The outspoken venture capitalist and Shark Tank star is making his big-screen debut in Marty Supreme, directed by Josh Safdie. The film also stars Timothée Chalamet and Gwyneth Paltrow, and is already being talked about as a potential awards contender.
O’Leary says the role came to him in a way that felt strangely familiar. Safdie called him about playing Milton Rockwell, described as the richest man in America in the early 1950s — and, in O’Leary’s words, “a real a--hole.”
Instead of being offended, O’Leary laughed. He’d heard almost the exact same pitch years earlier when Shark Tank was being cast.
Back then, reality TV mogul Mark Burnett told him they were looking for someone brutally honest, sharp-tongued, and intimidating. O’Leary got the job — and the persona helped turn Shark Tank into an Emmy-winning hit.
“I’m starting to think this a--hole thing’s working for me,” O’Leary jokes.
On Shark Tank, O’Leary became the show’s blunt enforcer, a role often compared to Simon Cowell on American Idol. His sharp exchanges — especially with fellow billionaire Mark Cuban — became a defining part of the series, which regularly drew millions of viewers.
One of those viewers was Ronald Bronstein, who co-wrote Marty Supreme with Safdie. O’Leary says Bronstein knew details about old Shark Tank pitches that even he had forgotten.
When Safdie asked O’Leary to audition in New York, the businessman wasn’t eager to leave his summer vacation in Canada. Instead, he invited the filmmakers to come to him. Safdie, Bronstein, and producer Eli Bush flew out and met O’Leary on the dock at his lake house.
That meeting sealed the deal.
A guest at O’Leary’s home read the script and reacted strongly, calling it “the craziest” story he’d ever seen. That raw, unprompted reaction convinced O’Leary the project was something special.
Not everyone agreed. His agent warned him that jumping into scripted acting without training was risky. O’Leary didn’t care.
“I don’t need more money,” he says. “I want to use my time to do things that are extraordinary.”
Despite never taking acting lessons, O’Leary says Safdie made the set feel natural and immersive. Acting opposite Chalamet also helped. He describes the Dune star as fully transforming into character in seconds, making it easy to stay in the moment.
Now, with strong early buzz around his performance, O’Leary says he’s been offered more scripts — though he’s not rushing into anything.
For him, it all comes down to one thing: the story.
“If the story isn’t good,” O’Leary says, “how could the movie be good?”
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