Kevin Supreme

“Kevin O’Leary, thespian” is the career pivot nobody saw coming. Did earning millionsMultiple outlets report that O’Leary’s current net worth is north of $400 million. in your sleep start to get boring? I’ve been an investor for many years, and I’ve been able to observe all kinds of different managers: CEOs, CFOs, CIOs. Over time, I’ve started to see a common attribute in the most successful ones: they spend about 20 to 30 per cent of their day outside of their comfort zone—doing something they don’t know how to do, that they’ve never done before. They run the risk of failing, but they force themselves to do it anyway, whether it’s skateboarding, painting or playing the cello.O’Leary collects guitars and has some mean chops himself. He owns a bespoke Mr. Wonderful amp from Allston. It doesn’t matter what, just that they are in unfamiliar territory. I was recently talking with an extremely successful watchmaker named David Candaux. I’m a big collector, and this guy has made a name for himself. When he’s not designing watches, he likes to jump off Swiss mountains on a paraglider. It had gotten to the point that I thought, Okay, there must be something to this idea of exercising the brain outside of its comfort zone. And then, just as I was considering it, this opportunity to act in a movie arose.

Did their people call your people? I got a call from director Josh Safdie and ­Ronald Bronstein, who co-wrote the screenplay for Marty Supreme. A24’s story of fictional ping-pong wizard Marty Mauser is inspired by the real-life rise of Marty Reisman, an American champ who started playing after he suffered a nervous breakdown at age nine and won 22 major titles between 1946 and 2002. Photo by Bettmann/Getty Images Ronnie is a huge Shark Tank fan, and he explained to me that they were casting for this character, Milton Rockwell, a wealthy socialite in 1952—and they were looking for a real asshole. They were very blunt about it. They said that they wanted someone the audience would dislike immediately, and that was me. It’s the same thing producer Mark Burnett told me two decades ago when he cast me in Shark Tank. He said, “Just be yourself.” I brought Marty Supreme up with my team at United Talent Agency, and they said, “Look, Kevin, this is not television. This is not a cameo. This is a serious, scripted role, and if you shit the bed, you’re going to destroy our business together.”

You mean being bad at something would weaken your brand? Yes. It would hurt financially, and it would be almost immediate. It’s that risk of being embarrassed or ridiculed that makes so many people stay in their comfort zone. You get monetary rewards, your life is at peace, but that’s not actually the right way to live. So I got the offer and I said, “Screw it.” The only way I’m going to know if I’m any good is if I try it.

Having seen the movie, I can say that you were very good. Did you take lessons? Did you study any masters? Learning the lines was definitely a challenge. That’s not something we do in reality TV. But, with the actual acting, the minute I was in character, it just started flowing. I think part of it was that I could relate to Rockwell. He was similar to Mr. Wonderful: a royalty guy who licensed the technology of his day, which was pens. And his tactics were similar to mine.

For example? I got a lot of heat when Shark Tank debuted because I would structure deals where I took dollars right off the top. Milton the character also figured that out. I could also easily fall into character because our sets were so meticulously constructed: the extras were all dressed in perfect period wardrobe, and everything down to a spoon in a café was entirely authentic to the period. I closed my eyes, and when I opened them, I was in New York in 1952, and I was Milton Rockwell. I admit that some days I didn’t want to go back to 2025.

Your 1952 hair was impressive. That was a prosthetic. It took two and a half hours to have it applied, probably an hour to take off. It was incredibly expensive to make. It definitely changed my look. Josh was inspired after seeing a photo of my biological father, Terry O’Leary, who died at 37. The first time they applied the wig, I fell asleep, and when I woke up, I was looking at my dad in the mirror.

That must have been emotional. Yes, it was.

Did your wifeLinda Greer married O’Leary in 1990. To save money, they hosted their wedding at home and ordered beer and pizza as refreshments. Photo by Alexander Tamargo/Getty Images like it? She loved it. She said I should keep it.

Was it intimidating acting opposite the biggest names in the business: Chalamet, Paltrow? Timothée—the guy has electric sparks flying off him, so you just feed off of that. I already knew Gwyneth because we had worked together on Shark Tank. And then, of course, Josh and his team are just the most incredible artists. I feel very spoiled because I now realize that I was working with the absolute upper echelon of filmmakingWith an estimated budget of $98.6 million, Marty Supreme takes the title of A24’s most expensive film to date.

How does a Hollywood set differ from the set of Shark Tank? I learned that a movie set isn’t a democracy. We would be doing take after take after take, and at one point, I turned to Josh and said, “I think we nailed it.” And he replied, “No, we haven’t nailed it until I say we’ve nailed it. Do it again.”

I’m surprised to hear that you can take direction. It wasn’t easy.

