The Adam Friedland Show (Cumtown) - KEVIN O'LEARY Talks Marty Supreme, Shark Tank, Millionaire Lifestyle

Episode Date: December 23, 2025

Get harder, longer-lasting erections with Ro Sparks: $15 off first order of medication to get hard at http:ro.co/TAFS -- See Adam on tour https://theadamfriedland.show/pages/tour -- JOIN THE FRIEDLAND FAMILY FOUNDATION / PREMIUM SUBSCRIPTION: https://www.youtube.com/@TheAdamFriedlandShow/join -- Patreon: https://www.patreon.com/cw/TheAdamFriedlandShow -- Buy our merch!: https://theadamfriedland.show/collections/new -- The Adam Friedland Show - Season Two Episode 27 | Kevin O'Leary X: https://x.com/adam_talkshow Instagram: https://www.instagram.com/theadamfriedlandshow TikTok: https://www.tiktok.com/@adamfriedlandshowclips YouTube: Subscribe to @TheAdamFriedlandShow here: https://www.youtube.com/c/TheAdamFriedlandShow Subscribe to @TAFSClips here: https://www.youtube.com/@tafsclips -- Go to Squarespace.com/TAFS and use code TAFS for 10% off your website or domain Use code TAFS at Monarch.com for 50% off your first year! — #adamfriedland #theadamfriedlandshow #KevinOLeary

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...and... ...and... ...and... ...and... I don't know. I'm going to be able to be. I don't know. And so on the

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the, and, and, and, And I'm going to be able to be. And... ...and... ...and...

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Oh, um, um, ooh, who, um. Um. Um. Well, I don't know, it was kind of smooth and slow. What do you think? Thank you. Thank you. Thank you.

Woo! Oh, my, good, a bit of a show, oh, my had a finished show, oh my

had a fan of the show on my TV. Hello and welcome back to the Adam Friedland Show. It's Adam Friedland second to last episode of the year. Merry Christmas, everyone. I hope you guys are having a great holiday season. I'm going back on the road, of course, Emerald City Comedy Club, Seattle, Washington, January 22nd and 24th. I'm doing five shows.

Get tickets at Emerald City Comedy.com. And also there's a link in the description. Caleb will be there as well. And as always, guys, a sincere thank you to our members here on YouTube.com. You guys have made this show possible this year. If you'd like to sign up, members get access to all of our episodes early, and if you join at a second or third tier, you get your name in the credits of this fine program.

If you'd like to join the Freedland Family Foundation, you can do so by clicking the join button here on YouTube.com Or by clicking the link in the description of this video. Also, there's a link for a Patreon if you prefer to support the show through Patreon. Hey guys, merch is available. Christmas is what? Two days, three days away? You can get it for maybe probably after Christmas.

I don't know. Yeah, you can get it for after Christmas. I'm not going to make any clip. You can get it tomorrow. New Year's gift. You can get it for a New Year's gift. My guest this week is legendary rock musician Kevin, Mr. Wonderful O'Leary. His nickname is Mr. Wonderful because he's known primarily for being wonderful at playing guitar

and dressing wonderful as well. Okay. We've all heard the tracks, but. Kevin is making the musician-go's actor-turn official with the release of Marty Supreme, Music and Movies. Music and movies, Alexander wept, for there were no more lands to conquer. Smart.

It's the end of the year, guys. I'm wearing the same clothes as last week. Guess why? Because we... Because I'm recording... We're dropping... I'm not saying it. Have a nice Christmas.

Enjoy this one. Marty Supreme in theaters everywhere. Support the movies, okay? Because pretty soon, pretty soon, pretty soon, there's going to be one fucking studio. And that is, what is it? That is Joe Max Productions.

I forgot the name of it. So guys, Kevin O'Leary, enjoy it. Bye, give it up. Go see the movies. Thank you to Roe for sponsoring this episode. I'm not a Roe Spark's user. but I'm excited to tell you what it's all about. Women can sense confidence in the bedroom.

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entertainment legend now, and now actor, he's in the movie Marty Supreme coming out Christmas. Everyone, please put your hands together for Kevin O'Leary. More noise. Thank you. Thank you. Thank you so much. I really appreciate it. That's great. So Kevin's a massive fan. He's been emailing us nonstop. I said you can finally do the show. Before I came in or I checked you out, you're okay. I'm okay. I'm going to give you 7.2 out of 10. I think that's reasonable. You may be able to increase your score depending on how today goes.

Oh, I think I think I'm going to be 9.9 after this. Really? I have a feeling we're going to be best friends. I don't know why. That's good. And I need a lot of advice from you. So I'm ready to give it. Oh, first of all, I want to congratulate you on the film, on Marty. I was at the premiere at Lincoln Center. Were you there or no? No, I have only seen the sequences that I did the voiceovers on. I intentionally waited, and I, you know, talk to Josh every day almost.

I'm going to do the SAG screening for the first time on Sunday and then do the LA premiere on Monday of next week, then come to New York. We're on a full promotional swing on this movie. Yeah. Obviously, 824 is excited about it. There's a good Oscar buzz for Timmy. I want to see him win it, obviously. That would be great.

What about you? I don't think they push us hard on the supporting actor role somehow, but we'll see. I was seeing that, honestly, at least a nomination. I love it. I mean, I've never acted before. I had no idea what I was getting into. And I have a theory that you may want to consider, and here's what it is. I'm really primarily an investor, that's what I do.

I invest in a lot of businesses and people. And so over the years, you invest in a startup or a nascent company, half of them fail. But five years later, maybe seven years later, the winning companies when you're exiting and you're getting 10,000 X on your money, the men and women that run those, do they have any common attributes? I started to ask myself, what do they have that's common, even though they don't know each other? even though the businesses are in different sectors, they're all different, and what is common? Well, there is one thing, and this is kind of unique.

