Kevin O’Leary on playing the villain and turning attention into power

0:09Welcome to another episode of the Mixed Signals podcast from us here at Semaphore where we are talking to the most important and interesting people shaping our new media age. I'm Max Taney. I'm the media editor here at Semaphore. And with me, as always, is our editor-in-chief, Ben Smith. Ben, happy new year. It's 2026, first episode of the year. How are you feeling? Any resolutions? I think my resolution is to see more movies in the theater. Loved seeing Marty Supreme for this episode. Loved all the trailers for the other A24 movies. I think that's my sorry, Ted Sarandos. That's the plan. And I was vaguely disappointed to see that then I could only get the new Knives Out on Netflix.

0:48You and I both actually saw Marty Supreme over the holidays, both because we enjoy the theatrical movie experience, but also because on this week's show, we are having one of the cast members of the film on the podcast. That is Kevin O 'Leary, also known as Mr. Wonderful. He's a Canadian businessman and investor, best known for his nearly two decades as a co-host as a shark on the show Shark Tank. But he was also somewhat surprisingly in this new movie, Marty Supreme, directed by Josh Safdie, starring Timothee Chalamet. Kevin plays someone who is somewhat similar to his character, his persona on Shark Tank.

1:24He plays kind of this asshole businessman. And he's receiving kind of these somewhat surprisingly, glowingly positive reviews for his performance. And so we wanted to have him on the show to talk about that. We wanted to talk about his support for Donald Trump. Ben, you had some other questions for Kevin. He's our second shark that we're having on this show. What were the kind of things that you think we should talk to him about? You know, a central source of kind of access and power is being in the media all the time, is ubiquitous media character. And as you said, in this film, this is his first scripted role, pretty major supporting role, in which he plays essentially the worst version of himself, a kind of sadistic, evil tycoon.

2:05But all, I think, with the goal of just being so deeply in the mix. And I think, you know, we're going to talk to him about how in the mix he is really right across the board of politics and culture. Well, we want to ask him about that. We want to ask him about the future of Shark Tank. We want to ask him some fun questions about Mark Cuban. But we'll get to all of that and a lot more right after this.

2:34Hi, I'm Joshua Spania, VP of Marketing at Google. And you might assume I have all the answers when it comes to marketing. The truth, I'm just as curious to learn, discover the answers to everything as everyone else. We are living through a total reset of our marketing industry. The old maps don't work, which means we get to chart a new path forward. It's dynamic, it's fast-paced, and honestly, there's never been a more exciting time to be in marketing. That is why we've started a new podcast, Frontier CMO. It's from Think With Google, and I promise it's not just a bunch of corporate waffle. I'm sitting down with people who really know what's going on.

3:18CMOs, creators, technologists, the lot. And we're having a proper, unfiltered chat about what's working, and quite frankly, what isn't. These are your notes from the frontier. So do me a favor, search for Frontier CMO wherever you get your podcasts, or watch us and subscribe on YouTube.

3:44Kevin, thank you so much for joining us. We're really excited to have you. So first of all, you know, I know that you've told this story a bunch already in print, but you know, for many of our listeners who might be familiar with you, mostly through your work on Shark Tank, it might be surprised to learn that you're in one of the hit movies of the year. Can you just walk us through what your reaction was to being offered this role and how you found out that you were up for it, I guess. It came through originally one of my lawyers in LA who knew, I guess, Josh, and he referred it to UTA. I got a call from Jay Suris, my guy at UTA, and he said, look, Kevin, they want you to consider a scripted role, and you're not a scripted guy.

4:27You're not an actor. We built a pretty big franchise with you over the last 17 years. Everybody's making money. the risk with this is you're going to shit the bed. And when you do that, you're going to cause a lot of damage to your business and ours. So we're not loving this idea. And I said, well, wait a second, how do you know I'm going to shit the bed? Where is that written that I'm going to shit the bed as an actor? Because the thing that I've learned, and this is sort of a tense and gentle statement, is I've been an investor for decades, and I work with a lot of CEOs and managers, and I was once myself one, the people that push themselves out of their comfort zone every day, they're basically, they're forcing themselves to exercise the most important muscle in their body, the brain.

