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Mixed Signals from Semafor Media
Kevin O’Leary on playing the villain and turning attention into power
00:44:41
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- [00:00]
A
Foreign. Welcome 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 Tawny. I'm the media editor here at Semaphore, and with me, as always, is our editor in chief, Ben Smith. Ben. Ben. Happy new year. It's 2026, first episode of the year. How you feeling? Any resolutions?
- [00:33]
B
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. I was vaguely disappointed to see that. Then I could only get the new knives out on Netflix.
- [00:48]
A
You 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 PO 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. He 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?
- [01:49]
B
You know, a central source of kind of access and power is being in the media all the time. He's a ubiquitous media character. And as you said in this film, this is his first scripted role, pretty, a major supporting role in which he plays essentially the worst version of himself, a kind of sadistic, evil tycoon. But 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.
- [02:16]
A
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. Kevin, 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, and 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?
- [03:02]
C
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, you're not an actor. We've 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 tangential 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 of 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. You 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, you know, 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. And so I play guitar. I'm a photographer. I used to work behind an Arriflex camera. I was a sound man, an 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. That'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 got me so intrigued. They sent me the script in 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 5am to watch the sunrise, and he starts reading. He doesn't know anything about the script, doesn't know anything about the film, doesn't know anything about anything. He just sees this thing. 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. That got me really intrigued, because you don't have a film without a great story.
- [06:37]
B
And once you find yourself in front of the camera, what was most surprising for you? I guess working with Safdie in particular.
- [06:43]
C
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. And 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, okay, 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. Like, 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, and as far as shitting the bed, I'll let the critics decide. And so far, so good.
- [08:11]
A
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?
- [08:26]
C
Well, 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, you know, 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, you know, 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, the 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. I just. 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 20ft 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's 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 gonna lay into him. It wasn't hard.
- [10:05]
B
I mean, you use the word asshole a lot. And that is. That's kind of the 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 you pause at all? Being cast that way, do you worry about being that person?
- [10:33]
C
Well, it is true. Twenty years ago at Shutters, which is near la, I think it's Santa Monica. It's a hotel. I 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. I'm casting for a new show called Shark Tank. We were supposed to meet for 20 minutes. We spent hours together talking about bunch of random stuff. And at the end I said, why am I here? Like, you called me here for what? Oh, he said, oh, yeah, yeah, yeah. Tomorrow we're gonna 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 won. The stuff you did in Canada, the stuff you're doing over in England, everybody calls you a dick. And I think I'm okay 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. Just show up the way you are and let's see what happens. And we never look back after. 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 gonna do about it? It's gonna bite you in the ass eventually. If you have a shitty idea, it's a stupid business and you're gonna go to zero and wipe out your parents mortgage on their house or whatever. And I think it serves me well. I don't really care what people think of me. The 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 gotta 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 got to admit, you nailed it on Marty Supreme.
- [12:24]
A
Yeah, well, I was going to say.
- [12:26]
C
I mean, what do you say to that? I actually wrote him back saying, well, that's a hell of a movie review.
- [12:31]
A
Yeah, 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?
- [12:40]
C
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, you know, content beyond business. I'm going to give a lot of credit to Josh because he's a. He's a very strange dude. And in fact, they, you know, 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. I'll just tell you how it works. You're on the set and Josh is directing it, but Ronnie's in the production tent, unseen 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, no matter how Many takes, you're going to keep doing it until Ronnie and Josh agree that they've got the scripted part nailed. And that could be 30 takes. And then somebody make a mistake, Chalamet makes a mistake, I make it, or Paltrow makes a mistake and he likes it. And 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 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.
- [14:43]
A
I 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.
- [14:58]
C
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 a 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 way you get respect is you execute. So if you've got a bunch of people working for you, as I do, that their family's well being is determined by my ability to guide a business forward, or an investment forward, or a new, you know, opportunity forward. They 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. A 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.
- [16:47]
B
You 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?