If you look and talk to them, because you get to know them after five years, and they say, you know, you ask them, how do you spend your time? I mean, I know you're working like hell, but what else do you do? In every case, they spend 20, 30 percent of their day doing something completely out of their comfort zone. crazy shit like paragliding going to Switzerland and jumping off a cliff and learning how to do that

which is I think nuts but they do it or they go to space they buy one of those things up in you know Virgin or whatever or they learn how to play the cello or what's yours well I like to think that the things that really keep me

passionate are my black and white photography that I still do with like a cameras and how I've been doing that my whole life. I remain an editor. I cut at least one of our social media posts every week on premiere because I used to cut film. I practice my guitar as much as I can. I collect watches.

Those are all different than what I do as an investor. But my point is, when you get an opportunity, so here's what happened to Ronnie Supreme. I get a call from Josh and Ronnie. And it actually came through my agent and he said, Kevin. Great guy, Jay Sears, I've known him forever, been all the way up through television for years with him. He said, you know, look, I want you to think about this seriously. You've built a big franchise here. But you don't know how to act, and you've never done this. You could go out there and shit the bed and totally destroy our franchise that we've built

together. And I said, Jay, fuck him. Well, I said, how do you know I'm going to shit the bed? How do I know I'm going to shit the bed? How do I know until I try it? My whole point is you've got to go do something that you, even though you may think, shit, it may not work. Why not give it a shot? Because 50% of the time you have a great outcome. Yeah. Which I think, hopefully, we'll let the audience decide in the case of the reviews look pretty good.

But I didn't know how to act. And they told me after we read the lines and they came out to my lakehouse, they said, look, we're looking for a real asshole. And you do that naturally. Yeah. So, okay. The answer is you did know how to act because you've been in show business. You've been on television. Yeah, but I wouldn't say that reality TV is the same as the cadence between scripted lines,

which is what I learned the first day of sure. Sure. Yeah. It's different. I will say, and I'm just some guy, but in my opinion, as a first-time actor, and it's a sizable performance. I mean, it is natural. I mean, you do not communicate as like, oh, this is a gimmick cast. You communicate as a great actor, and I, like, I commend you on it.

Well, I'm very, I'm really flattered. I'm glad you feel that way. But when you're, you know, what I learned and what I saw, and when I saw the rushes and I saw the cuts, what those guys, the way those two work, and I hope I'm not giving any industry secrets away here, is they wrote the script together. So they've been living this thing for seven years.

But here's what actually happens when you're shooting. Ronnie goes into the production text downstairs, wherever the hell it is, different sets in Tokyo or in New York or whatever. But he's in Josh's ear with an IFB. And he's the editor. Well, they cut it together, but he's kind of the lead editor guy. And, you know, I'm not used to being told what to do. So obviously I learned right away that a film set is not a democracy.

Because I'd say to Josh, what the fuck? I got it. We're done. We've shot it 10 times. I nailed it already. He said, you haven't nailed it till I say you've nailed it. Do it again. And then after multiple takes of the script, he'd say, okay, let's improvise.

We've got a cadence going here with Timmy or with, you know, whoever. And let's pick up on what you said on that last one or what he said on that last one. But when you see the final edit, what they did is they took some of the script and some of the improvisation, and they cut it together into what I think is masterful. They captured a moment. sometimes those two dudes don't agree and they take it outside because you don't want to be fighting in front of the cast but you know they just don't agree and it's three in the morning and they're going at each other and they come back with

a solution it's an intense like it's a it's a fucked up creative process that I think you can't emulate any other way than just doing it you know shooting it in some ways Josh was your first boss since Nabisco is that right you had that a since then. That's a great analogy. Listen, I've studied. No, I've never had a boss except back then. I've only been fired once, and I've never worked for anybody.

But I did work for Josh Safdi. I actually was an employee. That's how I felt. And he's a reasonable guy, but the hours we work, the hours, the immense hours, like 18, 20 hours. You might get them in trouble with the union. I don't know if you're allowed to say there. They worked regular hours and... Yeah, yeah, yeah, regular hours.

But when we were shooting the... Jimmy Hoffa might break your knees. When we were shooting the spanking scene, that happened at about 4 a.m. And it was intense, and it was really intense. And we didn't get it at the beginning. The cadence wasn't right. The vibe wasn't right. The room wasn't right.

Whatever the hell it was. We just kept going. And we had a stand-in ass. But... A stunt ass. A stunt ass. Yeah, yeah. But Timmy wouldn't, didn't want the stunt ass.

He wanted to immortalize his ass. That's incredible. And I said, look, I got to hit your ass with this. Because the fake ping pong paddle broke. Yeah. So now we're dealing with a real paddle, stiff wood. And Josh is saying, look, I want to hear that smackatino. I want to hear an explosion of ass here.

Yeah. I mean, there are women all over the country. And I'm telling you, I wound up. like a baseball bat and hit him and you fucked his ass up I his ass had imprints of the paddle rubber on his ass that's a that's a that's a hot ass right it's a hot it's a hot ass but it was very hot you're doing a little bit of a brag right now I am I think but I'm telling you all 12 ladies watching this are gonna are gonna be that very very proud of that scene but when I got back

did he say anything about me the whole time you were working with him I don't recall okay no I don't recall but when we when I got back to uh Casa Tua, I was staying there down on South Street in New York. It was 7 a.m. And I was fried. I mean, I was just wired, you know. And I said to the matri-D, look, I want some scrambled eggs and some, you know, smoked salmon. And a bottle of 2022 Puline Montresche.

He said, it's breakfast. What are you nuts? I said, well, it's not breakfast for me. I've been awake for two days. So I want the bottle. And I drank the whole, I put a straw in it. And I called my wife up and said, She said it's 7.30 in the morning.

So it's a guilty pleasure, but that's how I unwound that day. And I'll never forget it. It was a great experience, the whole thing. So you're, you just played music for us. You're a guitarist. You're a photographer. You're now an actor. You are a documentarian.

You've made a documentary film before in your early years. You are an entrepreneur. You are kind of an elder statesman of business in North America, I'd say. Would you consider yourself a modern-day Renaissance man, like a Da Vinci of sorts? You know, the journey of entrepreneurship is not a destination, it's a journey. And the reason you would want to do that now, and I tell everybody this, because I teach entrepreneurship at places like MIT and Harvard now, it's not about the grade of money

because you just listed off a bunch of things I couldn't do if I wasn't free to do them. That's what money buys you, the free time. It's not about the greed of money. I don't need more money. I need more time to pursue the things I really interest me.