5:15You have to do that. If you just sit there doing the same thing over and over again, you stagnate. You're not sharp anymore. And so to me, this was an opportunity to try something I'd never done, definitely outside of my comfort zone. The example I use all the time, some of the greatest watchmakers, I buy a lot of watches, I'm a huge watch collector. Some of the guys that I meet that make these pieces, these unique piece uniques are fucking crazy. Like they're just crazy people. One of them jumps off cliffs in Switzerland with a paraglider, risks his life every day. And that combination of yin and yang, the arts with the discipline of business is what I'm interested in.

5:53And so I play guitar. I'm a photographer. I'm a, you know, I used to work behind an Aeroflex camera. I was a sound man and eight plate video editor on film. I want to stay in that zone and I want to do what I do in business at the same time. So I basically said, look, screw that. I'm going to talk to these guys. They called me up and said, look, you got to fly to New York tomorrow and read the lines in our production office. And I said, I'm not doing that. I'm sitting on the dock in my lake house with ducks floating by in the middle of July. I get no time off. I'll send a plane for you. If you're serious, get in the plane and you fly up here.

6:26That's what they did. So I picked them up in Teterboro and they came up to the lake house and we got to work. And here's the interesting part that I think you should hear that really was, got me so intrigued. They sent me the script and a PDF file two days before they showed up. They said, read it first. So we're doing the lines with you. I went into town and I went to a print shop and I printed two stacks of this, two scripts. Then I forgot about it. I left them on the bar. And we had a big dinner. This is a place where family and friends hang out. And this guy named Gene McBurney from the Bahamas gets up in the morning at 5 a.m.

7:05to watch the sunrise. And he starts reading. He doesn't know anything about this script, doesn't know anything about the film, doesn't know anything about anything. He just sees this thing, says, I'm going to read this like a newspaper. By the time I get up four hours later, because we had a hell of a party the night before, he says to me, have you read this fucking script? This script is written by some very sick people. This is a very crazy story, but I can't put it down. Now, there's an independent guy, knew nothing about it, no idea what this was about, that is totally hooked to the story.

7:40That got me really intrigued, because you don't have a film without a great story. And once you find yourself in front of the camera, what was most surprising for you, I guess working with Safdie in particular. By the time we started shooting it, I had gone through multiple sessions with Ronnie Bronstein and Safdie. Those two guys wrote it together. And this guy named Eli Bush, the producer. And I didn't know if they'd be open to this, but I read the character, Milton Rockwell. And I said, guys, if I'm Milton Rockwell, I wouldn't say that, I'd say this. And if I'm Milton Rockwell, I'm not okay with this ending because this little fucker screwed me.

8:17And that doesn't happen today with me or wouldn't have happened in 1952. This guy is not getting away with what he's doing to me here. And they're saying, OK, we're all ears. Let's listen. So they actually let me recraft some of it so that it was in my head, in my way of who Milton Rockwell was. And that's pretty smart on their part, I think. They're a very intuitive director here and writer because once you get that latitude, you're the character. You're the guy. And when you go into the room and it's 1952 and everything's perfect, 52, the watches are 52, the linen's 52, the cutlery's 52, Gwyneth's in 52 outfit and Timmy, the same thing.

8:59Like, you're not acting. You're just there. You're in the moment. And I knew the lines and I knew the story and I knew where we were going, even though we shot it out of sequence. I don't think that was acting. That was just Milton Rockwell. And, you know, as far as shitting the bed, I'll let the critics decide. And so far, so good. You know, most people obviously know you through your many, many seasons on Shark Tank. Can you explain to the audience a little bit about the difference between being on camera for Shark Tank versus being on camera here? What are the skills that were kind of transferable?

9:33Well, that's a very good question because reality TV is not scripted. People might think it is, but it isn't. And after 17 or 20 years, whatever it's been of doing this, I don't see the cameras. I don't see anything. I just see four competitors beside me that I'm going to compete with to buy a deal that I want to buy as an investor, which I do in real life anyways. And so that is completely different than going into character in a scripted role. Obviously, it was my first experience doing it. And I didn't know what it was going to be like. So I didn't know what the differences are. but now I do because when you go, let's say you're acting across from Chalamet.

