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?

• 12:26Speaker 05

  Oh, oh, what is age rollover was and thought when it first came off, it's two different car. 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, like Pinafrin or whatever. You know, back in the twenties, thirties, forties, fifties, things were drawn by hand. So there's a, there's a.

• 13:05Barry Ritholtz?

  A flow?

• 13:05Speaker 05

  Yeah, a flow, yeah. Like 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 X K E. I 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, Lamborghini Countach. Those look like guy cars.

• 13:35Barry Ritholtz?

  Right.

• 13:36Speaker 05

  You drive one, the girls go, how old are you?

• 13:38Barry Ritholtz?

  Yeah. You boy toy.

• 13:39Speaker 05

  You pull them to Jag, you're like, ooh, I like that guy.

• 13:42Barry Ritholtz?

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

• 13:47Speaker 05

  Yeah, I mean, the trick is, well, if it speaks to everybody, then you have a Corolla. You know, the best cars, 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 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 that think it looks good and there's enough of them out there.

• 14:15Barry Ritholtz?

  For sure. So, so let's talk about, um, people have to ask you questions about cars all the time.

• 14:22Speaker 05

  But they don't have to, actually. Most of them just.

• 14:23Barry Ritholtz?

  People must, I assume lots of people do.

• 14:26Speaker 05

  Yeah.

• 14:27Barry 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?

• 14:34Speaker 05

  Well, you know, there are almost, oh, for an enthusiast or for transportation?

• 14:38Barry Ritholtz?

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

• 14:42Speaker 05

  Well, first they tell me what it is they're looking for. You know, I mean, obviously I 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.

• 14:55Barry Ritholtz?

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

• 15:04Speaker 05

  See, I paid for mine.

• 15:05Barry Ritholtz?

  So did I.

• 15:06Speaker 05

  Oh, you did?

• 15:07Barry Ritholtz?

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

• 15:13Speaker 05

  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 reason they don't like quartz watches. Quartz watches are obviously the most accurate you can get, but there's, they don't appear to have a soul to them. You know, with these kind of things, when you turn to hear the, you know, it's a sort of a, the car, 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 run, you know.

• 15:47Barry Ritholtz?

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

• 15:53Speaker 05

  Yeah, they do a beautiful job.

• 15:54Barry Ritholtz?

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

• 16:02Speaker 05

  Yeah, yeah. I, I've 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, if you lift it and turn it just a quarter of an inch, oh, it'll click in.

• 16:27Barry Ritholtz?

  Coming up, we continue our conversation with Jay Leno, live from the Newport Audrain Concourse d'Élegance, 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.

• 16:59Speaker 00

  At Brookfield, we believe you can own wealth that's measured in generations. Because true ownership looks beyond today and beyond cycles. For 125 years, we've built long-term wealth through expertise, discipline, and a clear vision for the future. Providing investors access to alternative strategies built for what's next. Brookfield. Own what's next. Learn more at Brookfield.com/own. This is not an offer to sell or investment advice. Investing involves risks, including loss of capital. Past performance is not indicative nor a guarantee of future results. Please review performance and offering materials before investing.

• 17:38Speaker 01

  This is the Bloomberg Tech Minute brought to you by ChatGPT. I'm Carol Muster. Getting hired at SpaceX requires exceptional ability and may include having Elon Musk review a candidate's resume. So writes Bloomberg Businessweek's Lauren Grush. She reports that the company culture is defined by Musk and job candidates must understand that a commitment to SpaceX means adhering to this culture and exhibiting loyalty to Elon Musk. To get hired, candidates must demonstrate their achievements from past jobs and hands-on experience matters more to recruiters than advanced degrees, with the company looking for people with raw, innate intelligence. A spokesperson for SpaceX didn't respond to a request for comment on its recruiting and hiring practices.

• 18:21Speaker 01

  But according to recruiters, advisors, and those who've interviewed for jobs there, it's the space exploration dream that draws people to the company. And Musk invokes that dream regularly to remind workers why they're there. Prospective hires are told that the job will require stamina, including in job ads that candidates quote, "must be willing to work extended hours and weekends as needed." One major perk for all that hard work? Employees' access to equity, either the right to buy shares or payment in the form of restricted stock units that vest over time. That's the Bloomberg Tech Minute brought to you by ChatGPT. Get started at ChatGPT.com.

• 19:05Barry 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 O'Drane concourse d'alegance. 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?