And so what you find out is that if you're motivated by money as an entrepreneur, you will never get it. You have to be so insanely passionate about what you're doing and all the competitors are pursuing you. And then one day you wake up and you're filthy rich. That's how it happens.

Every guy I've ever talked to that's had a huge exit has said I never saw it coming because I was just myopically focused on my business. It was the same for me. And then one day we were acquired for $4.2 billion. And then what I found was amazing for all of us, the people, the nine core people, we didn't know what to do the next day.

We just went back to work. I mean, that's all we know. And so we just kept doing other things. things and I've done many other successes and failures in that period but you know it's allowed me to do some really interesting things and that's what keeps me going and you know pursuing stuff yeah it's very interesting yeah but you have to be able to afford the time right the time is the problem you can't buy any and that's the one thing no matter how rich you get you can't buy you

can't buy health and you can't buy you know you can't be guaranteed health you got to be very careful and I certainly think about that a lot and I do try and use my time very carefully because I don't have to do anything so I've kind of I'm here because I want to be here and so I block this because you're a big fan yeah well also I just you guys do interesting work I've seen some of it and it's interesting I thought this could be good so you know um That's why. And then I'm going to do some other crazy shit tonight. What's that?

I'm going to have a dinner with the auctioneer of the F.P. Jorn, Francis Ford Coppola Watch, which I put on television about an hour ago. Oh, wow. Yeah, it's probably the most coveted watch on Earth. It's probably going to sell on Saturday for between $3 million. I wanted to hold it in my hand before it went into a private collection for a generation. So I suggested we bring it. to tell. Did you consider stealing it?

Yeah, the problem with that is I know, Jorne, I'm wearing one of his watches. The thing about watchmaking, which I really learned as time passed, is collectors now covet the independent watchmaker. And Jorne is now considered a living Picasso. He is making only 900 watches a year. There are thousands of collectors around the world

that want a Jorna. But he personally decides who gets each piece. Really? Yeah. And so... And they cost, what, over $1,000 probably? What's funny about that? Yeah, the secondary market would be in the millions.

Primary, you can get one as inexpensive as $18,000, but you can't. I mean, that's the problem. The elegant, which is the entry-level watch, sells for 18. Secondary market is $158,000. And that's a beautiful piece. Pretty simple. I want to try something because this is like kind of a free education for me because I'm a new I'm an entrepreneur of so I don't think of myself as one

I'm kind of you're you're supporting yourself with what you do I'm a staff now and I you have a responsibility yeah and I they look up to me and I you know they they see me as a friend more than a but but I bet some of the think you're an asshole that's probably true no I think that they think well okay um one thing that I've struggled with and I'm and maybe you can as an educational thing for the audience you could kind of impart some wisdom on me is um firing like I I've there is one individual who's not here today because you whack them no I because I and I've it's probably been a matter of three months that he's should have

been fired but every time I get close I just don't have it in me so perhaps if we could like act it out you could we could we could kind of, you could kind of show me, you could be me, I'll be him, and then you could kind of like, because I really, I don't know how to do this. I called my girlfriend's dad and said, how do you fire. What's his name? Uh, Paul. Okay, so you're Paul. No, no, the guy? Yeah. Oh, oh, uh, yeah. So, B-S. Hey, hey, Skip. Okay, so, listen. He's not here right now also. You know, I get it, but I'm going to give you, here's how it goes down. I want you to be happy

I really want to be happy and I have a feeling you're not happy and the reason I feel that way is you're not with the team anymore you're not on the same agenda and that must be that you're not happy now I'm happy I'm fine

I like it well the team isn't happy with you because they feel you're not happy and I'm going to make it very simple for you. We're going to end our relationship today, but the good news is I'm going to give you a fantastic exit package because I want you to be fairly treated. That's number one. How much? How much? How much? And number two is, you know... How much is exit package? I'm going to pay you three months of your salary. Okay. I don't have to. I could pay you

six weeks. To be a good guy, because I'm a good guy. Listen, that's why they call me Mr. Wonderful. Yeah. So I'm going to give you three months. I call myself Mr. Wonderful. What's, but what's important is, that we go our own ways now. I don't why you're sitting around. In fact, I've cleaned out your whole place. There's a box outside on the street. It's waiting for you. Yeah, okay.

But I've got you a limo. The box is in the limo, and it's going to take it wherever you want. Okay. Can I just do that right now? I swear to God. Yeah. Yeah.

Well, that's how you do a fair... A fair... Yeah. A shit can. Okay. I mean, I'll be nice about it, but... Okay, I mean, just give me a minute. I know we're pressed for a time.

but I'll just I'll just get him out of here because it's been driving me nuts because well I think you got you got to make a decision that's my whole point hey hey hey hey hey where are you what you what I'm home yeah well why aren't you here right now I'm noticing I had a family emergency he's a fucking hold on one's like he bullshit It's the worst, it's the worst bullshit I've ever heard. Well, wait, give you a thing, yeah. Okay, well, you know, I got to say I'm starting not to, listen, it doesn't matter, but I don't, I, it's been.

My son is in the hospital right now. He is? Yeah, he relapse. You know, I know that you have issues, but he, he, is he okay relapse he overdone he overdosed he's gonna be he's not dead or anything he's he's okay but he is um he's it it was pretty bad um i'm sorry dude and since you know since your since your wife yeah i know he's got the same because it's a disease yeah i know and it's just like it's happening again and i just i can't lose in both and it's just i'm sorry i didn't text you i thought i did

Well, here's what I'm going to do. I can tell that you're not happy, and the team isn't happy with you. Yeah, and what I'm going to do is offer you a very generous package. Are you firing me? What I'm going to do is I want you to be happy. So I'm going to offer you three months of your pay, and then, and then I'm going to You're bought, I packed up a box and your stuff is outside right now. My son is in the hospital right now.

And you're telling me I'm going to lose my health insurance. Well, listen. That I get through this show. This is, this is, it's business. Are you filming this right now? No, I'm not filming this. No, I wouldn't, no, come on. No, no, I'm just saying, um, I got to, but no, no, I got to go.