10:14The first day we started shooting together, I'd only met him for five minutes the day before in Josh's office. And, you know, I didn't take any acting lessons or anything. He just said, look, just be that asshole you are in Shark Tank. Don't worry about anything. And so the way Chalamet works is you're sitting down, they're setting up the lighting and we're just talking, Chalamet and I, but whatever, you know, whatever, nothing to do with the film. Then we know we're going to roll. he gets up he walks about 20 feet away he does this every time and when he comes back he's not chalamet he's marty mauser and he's wired into marty mauser like he's that little asshole across from me so it was really easy for me to go at him because now we're at it now we're in it and it and we're just he's he obviously the guy is amazing but it made it very easy for me here's this little dick screwing me around and of course I'm going to lay into him.

11:11It wasn't hard. I mean, you use the word asshole a lot and that is, that's kind of a character that Mark Burnett, I don't know if he cast you for it or if he created it for you on Shark Tank, but you're then cast in a movie where you're an asshole and everybody's an asshole, like Chalamet's character, obviously, and then Gwyneth Paltrow's character too are these egotists who really don't care whose lives they ruin in their kind of path to their own dreams. Did that give you pause at all, being cast that way? Do you worry about being that person? Well, it is true. 20 years ago at Shutters, which is near LA, I think it's Santa Monica, it's a hotel.

11:49I met Mark Burnett for the first time. I was working over in London on a Discovery Channel project called Project Earth. And he sent two tickets over and said, get over to LA and I'm casting for a new show called Shark Tank. We were supposed to meet for 20 minutes. We spent hours together talking about a bunch of random stuff. And at the end, I said, why am I here? You called me here. Oh, he said, oh, yeah, yeah, yeah. Tomorrow we're going to do a pilot on this new format called Shark Tank. And I'm looking for a real asshole, and you're it. And I said, well, why do you know that? He says, well, because the British one, the stuff you did in Canada, the stuff you're doing over in England, everybody calls you a dick.

12:24And I think I'm OK with that. And I think we need the dick in this show. And I said, well, I don't know whether to take that as a compliment or not. He said, it doesn't matter. I just show up the way you are and let's see what happens and we never look back after that. I mean You know what happened with shark tank is legendary. It's on in 54 countries I don't think i'm an asshole. I just simply tell the truth and you don't like it You're offended who cares? It's still the truth. What are you going to do about it? It's going to bite you in the ass Eventually if you have a shitty idea, it's a stupid business And you're going to go to zero and wipe out your parents You know mortgage on their house or whatever and I think it serves me well I don't really care what people think of me.

13:03The only people I care about are my immediate family and maybe 20 other friends of mine. And if you read, I've got millions of followers now, and I respect, you know, when they write an essay about how much they hate me, and it's two pages long, you got to respect that. Imagine the amount of time they're spending doing that. I got one yesterday that my social media people sent to me. It said, I hate you so much, but I I got to admit, you nailed it on Marty Supreme. Yeah. Well, I was going to say, has... I mean, what did you say to that? I actually wrote him back saying, well, that's a hell of a movie review.

13:38Yeah. I feel like your performance has been critically lauded. Has being in this movie changed anybody's perception of you as far as you can tell? I think what it's done, particularly in the last, I don't know, three days, it's brought a whole new audience into my world. I mean, just a whole new audience of people that are moviegoers, that are interested in content beyond business. I'm going to give a lot of credit to Josh because he's a very strange dude. And in fact, both of those guys are crazy chickens. They really are because the way they work, and a lot of people don't know this, so I'll just tell you how it works.

14:17You're on the set and Josh is directing it, but Ronnie's in the production tent on scene somewhere out in the street and he's watching every take. these guys are collaborators they edit this stuff together too and there's a script person making sure that every single line that's in the script she's listening to gets nailed that no matter how many takes you're going to keep doing it until ronnie and josh agreed that they've got the scripted part nailed and that could be 30 takes and then some somebody make a mistake Chalamet makes the mistake, I make it, or, you know, Paltrow makes the mistake.