I’m going to issue a spoiler alert. There’s a scene where your character brutalizes Timothée’s bare butt with a ping-pong paddle. I’m not even sure what to ask. They offered Timmy an extra to take the hits, but he insisted on doing it himself. At first, I was trying to be gentle, but Josh said, “You’ve got to hit him! Do it like it’s real.” By the end of the shoot, Timmy had an indentation of a paddle on his ass. That was also the day that my wife and daughter came to set to watch. They saw Timmy work from probably midnight to 2:30 a.m. By the time we wrapped, it was after 4 a.m. I didn’t get back to my hotel, Casa Cipriani, until 7 a.m. They had started breakfast, and I said to the maître d’, “Listen, I need you to go down to the cellar and get me a 2022 Puligny-Montrachet.” He said, “Sir, it’s 7 in the morning.” I said, “And I want some eggs and smoked salmon to go with it.” I was so wired. My wife came to join me, but I finished the whole bottle before she got there. It was really an amazing experience. I think it ended up being one of the best scenes in the movie.

Your studio obviously agrees. A24 is currently running a campaign to get you an Oscar nomination for best supporting actor. I’m very proud that they consider my work worthy of investment, because that’s what an Oscar campaign is. Look, I want to be successful. I want the movie to be successful. I want the work and the hours that I put in to be validated. I want to feel like I achieved my objective of not shitting the bed.

You recently said that AI could be used to replace extras in a movie like Marty Supreme. How do you think that’s going to sit with Academy voters? Let me explain what I said, because my words have been mischaracterized. The comments that I made about AI and extras were in the context of giant crowd scenes—the kind where technology has always played a role. If you go back to the gladiator movies of the ’60s, they had to put 10,000 people in the Colosseum to watch the big fight scene, and they did that through a very arduous green-screening process. Or think about Kirk Douglas marching with thousands of soldiers behind him in Spartacus. That could be achieved using AI, and it would mean huge savings, meaning more money to make more movies. I was not talking about extras who interact with principals and deliver lines or serve a distinct purpose.

Okay, but you did say that Marty Supreme could have saved millions of dollars by replacing extras in scenes where there were at least 100 of them. It sounds like you’ve shifted away from your original comments. I mean, now that I’ve actually seen the film, I’ve seen how much interaction there is between the principal actors and the extras. There is a nuance when you have that interplay between two human beings, even if there are no words spoken. There is too much improvisation and reacting to things in the moment, which AI is not capable of. The other thing is that I am a huge supporter of SAG-AFTRA.Hollywood’s biggest union is made up of roughly 160,000 members.

Always? Or since you launched your Oscar campaign? I have seen how Hollywood works, and the only reason that I have health care, and everyone else that I work with has health care, is the power of SAG. Without that union, there would be a lot of people getting screwed in the arts. Every time someone comes to me and says, “I want to use your likeness,” I tell them it has to be SAG compliant. I’m not a big union supporter, but it’s different with the arts. Artists are crazy. Making art is not the same as running a business. You have to give a lot of latitude to draw out the creativity. The best people I have worked with are from other planets. By that I mean they are not normal people. Josh and Ronnie? Strange dudes. And you need the structure of a union to make it work. I do think that the union is going to get to a place where they allow background scenes to be AI-generated, but they’re not going to let AI work with prime actors. What director would allow it?

Elon Musk recently said that his chatbot, Grok, will create an excellent AI movie within the next couple of years. He can give it a try. Definitely these conversations are happening. There is Musk, there is a German company talking about doing an AI sci-fi, there is Tilly NorwoodAI actor Tilly Norwood was created by AI production company Particle6, which says she has “girl next door vibes.” or whatever her name is. I work in this space, I am developing my own agentic AI, and I can tell you they are a long, long, long way from replacing people.

I want to go back to what you said earlier. Serious question: Do you consider yourself an asshole? I don’t. I just tell the truth. The thing to understand about business is that there is no grey zone: you either make money or you lose money. After investing for so long, particularly in venture portfolios, I found that, in leadership, it’s not important that people like you; it’s important that they respect you. You have to make tough decisions all the time. Not everyone agrees with them, but the only thing that matters in the end is that you’re successful. People will follow someone who executes successfully. That’s something I learned in the ’90s working for Steve Jobs.“The toughest bastard I’ve ever met,” is how O’Leary describes his former boss. This guy was not a nice guy. Just not. However, he had a very simple concept: workdays, he said, boil down to tasks and distractions—what he called signal and noise. Signal is the important stuff. Noise is everything stopping you from getting to the signal. And he said that you must have an 80:20 signal-to-noise ratio to be successful. Unfortunately, when you are that myopically focused on getting things done, you will not have time for niceties. Niceties are noise. The only other individual I know who has a higher signal-to-noise ratio than Jobs is Elon Musk. He’ll walk out of a conversation the minute he feels it’s useless.