It just, um, good luck with everything. in three months and just okay anyway well oh man that's that's a horrible story if it's true if he made that up he's a bad person right I don't know I don't know I feel like an asshole right now well I think you know there could be asshole factor six in you I don't know was it not the right time should I not have done it then it unfortunately these two things are horrific they're both bad but you know there there has to be some there has to be some there to be an outcome. That's the whole point. Because I don't think it's going to get better for him. I mean, this is, listen, my heart goes out to him if that, if that story's true.

Yeah, I didn't know that at all. Well, do you know that? Well, I know that there have been problems in the family, and he is dealing with the life. Well, that's a very, very tough situation. I mean, I don't wish that on anybody, but... Should I say sorry? Should I hire him back? I feel like I should... Why do you think it'll be better? I'm like he's him off No but the whole point is Why is the original problem still

It's still going to be there Whatever it was I mean I don't know the details Listen you know business you're right You know what you're talking about It's kind of like you have to take care of The remaining employees That's what matters

You could be more generous if that story's really true Maybe six months Or maybe a year Or maybe a raise Maybe Well okay move out because we have this episode is brought to you by squarespace try code t a f s for 10% off your domain or website the following ad spot is best experience as a video which you could watch

at the adam friedland show on youtube I'm going to be able to be. We're going to be able to be able to be. I don't know. I'm going to be able to be. I'm going to be able to be. Hey. Hey. Listen, um, I know I'm not who you're looking for. I know I'm not the usual type of girl that gets the guy at the end of the movie.

I know I'm definitely not Macha Girl. But when I saw the words on your website that you made using Squarespace.com, it made me want to be wanted the way that you wanted Macha Girl to be wanting you. Look, I know I'm a loser. I'm a freak. And I can't imagine why someone like you who could make such an amazing website on Squarespace

using their built-in tools like AI-assisted blueprint and search engine optimization and their... Oh, scheduling. Yeah, they're scheduling. Could ever want me. But just so you know, if you ever did, I love you.

I'd love you until... Yeah, yeah, sure. You want to go? Oh, all right. Okay. Yeah, yeah, thank you. Wow. holiday plans, this is when I need my wardrobe to just work.

That's why I'm all about quince. They make it easy to look, sharp, feel good, and find gifts that last. From Mongolian cashmere sweaters to Italian wool coats, Quince pieces are crafted from premium materials built to hold up without the luxury market. Quins makes essentials that every guy needs Mongolian cashmere sweaters for $50. wool coats that look and feel designer and denim and chinos that fit just right. Their outerwear lineup is no joke, down jackets, wool top coats, and leather styles that are built to last.

Each piece is made from premium materials, trusted factories that meet rigorous standards for craftsmanship and ethical production. By cutting out the middleman and traditional markups, Quince delivers the same quality as luxury brands at a fraction of the price. It's everything you actually want to wear, built to hold up, all see. season long. Finding the right winter coat was easy for me with quits. They've got plenty of options and prices actually made sense. Quince has gift giving covered beyond clothing too. I in fact picked up the pumpkin cardamom candle for my father-in-law. Get your wardrobe sorted and your gift list handled with quince. Don't wait. Go to quince.com

slash T-A-F-S for free shipping on your order and 365-day returns. Now available in Canada, too. That's Q-U-I-N-C-E-E-D-com. slash t a f s free shipping and 365 day returns queens dot com slash tafts this episode is sponsored by lucy one hundred percent pure nicotine always tobacco-free lucy breakers or nicotine pouches with an extra surprise each pouch holds the capsule and they can be broken open to release extra flavor and hydration set yourself up with a subscription to have lucy deliver straight to your door what's my favorite it's the mint what's the strength the strongest one when do i throw it in before i have so guys let's level up at your nicotine routine with lucy go to Lucy.co slash TAFS, use promo code TAFS, get 20% off your first order.

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As I'm saying, I'm a nascent entrepreneur. But like I happen, like I have business partners that kind of engage in the business side. I get to focus on the creative. And I fancied myself a businessman for far too long and I realized I got my shit handed to me too much. And then what's important is that I'm good at this part and I have business folks that do the other part. So like how would you to an idiot, a real dumb dumb, like explain. like what like what is like economics like in your like and you're talking well I you know the thing about entrepreneurship it's very binary you either make money or you lose money

there's no gray you it's one or the other and so you should put time into the equation you say to yourself I'm starting a business and if I can't make money in 36 months I'm going to take it behind the barn and shoot it because at that point you've run out of an That idea is not working. If we weren't able to prove that you could acquire customers economically, the business is unprofitable, and you're burning cash, and you're bankrupting yourself if you're borrowing money against your house or whatever it is. No, we're doing good. Okay, so the idea is that entrepreneurs fail sometimes, but they shouldn't spend all their time wallowing in failure. And entrepreneurs that are unsuccessful don't have the guts to take it behind the barn and shoot it.

Yeah. That's what you have to do. Bad businesses are like a cancer. They kill your time. Yeah. So you got to shoot it. Yeah. That's it.

Yeah. And I've done that, you know, I've had good ideas, bad ideas, but I never, never let them spend. Like these days, if I can't figure it out in 18 months, I shoot it. This thing is, I mean, it's a good product. People like the product. But once you know it works, you've got to spend 110% of your time on it. Oh, I'm married to this. Yeah, of course.

What do you do when you get in trouble from the lady? for working too much well that's a big challenge for everybody you know you should basically set aside some quality time for me i try and make it weekends and i'm very fortunate i can say look where does the family want to go this weekend you want to go to geneva you want to go to thailand you want to go to paris let's go uh take the tickets on me spend the weekend together and then after that we all disperse again because i'm traveling all week yeah so you know it's quite and lately particularly on this marty supreme uh promotional tour We're going everywhere.

Yeah. My wife, Linda, said, I want to go with you to see what it's like. And after the first week, she went, wow, I don't want to get another airplane. I said, well, we're just starting. Yeah, yeah. Because you spend most of your time hopping cities. Yeah. Sometimes three cities in a day.