- [17:04]
C
I remember back in Boston, after we'd sold the Learning Company, there 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? We'll work together. We know you very well. 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 television network. They want to do some stuff. I said, no, no, no, we don't do tv. You got to stay low profile. Don't go in. I said, 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.
- [17:52]
B
And is that because you have a screw loose or is that like a business strategy?
- [17:55]
C
No, I don't know how to take direction. I've never worked for anybody, so I don't know how to do it. And so 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 out there is the media.
- [18:15]
A
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?
- [18:24]
C
Well, 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.
- [18:32]
A
How much longer do you want to be doing it? You've been doing Shark Tank in a show that was very similar to Shark Tank for quite some time.
- [18:38]
C
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 Arab 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, it'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 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. They 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 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. And 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.
- [20:08]
B
A contractual issue.
- [20:11]
C
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 got Amazon, you got mgm. You got a lot of cooks in the kitchen. And you have to respect what they've built. There's 150 people working on that show, some of them for the very first days. And 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.
- [21:04]
A
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.
- [21:16]
B
In this week's branded segment from Think with Google, I spoke with Google's VP of Marketing, Josh Spanier, about the impact of AI on creativity. In this age of automation, there's a lot of questions about where creativity comes in, whether AI is going to replace, in some sense, human creativity. When you're looking at the marketing industry, Josh, are you seeing any evidence that marketers are losing creative ambition?
- [21:38]
D
I'm really not. In fact, the reverse is happening. And if you see Nano Banana and like the hundreds of millions of people who played around with nano Banana, there is more creativity happening because of AI than ever before. I speak with a lot of creative teams. I was just speaking with Rob Reilly, he's the Chief Creative Officer of wpp and he's telling me that the creative teams have embraced this AI moment. It's not a fear anymore, it's an opportunity. And when they track who's using their AI technologies within wpp, the creative teams are using it more than any other team. You're seeing a real flourishing of creativity. It's a new tool set in the armory to use to actually make stuff inside of Google Marketing. We've actually launched a couple of new campaigns using fully generative ads. We have our newest one for our Pixel phone, which features Santa getting dressed, using AI, changing up his outfit. What's really fun about it is this is creativity that wasn't possible before because it, while it's in a stop motion style, there simply wasn't the budget or the time to make this happen using generative AI. The creative team had an idea and they could actually conceive it, pitch it, sell it and make it work real in a much shorter timeframe and actually put a really fun ad out in the world.
- [22:52]
B
Where can people find out more about this?
- [22:54]
D
Head on over to thinkwithgoogle.com there's a great article about WPP and their creative production transformation. And you can also on google.com search for frontier CMO and sign up for our new marketing podcast that I'm hosting with Think with Google as well.
- [23:09]
B
You buried the lead. Congrats on the new podcast.
- [23:12]
D
Thanks Ben.
- [23:12]
B
Thanks Josh.
- [23:23]
A
I'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 in 2025, 2026. Do you see Shark Tank making a kind of transition eventually from television to just streaming? Talk a little bit about that kind of evolution.
- [23:56]
C
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. You can see these Paramount, all these deals that are going down in cons 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.
- [24:40]
A
Where do they see it?
- [24:41]
C
They get it on YouTube. They get it on YouTube TV. They're not bound to any one location or device. They're just My son watches Shark Tank on his phone.
- [24:53]
B
I saw the show movie with my 16 year old and I assumed he wouldn't have heard of you. He's not like a Shark Tank demo person. Then he thought it was ridiculous that I thought that he hadn't heard of you. Cause he said any human being on planet earth had heard of you.
- [25:04]
C
The content's relevant no matter how you consume it. The hardest part about Shark Tank when you think about it, is curating there's 100,000 plus applications. Now, which ones of the 240 that eventually make it to tape should make it which ones, because we're not allowed to see them. That's the game show laws. So it's taken a long time to get the right people, the right team to be able to curate, because that show is created by curation of deal flow. Some of the craziest deals that are so wildly successful are ideas that you would think are total shit. And that's the serendipitous nature of venture investing. And I think recently, the one I use so often as an example, this woman named annaskaya, she's almost 6ft 2 or something, kind of a Russian model, but a biologist scientist, comes out with a white coat on and has a cat and a Q tip. And she basically shoves the Q tip up the cat's ass or whatever. I can't remember which end it went in. And she said, for $29, you can send this Q tip back to me and I'll give you a DNA test that'll tell you what foods to feed your cat to extend its life by 30%. And I said, anna, this idea is so stupid. I can buy a new cat. Five bucks.
