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David Spade
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Dana Carvey
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David Spade
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Kevin O'Leary
They came to see me and said, look, we're looking for a real asshole in this and you're it. Well, listen, I met Barbara in Vienna in 1601. That was my first dance with her.
Dana Carvey
She was there too.
Kevin O'Leary
Now the only reason she gets to LA every year from New York where she lives here. As I buy her a new broom, I give her the latest model. I said, timmy, I mean, I admire you. An ass is an ass and there's only one ass. Make it your ass, celebrate your ass and put it in this film for generations to come. I can't believe how good I look. I look spectacular. It's ridiculous how good I look.
David Spade
Kevin o'. Leary. Kevin o' Leary is Kevin.
Kevin O'Leary
Kevin o'.
David Spade
Leary.
Dana Carvey
Different move for us, but I think, you know, he does financial advice.
David Spade
Shark Tank for years. Yeah.
Dana Carvey
At least 10 years of that. That shows everywhere, worldwide and Interesting guy. And also he was plucked. Was it by the Safdies or.
David Spade
Yeah.
Dana Carvey
To be in the new Marty Supreme. Yeah.
David Spade
Mari supreme. So he. It's really interesting. Like the guy's never been an actor and all of a sudden he. He's in this big movie and it's really funny. He talks about how he. He was spanking Timothy Shallow and how awkward and all that stuff that happens. But yeah, he's pretty, pretty funny. He's a confident guy, knows a lot about business. But him in kind of a, you know, like a Oscar winning movie for your first role. It's really interesting.
Kevin O'Leary
Yeah.
Dana Carvey
With the Safdies. I mean, my God, it's as cool as it gets. And a big movie that's out there right now still. And listen to what he has to say about. Here he is, Kevin o'.
David Spade
Leary. Listen to what the man said. Kevin o'. Leary. You know, he's really interesting. Oh, oh, he's on.
Kevin O'Leary
Oh, yeah. All right. Let her rip.
David Spade
He goes, that sounds like a product. That sounds like a name of a toy or something called Let it Rip. I like it. Let's go with it. We get some funding. Spade, knife. Throwing a couple hundred.
Dana Carvey
Dude, if I had Kevin's money, I'd throw mine away.
David Spade
Do people who are very wealthy. If you walk in a room and you're very, very, very wealthy, but then you've got billionaires. Multiple, multiple billionaires, do you feel small?
Kevin O'Leary
You know, I mean, I don't need any more money. I just need more time. That's my real issue.
Dana Carvey
Yeah, right.
Kevin O'Leary
Like this. You know what? I think there's always a guy way richer than you. Yeah, always. And so I don't really give a about that.
Dana Carvey
When I go in a room, I go, what if I walk in this room and someone's better looking than me? I mean, the chances are low, but there's a chance.
Kevin O'Leary
No, that that never happens to me.
David Spade
Here's my way of thinking about it. Like it's just a bigger room to watch tv. I think that was in a movie.
Kevin O'Leary
No, no, listen, I. I look fabulous all the time. I can't believe how good I look.
Dana Carvey
It's ridiculous. You look great.
David Spade
And no after shave. Is it moisturizer? Is it just your attitude? Because you do.
Dana Carvey
Yeah.
David Spade
You look fresh.
Kevin O'Leary
Fresh and exciting.
Dana Carvey
You know, I see you on a lot of these shows, Kevin. Not only Shark Tank, but I see you when you're on some business shows. And you always have good energy. You always have a lot to say and you're very articulate and you can speak well. And I think that's a big part of your success. You have opinions and you lay them Out. You don't sort of mince around.
Kevin O'Leary
Yeah. You know, I mean, the way I look at it is just tell. My mother told me when I was 16. Just tell the truth. You never have to remember what you said. Now, some people don't like it. They get.
Dana Carvey
That's true, all that stuff.
Kevin O'Leary
But I can't keep everybody happy. What am I supposed to do? I care about my family and maybe 15 friends and everybody else. I don't give a shit.
David Spade
I'm with you. I don't give a shit. No, it's good. I mean, when you're on, like, a cable show, then you've got to do the sound bites. You got to be really succinct. Now you're on a podcast, so it is a little more interesting. Right, for you. Or you can just say whatever you want or.
Kevin O'Leary
No, no, but listen, I respect. I mean, I gotta admit, you know, I got a lot of followers. I don't know, 11 million followers. And they. Sometimes I get like an essay, maybe four pages, well written, just blasting me about something. I said, imagine four pages. Imagine somebody spent like an hour writing it.
David Spade
Really?
Kevin O'Leary
Well, I mean, I don't know if it's AI generated or not, but they really worked on it. And I gotta say to myself, well, I gotta respect the amount of time. Why would you waste your time on that unless you were very passionate about it? And those are the people that I actually respond to. Most of us hate mail. And then there's about two and a half percent, which I call the lunatic fringe, which is just. They're completely fucking crazy. And what am I supposed to do about that? Nothing. I can't do anything about it. And so that's it. I mean, you know, I kind of. I've been dealing with it for 20 years, and I've kind of found a place to live and float in the sea of happiness.
Dana Carvey
You're doing good. Now, when Shark Tank came out, how long did it take for that to sort of catch on? Or was it immediate? I can't remember.
Kevin O'Leary
No, it got canceled three years in a row. The story was legendary. I mean, every year it got canceled, everybody hated us.
David Spade
But.
Kevin O'Leary
But Willow Bain was married to Iger. And I met her way back in the NBC days and she was raising kids with Iger, and they loved the show. And so every time he'd come home saying, ah, we whack those guys on Shark Tank, she said, no, no, no, no, no. We're not whacking Shark Tank. Our kids like it, other families like it. It's the only thing on TV that doesn't have everybody naked screaming about sex.
Dana Carvey
Yeah.
Kevin O'Leary
And so it became a family hit. And in the fourth year, it just went geometric. I mean, poo poo happens, you know, Geometric.
Dana Carvey
I'm glad they didn't go into, like, Shark Tank island, where. And then it's. They're all dating. That's what it should have gone into because that's. That's what most shows are on tv.
Kevin O'Leary
It was called beyond the Tank. Right into the poop shoot. That's what happened.
David Spade
Excellent. That's the first time someone has said poop shoot on this podcast. Thank you for that.
Dana Carvey
You'd think it would be a lot. It's not. No one said it.
David Spade
You think it'd be a comma, but no. Ever had it.
Dana Carvey
So Willow Bay helps out because it is sort of a family show where you. It's fun to sort of figure it out, and it's fun to decide as a family. Is this something that's a good business? You know, you learn about a lot of things.