14:58And he likes it. He says, wait a second, let's riff off that. Let's do some more takes. Let's riff off that. And then you're in your improv mode. So he is pulling from his performers, his actors. He's pulling new shit. And that's what he did with me. He pulled stuff out. I remember being frustrated with the scene where I first meet Chalamet when I meet Marty Mauser when he's buying me dinner I don't know we're into like take 50 and we're like I'm saying fuck it we have it like he said we don't have it till I say we have it and the next take I said I could smell bullshit a mile away and he says wow let's do that one again and that ended up in the movie So here's a director pulling something out of you.

15:50I want to return to the asshole question just for a second here. How has being seen as an asshole to a certain segment of the public changed your life? And has that changed you in any way? You know, the expectation from people in the public that maybe you're not a very nice guy. Here's what I know from business, okay, that I learned a long time ago, being a manager, a CEO, a founder, an investor eventually. you can't make everybody like you it's not possible no matter how nice the person you are that you can't make everybody happy what you can achieve is respect they can respect you you want people to respect you not like you and the the way you get respect is you execute so if you've got a bunch of people working for you as i do that fat their family's well-being is determined by my ability to guide a business forward or an investment forward or a new opportunity forward.

16:46They don't like me necessarily. I know they don't like me. I'm a really tough guy. And I learned this from Steve Jobs back in the early 90s when I worked for him. I did all of his educational software for 110 ,000 school buildings, and he was not a nice guy. But he said one thing that was right. He said, look, every day you got to get three things done. And that's called the signal. You have to get the three things done. Everything that stops you from getting the three things done is called the noise. And if the ratio is less than 80-20, 80 signal, 20 noise, you're fucked. You will fail. The trouble with being 80 % on signal is you piss off a lot of people.

17:22A guy walks into your office or a woman says, hey, I'd like to talk to you about this. You say, I have no interest in that. I do not want to talk about that. That does not help me with my three things. Get out of here. That's how it happens. But they stay with you because you're executing, you're successful, you're hitting your targets, you're driving forward your business. When people say, oh, he's an asshole, I don't care. Like, I swear I don't, not a single second do I give a shit about that. It's whether or not they respect me. You can still hate me, but you have to respect my ability to execute.

17:54You know, you mentioned that you came up in educational software, you had a huge exit to Mattel. And I'm curious how you think about the relationship between you're having been a business guy, an investor, and being a media guy, which you clearly are in many ways now. What's the relationship between these two parts of your life? I remember back in Boston after we'd sold the learning company, it was a huge exit for the nine of us that were founders. And I went over to see Scott Sperling and Thomas H. Lee. They're one of our largest shareholders in Bain Capital. And he said, listen, why don't you park yourself here for a while you've got a ton of money why don't you go sniff around for deals i will work together we know you very well you know but why don't we just work together for a while i said that sounds good scott i said by the way i got a call from a television network they want to do some stuff you what i said no no we don't do tv you got to stay low profile don't go on well why not he said well that's not how it works in private equity you keep a low profile you don't make a big deal out of anything and you go get returns for shareholders i thought about it i said screw that and I went and did it.

18:59And is that because you have a screw loose or is that like a business strategy? No, I don't know how to take direction. You know, I've never worked for anybody. So I don't know. I don't know how to do it. And so, you know, I'm interested in the input, but in the end, I got to make my own decision on everything. I want to be in the narrative. I have opinions. I think they matter. You don't have to agree with me. The only way I'm going to get them out there is the media. We had Mark Cuban on the show also a few months back. I think Ben asked him a similar question. I wonder how much of it is that people are out there in the media a little bit more.

19:31Well, I mean, you know, I've known Mark a long time and I got to get him back on Shark Tank, by the way, because he's my grasshopper. He's learning from me. How much longer do you want to be doing it? You've been doing Shark Tank and a show that was very similar to Shark Tank for quite some time. I think it's a very important platform. It's like a ambassadorship for me all around the world. I can go to Saudi Arabia, United, out at Emirates, Switzerland, France, I can meet with the leadership because they want Shark Tank pictures for their kids. I mean, it's like unbelievable. The number one export of America is not technology.

20:00It's not energy. It's the American dream. And Shark Tank encapsulates the American dream beyond politics. It's bipartisan. It's the concept of being free to take a chance and create your own freedom down the road, which is the essence of the American dream that every country on earth understands. And it's embodied in watching those people walk out. I think it's a very important platform. I mean, I do it now because I want to be part of that platform. I'm proud of what we built together. And I think Mark feels the same way. By the way, he came to, I invited him to the New York premiere and he came with his daughter.