- [26:32]
B
Maybe a blind spot for you there.
- [26:34]
C
That pissed off Cat Nation in America because there's 110 million cats. This is pre pandemic. That company sold to a major pharmaceutical company for a wild amount of money. So large that we had to do an NDA. We couldn't disclose it on Shark Tank. That was my deal. But there's an example. You would never think that would work, right? But I talked to Mindy, Casting, as we call her. She's been around since the beginning. I said, where did that deal come from? She said, I don't know. She was just so persuasive in this, you know, we loved her. That's amazing. That's how it works.
- [27:07]
B
I was curious if the Marty supreme experience changed how you think at all about movies and movie theaters.
- [27:12]
C
Well, my mind has been changed in the last couple of years about the role of theaters and whether they will go away. And my answer is they won't. And let's put it in the context of Marty Supreme. It's very important that you go see that movie with a community around you because it's got a lot of troubling themes in it. Most of the characters are broken people. They are dark. You know, that's part of the whole Safdie thing where he gives you comic relief. But really, you continue down into hell, that's where you're going. That's the same with uncut gems. But when I realized, you know, in the early screenings that some that were done with directors, and then we went to some of the premieres in LA and New York, for example, and some of the SAG AFTRA screenings where we were asked to answer questions, the audience was a very. Was very. It was very important to have that sense of community that you were with people that were experiencing the same thing you were experiencing, because it was a tough film in that respect in some of the moments. And I realized, wow, this is. If I was just watching this in my man cave, it would not be the same thing. When you see the 70 millimeter print, I mean, whoa. It just, you know, with the sound, Dolby Six or whatever it is, you're. You're immersed into 52. So I think that experience will continue forever because you can't emulate that on your TV screen at home. No matter how big your viewing thing is, you're not gonna be sitting there with a thousand people. And to me, that really mattered. You know, I'm like a big James Bond fan and I like action films. I never see. I don't wait for them to come out. I go see them in a theater. I pay my 20 bucks or whatever it is, and I, you know, put a ball cap on and just go in there and watch it, and I love it. And I go with my son sometimes. It's an experience. It's like an experiential thing.
- [29:05]
A
With the last few minutes that we have, I wanna ask you some questions. Obviously, we have a lot of people who listen to the show who are interested in politics. I'm sure many of them have, either on Fox or on cnn. You've been asked on a lot, particularly on cnn, to go on and defend Trump. I'm curious, like, what's the benefit for you of going on television to defend Trump? Has it been good for, you know, opening you up to a certain audience? Is it just. That's how you feel and you get asked to do it, so you do it. And I'm also curious, do you hear from Trump? I mean, he loves to watch tv. Do you ever hear from him after you do these hits?
- [29:37]
C
The important part of that answer is I don't shill for politicians, including Trump. I shill for their policy. And so that's why there are times when I disagree with Trump's policy. In aggregate, though, I care about policy that supports small business. 72% of jobs in America created by companies, 5 to 500 employees. And that's where I spend the majority of my time as an investor. And if you look at my 52 portfolio companies, they all fit in that genre, and they're in all 11 sectors of the economy. So I care about policy. And I'll give you an example. When Trump's tax bill was being crafted, a lot of people don't know this about how it works on the Hill. It's the staffers of the senators and the representatives. It's the staffers that write that law. You don't know anybody that read that bill. But I did read it, and I found some very disturbing aspects of it. And I was very, very fortunate to be able. And this is the great thing about why I do media. When you have a narrative and you're known in the media and you're known for supporting job creation, which is bipartisan, you can go to Rick Scott in Florida, or you can go to Ron Johnson, or you can go to Hagerty and his staffers and say, guys, this paragraph is a bad paragraph for small business. You gotta change this and you gotta fix it, because I'm telling you right now, this is bad. And to be able to have that dialogue and actually negotiate those subtle changes, which I did.