Kevin O'Leary
Well, I think the reason it works is that we don't know. You don't know what's going to walk through those doors. It's the essence of the American dream. I mean, the idea that you can come up with a product or service that solves a problem, become a multimillionaire, which we've done countless times in 17 years, we've sold billions of dollars worth of product. You got eight minutes on network TV and 110 million eyeballs on syndication in 54 countries. I mean, come on. I mean, it's this podcast. You just need to find some product that you're beyond just your grandmother and your uncle buy. You got to find something that really people need. And it's all kinds of crazy stuff. I mean, I think about, you know, pet DNA tests and stuff that you would think would never work. Makes hundreds of millions of dollars.
Dana Carvey
Yeah, you don't. And that's the thing. You got to sort of troubleshoot it in a short amount of time and say, how much will I invest? And if you do, then you go, oh, now I got to beat someone else. Now I got to go higher than I wanted to go. That's part of the intrigue.
Kevin O'Leary
I mean, the first million is easy because you do it yourself. But getting, like, when you hit 5 million, you got to start hiring people. You have to find out if you're a manager. A lot of people shit the bed when that happens. They blow up. But if you can get to 5, you can get to 50. If you get to 50 million in sales, you get to 500 million. We've had that happen lots and lots of times because basically you've proven that the product works and people want it. Now you have to scale it. That's a different skill set often and you have to find other people that can help you do it. But it generally takes three to five years to prove out a company. But it happens quickly. When it's a hit, it's a hit.
Dana Carvey
Yeah. That must be the fun is the.
David Spade
Idea kind of sort of figuring out what people need before they know they need it.
Kevin O'Leary
I think what happens is to the big ones is they find some pain point that they look around them and everybody has that pain point. Now, I mentioned it earlier, but I'll give you an example. Most cats die at around 12 to 13 years. I'm not a cat guy, but I'm giving you data. I know because I invested in this company called basepaws. However, cats in ancient Egypt, Chocolate point siamese, lasted past 30 years. How'd they do that? Because the ancient Egyptians knew what to feed them. And so they'd give them food that they would not abscess their teeth. So we give them shit food and they die really quickly. So if you get a cat DNA test and you find out which of the three genres of cats it comes from, because there's only three big pools, you can actually feed the right food to a young cat and have it last half of your life or maybe 40% of your life. And so this thing called base paws, where you stick a Q tip where the sun doesn't shine in a cat and send it in and get this analysis, $29. So when she came on the set of Shark Tank, I said, well, excuse me, I can buy a new cat for five bucks. Why would I spend 29 on a test like this and. And 110 million cat owner on me. But, you know, I eventually figured out I wanted to do that deal and I did. And we made a lot of money, a ton. It was bought by a giant pharmaceutical company later for the data.
Dana Carvey
It's cheaper than moving to Egypt, right?
Kevin O'Leary
Basically, yeah.
Dana Carvey
Yeah. You know, it's funny because when my brother ran that Kate Spade company, he was just a guy from Arizona with kids, Katie. And it kind of blew up pretty fast. And I remember seeing him in the office when he's like, I just had a dock worker in here telling me, he's going to break my legs if we don't do that. He goes, I Don't want to do this part of it. That's what you're saying about management. That's what I thought is like he was into designing stores, he was into putting the bags. But when you start getting it's too big. Then they did wind up selling because it just was out of their reach. That's not what they were trained to do. And it's so fucking complicated to run a big operation.
Kevin O'Leary
Well, it's true executional skills are an them impossible to find. And so you know, you're right. Big is 50 million and after that you need executional skills. And most people that found at the company don't have them and they, they go to zero because of it. They buy too much inventory or they don't manage their systems. And whatever it is, I see it happen all the time. That's why I make a lot of changes at around the 50 million rate and I say, listen, I'm going to help you out. You're going to go off the board. I got to whack you now. Which is a good thing.
Dana Carvey
Well, you need someone that knows what's going on. Who's done this before. Right. Because it's like a movie. You go, you make your own movie and you go, I don't know how to make a movie. You think you do. And it's. There's so many people that do each job better than you. You need to keep hiring people to make sure they've done this before. It's too many moving parts.
Kevin O'Leary
Yeah. A movie making stuff. I just finished one of those. That's.
Dana Carvey
Yeah, we're excited about that. I mean the Safdies. Is it both Safdie brothers that directed it.
Kevin O'Leary
One. No, no, no. This is Josh.
Dana Carvey
Okay.
Kevin O'Leary
Wrote the script with Ronnie Bronstein, the same guy that did Uncut Gems. They are very disturbed individuals.
Dana Carvey
Yes.
Kevin O'Leary
Yeah, I know them a little bit. I know puppies.
David Spade
Well.
Dana Carvey
Uncut Gems was a sweaty, fast paced movie that was really well done and they, they, they know what they're doing for sure. And this one already has a lot of attention and sounds from. It's going to be great on the awards.
David Spade
I honestly, honestly Kevin, I thought you'd be a cameo. When I first heard. I thought you'd come into one scene or something during the entire movie and you land at the end.
Kevin O'Leary
They came to see me and said look, we're looking for a real in this and you're it.
David Spade
Right. Someone who's just incredibly cruel and mean and really cocky and then they thought of you.
Dana Carvey
Yeah.
Kevin O'Leary
I don't know how that happened.
Dana Carvey
I don't know how I didn't get called it.
David Spade
Did you say at the end of the movie, I was born in 1601? Did I hear that right when you talk?
Kevin O'Leary
I was very unhappy with the ending. And Josh and Ronnie and I fought about it for a couple of months. I said, this guy, this Marty Mauser, if he really did this to me in real life, I would fuck him over so badly. You have no idea. And why am my character letting him off this easily? I just. I'm so unhappy with this. And we started to negotiate. I wanted to kill off Rachel. I wanted Marty to die. I mean, that was me.
David Spade
And they said you were just a hired actor.
Kevin O'Leary
Well, I mean, listen. At least they listen to me a little. Yeah, I just don't feel right about it as Milton. I'm really pissed. And so we came up with this idea that maybe. And I suggested to them, perhaps I'm a vampire and I bite him and he lives in hell in perpetuity. That seems fair. And he said, well, we're not going to put fangs on you and have blood spurting all over the place. I said, why not? That your. That's your kind of movie, guys. Look at the stuff you make.
Dana Carvey
Hey, you weirdos.
Kevin O'Leary
And. And they. And they said, no, but you could maybe hint at it. And that's our comp. That's the compromise. And listen, I've been to the couple of premieres, and people are howling at the moon at the end, saying, wait a second. It's a huge narrative, a big disagreement about whether Marty paid the full price. He should have. And I think that's what make these guys magic. They get people.
Dana Carvey
People talk. It's like the. The Instagram comments. You want people to fight. Yeah, I mean, look, comments, more people talking.
David Spade
Well, I mean, has this ever happened before in the modern era? Like, this is. This is a movie that's on. It's. It's a great movie. It's on the award circuits. Everything you'd never done acting in a film. I. And then you're in this film. I mean, does Larry Kudlow have a deal? Or Jim Cramer? I mean.