• 19:36Speaker 05

  Tesla Plaid'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. You're not going fast. You're not... You're just annoying people and poisoning the atmosphere. So you take your electric car. Then in 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, you know?

• 20:07Barry Ritholtz?

  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?

• 20:23Speaker 05

  Well, 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 showroom, 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 you all doing? Woo! Anybody from Boston? Woo! Boston, yeah!" Okay, that's not comedy. You wasted 40 seconds, you know?

• 20:44Barry Ritholtz?

  Filler.

• 20:45Speaker 05

  Yeah, keep it moving. You know, when you watch Rodney... Rodney was a... I was a big fan of Rodney and his film. And 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 worked at a 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."

• 21:20Speaker 05

  I mean, okay, but it's quick. Boom, boom, boom. You're not wasting people's time.

• 21:26Barry 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.

• 21:38Speaker 05

  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. Write 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 gotta 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 what you're dealing with. You know, my favorite TV line of all time, when NBC was letting me go,

• 22:20Speaker 05

  I said, "You know, I've been number one for 22 years." Well, for 18, 18 of the 23 years. And they said, "We want what's above number one." I said, "Okay, what is above? What is above 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 above? Just tell me. Somebody tell me what it is." Yeah, it just made me laugh.

• 22:42Barry Ritholtz?

  So, since this is Bloomberg, a financial network, let's talk a little bit about money.

• 22:47Speaker 05

  All right.

• 22:48Barry Ritholtz?

  You are known as someone who is savvy with your money. You only spent the money you earned doing stand-up.

• 22:53Speaker 05

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

• 22:55Barry Ritholtz?

  Yeah.

• 22:56Speaker 05

  Okay, so consequently, I don't really understand it. All I know is money. I work and my money relaxes. That's my thing. I don't want my money out working for me because it's gonna screw up somewhere. I don't want that. Whenever I hear, and there's minimal risk, and I hear the word risk and minimal, that means I'm gonna lose something.

• 23:16Barry Ritholtz?

  Right.

• 23:16Speaker 05

  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...

• 23:28Barry Ritholtz?

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

• 23:30Speaker 05

  I never touched a check in 22 years in The Tonight Show.

• 23:33Barry Ritholtz?

  That's amazing.

• 23:33Speaker 05

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

• 23:46Barry Ritholtz?

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

• 23:52Speaker 05

  No.

• 23:53Barry Ritholtz?

  Or this valuable?

• 23:54Speaker 05

  No, I never thought that. No. 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 was 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 horrible.

• 24:13Barry Ritholtz?

  That, really, on the road, you were that hard-travel?

• 24:16Speaker 05

  On 44th and 9th, there was Dyke's Lumber Yard, right across the way. From, from the alley where I slept a couple of nights, I could see Dyke's Lumber Yard. I always had that in my mind. The hookers would come in, and it's just 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.

• 24:41Barry 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 barns?

• 24:48Speaker 05

  No, no, 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-

• 24:55Barry Ritholtz?

  You had it on the show?

• 24:56Speaker 05

  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.

• 25:01Barry Ritholtz?

  Didn't you find a number of barn finds, cars?

• 25:05Speaker 05

  Oh, yeah, sure, sure.

• 25:06Barry Ritholtz?

  What are some of the more memorable ones?

• 25:07Speaker 05

  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, guy's right across the street. My uncle's had some kind of car, we didn't know what it was. And it was a Jaguar. And I, I said, and this is really the best, right? I said, look, Google it, find out what's 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

• 25:50Barry Ritholtz?

  Seems fair.

• 25:51Speaker 05

  Yeah, I 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 go, you don't want any of that.

• 26:01Barry Ritholtz?

  Any cars on your list that you're still hunting for?

• 26:05Speaker 05

  No, you know, I buy I buy the story as much as I buy the car.

• 26:09Barry Ritholtz?

  Really?

• 26:09Speaker 05

  Yeah, I mean, to me, the fun, you know, I had a lady call me. Ninety four years old. And she and her husband bought a fifty one 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 thirty years. He died sometime in the early nineties. She calls me about two thousand, I guess, three, four.

• 26:36Speaker 05

  Oh, my husband died like twenty years ago. We got this car. I say, I already have a fifty three Honda. Will you come look at it? Okay, so I got to look at it. She's ninety four. No hearing and no glasses. And she said, would you give me five thousand dollars 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, what's Jaylen off? The car's all finished. You want to go for a ride? She's okay. Now she's ninety six. 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 seventy four and seventy two. 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 blind. Oh, and she starts crying.