Are you saying that the most successful people in the world shouldn’t have to concern themselves with kindness?
Kindness doesn’t matter.Billionaire Warren Buffet tends to disagree: “When you help someone in any of thousands of ways, you help the world. Kindness is costless but also priceless.” Photo by Kevin Dietsch/Getty Images Millions of people follow me on social media, and 50 per cent of them hate me. They write me long diatribes, and I read them because I respect their opinions. They don’t have to like me. That’s not important. I have the ability to lead people into the battle of business because they trust that I’ll get them out the other side. If that makes me the mean shark or the asshole, I’m okay with that. Just try and compete with me.

Speaking of stiff competition, you are currently leading the proposal for Wonder Valley,O’Leary Ventures has dubbed the potential project the “largest AI compute data centre park on Earth.” Its promotional video appears to be entirely generated by AI. a $70-billion data centre in Alberta that stands to be the largest in the world. Can you provide an update? At the moment, we are going through the permit process. We’ve already invested a lot of capital. This happened because I’m a real estate guy. Data centres are a new category of real estate, and they are complex because they require fibre-optic cables, water and sophisticated people in terms of engineering—not just to build but to maintain. You can’t just stick one of these in the middle of the desert. You need workers to live there, and they need to have grocery stores and schools for their kids. But the number-one thing that you need is a lot of electricity. I visited various sites around the world, including in Norway and Finland, where they have a lot of hydro and nuclear power. Then, about two years ago, I got a phone call from a member of the Conservative Party of Alberta. He said, “Mr. O’Leary, why are you not looking at sites in Alberta?” I said, “Well, everybody knows that you can’t get a permit.” Back then, the entire Canadian economy had been shut down by the Impact Assessment Act,The act was meant to help determine the pros and cons of proposed projects. Alberta’s energy sector, in particular, argued that it complicated approval processes. when Trudeau was still prime minister.

You’ve made no secret of your feelings about the former PM. I’ve framed him pretty negatively, but the numbers tell the story: he was the Idiot King, and he brought the country to its knees. He destroyed the Canadian economy by never allowing it to flourish with the one asset it has that no other country has: unlimited energy. I think the current government understands that the world needs power and Canada has it. But, going back to the Wonder Valley project, Premier Danielle Smith herself invited me to visit Alberta, and I was blown away. We took helicopters all over the province.

Aside from abundant space, why exactly is Alberta a perfect site to build data centres? Why not Ontario? The price of power in Alberta is lower, but the other thing is permits. If you told me I could get a permit to develop in Ontario or Manitoba, I would be interested, but I don’t think that’s the case. Danielle has fought hard against the Idiot King’s Impact Assessment Act. That doesn’t mean I have permits yet. I am going through the process. I know that I have a fighting chance, which is why I’m willing to put millions of dollars down.

You and Danielle Smith made headlines for your visit to Mar-a-Lago last winter, just as Trump’s 51st-state rhetoric was heating up. A lot of Canadians saw that as a betrayal. I know Danielle took a lot of heat for that, but look at her now: better off than any other premier in terms of the tariff situation because she took the time to go and meet Trump’s administration on an informal basis. She understood that Trump is a transactional guy. He holds court that way—mano a mano, or mano a womano. Smith sat down with Trump, just the two of them, to let him find out what she was all about. That has worked out pretty wellSince Trump’s tariffs hit, Alberta’s oil-and-gas sector has lost 5,000 jobs. Photo by Bloomberg/Getty Images for her.

You don’t consider her invocations of the notwithstanding clause to be somewhat authoritarian? A lot of people take issue with politicians who bypass the democratic process. You call it authoritarianism, I call it getting stuff done.

Dictators get stuff done. I wouldn’t consider her a dictator. She has to be elected. I’m just saying that any politician is going to have 50 per cent of their constituency not happy. That’s the nature of politics. Danielle is a maverick. I predict she will be prime minister one day.

It’s hard not to see that as a diss to Doug Ford, who also has designs on the big chair. Doug Ford is a great guy—a great leader—but those Reagan ads he commissionedPrime Minister Carney privately apologized to President Trump for the commercial, saying, “It was not something I would have done.” were the worst thing he could have done. I mean, read the room. That ad ran before elections in multiple states, and it made a lot of people think they were being manipulated. I have no problem with diversifying trade with other countries, and that’s what Carney is doing. But the US is a very large market. I don’t see why we can’t work these problems out, get to some kind of reciprocal tariff arrangement and move forward.