Kevin O'Leary
The rules are, I don't give a. I mean, I just look to me as you. You walk into a room. You know the story, you know the script. You read the room. It's 1952. It's so beautifully, you know, set. It's amazing. And then you just go at it and. Yeah, well, I mean, I don't. Maybe that is acting. I Don't know.
Dana Carvey
Right. They're there to steer you anyway, so. And you're on camera all the time, and you've got a little bit of that beats. You're ahead of the game and you're already sort of that personality. So if you can get the lines down and not freeze up like Cindy Brady, you can probably get through it.
David Spade
You have a career, gigantic career. So you walk on a set when we were in our early days trying to audition, getting past the terror and the fear of not doing it right. Or am I? And for you to walk in with as a wealthy businessman and TV star, I mean, I guess that's part of the reason, or just your nature that you were that relaxed acting across from Timothy Chalamet, who's kind of one of our great actors.
Dana Carvey
Huge actor.
Kevin O'Leary
Yeah, he was great. And I think he was kind of a, you know, I figured him out, and he figured me out in the first couple of minutes when we started shooting. Our first day was seven pages, a lot of text.
Dana Carvey
That's a big day.
Kevin O'Leary
And we. We just found the groove. He kind of snaps into his character, and then I could just beat him up. That was what I thought, you know.
David Spade
Well, the way you did deliver the request and the way they shot that of the. The infamous now maybe paddle scene and make him go get this paddle. You did have a kind of a very devious thing about character that has nothing to do with this.
Kevin O'Leary
We had an ass double, and he did. And it was three in the morning, and I said, look, the fake paddle we were going to use got broken the first hit. It got broken immediately because it had a hinge and it was made of foam and it was crap. Then we had to go to a real paddle, and the ass double guy was going to take the hit, but Timmy said, no, I want to immortalize my own ass in perpetuity. And so I said, I have to hit your ass. It's going to hurt. So he rotated cheeks so that they were equally red through 20 takes. And finally Josh said, you know, you're not hitting him hard enough. You're holding back. You got him lined up like, I'm happy to do it. I mean, I'll do it. I'll happily do it.
David Spade
Why happily?
Dana Carvey
I'll break his head.
Kevin O'Leary
I did. I mean, you know, my character should have done more than that to him. Yeah, right.
Dana Carvey
Yeah, we've all had that conversation, I think, with someone.
Kevin O'Leary
Here. Hold on.
Dana Carvey
Oh, yeah, there's a sign in here. Is that the real background? What is that?
Kevin O'Leary
No, that's that's New York City right out the window. I'm at the Whitby right now. I love this place.
David Spade
Whitby Hotel.
Kevin O'Leary
Okay.
Dana Carvey
A Whippy. What's that?
David Spade
Fifth Avenue?
Dana Carvey
I think it's a write off because you're doing this good job.
David Spade
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Dana Carvey
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David Spade
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Dana Carvey
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Kevin O'Leary
N s.co what's up world is Vaughn Miller, Super Bowl MVP, chicken farmer and now host of Free Range. This is a show where I go off the field and off the script. We're talking what's hot in music, film, trending news and everything blowing up your feed. If you love football, you'll feel at home. But if you're here for the vibes, the Internet deep dives the conversation. This is your podcast. Join me every Wednesday. Follow and listen to Free Range with me, Vaughn Miller. Everywhere you get your podcast. Well, the holidays have come and gone once again. But if you've forgotten to get that special someone in your life a gift, well, Mint Mobile is extending their holiday offer of half off unlimited wireless. So here's the idea. You get it now, you call it an early present for next year. What do you have to lose? Give it a try@mintmobile.com switch limited time.
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Dana Carvey
We have the crummiest backdrop. Mine doesn't do anything. I'm just a rocket ship. I have a lava lamp. Is that a little sad fern?
David Spade
Yeah. What is?
Dana Carvey
I don't know. I thought that was a little monster, but I think it's a fern.
David Spade
Please stand by.
Dana Carvey
Is that Andy's book or Norm's book?
David Spade
Is that on a TV screen or.
Dana Carvey
It doesn't look real. You mean Kevin's?
David Spade
Yeah.
Dana Carvey
We keep all this on because we're authentic.
Kevin O'Leary
No, no, it's 100 authentic and you're getting real time. Listen, this is good. Tonight is the big premiere in New York. Oh, it is. We got. We got Timmy, we got.
Dana Carvey
What do you say to Kylie Jenner tonight? What do you think? And.
Kevin O'Leary
And we have the Sharks.
Dana Carvey
Your whole team's coming.
David Spade
Your whole team.
Kevin O'Leary
Yeah. I got Cuban flying up from Washington where he's changing the health care system.
Dana Carvey
Okay.
Kevin O'Leary
And good for Mars. Hey, I got them all. They're all showing up. We're going to do Shark Tank meets, you know. Oh, Marty. Supreme. I think that's a great idea.
Dana Carvey
Now, how many Sharks are there total?
Kevin O'Leary
Well, including the guest sharks, 4,000. But you know, the original sharks were six.
Dana Carvey
Was it six sitting there? That's a lot. Is six too many to cover and all that? How long does it take to do one pitch?
Kevin O'Leary
Well, listen, guys, that's hard work because we started as, you know, making reality tv. You try and shoot three episodes in a day, start a five in the morning, gross at night. You got to rotate the talent, otherwise they're going to drop dead on you for sure.
Dana Carvey
And you're in your 40s now, so it's probably getting tougher.
Kevin O'Leary
I'm 28 years old and I'm tired, okay?
Dana Carvey
Right.
Kevin O'Leary
You know, remember, I'm in vampire years. I'm not.
Dana Carvey
That's right. We can't give away everything. But, you know, that's. That's why he's drinking pe. He's a vampire. So listen, you have. It was first. First Sharks. Were you Barbara? Maybe?
Kevin O'Leary
Well, listen, I met Barbara in Vienna in 1601. That was my first dance.
Dana Carvey
She was there, too.
Kevin O'Leary
Now, the only reason she gets to LA every year from New York, where she lives here, is I buy her a new broom. I give her the latest model.
Dana Carvey
I love it. And there's Cuban. He Came on later, didn't he?
Kevin O'Leary
Yeah, I think season four, he came on.
Dana Carvey
He's a new guy.
Kevin O'Leary
Well, he's my grasshopper. He's still learning.
Dana Carvey
Yeah, he's still learning that.
David Spade
Have you and he done business together or is it just on the show? Do you guys have things you own together and plan together or just friends?
Kevin O'Leary
No, we have many deals together. Our teams work together. I mean, there's so many companies we've invested in.
David Spade
Yeah.
Kevin O'Leary
You know, he likes equity, I like royalties. So he's a little bit country, I'm a little bit rock and roll, that kind of thing.
David Spade
Okay.
Kevin O'Leary
And. And that's what makes it interesting. We've, you know, we've taught America about prep shares, convertible debentures, equity versus debt, royalties, you know, all that stuff. I think it's terrific what we've done.