You seem like the concept of a businessman, like a successful person, I guess maybe it comes from movies, is that because they're making big bets and there's a rush coming from it, that they also have other, like, vices. But you seem like relatively well-adjusted in your life. Well, what I try and do, and not everybody has devices, but my routine is I get up at five. I live in Miami. I live on the beach, and we have a 22-mile boardwalk.

Fabulous. So when the sun rises at about, so at five to six, I'm kind of listening to all the news feeds because I do a lot of live TV during the day. There's usually five news stories worldwide. I listen to them. You know, the outlets I listen to, I try and get balanced. BBC in London is very good.

Al Jazeera, Fox, CNBC, BBC in Canada. There's a lot of stuff going on between. You guys have a BBC, too? No, BBC is England, but CBC is Canada. CBC, yeah, CBC. But the point is, they all have the same five stories with a different tilt on it. So by the time I'm finished like 40 minutes of that stuff, I've got a pretty good idea of what's on the plate for the day.

And I get on the bike and I ride for about an hour and 20 minutes with thousands of other bikers as the sun is coming up There's only bikes and dog walkers. That's it. Then I go to the gym for 20 minutes I don't eat breakfast. So I fast for 16 hours a day and then I eat it 2 o'clock My only I don't take drugs. I don't smoke my only vice is wine. I like wine So I have to limit myself, you know, I don't drink till 6 o'clock. I have a glass of lingerche. The thing about wine the problem with wine is if you drink it before you go to bed you don't sleep well

if you can get seven hours of sleep a night you feel amazing you know don't eat shit food get some exercise and don't drink too much so that's the problem and that's where I

you know that's my advice I love it happy yeah you know the thing is the key is Are you a happy person? Yeah I'm pretty happy I should be drinking at breakfast that way I'd have

plenty of time before I went to bed. Yeah, yeah. Trying to convince my wife of that. Let's do some more Montresche in the morning with eggs. Well, I can talk to her. At your level of elite entrepreneurial business people, you must have met some real freakazozoids that outside of the boardroom.

Well, where I see the guys from other planets is in the technology deals I invest in. The programmers, the coders, the firmware developers. And what are they doing? They're just eclectic dudes. The really good ones are, really great engineers are not normal people. They're just unusual people.

And they have the ability to be extremely focused on the signal of the work they're doing and they don't let noise get in the way. They're very eclectic. And I've been working with guys like that and women like that for 20 years. So the guys that wrote missed. It's a title from way back that became very famous.

Five guys in a house. house, they all had Ferraris, using unusual, they were unusual. But they wrote this software. Unusual how? Well, you know, I don't want to say, but they were on the edge. They're on the edge. But they wrote amazing code, and I have to go out there and get them to finish it on time so we'd ship 12 million copies to Walmart. And they keep trying to pull you into a cuddle puddle. Yeah, but the thing is, my coders, they never want to stop. They just want to make it better and better, but at some point you have to. cut the version and ship it.

But I did that my whole life and so I've got a pretty good respect for what they do and that was one of our competitive advantages. Developers like to work for me because I gave them a lot of slack on the creative creativity but was able to manage their time and say look we gotta ship it next month. It's got to ship

because you're trying to fill shelves for holiday and whatever else but and I still do that to a certain extent but I'm not an operator anymore, I'm just an investor. When you see like in New York City when you see someone on the street like a homeless person like what do you make of the what's your what's your whole take on that it's sad but usually it's mental illness yeah what it is and yeah our society is a very hard time you shouldn't tell them to

take it outside it's it's kind of inhumane it's it's you look at other societies like Asian societies for example or even even in Europe and Switzerland they covet the elderly yeah they want to to bring them into their homes and they keep their grandparents around because that's how the family values work. We don't have that in North America. I feel like in the future, have you seen the show Mad Men?

Yeah, of course. Like there's a, you remember they're going for a picnic? And then they shake out all their garbage into a field and you're like, oh, they didn't know what littering was. I feel like in the future they'll look back at us and they'll be like, you just walked past a guy just suffering and dying on the street? Yeah, so there's homeless in every society,

but usually if it's mental illness, It's being supported by a family somewhere, so there's less of it. Certainly, the Asian countries are the same. Can we do a thought experiment? Sure. You go to bed, Miami, beautiful life, beautiful house, you're Mr. Wonderful. You open your eyes. You have zero dollars.

And you go around and you're like, I'm Mr. Wonderful. People are like, I've never heard of Mr. Wonderful, okay? What do you do? Seriously, the first day... Well, maybe that will happen to me in a dream, you never know. But I'm saying, let's a thought experiment, you wake up, you're on the street, and you have zero dollars, what do you do your first day to get back on your feet? Make money. Yeah, I would probably go be a laborer as I did when I was young.

I was a brick layer, and then I washed dishes. You can't really go, you can't really go up that way, right? No, no, but you have to get some cash. I mean, you ought to be pragmatic. You know, you've got to get some clothes, get some cash. I would probably go and use my skills in photography and, you know, find a job. in doing social media or something because that's a growth area but you got to start at the bottom again and you know basically there's a lot of work for

people that want to work it's in the field or maybe it's you know in in service industries they don't want to do that though yeah so how long would it take you to get a million dollars from zero if just the thought experiment from that circumstance no one knows who you are you're not a star of screen and yeah and and small so I think I could do it again do you think three months you get a million I don't think if I I'm not sure I can do it in in three months but I would assume three weeks you know the way the way you you make a million dollars is you don't buy shit like you actually have money to invest really that's how I figured it out took me a while to figure it out you know I was able to make a million when I was pretty young by by just I had you know when you go into someone go Go into your own closet and look at all the shit you bought over the years you don't I mean it's such an easy one to see but you're a you're a day or you're a you're a you can afford you can afford it I can afford to get great clothes now and I have a lot of fun

you know between the different brands right now I'm working with Dolce they're doing really that's because of Marty Supreme don't that the Dolce is doing thank you thank you what I like the weakest applause every you know what the hell is great But they are working with material and designs from the 30s and 40s, which kind of fit the whole Marty Supreme vibe. So for the, I've got some very crazy shit coming for the premieres in New York and L.A. No. Like Laida Gaga level? I think I might beat her on these. You're going to wear meat?

