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Kevin O’Leary once told the student to choose his business over his fiancée

  • If the person you’re dating makes you choose between them and your business, choose your business.
  • Kevin O’Leary said this to a startup founder whose fiancée was threatening to leave him.
  • The “Shark Tank” investor said business success and wealth gains can open up more romantic options.

If the person you’re dating is forcing you to choose between your business and them, you should probably ditch them, says Kevin O’Leary.

The “Shark Tank” star was teaching a class a few years ago when a student asked him exactly that dilemma, O’Leary recalled in a clip from the “Impaulsive with Logan Paul” podcast that was recently posted online its socialization.

The student said he runs a software business out of his dorm room with $5 million in annual free cash flow. “I don’t hear any problem,” O’Leary joked.

“That’s not the problem: my fiancee came to me today and said she’s going to leave me,” the student said. She was upset because he wasn’t spending time with her family and wasn’t free on weekends, he explained. “I can’t because I’m so busy and I have to maintain my business, I have to get my degree. What do I do?”

The rest of the class waited in rapt silence for his answer, O’Leary recalled. “Wow. OK. I’m no Dr. Phil, but let me give you some advice here: Which is easier to replace – the girlfriend or the business?”

The celebrity investor said the student had to ask herself that question because “she was making $5 million and every woman in this class now knows it. I’m going to guess that if you can’t work it out, you’ll just do well.”

“He’s not the right person if he doesn’t support this journey that you’re on,” O’Leary continued. “Obviously you’re going to be wildly successful, you’re going to get someone else.”

O’Leary said his straightforward advice sparked a 45-minute debate about how people value their time and what’s important to them. He argued that entrepreneurs should look for partners who understand and support what they’re doing “because ultimately, that’s how you’ll be personally free one day.”

The business guru known as ‘Mr Wonderful’ said he would have liked to check on the student a few years later. “I bet he’s making a fortune, and I’m sure he’s got plenty of options.”

O’Leary told a similar version of the story in an interview clip he shared in June on LinkedIn. In this story, the student said that he worked every weekend and all night, so he had no time for his fiancée, and she had given him an ultimatum: choose her or his business.

“Look, let’s be pragmatic about this,” O’Leary replied. “Which is easier to replace? Your business or your fiancee?”

The Canadian multi-millionaire has dished out plenty of memorable advice over the years. He warned couples against combining their finances, warned against lending money to family, urged people not to wait too long before getting married and having children, and recommended buying fewer but higher quality products, with a higher resale value.

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