David Spade
Is it weird in Hollywood? Like, I was on David Spade's talk show and I got, I think, 0.05 cents for a rerun.
Dana Carvey
Yeah.
David Spade
I mean, the Hollywood. I don't know.
Dana Carvey
You got to put that away.
David Spade
The royalties are pretty funny.
Kevin O'Leary
Don't give up your day job.
Dana Carvey
Yeah, he's sock it away. They add up.
David Spade
I'm equity. I don't. I'm not a royalty guy.
Kevin O'Leary
Okay. Well, I mean, you know, in. In Hollywood these days, I think you want to buy out the forwards. That's my view. Get the cash now, invest it yourself. Because you don't know what's going to happen to syndication. Not that we want to get technical here, but the world's changing so much.
David Spade
Oh, no, that's.
Dana Carvey
No, we can get technical.
David Spade
Died a long time ago. There's no more.
Dana Carvey
Yeah, My, my, You know, bread and butter was sitcoms and then. And even movies like you can do.
David Spade
All right.
Dana Carvey
Just reruns and reruns and reruns. And it goes to hbo, then it goes to somewhere else and it goes, you know, grown ups, we joke it's keeping the lights on at TBS over there. It's on seven times a day. And then it's grown ups, too, so.
Kevin O'Leary
Well, same for us. Shark tanks on four hours straight on CNBC at night. So, you know, things go through the syndication process, obviously. By the way, I'm a big fan. I haven't told you that yet. I think you're pretty good. You know, I don't have a big enough ego to say that, but I'm happy to do it.
Dana Carvey
Okay. You're talking to me or Dana? Don't say Danner.
Kevin O'Leary
Both of you guys. Okay, good. Absolutely. Both of You.
Dana Carvey
I appreciate that. Was nice of you to come on. By the way, we. We like what you do. And I watch on these shows and, you know, Shark Tank is one thing. And then when you see on these shows and you're. You're talking, I like that you hold your own against everyone and you're not very political. You say, I'll take it down the middle. Give me any president. Just let's make some money.
Kevin O'Leary
Yeah. You know, this whole thing with the way I've stayed out of trouble on this, particularly in L. A which obviously is to the left and then the New York left and left and right. I don't care about that stuff. I'm a policy guy. Does this make sense? Because I don't show for politicians. How can you. They come and go like crazy. So I don't care about that. I care. Is this good policy? And I invest a lot. So I say, this is a good idea, it's a bad idea. This policy works. This doesn't work. You know, whatever. And that seems to have kept me out of trouble. I do as many hours on CNN as I do on Fox.
Dana Carvey
Yeah, I've seen you on both.
Kevin O'Leary
Yeah, I do it on both. And I say, hey, listen, this is what I think. And if you don't like it, it's really interesting how split and divided the country is now.
David Spade
Wow.
Kevin O'Leary
It's crazy. And I don't know why. Because the essence, the number one export of America is not energy or technology. It's the American dream. It's the number one economy on Earth for all its faults and everybody this and everybody that. I mean, I don't see people going under barbed wire in a river to try and get into North Korea. They're not doing that. That's happening here. And so people still want the American dream wherever I go. And the Shark Tank thing's on in 54 countries. So I can go to Saudi Arabia, meet the leader, because the kids want Shark Tank pictures. I'm not kidding.
Dana Carvey
Yeah, for sure.
Kevin O'Leary
It's an amazing passport. I'm an ambassador to the American dream. I'm proud of it. And that's not red or blue. So I go to Washington to complain about policy. They let me in both sides because everybody wants to create jobs in their state. Who hates jobs, right?
David Spade
What is our secret sauce? You think in America, is it. We have more freedom than other countries to. We don't have the government on top of us too much compared to other countries. Because usually in a lot of countries, if you make money, you're Kind of in the bullseye a little bit. Especially living in California, you are kind of public. You are in the bullseye one. You are the rich who don't pay their fair share. So it's a little disconcerting, but I guess we're just better than any other country if you want to pursue your dreams with hard work.
Kevin O'Leary
Well, I think it's about personal freedom. You know, entrepreneurship's not money or greed. It's about pursuit of personal freedom to do whatever you want with your time. And that's the American dream. And if you get it right and some many people do, you get you're able to do that, provide for your family. Now, California, I don't think you guys are paying your fair share. You should be paying 99% tax.
Dana Carvey
I thought we did.
Kevin O'Leary
That's good, that 1%. That's good. And then here in New York we have the big communist experiment going on. And I'm cool with it. I mean, I don't live here. I visit and I wish everybody the best. And they're paying their 99.99% tax. And that's their fair share, all of it. You know, remember that song Tax man by George Harrison?
Dana Carvey
Oh, yeah.
Kevin O'Leary
That was 99.2% tax on the Beatles when they moved to. Francis said, screw this, right?
Dana Carvey
Oh, is that how bad it was? How bad was it?
Kevin O'Leary
Yeah, yeah, it was. It was 19 shillings out of 20 shillings in a pound.
Dana Carvey
Oh, my God. Because they were making the most money.
Kevin O'Leary
That's why he wrote that song. And I think that gives you an idea that you don't. The great thing about America is the competition of states. You don't have to stay in New York or California. You can visit like I'm doing. I love New York. I love the Rockettes. I went downstairs and bought some gloves today. I'm supporting the economy here, but I'm not living here. And I've got my app making sure I'm here six months less a day. And I wish.
Dana Carvey
You live Vegas.
Kevin O'Leary
Best real estate agent in Florida is Mondami. He is selling houses down there like you can't believe.
David Spade
Just the planes they have to get extra flights, just people.
Dana Carvey
Palm Beach.
Kevin O'Leary
I'm telling people, stop moving to Florida. The traffic sucks.
Dana Carvey
Oh, that. Is that where your base is?
Kevin O'Leary
Yeah. Everybody lives in Florida now. All my Boston neighbors, all the neighbors here, every hedge fund manager I know, every finance guy, they live in Florida and they visit New York. I don't know who's going to pay the taxes here, but I. This isn't going to work. Wow.
Dana Carvey
It's a tough spot.
David Spade
Interesting.
Kevin O'Leary
Believe me, I can't sleep. I can't sleep about it.
David Spade
So do you have anything? Just because we have you here, you're our first kind of person like you on the show. Well, what's your take on it?
Kevin O'Leary
Like me?
Dana Carvey
Yeah.
David Spade
Well, that knows business. We can ask you just basic things about.
Kevin O'Leary
Okay, Well, I know wine, too. This is a Poulinay Montrache 22. Absolutely spectacular. And I deserve it because in about an hour, I've got to head off and do that whole red carpet thing with Timmy and Gwyneth and all the rest of that. I'm taking my whole family with me, bringing my kids up for this. And, you know, I. I've never done this kind of gig before, but boy, it's crazy.
Dana Carvey
They're going to be so jealous.