- [30:59]
B
Was there something in particular?
- [31:00]
C
Yes, it was the audit period for those companies that took government support during the pandemic. They wanted to extend it from three years to nine. That's insane, because then they could have never borrowed money while the threat of an IRS audit is sitting over their heads. And I wasn't the only guy complaining about it. But that was a big problem. They were able to fix that. And I'm very appreciative on a bipartisan basis that they would do that. Trump is the. Everybody knows by now. If you don't know how Trump operates, you know, and I understand that 50% of the world, including 50% of my family, have. Has Trump derangement syndrome. I don't have that problem. I don't spend my energy on noise. When he puts his name on the Kennedy center, he loves doing that because he knows it drives his adversaries crazy. He's having fun with it. It's noise. What does that have to do with policy? Nothing. I don't spend a single ounce of one calorie of energy on that. I don't care about that. I care about his policy. So, yeah, I get feedback from him. But more importantly, the administration, I talk to them all the time. I'm in Washington every two Weeks, for a couple of days. I meet with lots of senators, lots of governors, and here's another thing you gotta know. One of the areas I invest in, which is I've always been a real estate guy, is data centers. These are multi billion dollar projects. You're not gonna get those done unless you have the governor on board, the mayor of the town on board, the senator of that state on board. You gotta do a lot of work in Washington, and that's how you pave the way for developing a project like that. And so that's why I stay in the narrative. You know, I think you're. You could. The reason I do as many hours on CNN as I do on Fox, and I do MSNBC and I do cnbc. I'm just a policy guy. I want to talk about policy. Trump's thing on not letting foreign students in. I don't agree with that. I teach those foreign students, they're the smartest people on earth. If we don't teach them, they'll get taught in Russia or China. Why the hell would we let a genius from Pakistan go and work for the Chinese? Why the hell would we do that? That makes no sense. Put them in Harvard, put him in mit. That's my attitude, because I teach in those places. And so we have disagreements, but he's a pragmatic guy. He's not crazy. He'll listen to different directions. Ultimately, he makes his own decision. And I'd say so far the scorecard, which is GDP and the market is liking what they see.
- [33:17]
B
People occasionally mention you as a Canadian, Trump. You still thinking about getting involved in Canadian politics?
- [33:22]
C
No, I don't think so. I think I did that in 2016. And I'll tell you the difference. A lot of people don't realize, when you're a celebrity, 50% of the population doesn't like you. That's just how it is. They don't like you. But when you're a politician, 50% of the constituency hates you and two and a half percent of them want to kill you. That's the difference.
- [33:47]
B
Yeah.
- [33:48]
C
And that is a very big difference, if you understand what I'm saying. Because I experienced some of that when I was running as a conservative, even in Canada.
- [33:57]
B
Yikes.
- [33:57]
C
Oh, yeah. Oh, yeah. Yeah.
- [33:58]
B
I thought you guys were nicer.
- [33:59]
C
No, there's always a 2.5% lunatic fringe, no matter where you are. It's pretty scary. And it's tough on your family. You're causing pain to your immediate family. They're worried about your safety, Their safety You know, where you live and everything else. Which is why I have respect even for aoc. I don't agree with any of her policy. Monda me, I met at the opening of Marty supreme in New York. Very charismatic guy.
- [34:22]
A
Wow, really?
- [34:23]
C
Yeah, yeah, no, he came to the opening, he met with all of us and I had a chance to talk to him and I said, look, you know, I don't agree with anything you're proposing. I'm not a big fan of communism, but I have to respect what you achieved because I have never seen social media so effective. Who did that for you? And I met his team, they're basically data scientists. He cleaned up because he understood how to use each platform the right way. I'm going to meet with him soon because we're going to talk about policy on housing where I invest and you know, just to see. I really found him a very pleasant guy, you know, I don't, I don't like his policy. Elizabeth Warren, I respect her, but I don't agree with her policy. But I know how hard it is to be that politician. That's why I respect all of them, but I don't have to agree with their policies.