Ford has called that ad the “most successful in the history of North America.” I don’t want to be in a war of words. I would rather grow the GDP. We had deals on the table in uranium, aluminum, other commodities—all of those deals got blown up because of that ad. But I think the bigger issue is that a premier shouldn’t speak for our country. We need one voice to negotiate. Trump respects Carney right now, so let him go down there and make a deal. I didn’t vote for Carney, but I want him to succeed. He’s a very pragmatic guy. He has execution skills that he’s proven over a long career.

What do you make of his current approach to building Canada’s data sovereignty?Data sovereignty is the idea that a nation owns the data it generates and stores on home soil, thus subjecting it to domestic laws and governance. I’ve known the new minister of AI, Evan Solomon, for years, and he understands the importance of data sovereignty. Canada is such a stable place. We have a singular problem right now: that we don’t have a fibre-optic cable network from coast to coast. I believe Rogers is going to fix that, probably using the Trans-Canada Highway,Governments and corporations often hide fibre-optic cables within existing infrastructure. Toronto, for instance, has them running under the 407. so that we can offer data sovereignty to anybody on earth if they wish to work within Canada.

But wouldn’t Canada then control those countries’ data sovereignty? I haven’t heard of a single country in the G20 that doesn’t want to work with Canada and take advantage of our power and infrastructure. If you’re Britain or Germany or France, what you want to know is: if you park your data in Canada, do you have rights? So we need to make sure that the policy is in place and that these client countries understand that Canada wants to provide data sovereignty to nations that are willing to invest their capital here. I think Carney has been doing a pretty good job of getting the word out.

Pierre PoilievreDuring the Canadian federal election, President Trump attacked Poilievre for not supporting the MAGA movement and said he’d rather deal with a Liberal. Photo by Geoff Robins/Getty Images will face a leadership review in January. He says he’s confident. Should he be? He’s got a tough road ahead. He missed an open net, and the Conservative Party has been pretty cruel to leaders who do that—not some of the time, 100 per cent of the time. It’s easy to have 20/20 in hindsight, but I do think Poilievre made an error in not going down to the US to form a relationship with Trump. Maybe then Trump wouldn’t have dismissed him the way he did, which really knocked him out of the box.

Would you ever return to politics?O’Leary abandoned the 2017 Conservative leadership race, citing his poor French. His campaign amassed roughly $500,000 in debt. I’m pretty busy with everything else I’ve got going on. I will say that you don’t understand how immensely hard that job is until you try to do it. In my world, which is celebrity, the people who disagree with you may not like you, but in politics, they want to kill you. Regardless of my feelings about Trudeau’s lack of execution skills, I certainly respect that he had a hard job.

Have you been following Trudeau’s post-political life? Yes, and I think the best thing Katy Perry could do is use my company, HelloPrenup, right away, because he bankrupts everything he touches within 90 days. She can consider this a public offer: I will provide a prenup for Katy Perry free of charge.

You mentioned you’re developing agentic AI. Did you mean an AI Mr. Wonderful? Yes. This is something that I’ve been creating in the UAE, where they’re doing the most advanced AI work. I go over there and the model keeps learning more about me: my motions, my eyes, how I move. The idea is that AI Kevin will be an agent attached to various businesses. For example, I have a watch insurance company, WonderCare. Three thousand people a day have questions for me, and I can have all the answers built into a giant AI learning model. They’re happy to talk to AI Kevin, because their questions are very specific and the information is all there. But here’s the dilemma: when you see AI Kevin, should I disclose that it’s AI Kevin? Or is it okay to not disclose that? My decision is that you have to disclose. I would say that what you’re looking at is not me, it’s my AI brother. He’s here because the real Kevin is asleep. And when we use AI Kevin on a commercial, we would pay our SAG dues.In July of 2025, SAG-AFTRA members ratified an agreement that includes consent and disclosure requirements for AI avatar use. That’s how we’re going to resolve this in the creative community: disclosure, transparency, honesty. AI technology can advance the arts, but I don’t want AI Kevin performing in a movie. I want the real Kevin.

Could AI Kevin be a companion? Not for me. I have maybe 25 people in my life that matter, and that’s where I put my energy. People expect too much of AI. It’s a great tool, just like a spreadsheet, but in the end, it’s a human tool. It won’t be able to replace us, certainly not in the arts. Tilly Norwood looks like AI, and I don’t want to act beside her.

Spoken like a true diva. Have you booked any more acting gigs? For now, I’m looking forward to reading the reviews.Marty Supreme hits theatres Christmas Day. I’ve heard great things from my family and friends. But I want people who don’t like me to say that I did a good job. If the ones who think I’m an asshole have good things to say, that’s what I want. I have heard from a few directors—people who have seen advanced screenings and have reached out or sent a script. I can’t say who at this point.

Would you ever play a nice guy? I prefer to be the antagonist. Nine times out of 10, that’s the more interesting role.

This interview has been edited for length and clarity.