I should wear meat, but I've got an amazing jacket from sort of Louis XIV, kind of vibe. Whoa. I love that for you. That's actually pretty cool. It's definitely me. Yeah, yeah, that's you. That is wonderful. It's a wonderful kind of, you know.

Anyways, it's fun, and I bring it home, and my daughter and wife just go out of their minds when they see this stuff. Your wife gets turned on a little time. Well, I remember when I bought my first Porsche, I collect Porsches, and, you know, I drove at home. It was a 9-11? Yeah, it was a 9-11 turbo convertible cabriolet stick shift. And all she said to me was, oh, great, another bald asshole in a Porsche. They don't understand how cool, cool stuff is. I love that car, and I like the new Porsches.

I got the 50th anniversary. These cars are amazing. You know, German precision, all that stuff. It's like a watch. I might put 1,000 miles on it a year. I don't drive it very often, but I like to just look at it. Come on, dude. Yeah.

Why don't you just look? I think about a car. I'm a young you. Watchers are easy to. collectors you can actually store them in a bank vaults but cars you've got to get a garage climate control facility and tricklers and all it's a complicated yeah it's a lot of headache and the maintenance yeah nuts yeah yeah guys I want to talk to you about monarch money guys the holidays season could be

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in your browser for half off your first year. That's 50% off your first year at Monarch.com with code T-A-F-S. All right, that's the last out of year. That's the last out of year. You have a really interesting, like, background, like, in childhood. Like, and I wouldn't have expected it. You know, like, I kind of knew you from TV. I'm like, oh, this guy's, like, I don't know, blue-blood, like, Wharton boy.

But you lived, you were born in Canada, obviously. Montreal moved to Champagne or Ben. Yeah. Outside of Chicago in Illinois, went to, you know, school there, Bottenfield, I'll never forget it. I lived, uh, bought and field at school. I don't even know if it's still there. But you lived in Cambodia as well, before the, before the Khmer Rouge?

Yeah, after that one, my stepdad, because my original dad died, my stepdad was graduating from the University of Illinois and he became a PhD in management and he got a job with the ILO, the United Nations, and we traveled every two years. He worked on infrastructure projects like water and highways. He was a spook. Sounds like a spook to me. Well, he did a hell of a job for the UAE. He was there when the founder was there, and that's how I got my residency there. He helped get the water system going for those guys. Now look at them. Yeah, they're doing okay. They're doing all right. Wait. Yeah, they actually were pretty smart about how they made that country. You met highly Salasi as a kid. And is it true? Is he, is he, is he, is he,

jaw? He was. Are you Rastafar-I kind of guy? Yeah, he, well, he is the leader of the Rastafarians. Yeah, I know. He also, I met his lion cubs. I met Paul Pott, who went nuts and killed everybody in Cambodia. What are you, James Bond? It was just random. I mean, you know, the expats would always get together at these cocktail parties and they would throw them at the palace. Uh-huh. And, you know, the ILOers would bring their kids. And that's how I met I just... And you play poker against a guy with an eye patch? Well, I met Ciannuch, too.

I mean, that was when the Vietnam War was spreading into Cambodia. Why? Everywhere you go, war follows? It was tough. I mean, that was tough. You're the angel of death, Kevin. Wait. But, you know, I've been to some interesting places.

So you're raised by your stepfather primarily? Yeah, he was very pragmatic with me. And your parents split up after you'd moved or before? No, my parents, my original father, They got divorced and then he died actually when he was 37. When did he die? When you moved or around the time? No, we, he had, they were divorced already.

My mother was now, you know, starting dating, I guess, my stepfather. But then he passed away, my original father. And then they moved to finish off George's Ph.D. That's what happened. And did you, you didn't get a chance to say goodbye or? I did. I knew, you know, I spent weekends with him, but one day he was just gone. It was tough. My brother's two years old. It's really hard. It's really hard on him. That was difficult. But, you know, when I started moving every two years, I thought everybody lived that way. But it's not true.

But it ended up being a huge advantage for me because I've been to every culture in the world. Yeah. So, you know, Iceland and Norway and France and Switzerland and Germany and Japan and Ethiopia, all of those places. Yeah, and another thing is, well, a funny thing. thing, correct me if this is wrong, but your stepfather at the end of high school asked you what you wanted to do, and you said, I want to take photographs of hot chicks. He said, you're not good enough. That's so us, by way. That's awesome. That is the most awesome answer I've ever heard. And he said, look, you're not good enough. You'll starve to death. Why

don't you just take a couple of years off and go get a business degree? Then you can figure out what to do. He was right, but I went right back into photography. I founded a company special event television. We did all the hockey programming on Saturday nights for the original six teams. And you developed the technology for like digital graphics. Yeah, we did that.

Yeah. That turned in the learning company. There was a bunch of things that happened in that journey, and you just don't know what's going to happen when you start a company. But we did Don Cherry's Grapevine. The original six was another format we owned.

I didn't know what a television format was, but I owned it. And so somebody came along and said, I don't want to buy it. That was the first exit we had. We took that money, started the learning company, and the rest is history. Yeah. When, another surprising thing about you is that you, you know, I'm, old pinko glasses, New York Jew over here. I would assume like, I would never have assumed that you'd be an environmentalist. So you studied environmental studies. You made a documentary. Yeah. And you happen to be one to this day, you think? I was one of the first

cohorts with Sally Lerner and Reg Mikkelatsky were the two of them. They founded it in the architecture department. But what Sally told me, which I'll never forget, she said, you know, Kevin, you should pursue entrepreneurship. You should go start a business because

you don't look to me like a guy who's ever going to keep a job. You just don't know how to work for anybody. And it could be bad, it could be good, but But she was one of the ones that really edged me on. And I'll never forget that. It was, because she was right. I mean, in the end, I never was able to hold down a job for anybody. I never will.