- [35:06]
A
It sounds like you might be getting a phone call. I know we've got a rap soon. I wanted to ask one more question here, just a fun one to end so we don't have to end on death threats or anything like that. Though I loved, loved hearing some of that as I was talking to some people as well, you know, over the holidays. I was mentioning that we had you on the show this week and a few, a few friends of mine mentioned that they follow these fan accounts of yours, but for your music, are you aware that there are like these accounts that aggregate your musicianship?
- [35:31]
C
The thing about guitar, I've been playing a long time is you can't get better unless you practice. There's no way to get better. And my time is so compressed that I have guitars all over the world. I have some sitting in hotels in New York and la, just so when I get there I can pull it out and practice. John Mayer is a big Shark Tank fan and he came to the set a few years ago, he said, you know, I'm recording at the Capitol Studios, but if you're interested to come down, you know, give me your number and I'll just call you when I have. But it could be two in the morning. It's just sometimes I get inspired and I just go into the studio and sure enough, a couple days later, phone rang. At like 1:30 and said, hey listen, I'm going to the studio, do you want to come and watch? And I went with my wife and we watched John write it. Basically write a song that's on his most recent album. And I was talking to him about his playing because I really like. He's one of my favorites in terms of people that I try and emulate in, in the way he, he interprets the blues on the guitar. What I learned from him was slow it down. Like you don't need 30 notes in four seconds, you need three. But you gotta make it, you gotta make it feel you have to pull it out of the guitar. And boy was that great advice. But in order to do that, which sounds easy, it's not, you have to practice. And so what I do often is sometimes at 2 in the morning I'll just set up the, you know, my phone in some place that I'm at, in a hotel or maybe it's a condo or something and I'll pull up my guitar and I'll do like, you know, a 10 minute session on Instagram Live. And then I and I post it and just get the feedback. And a lot of hardcore players will critique it constructively and say go to the B flat here or you know, just, or whatever they say. And I listen to that and I think it's a form of, you know, getting my head out of the day of, you know, an all day press just getting loose in a different way but also listening to. And I've become a much better player in the last two years. I'm way better than I was two years ago and I've slowed it down and that's why I do it. And so any of this feedback you're talking about, I'm aware of these sites, they aggregate it and what's interesting is some of it's like from five years ago versus like last week and you can see the difference.
- [37:51]
A
Well, Kevin, thank you so much for joining us. Much better place to leave it than the threats of political violence.
- [37:56]
C
It's the world we live in. It's the world we live in. But anyways, thanks. It was great. You know, let's see what happens with Marty Supreme. Did I shit the bet or not? That's the question.
- [38:15]
B
So thank you for bringing Kevin by. That was. He's got a very, very wide range. But to start, did you hear any news in there?
- [38:21]
A
I actually think he did make a little bit of news on our show or he hinted at a few things. Kevin mentioned that he was Trying to convince Mark Cuban to come back on Shark Tank and kind of got a little bit at what might have been some of the issues there. I had kind of assumed when we talked to Mark, my assumption was kind baked in that he wanted to not do the show anymore because he was kind of sick of doing it for several decades. But the reality, it seems like, may be that there was more of a contractual dispute or contractual disagreement, you know, around distribution, which. Which I thought was pretty interesting.
- [38:57]
B
Yeah. That Cuban maybe wants it more widely distributed than the owners of the show are going to allow. Well, he wants to stream it everywhere.
- [39:04]
A
The other thing I thought was really interesting as he talked about his new relationship with New York City Mayor Zoran Mamdani. He talks about meeting him at the Marty supreme premiere and that he was going to talk to him soon about housing, which he's an investor in. And of course, he also talked about how he got some parts of the tax law changed as well. I thought that all of those bits I hadn't heard him talk about before, and I thought that they were really interesting and demonstrated his kind of insights into just how to wield his media power. I don't know. Ben, what did you think about his answer to your question about how he thinks about his relationship between being a media guy and an investor and that kind of matrix?