Kevin O'Leary
You guys have done it. I haven't done wild.
David Spade
It's going to be loud and you're going. How will you. You're going to get a lot of compliments.
Dana Carvey
Yeah.
David Spade
You were so great in this.
Kevin O'Leary
I love it when people suck up to me. I really do.
David Spade
You're going to get. You're going to be sucked up beautifully tonight.
Kevin O'Leary
I don't.
David Spade
And it's going to be loud and it's going to be. Kevin, Kevin, Kevin.
Kevin O'Leary
Yeah, I'm good. I'm good with it. I'm good with it. Then the after party. I'm against drugs, but not rock and roll.
Dana Carvey
Right.
David Spade
Okay.
Dana Carvey
Are you gonna. What if they go picture you and Timmy? Give them a little spank. Give them a little spank.
Kevin O'Leary
Yeah, we've done that already last night.
David Spade
Are you wearing a classic?
Kevin O'Leary
I think has callous on it now.
Dana Carvey
After what I did. Yeah, his ass is one big callous. I think I saw that.
Kevin O'Leary
I admire him for saying, look, I'm not letting a stunt ass immortalize my ass in perpetuity in a film. I'll take the hit. So it's my ass. That was 3:45 in the morning. I said, timmy, I mean, I admire you. An ass is an ass and there's only one ass. Make it your ass. Celebrate your ass and put it in this film for generations to come.
David Spade
Well, this is a very. I looked this up earlier. Chalamet is French for ass bank, which I thought was so.
Dana Carvey
Yeah.
David Spade
Ironic. Just bizarre. You didn't know that. Now your tuxedo. Are you going classic Cary Grant, George Clooney, or are you going to be colorful?
Dana Carvey
Not tuxedo. He's wearing a suit. You're just Wearing.
Kevin O'Leary
No, I'm going to. I'm wearing. You know, I love it. What are you wearing tonight?
Dana Carvey
What are you wearing?
David Spade
No one else would ask you that.
Kevin O'Leary
You know, I was talking, like, I'm talking to all the. I wear Prada and Dolce, but Dolce lately said to me, look, we can make you a tux from 1952 with the thread from 1952. And I think it's going to capture the moment. I said, I'm good for that, so I'll be wearing Dolce.
Dana Carvey
Nice.
Kevin O'Leary
I'm wearing Dolce, you know, tuxedo slippers. I can't believe how good I look. I look spectacular. It's ridiculous how good I look. And so, you know, I'm almost embarrassed how spectacular I look.
Dana Carvey
But don't outshine everyone. Don't outshine Kylie.
Kevin O'Leary
I gotta be careful. I don't really want to do that. I'm just a supporting actor. But I think I'm gonna walk out there and the light's gonna shine and grown men are gonna weep.
Dana Carvey
It's a good way.
David Spade
How were your friends handle this new thing you've got? You're a movie star, basically now, along with everything else.
Kevin O'Leary
I mean, Mark, I know they're. I know they're my friends because they don't give a.
David Spade
Okay. No one's jealous.
Kevin O'Leary
The guys I hang with, I've known for, like, 30, 40 years. I mean, you know, before I had any money and before I, you know, did TV or any of this movie stuff. Those are the. Because, you know, obviously I have a lot of new special friends.
Dana Carvey
But, yeah, they're better.
Kevin O'Leary
You know, that's your friends in Quebec a long, long time.
David Spade
We have a lot of.
Dana Carvey
Quebec.
Kevin O'Leary
Yeah.
Dana Carvey
From Canada, Mount Royal.
David Spade
Oh, you're Canadian.
Kevin O'Leary
Yeah. I was born in TMR and I moved to Boston. My kids were all born there and grew up there. So we have really interesting Thanksgivings, dinners, because my whole family is American except me. And so you know how Canada and us are on each other these days.
David Spade
Oh, yeah.
Dana Carvey
Yeah.
Kevin O'Leary
Personally, what I think should happen, you know, forget about the rhetoric, is we should just join forces in terms of the economies. Canada has all the raw resources and the US is the largest market. And bulk up go to the American dollar as the common currency because that's what everything's priced in in Canada anyways. And then tell the Chinese to fuck off. Whoa.
David Spade
Does Trump know this? Have you talked to him?
Kevin O'Leary
I have talked to him about it, yeah.
David Spade
The Canadians are very proud. They didn't like the.
Kevin O'Leary
Listen, I get It, I get it. But they will one day realize the enemy is China. I don't dislike the Chinese people, but that government's nuts. And they wanted world domination on everything. AI army, economy, resources. I mean, if people don't understand that about China yet, they're nuts because that's coming. And so at some point, this whole crapola between Canada and the United States because it shares the largest border on earth and it's the two richest countries on earth in terms of resources and economy, you get together and you say, look, China, don't fuck with us. That's what's going to happen in the next five years. You heard it here first.
David Spade
Does Canada have rare earth minerals ready.
Kevin O'Leary
To go big time? Big time. They got everything, but they don't have the money to dig them up as a stock certificate. Look, it was run by an idiot king for 10 years and now he's gone. Now there's a new guy. I didn't vote for him, but I want him to win. And I think he's smart enough to understand to get the economy back rolling again. Canada's a very, very rich country run by idiots.
Dana Carvey
Yeah. Is it Katy Perry's boyfriend still or is it someone else?
Kevin O'Leary
No, I mean the Katy Perry idiot king combo. I offered her a free prenup. I have a shark tank company called hello Prenup and I'm providing her with a free prenup because everything the idiot king touches goes to zero. Like it is. I'm known as the Merchant of Truth.
Dana Carvey
I love it.
David Spade
All right, pick one of these to talk about. AI Bubble Bitcoin affordability. The catch word of the day, the tariffs, fed interest rates or anything else.
Kevin O'Leary
You really want to talk about that?
David Spade
No, I, I'm just saying if you had any hot take. We, we. Our, our audience is highly under educated when it comes to finance or uneducated.
Kevin O'Leary
Let's touch on crypto because I spent a lot of time on that and I did a lot of work on the crypto bills. All you need to own in crypto, if you're going to get into it, is Bitcoin and ethereum. There are 10,000 shit coins. You don't need to own any of those. 97% of the Alpha, which is the price volatility of the entire crypto market, are two just Bitcoin and Ethereum.
Dana Carvey
Oh, I didn't know that.
Kevin O'Leary
But just dump all the poo poo coins. You don't need to own bitcoin.
Dana Carvey
People come up with a coin. How does that work? They just Say I'm going to do a poop coin or fart coin and then you go, okay, oh, it's up a million dollars.
Kevin O'Leary
Poo poo coin, its now. Okay, so I mean it's just like a Vegas speculation, but that's not where the institution is putting their money. They're buying Bitcoin and Ethereum, but it's no different than digital gold. Don't own more than 5% of your portfolio in it. You can make about 3% yield on it, which is not a lot. I mean, don't speculate too much. I mean, some people just never own Bitcoin because they don't understand you can't touch it. But it's sort of like a digital version of gold. Gold's been around for 2,000 years. Bitcoin's been around for 16 years. So a lot of people don't trust it yet.
