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

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

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.

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).

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.

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)

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)

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)

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)

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)

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)

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)

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)

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

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.