KEVIN SUPREME

KEVIN O’LEARY IS MANY THINGS: REALITY TV BULLY, TRUMP APOLOGIST AND, NOW, LAUDED ACTOR. IN MARTY SUPREME, HE PLAYS A SUPERVILLAIN— IN OTHER WORDS, HIMSELF. A CONVERSATION ABOUT THE OSCAR RACE, HIS AI OBSESSION AND HIS QUEST FOR WORLD DOMINATION

- BY COURTNEY SHEA

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. 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. 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?