Dana Carvey
And is there a, is there a government owned crypto or is that, is that going to hurt Bitcoin if that happens or has already happened?
Kevin O'Leary
The government approved Stablecoins, which are, is a digital payment system backed by the U.S. treasury. That made sense and it's being used like crazy. It's only about four months old, but all the banks are starting to make their own Stablecoins. You can get, if you want to use a Stablecoin, just get Robinhood or Coinbase, put it on your phone, a thousand dollars into it and learn how it works. It's very easy to transfer, very low cost, very transparent, very fast. Certainly beats a bank transfer or Fed wire. So if your kids in college, you want to send them 400 bucks, much better. And believe me, your kid has a Stablecoin wallet already.
Dana Carvey
Yeah, Coinbase was tough to get on. I mean, I think is that Heather? I was getting on and throwing some, you know, I got a few beans in my jeans. Kevin. I don't know if you've read the papers, but. So I put a little money in.
Kevin O'Leary
No, you were definitely a beanologist.
Dana Carvey
So I put it in. But getting on Coinbase, I was literally calling them and begging them to like take my driver's license and all my bank account numbers. I go, God, if they wanted to.
Kevin O'Leary
Police me and stuff is brutal.
Dana Carvey
It's unreal.
Kevin O'Leary
I was like, but once you get the account, it's useful, you know, just call me, I'll call the CEO for you.
Dana Carvey
Okay, thank you. That's really what I was heading for.
Kevin O'Leary
Brian, he's the guy.
David Spade
Yeah. What's the most impressive? Oh, sorry, go ahead, David.
Dana Carvey
No, I was Just talking.
David Spade
You mentioned CEO. I'm curious about the. The how much influence a CEO has on a company. What do you think is one of the smartest ones you've ever met?
Kevin O'Leary
Elon Musk.
David Spade
That's what I thought you'd say.
Kevin O'Leary
This guy is. He's only a third of the way through his career and look what he's achieved. The guy is 100% signal, no noise. A little awkward socially. My son worked for for him for five years. Mark Burnett's house a couple of times. A big party Mark used to have. Doesn't do it anymore because he lives in England. But as soon as he realizes he's not gleaning any information of use or value to him from you, he just walked away.
Dana Carvey
Yeah.
David Spade
Without. I actually.
Dana Carvey
I like that. That's funny. He does seem like all biz, no bullshit. But there's tunnels under Vegas.
Kevin O'Leary
Smart as poo poo.
David Spade
I can't imagine an engineer first in some ways at least that how he sees himself that he goes, if there's a problem, he goes and sits with the other engineers. Starlink is the.
Kevin O'Leary
I mean, that's the thing. All the engineers on earth want to work with him, including my son, who's an electrical engineer. His whole cohort that he, you know, he beat MIT with an electric car F1 race. Elon hired all of them, moved them to Fremont. He worked on the Low Voltage team for five years. And then he said, look, I want to go get a design engineering degree and an mba. And I said, listen, good luck with that because there's only 20 seats at MIT and 22 at Harvard. And you're not getting into either of those. But he got one of the directors at Tesla to write him a letter and he got into both of them and he went to Harvard because there's more girls there. So I applaud him. And he's coming to the opening. Applaud him.
Dana Carvey
Oh, he'll be there.
Kevin O'Leary
I bought him a tux in Boston. Right on.
Dana Carvey
Oh, from nineteen six.
David Spade
He's coming to the show tonight. He'll be there.
Kevin O'Leary
Yeah, I got the whole family coming. I'm bringing the whole crew and my daughter's new boyfriend. I love him. He's got a job. That's fantastic.
David Spade
You're kidding.
Kevin O'Leary
I'm very excited about that.
Dana Carvey
All right, I have another boring question. Just because this got too interesting. I just read Ford's F150. They lost 19 billion on the electric truck. Is it because guys don't want electric.
Kevin O'Leary
Truck if they're a ford truck guy, 19.2 billion. One of the largest write offs in automotive history. Bad policy, this idea that everybody in America wants to go green, but if you're in Fargo, North Dakota, there's no green. When it's 40 below zero. You need a truck with diesel or gas in it. So I guess they didn't think that one through too much. And China's dumping low cost ev. The only thing we got going in America is Tesla. It's the best EV in the world because it's designed from scratch, but it's not a low cost vehicle. They're going to try and do that with the Y version. There's a competition. China is subsidizing ev, selling it to every country on earth at half of what it really costs. I'm telling you, we're in economic war with those guys. They're not good guys. And that's why I think we should bulk up in our economy and say to the Chinese, don't mess with us.
Dana Carvey
I might join in.
David Spade
That, that's their, Is it called byd, is their little electric vehicle that's selling all over Europe.
Kevin O'Leary
I think they're called shitball expresses, but it doesn't matter.
David Spade
That was my second question.
Kevin O'Leary
They're very, very inexpensive.
David Spade
Yeah.
Kevin O'Leary
You know, and they, every country on earth is, is buying them because where else can you get a fifteen thousand dollar shitball express?
Dana Carvey
Yeah, I see little trucks they say they want over here that are, looks like they're way cheaper than everything in.
David Spade
The end of the day because you're looking at America and it's, it's controlled chaos in a sense because it's a free market and it's ad hoc and we see, and then we see a command and control dictatorial economy in China. And sometimes you go, wow, they can just build that, do that. But it seems in the end of the day all the cool stuff comes from America, you know.
Kevin O'Leary
No, they just steal it all. And then they steal everything. In China, if you go back to the tech and go back 20 years, you're going to find American and German, French source code in it. They steal everything. They have no IP laws, you can't sue them. The World Trade Organization, they joined it, you know, 2020 and they've never abided by the rules. I've tried to sue them. Nobody can they rip off everything. I mean, I'm just telling the truth. And that's why I'm glad, you know, whether you love Trump or you hate him, at least this administration is taking them on saying, okay, we've had enough of this crap and we're going to give you some consequences. And he started with 100% tariffs. I mean, it's a difficult conversation, but they steal, they cheat, they don't give a damn. And I think it's gotta end. It's not a level playing field. I would love to sell Chinese people's stuff. I don't want my IP ripped off. And that's what happens. And so it's a very. We can delist our companies off our exchanges. We can not allow them to sue our. They sue us in America and we can't sue them in China.
David Spade
Right?
Kevin O'Leary
Hell is that. Yeah, don't let them have access to the courts.
Dana Carvey
Can they buy land here? We can't buy land there.
