When Kevin O’Leary talks about entrepreneurship, he doesn’t talk about work-life balance. He talks about priorities.
In a 2022 appearance on “Impaulsive with Logan Paul,” the “Shark Tank” investor told a story about teaching a night class for a group of graduating engineers. With five minutes left in a three-hour session, a student who’d been silent all evening raised his hand.
“I’ve been running this business out of my dorm, and I’m about to graduate,” the student said. “It’s a cloud business that provides compliance software for hedge funds that have $250 million or less. I’m making about $5 million a year in free cash flow.”
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O’Leary told the podcast, “I don’t hear a problem.”
But the student did.
“My fiancée came to me today and said that she’s going to leave me,” he said. “I’m not spending any time with her family. I don’t have any time on weekends… I just can’t, because I’m so busy, and I’ve got to keep my business going. I’ve got to graduate my degree.”
O’Leary continued recounting the moment to “Impaulsive”:
“The class is like—you could hear a pin drop in there, right?”
Then he gave his answer. “I said to him, ‘Wow. Okay. I’m not Dr. Phil, but let me give you some advice here. Which one is easier to replace—the girlfriend or the business?'”
And he didn’t stop there:
“You’re making $5 million a year, and every woman in this class now knows this…If you can’t work this out, you’re going to just do fine.”
O’Leary framed the decision not as emotional, but strategic—something every entrepreneur will eventually face.
“She’s not the right person if she’s not supportive of this journey you’re on,” he said he told the class. “You’re obviously going to be wildly successful. You’re going to get somebody else.”
That sparked a debate in the classroom that stretched for another 45 minutes, O’Leary said, about how entrepreneurs should spend their time, and who they choose to build their lives with.
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