Tell us about the cat food. Yeah, that was a summer. I had to have a summer job. And I worked for a guy. But that ended up being a very important lesson because he took me to show how cat food was made. And it's just two engines. It's Sea of Japan, tuna, the belly. That's for the fish protein.

and the other is chicken faces and beef faces and all the parts that we don't eat of a cow and they get sort of melted into a mush with papaya juice and then squeezed out and that paste is the protein that is basic. Chicken McNuggets and McDonald's. These are for cats, but think about the idea it's either Sea of Japan tuna on this side

or the chicken faces on the right. Sounds nicer the tuna. 15 years later I'm sitting with my partner with the learning company, we're buying all these software companies with their developers, making educational software. And the only two things we're doing is math and reading scores. We're doing hundreds of millions of dollars of sales advancing math and reading scores. Yes. And I said to Mike, let me tell you this story about cat food. And I said, why don't we fire all

the developers that we don't need and just have one chicken face team and one Steve Japan tuna team? The Steve Japan Tuna does the reading software. The other guys do the math. And then all we do is take the titles. Because when you make cat food, you add bacon bits, a little egg bits, or, you know, and you call it, you know, souffle or whatever. But it's just the same paste. We did the same thing. We took, we licensed, you know, characters from Disney and characters from.

Mattel, right? Yeah, Big Bird. We had all these titles. We pay a royalty on it, and our cost of development dropped by 30%. But didn't you try to rebrand the cat food, and then they said, would you eat it? Yeah. That's what I was asking for it. I did have to eat it in front of the sales force, but apparently that's sort of like a hazing thing they did at that company.

Really? They made the young guy eat the food, and I knew how it was made, so it really made me sick. Yeah, yeah. And then you were like, I'm not going to have a boss ever again. It's kind of for a good reason. Well, it was an important lesson. And I think you learn these things in life, and they come back and they're very good for you later. That's the whole idea.

But that was an important lesson, the two engines of protein, because that changed the outcome of the learning company a big way. I want to talk about your turn into entertainment. I mean, like, I'm a comedian. I've gone on the road. I've watched thousands of hours of Shark Tank. It's just the best show. And like you are just a fucking hit. You know that.

Well, it's been on for 17 years. We're shooting our 18th season. I actually have a theory about why that happens. The real stars and the reason people keep watching it is every time someone walks through those doors, they've never seen that product or service before. They can't believe someone else thought of it instead of them. It's why didn't I think of that?

Because half of these things turn into huge successes, and the other half go to zero. But every once in a while, you get some crazy idea that ends up being fucking huge. Yeah, yeah. And we've seen it happen. You missed on that ring door thing, you guys. Ring was huge.

Cat DNA was huge. What's that? Wicked good cupcakes. It was called base paws. It was a monster hit. Cat DNA? Cat DNA. You stick a cute up up the cat's ass.

You send it in and it tells you what to feed it to extend its life by 30%. That's a dog. That's not a gym. What's your thing? A dog or a gym? No. A dog or a dog? a dog or a business dog or a business gem?

Well, I'd say, look, it's a howling dog from hell. That sounds like the dumbest idea for anything. That pisses me off that's successful. Yeah, but, you know, I've seen so many pitches now. I kind of have an idea what's going to work and what is it. I like when you're mean to kids. I don't like kids. Yeah, yeah.

When they're like, I'm three years old and I have a business. And you're like, you're an idiot. Get off the way I get out of that problem is like, save the parents. I'll invest in the three-year-old if you take him out of school for the rest of his life. Yeah. So that he can work for me full time. Yeah, he shouldn't be going to school. I don't know why anybody would

invest in a kid in high school. It's a gimmick. It's a graduate. And I'll do it. I think it's dumb. But you know, it's TV, and so it happens. You crush it on that. How much of Mr. Wonderful is a character? Because I'm meeting you right now, you seem like you're just a what, like calm, friendly,

well-adjusted, zend-out, dude. Well, I don't think, I don't think you can... He should never work again. You can't... You really, you turn it on. No, no, you can't fake it for 17 years. You can't do that. That's who I am when it comes to investing.

I scrutinized deals. I am not acting. I'm not faking it. That's how I am. And you can ask the people I work with my team. That's how I am. Yeah. And so, you know, it's sort of like...

For me, Shark Tank, I don't see any cameras on Shark Tank. nor does anybody else. We've been doing it for so long. I mean, it's just bring it on. Let's have a look at it. But if it's dog shit, I'm going to say it's dog shit. You tell the truth. I think telling the truth is extremely helpful in the case of business

because you don't want them to waste the money. You want them to actually say, maybe it is dog shit. If everybody won't invest, I find it very disingenuous when Barbara O'Lauri say, well. That pisses me off, too. Oh, you're so nice. And I think you're wonderful. you should just go do what you do.

You don't need any of us. What they're saying is your product's a piece of shit and I would never invest in it. I just say your product's a piece of shit and they're setting them up. They're going to lose them money. And I'm gas-liding them. You know, barbers on this side, Lori's here and say,

what are you doing? You're lying through your teeth to these people. You're giving them such bad advice to tell them to keep going on this dog-shit crap they have. Like, why? Why don't you just call it what it is? Dog shit crap. Do them a favor. Tell them the truth.

Because in reality, those people are going to think that it's not dog shit crap, and it's going to cost them time and money. It's so bad I can smell the odor of dog shit off the product. It's just from, I mean, they're in a room 10 feet away saying, it's horrible. Shoot it. It's like they're being kind, but they're not being kind. In fact, you're being kind by telling that kid to kill himself. Thank you. Finally, somebody realized it.

Yeah, I mean, I do. Look at the heat I take from everybody. Oh, you're the mean shark, you're the bad shark. No, I'm not. I'm just telling you across the piece of crap. You're the star of the show. You sit in the middle. The point is, it's a piece of crap.

Yeah. It is. And they're going to waste their lives on it. And their parents' money. And their parents' money. Yeah, yeah. Yeah. That's the real problem. Yeah, yeah.

Do you respect people that just didn't have to work for it to have a lot of money? Or do you think that they're pussies? Sorry for saying that word. I don't know. Well, you mean they've inherited it. Yeah, like you're a fucking, looker than that. Let me tell you what happens. You've grind it.

Inherited wealth is generally dissipated. within two generations. Yeah, yeah. So you shouldn't give your money to the idiot cousin. It's not a good idea. You know, if you have a business, nepotism destroys it. What you do is you put the kids at the board level and you hire professional managers.