Kevin O'Leary
Not the Chinese people, just the Chinese government. They understand the stick. You gotta hit them with the stick. They like, they understand power. That's why we gotta bulk up the economy. That Canada resource combo with the US economy. I know all the crap going on with, you know, the Canadian versus US crap, but I'm a guy with a foot in both countries with a family on both sides, and I understand the opportunity. I'm not a negative guy. I'm saying by the, by the time this is over, everybody in Canada's gonna say we gotta bulk up because the Chinese are gonna come right over the top. And I don't, I definitely don't ever want to work for the Chinese guys.
David Spade
I. Yes, I have a lot of affinity for Canada. My wife was. Is half Canadian and I'm from Montana, Alberta and all that. I mean, so it would be nice if we could become incredibly cooperative this way.
Dana Carvey
We will.
Kevin O'Leary
Out of economic necessity. All this bullshit will be over soon. I'm an optimist about that. And, you know, I go back and forth all the time too. I don't like the winter anymore, so I live in Miami where the taxes are. Everybody lives in Miami six months and a day. Everybody, you know, lives there.
Dana Carvey
So they're citizens. Is that what it is?
David Spade
And they're citizens.
Kevin O'Leary
It's, you know, Miami beach is its own country.
Dana Carvey
It's great.
Kevin O'Leary
Yeah.
David Spade
And Tennessee, we have friends in Tennessee. And also Texas.
Kevin O'Leary
I like Tennessee, but it doesn't have zero sales tax.
Dana Carvey
Right.
Kevin O'Leary
Talking to Hagerty about that. Let's get that done. I have to pay some sales tax on my new Gibson. Mr. Wonderful. I mean. Oh, yeah, I made a guitar with those guys. It's actually a 355 George Harrison Red with a 335 neck. If you're into guitars that's a pretty cool guitar.
David Spade
Wow. Or do you play? Or you're just a collector?
Kevin O'Leary
I like to think so. Thank you.
David Spade
Okay. Acoustic or electric or both?
Dana Carvey
Both.
Kevin O'Leary
I got a lot of guitars. I used to own a piece of Fender, so. I got a lot of Fender guitars, too. I like. I like them all. But a Gibson SG Classic and of course, a 355 Hollow body. That's got a sound. A lot of the Beatles tracks had that on it. You know, It's. It's very interesting.
David Spade
58. Les Paul was a good one. I like music, too, but I'm learning.
Kevin O'Leary
I'm learning how to play better because I. I just don't get enough time to practice. But in this hotel, I keep a guitar and an amp. And what you want to do is slow down. You listen to the old blues guys from the 40s and 30s, they weren't running up and down. They were keeping it slow.
David Spade
Do a great note, don't we? My brother and I used to call him typewriter guitar players. Just. And then you'd see someone like Albert King or something and go, okay, this note is, like the last note he's ever gonna play. He's just not going to play that many notes. But they're just magic, so. I totally agree.
Kevin O'Leary
You play less notes with more feel.
David Spade
That's it.
Dana Carvey
Yeah.
David Spade
Yeah.
Dana Carvey
Do you like being called Mr. Wonderful still? Did you like that? Or is that.
Kevin O'Leary
Oh, look, it's the. You know, it's just the truth. What am I supposed to say?
Dana Carvey
Well, we. Anything else for this young man, Dana? He's been nice to sit there.
David Spade
I just. I love that we. We got to get together with Canada. This is my takeaway. I love that you play electric guitar in your room and you kind of have fun with the idea of your confidence. And I want to adopt a little.
Kevin O'Leary
Listen, go. If you're going to go see Marty supreme, let's do a plug for the movie. Don't go alone. It's an emotional wrencher. And go with the community. Go see it in a theater. Because it was shot on 35 mil film. It's not by the Darius guy. I hated him when we were shooting it because he would take two hours to set up a single shot.
Dana Carvey
Oh, yeah.
Kevin O'Leary
Now that I see it, yeah. By the way, do you really think he was punished enough for what he did?
David Spade
Well, he plays not a. An incredibly aggressive person who's very unscrupulous. So I don't know. The very, very end when she said, I don't want to give it away. They did this.
Kevin O'Leary
I don't want to give it away either, but I won't. I mean, he did not. You can't over that way and get away with it. That's what I kept telling.
Dana Carvey
That's the whole thing.
David Spade
Well, you, you have a point. But it's an interesting end. It's a very intense ride and you're all, all the performances are great, all the character actors.
Kevin O'Leary
Go see the movie. It'll entertain the hell out of you. But yes, I got over.
Dana Carvey
Yes, Josh Safdie makes a good movie and I've.
David Spade
Kevin o' Leary gets people like over an Academy Award winning ending sucks, says o'. Leary.
Kevin O'Leary
Okay, Kevin, it sucked because my wife said it was perfect. My daughter loved it. It. My kids loved it and I said no, it's not enough punishment for him.
David Spade
And anyway, you have a point. But it was. It's a great movie. Congratulations. Enjoy the premiere tonight.
Dana Carvey
Yeah, take care. Hey guys, if you're loving this podcast, which you are, be sure to click follow on your favorite podcast app, give us review, five star rating and maybe even share an Apple episode that you've loved with a friend.
David Spade
If you're watching this episode on YouTube, please subscribe. We're on video now.
Dana Carvey
Fly on the Wall is presented by Odyssey and executive produced by Dana Carvey and David Spade, Heather Santoro and Greg Holtzman, Maddie Sprung Kaiser and Leah Reese Dennis of Odyssey.
David Spade
Our senior producer is Greg Holtzman and the show is produced and edited by.
Dana Carvey
Phil Sweet Tech booking by Cultivated Entertainment.
David Spade
Special thanks to Patrick Fogarty, Evan Cox, Maura Curran, Melissa Wester, Hillary Schuff, Eric Donnelly, Colin Gaynor, Sean Cherry, Kirk Courtney and Lauren Vieira.
Dana Carvey
Reach out with us. Any questions to be asked and answered on the show? You can email us@flyonthewalldecy.com that's a U D A C Y.com car.
Episode: Mr. Wonderful aka Kevin O’Leary: Shark Tank Meets Marty Supreme
Date: January 15, 2026
In this lively episode, comedians Dana Carvey and David Spade welcome Kevin O'Leary—known to millions as "Mr. Wonderful" from Shark Tank—for an offbeat, insightful, and very funny conversation. The trio discusses O’Leary’s unexpected leap into acting with the Safdie brothers’ much-hyped movie Marty Supreme (co-starring Timothy Chalamet), the inner workings and evolution of Shark Tank, the realities of entrepreneurship, and O’Leary’s signature take-no-prisoners views on business, politics, and global economics. The episode is a wild ride blending showbiz banter, behind-the-scenes movie stories (highlighted by Chalamet's now infamous “ass double” anecdote), and hard-nosed financial wisdom—with plenty of irreverent humor throughout.