• 27:21Speaker 05

  You want to go for a ride? 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, right? And and she turns around. I I told you kids, and she's whacking the crap out of them. Mr. Monroe 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 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 a hundred and six.

• 27:53Barry Ritholtz?

  Wow.

• 27:54Speaker 05

  And every time I get in that car, it makes me laugh because it was just so funny to see these two old men. And they all look the same age, you know? She's ninety six, he's seventy four. And and she's just whacking the crap out of them. Hilarious.

• 28:08Barry Ritholtz?

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

• 28:14Speaker 05

  No, I don't have a hole in my collection. No, I haven't enamored with this. No.

• 28:16Barry Ritholtz?

  It's just about the stories.

• 28:17Speaker 05

  My key to success is low self-esteem.

• 28:20Barry Ritholtz?

  I've heard you say that before.

• 28:21Speaker 05

  Yes, 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, wait, 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? Sometimes. But everybody felt they had a say in what was going on.

• 29:02Speaker 05

  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.

• 29:16Barry Ritholtz?

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

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• 32:07Barry 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 O'Drane Concourse d'Allegans.

• 32:28Barry Ritholtz?

  So, so let's stay with the Tonight Show and comedy.

• 32:32Speaker 05

  All right.

• 32:33Barry Ritholtz?

  You've interviewed a few presidents, right? You interviewed Barack Obama. What other presidents did you interview?

• 32:41Speaker 05

  Uh, Barack Obama.

• 32:44Barry Ritholtz?

  Was Reagan before you started on?

• 32:46Speaker 05

  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.

• 32:55Barry Ritholtz?

  Mm-hmm.

• 32:56Speaker 05

  Barack Obama, Hillary had the nomination locked up. And then he announced he was running for president. So, I called him up and said, "You want to come on the show?" "Oh, no, no, thank you so much." He rented a car, drove himself to the show, you know. Walks out, goes, "Jay, my name's Barack Hussein Obama. I'm running for president of the United States." I said, "Okay, black guy from Chicago named Hussein." I said, "You know, you shouldn't even have to campaign. I just think you're a shoe-in with that." And, you know, he got the joke and he laughed. 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 ever did. And the whole parking lot was tinted.

• 33:37Barry Ritholtz?

  Mm-hmm.

• 33:38Speaker 05

  So, the satellite could not see where-

• 33:40Barry Ritholtz?

  When he came in.

• 33:41Speaker 05

  Where it came in. Yeah. And, I mean, I've told this story, but this is... I have the same idiot friends I had in 8th grade. So, I'm telling them, "I had Barack Obama on the show and he gave me his phone number."

• 33:56Barry Ritholtz?

  "Nuh-uh, uh-huh."

• 33:57Speaker 05

  "Nuh-uh, uh-huh." "You didn't get it. You said, 'Nuh.'" "All right, let's call him up." I go, "It's the President of the United States. I'm not gonna call him up." "No, you don't have it." "Nuh-uh, uh-huh, nuh-uh, uh-huh." So, I take out my phone book and I cover the phone and I go, "See what it says there? Barack Obama, President of the United States. His phone number's right over here." "You know, you don't have it." I said, "All right, all right, I'll call him. You want me to call him?" "I'll call." It's like 3 o'clock. I figure, "Okay, what can go wrong?" "Hello, Barack here." "Mr. President?" "Yeah." "Jay Leno." "What can I do for you, Jay?" "I'm just here with some of my friends." "What is this number, Jay?" "Click."

• 34:31Barry Ritholtz?

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

• 34:39Speaker 05

  Well, I used to get quoted every day in the New York Times. We tried to make fun of both sides. Yeah, that's the way we did it. That's not the way everybody else does it, but that's okay.

• 34:49Barry Ritholtz?

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

• 35:05Speaker 05

  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 free, 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.

• 35:47Speaker 05

  I didn't like what they said, but I agree with their right to say it if they chose.

• 35:52Barry Ritholtz?

  You have Dave Chappelle speaking at the Comedy Festival in Saudi Arabia, saying he feels like free speech is under assault in the US. Not that Saudi Arabia is a hotbed of free speech.

• 36:05Speaker 05

  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 then, how about when he said this? Again, whatever, I don't have to agree with it. You know, it's like the Nazis marching in Skokie. Okay, they, they have the right to do that. I don't agree with it. Well, 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 was to run. Okay, it's fine with me, you know, I might even cheer him on, but I'm, no, I, I, I, again, I think you, it's America.

• 36:47Barry Ritholtz?