- [39:43]
B
I think it's what you just said, that this is how power works now, that the currency of attention is more valuable than money. Actually, rich guys dime a dozen trying to get meetings with Donald Trump. And if you pay enough and you give some money at the, you know, to fund various family projects, you know, maybe you can get a pardon. But this other path, which is more valuable, is to have a big media following. And that's what that contemporary public figures like Donald Trump, like Zoran Mamdani, value more than money.
- [40:09]
A
And one of the other things that I got from. From talking to Kevin was just that this stuff is. Is no accident. And he really is thinking very deliberately about all of the moves that he is making. It's not random. And one bit is informing the other. It doesn't surprise me at all that he was, you know, at the premiere with Zoran Vamdani talking about his other businesses. Right. That's a direct line between being in Marty supreme, doing this kind of fun thing that was out of his comfort zone, directly impacting the things that he's working in. And of course, it's the same thing with his appearances on CNN supporting Trump. I mean, one thing that struck me and we kind of hinted at this a little bit, we got at this a little bit in the interview is how much he disagrees with Trump on a lot of things. He's disagreed with him on various elements of the tariffs. He's disagreed with him on the high skilled visas. He clearly disagrees with him to a certain degree on the, you know, what he described as noise with the Kennedy center stuff. I mean, I actually wrote it. He said he disagreed with him on the 50 year mortgage plan, that somebody in the White House was floating, his attempts to meddle with the Fed. And yet, you know, he's on TV oftentimes defending Trump in part because it's very helpful. And Trump calls him on the phone. He mentioned that in the interview. And so I think he. He's very strategic and deliberate about what he's doing and he knows exactly what his appearances in the media are going to do for the rest of his.
- [41:31]
B
I mean, also, though, obviously he loves it, right? Totally.
- [41:33]
A
Yeah, totally.
- [41:34]
B
He's a total guy who likes being in front of the camera. I mean, though it is interesting. One sort of final observation is just that, you know, he is a sort of embodiment of the way in which contemporary media encourages you to be your worst self in public. If you had to become like the worst version of yourself in public, what would it be? Do you think?
- [41:49]
A
Oh, God, I could become a much like, I think, less forgiving reporter in some ways. You know, I feel like I could just fire shit off and just basically not run anything that anybody thinks is contrary to what's in the stories and, I don't know, just pop off. I guess I could just mock people on Twitter, maybe a little bit more of what I used to do, which was like kind of dunk on more people on Twitter. I think that's probably what it would be. I don't know, I feel like you.
- [42:12]
B
Exercise a lot of restraint.
- [42:13]
A
I've started to. I've started to. I started to not fight with people on Twitter. I see how it goes. It never ends well. Well, that is it for us this week. Thank you so much for listening to another episode of Me Mixed Signals from us here at Semaphore. It's our first one of 2026, first of many. Our show is produced by Manny Fadal and Josh Billinson, with special thanks to Anna Pizzino, Jules Zern, Chad Lewis, Rachel Oppenheim, Tori Kaur, Garrett Wiley and Daniel Haft. Our engineer is Rick Kwan and our theme music is by Steve Bone. Our public editor is David fankel. Who runs a 24. David, I know you're sometimes breakfast buddies with Ben, but so far have turned us down for the show. Come on the show. Look at how fun it can be. It can be great if you're watching.
- [43:03]
B
On YouTube, whether or not you're David. Please subscribe and follow us wherever you get your podcasts.
- [43:07]
A
And feel free to leave us a review. I made the mistake over the holidays of reading some of the comments. Most of them are nice, but you know, you see the occasional one in there. Inundate us with positive reviews. If you have any sort of positive feelings for us, that would be a.
- [43:20]
B
Very nice holiday activity.
- [43:21]
A
Yeah, exactly. Sinking into the comments about how I pronounce certain things and how many ums I use. And if you want more, you can always sign up for Semaphore's media newsletter, which is out every Sunday night.