Casting for a “Real Asshole” (01:34, 14:11)
"They came to see me and said, look, we're looking for a real asshole in this and you're it." – Kevin O’Leary [01:34, 14:11]
"I was very unhappy with the ending... if he really did this to me in real life, I would fuck him over so badly... I suggested to them, perhaps I'm a vampire and I bite him and he lives in hell in perpetuity." – Kevin O’Leary [14:33, 15:02]
Working with the Safdies and Timothy Chalamet (13:22–18:41, 32:22)
"Timmy said, no, I want to immortalize my own ass in perpetuity. So I said, I have to hit your ass, it's going to hurt. So he rotated cheeks so they were equally red through 20 takes... I admire him for saying, look, I'm not letting a stunt ass immortalize my ass in perpetuity in a film." – Kevin O’Leary [17:31, 18:40, 32:22]
Red Carpet & Industry Surrealism (31:05–33:47)
"I've never done this kind of gig before, but boy, it's crazy... I love it when people suck up to me. I really do." – Kevin O’Leary [31:12, 31:47]
From Audition to Family-Sized Hit (04:10, 07:04–09:20)
"It got canceled three years in a row... In the fourth year, it just went geometric." – Kevin O’Leary [07:10, 07:45] "It's the essence of the American dream... you can come up with a product... become a multimillionaire, which we've done countless times in 17 years." – Kevin O’Leary [08:31]
Key to Entrepreneurial Success (09:33–13:05)
"The first million is easy... But getting, like, when you hit 5 million, you gotta start hiring people... A lot of people shit the bed when that happens." – Kevin O’Leary [09:33] "Big is 50 million... Most people that founded the company don't have [executional] skills and they go to zero because of it." – Kevin O’Leary [12:36]
Notable Deals: Cat DNA Test Example (10:23, 11:56)
"Cat DNA tests... I can buy a new cat for five bucks, why spend $29 on a test? But... we made a lot of money, a ton. It was bought by a giant pharmaceutical company later for the data." – Kevin O’Leary [10:23, 11:56]
Philosophy on Wealth and Self-Confidence (04:10, 05:00)
"I don't need any more money. I just need more time. That's my real issue." – Kevin O’Leary [04:10] "I look fabulous all the time. I can't believe how good I look." – Kevin O’Leary [04:45, 33:34]
Truth-Telling and Dealing With Hate (05:21–06:22)
"My mother told me when I was 16: just tell the truth, you never have to remember what you said... I care about my family and maybe 15 friends and everybody else. I don't give a shit." – Kevin O’Leary [05:21]
Shark Tank Dynamics & Relationship with Mark Cuban (22:29–24:51)
"He likes equity, I like royalties... He's a little bit country, I'm a little bit rock and roll." – Kevin O’Leary [24:34]
Political Neutrality & The Policy Lens (26:34–27:21)
"I'm a policy guy... I do as many hours on CNN as I do on Fox... I care: is this good policy? And that seems to have kept me out of trouble." – Kevin O’Leary [26:34]
On America's “Secret Sauce” (27:21–29:09)
"The number one export of America is not energy or technology. It's the American dream." – Kevin O’Leary [27:21] "Entrepreneurship's not money or greed. It's about pursuit of personal freedom to do whatever you want with your time." – Kevin O’Leary [28:45]
Views on High-Tax States and Mobility (29:09–30:58, 35:02–36:34)
"California... you guys are paying 99% tax." – Kevin O’Leary [29:09] "Everybody lives in Florida now. All my Boston neighbors... they live in Florida and they visit New York. I don't know who's going to pay the taxes here, but this isn't going to work." – Kevin O’Leary [30:37]
Canada-US Economic Alliance & China Skepticism (35:02–36:34, 43:43–45:48)
"Canada has all the raw resources and the US is the largest market... and then tell the Chinese to fuck off." – Kevin O’Leary [35:03] "China is subsidizing EVs, selling it to every country at half what it really costs... We’re in economic war with those guys." – Kevin O’Leary [42:14, 44:04]
IP Theft and Trade Realpolitik (44:04–45:11)
"They steal everything. They have no IP laws, you can't sue them... I'm just telling the truth." – Kevin O’Leary [44:04]
Crypto for Beginners (37:02–39:46)
"All you need to own in crypto... is Bitcoin and Ethereum. There are 10,000 shit coins. You don't need to own any of those." – Kevin O’Leary [37:13] "Don't own more than 5% of your portfolio in it. You can make about 3% yield on it, which is not a lot. Don't speculate too much." – Kevin O’Leary [38:00]
On Elon Musk (40:13–41:58)
"This guy is 100% signal, no noise. A little awkward socially... but he's only a third of the way through his career and look what he's achieved." – Kevin O’Leary [40:13]
Music and Guitars (46:30–47:47)
"I made a guitar with [Gibson]... a 355 George Harrison Red with a 335 neck. If you're into guitars that's a pretty cool guitar." – Kevin O’Leary [46:38]
On Celebrity & Self-Image:
"I can't believe how good I look... It's ridiculous how good I look. I'm almost embarrassed how spectacular I look."
— Kevin O’Leary [33:34]
On Shark Tank’s Appeal:
"The reason it works is that we don't know. You don't know what's going to walk through those doors. It's the essence of the American dream."
— Kevin O’Leary [08:31]
On the “Ass Double” Scene:
"Timmy said, no, I want to immortalize my own ass in perpetuity... An ass is an ass and there's only one ass. Make it your ass, celebrate your ass and put it in this film for generations to come."
— Kevin O’Leary [32:22]
On Entrepreneurship:
"It's not money or greed. It's about personal freedom to do whatever you want with your time."
— Kevin O’Leary [28:45]
On Political Divides:
"The number one export of America is not energy or technology. It's the American dream."
— Kevin O’Leary [27:21]
On Dealing with Hate:
"Most of us hate mail. And then there's about two and a half percent, which I call the lunatic fringe, which is just... completely fucking crazy. And what am I supposed to do about that? Nothing."
— Kevin O’Leary [06:22]
| Segment | Timestamp | |-----------------------------------------------|-------------| | Shark Tank origins and family appeal | 07:04–09:20 | | O’Leary joins the Safdies' film | 13:22–16:38 | | Timothy Chalamet paddling scene | 17:31–18:41 | | Crypto advice & stablecoins | 37:13–39:21 | | Praise for Elon Musk and story | 40:13–41:58 | | Perspective on America, taxes, and rivalry | 27:21–30:58 | | US-Canada economic strategy and China | 35:03–36:34, 43:43–45:48 | | Red carpet preparation, tuxedo fashion | 31:05–33:47 |
This episode delivers a fast-paced, funny, and unexpectedly deep conversation that spotlights Kevin O’Leary’s larger-than-life persona, his quick wit, and blunt business wisdom. Are the Safdie brothers "disturbed individuals"? Is America still the best economic game in town? What should we really do about China? And, most importantly—should every actor immortalize their own ass on film?
Whether you're a Shark Tank fan, curious about the modern business landscape, or just in it for the showbiz gossip and laughs, this episode provides an entertaining and insightful look behind the scenes with "Mr. Wonderful" himself.