  And, 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, 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?

• 37:06Speaker 05

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

• 37:23Barry Ritholtz?

  Or Jay Leno for 45 minutes unscripted.

• 37:25Speaker 05

  Yeah, but, yeah, I mean, to me, I think it's just the nature of television. It, 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, that you can, that you can use, so. The thing that really kills late night is the incessant number of commercials. After 11:30, you can run like nine minutes at 12 o'clock with some crazy.

• 37:54Barry Ritholtz?

  Yeah, it's crazy, it's wild.

• 37:56Speaker 05

  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, you know. To me, that's the thing that's really hurt late night. It's not necessarily people, it's the fact that people, oh God, another commercial, you just, you know, just read through.

• 38:14Barry 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 wanna, I wanna do a speed round.

• 38:23Speaker 05

  A speed round.

• 38:24Barry Ritholtz?

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

• 38:34Speaker 05

  A Duesenberg.

• 38:35Barry Ritholtz?

  What's your favorite motorcycle in your garage?

• 38:38Speaker 05

  A Brossa Pire.

• 38:40Barry Ritholtz?

  What car offers the best bang for the buck?

• 38:42Speaker 05

  Corvette.

• 38:46Barry Ritholtz?

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

• 38:51Speaker 05

  Uh, McLaren F1.

• 38:52Barry Ritholtz?

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

• 38:58Speaker 05

  Uh, my 1925 Dobell steam car.

• 39:01Barry Ritholtz?

  The one that kinda blew up? Is that the one we're talking about?

• 39:04Speaker 05

  That blew up, but that wasn't the one that actually blew up in my face.

• 39:07Barry Ritholtz?

  Any cars you have any regrets passing on?

• 39:11Speaker 05

  Oh, yeah. Uh, what's all?

• 39:14Barry Ritholtz?

  What modern car features do you find most annoying?

• 39:19Speaker 05

  Uh, probably the infotainment system. Uh, you know, I have my 51 Hudson. I reach out, I press a button, I get a station. I don't have to stop and look at it. Are you happy to see this? Yes, would you make this section again? Yes, others have made this section. Would you continue? Yes, I would. You know, would you pick your language? English is good. Thank you. You know, it's just a word.

• 39:39Barry Ritholtz?

  Annoying. Um, what car do you drive the most often from your collection?

• 39:45Speaker 05

  Oh, I don't know. Uh, well, hmm. I drive a lot of them, quite a lot.

• 39:51Barry Ritholtz?

  That's what they were made for.

• 39:52Speaker 05

  Model T's kinda fun. I guess I don't drive it that much. Uh, probably the Mustang. That's pretty good. Well, actually, the Tesla when I have to go to the airport. No, those kind of things.

• 40:01Barry Ritholtz?

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

• 40:07Speaker 05

  Well, that would be the Dobell steam car.

• 40:09Barry Ritholtz?

  Mm-hmm.

• 40:12Barry Ritholtz?

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

• 40:16Speaker 05

  No, no, not one of them.

• 40:17Barry Ritholtz?

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

• 40:19Speaker 05

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

• 40:30Barry Ritholtz?

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

• 40:36Speaker 05

  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 a 1906 Stanley Steamer and it's on fire. People like, oh, my God. Your car's on fire. Yeah, I know.

• 40:50Barry Ritholtz?

  It's supposed to be.

• 40:51Speaker 05

  You carry open flame.

• 40:54Barry Ritholtz?

  What's the most recent addition to the collection?

• 40:57Speaker 05

  A Mustang GTD.

• 40:59Barry Ritholtz?

  What's the best sounding engine you own?

• 41:04Speaker 05

  Porsche Carrera GT V10.

• 41:06Barry Ritholtz?

  And final question, is there one dream car you're still hunting for?

• 41:11Speaker 05

  No, no, I'm quite happy with what I have. I guess I'd be happy with what you have, just make sure you have enough.

• 41:19Barry Ritholtz?

  There you go. Thank you, Jay, for being so generous with your time.

• 41:22Speaker 05

  Thank you, thank you.

• 41:26Barry Ritholtz?

  That was my live interview with Jay Leno at the Newport Audrey concourse de 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.

• 42:09Barry Ritholtz?

  Alexis Noriega is my video producer. Anna Luke is my podcast producer. Sean Russo is my researcher. Sage Baumann is the head of podcasts here at Bloomberg. I'm Barry Ritholtz. You've been listening to Masters in Business on Bloomberg Radio.

• 43:05Speaker 07

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