20:34They had a great time. And I talked to him about Shark Tank. He is very much part of the DNA of that show. He and I together. I mean, because we disagree on so many things and it's very educational in disagreement. He hates royalties. I love royalties. You know, he hates complicated structures. He overpays for all kinds of shit. I refuse to do that. And it's sort of like that is educational because that is the real world. And we are in deals together. I like his team. I like him. And also, you know, he was getting involved in politics at the same time I was in 2016. So we have that. I really like the guy and I would like to see him back.

21:08And I know why he's not back. It's an off-the-record conversation, but he is interested in coming back. Certain things have to change. Is it a contractual issue? Mark's very opinionated about distribution of content because he comes out of that world. He comes out of that world. And I don't disagree with him. There's a lot of partners in Shark Tank. You've got Sony, you've got Disney, you've got ABC, you've got Amazon, you've got MGM. You got a lot of cooks in the kitchen and you have to respect what they've built. I mean, yeah, there's 150 people working on that show, some of them for the very first days.

21:47And in fact, we found 21 people that were there at the pilot that still work on the show as of last year. And Rolex Tudor dedicated 21 watches made of silver with their names on them. And I gave them out. I funded that project with a Shark Tank logo on a silver watch. You know how hard that was to get done? Took two years of negotiations. Well, we have a lot more that we want to get to with Kevin, but we have to take a short break and we'll be right back after this.

22:23In this week's branded segment from Think with Google, I spoke with Google's VP of Marketing, Josh Spanier, about what he saw at CES. So Josh, you were at CES at the beginning of this year. Why does that event matter for CMOs? So CES gives us a real view into how people are going to be living their lives and spending their money in two, five, even 10 years' time. I know from the outside, it looks like a giant toy show. There's smart rings and foldable laundry robots and flying cars. But I was chatting with Shelley Palmer, who I interviewed for my new podcast. He's an AI visionary and tech leader.

23:02And he swears by, and I agree with him, that the ability to see patterns amongst all the gadgets is actually really, really compelling for near term and into the future. So what did you learn from that conversation? Well, the gadgets aren't really the thing. Stuff gets announced. Some of it launches. Some of it doesn't launch. What you're really looking for are business model changes, the new paradigms that are emerging. So two that I saw and we spoke about. One is around agentic commerce. Google announced during CES and just after CES a whole bunch of partnerships with Shopify, with Walmart, with Target around agentic commerce.

23:41Super interesting building the new protocols for machines doing the shopping for you where appropriate. And then separately, I also saw a lot of expansion of what you might call intelligent ecosystems. systems. These are technologies from different companies coming together, meshing together to enable you to do more interesting and engaging things. And again, with Google and Gemini leading the way. They're really fascinating forerunners of where we're all going to be in the near and medium term. And where can people listen to the whole thing? You could listen to my conversation with Shelley Palmer in my new podcast, Frontier CMO, on YouTube or wherever you download podcasts, or you can sign up for my weekly newsletter over on LinkedIn.

24:23Great. Thanks, Josh.

24:36I'm curious, how have you seen reality television change over the course of the last 20 years? And as we're moving into this zone where fewer and fewer people are watching television, more people are watching things like this, I saw that you did the Adam Friedland show. Adam's come on our show before. You know, kind of a strange thing that could really only exist, you know, in 2025, 2026. Do you see Shark Tank making a kind of transition eventually from television to just streaming? Like, talk a little bit about that kind of evolution. I think even beyond Shark Tank, I think linear television and streaming are going to go through a phase of where they'll be in sync, they'll be simultaneous, to eventually all being streamed.

25:21You can see these paramount, all these deals that are going down in consolidation of the industry, you're either on the content side or you're on the distribution side. But now business models like Netflix, they're in both, and they end up being the most powerful entity in the world right now. Because they have distribution in so many countries, they can create their own content, and they do. And so I think that my own kids, they don't watch linear television. They don't have cable. But they see Shark Tank, and they just get it. Where do they see it? They get it on YouTube. They get it on YouTube TV.