Yeah. And that way you can sustain the family for, you know, long after you're gone, as long as they don't try and run it. Most people can't do what their parents did. Yeah. Sometimes... It's like the Bush administration, right?

it's difficult but you know you don't want to sometimes there's exceptions but not often and so if you're going to be an entrepreneur it's better to try and do it in your 20s when you can take a hit you don't have a lot of responsibility you don't have a family you don't have a mortgage just go do it

and in 18 months you'll find out if you can pull it off for it and if you do it sets you free there's something wonderful about being able to do what you want to do and the only way in America you get there is you've got to be successful in the American dream there's a competitive element to business right You want to win?

Yeah, of course. It's a joint competition. So you have to fucking hate the other guy at some point a lot of the time, right? Like, who's the biggest fucking fraud? Just name, names. Well, I mean, you're talking about the other sharks? No, no, no. No, those are our friends.

We love them. Well, no, let me tell you how friendly I am. Dude, when Mark quit, you're genuinely emotional. I think I can get Mark back on the show. You're trying to get it back. You're missing. I am, I am. That's your boy.

Because I think we have a great dynamic. You do. him and he's learning for me and it's fantastic yeah yeah and he's like the sense in the student and bar you know he's my grasshopper yeah barbara the only reason that she makes it to the set each year as I buy her new broom that's how kind of you mentioned you're keeping the band together you're like Paul McCartney every year brand new the latest broom for the witch mark it Mark is like John Lennon he's up with Yoko doing heroin you're like you just

get to the studio let's make Abby wrote get back in the chair let's get back I love it. So you're like the Capitan a little bit. I'd like to think that way. Yeah, yeah, I like that. Call me El Capitan. This is cool for me, because I'm a massive fan. This is cool to hear this. Look, I don't think of myself as the star of the show because I know with certainty

if we didn't have the pitches, there'd be no show. What we've learned is what's really good now about Shark Tank is the 100 plus producers that after 17 years can curate great deals. They go out there, just like an American Idol. They listen to pitches, thousands of pitches, thousands of pitches. And the woman has done it from the beginning, he's named Mindy Casting, I don't know what a real name is, but I call it. And she has seen every pitch.

Can you imagine that? And so, holy shit. And then she says that one, that one, that one, that one. Then she sends it into the, you know, the editorial team that says it's appropriate, it isn't. But she has done such an incredible job with her team that that's how, why the show works. I assume there's due diligence, though, after you make a deal. There is. Afterwards, and there's also diligence before.

What's the craziest thing that's come out in due diligence after making a deal with some... The guy was in prison. The guy was... One of our deals... They let him out of prison to do Shark Tank? He didn't tell the truth, obviously. He was a felon. That's not useful.

I think it's better to tell the truth. I'm not against felons. I think they've redeemed themselves. They've served their time. That's what Miami's all about. Well, it was built on larceny. But the point is, you've got to disclose that. You have to tell.

You think Timothy would have fun on the show? I do. I do. And I think his, and I've met many of his friends when we were shooting. I think he would have. I've met him before. He's awesome. He's a great guy.

Yeah, he's really cool. You know, he's dating with the Kardashians. Because he gets into the zone and you shoot the scene and then he checks out. and, you know, he's quite something. What lessons did the other actors impart on you on set? Did they help you? As you saw in the movie, there's a lot of interaction between a lot of people simultaneously

in those big scenes and restaurants. Kind of like Robert Altman, kind of, yeah. Yeah, and so it's a roaming camera, and you do those sequences multiple times, and you get new cadence of what the script is. There were some great people in that thing that really knew what they were doing, and that made it easy for me.

Yeah. I mean, I thought probably, Probably by the fourth or fifth day, I was into the kind of groove of how that, you know, Josh and and Ronnie worked. Did Gwyneth ask you for, like, tips for her goop company? Actually, we met two years earlier on Shark Tank. She was a guest shark. Yeah, because she's an entrepreneur. Yeah, she was.

Goop. Yeah. The ladies love this stuff, yeah. You know, she's, that's a tough gig. I don't even know what it is, yeah. And so we knew each other already, so it was very easy to roll into the husband-wife scene. It was very easy. Yeah, you felt like husband and a wife already from Charleston.

Yeah, but a loveless marriage, she was a horrible person to me. Yeah, you felt like she was a bad, she hated you. Did you felt like you were being when you were shooting a scene? Like you were the guy, you were the guy. It was really interesting because it was easy to get into that character. You know, Milton in 1952, that was quite something. I didn't have a hard time becoming Milton. That was good.

Yeah, it's good for me. Yeah. You killed it, dude. I mean, seriously, I'm genuinely impressed. Can I tell you what happened to me at the premiere? Sure, tell me. We'll end on this. This guy, I was with this guy there.

Josh is on stage. She said, I finished editing this last night. This is the movie. Enjoy it. The lights are going down. I'm walking down my row. And I have a pair of pants, and they have a snap button on the back. There's a woman in the row.

My pants brushed past her hair, and her hair got stuck in my hair. And then the lights are going down. And she's screaming. And she's like, ouch. And then her friend, she was with her gay friend. He was like, you're hurting her. And then everyone on the other side of me was like, sit down. The movie's starting.

So I'm like going like, sorry, sorry, sorry. And it was a, and he's sitting there. And he's just laughing in my face at it. And it was perhaps, so that's how I started, the movie started for me, actually. Yeah. I was apologizing to a woman for. her hair. And I couldn't get it out.

I think you deserve the abuse. I mean, you know. It's not my fault. I don't know what kind of pants for those. That's crazy. They were from double R.O. Oh, no kidding. Yeah, it's a nice line.

I wear a lot of, you know, I have it here. I see that. Do you know, lift shits? Ralph? He's a good guy? I think the thing is, it's a shame that happened, but a little excitement doesn't hurt. No, it's hilarious.

But, you know, I was getting, I think you were at a screening where I had some friends and they were texting me. during the, that's the first interaction. We just saw the most Jewish man in the world. No, I think they said there's some asshole pulled up some woman's hair. Kevin O'Leary, everybody.

Thank you. Thank you very much, man. This is been a pleasure. Thank you. Thank you.