Shark Tank's Kevin O'Leary once asked a student which one is easier to replace — girlfriend or business?
Kevin O’Leary, known as “Mr. Wonderful” on ‘Shark Tank’, is notorious for being brutally honest, especially when it comes to business. Recently, he gave eyebrow-raising advice during a classroom session: when faced with an ultimatum between a fiancée and a business, choose the business. This came after a college student shared his predicament—he owns a software business generating $5 million in annual free cash flow, but his fiancée was upset over the lack of time he spent with her. She issued an ultimatum: her or the business.
During an appearance on Logan Paul’s 'Impaulsive' podcast, Kevin O’Leary shared the story of a college student who sought his advice on the dilemma. “My fiancée came to me today and said that she’s going to leave me,” the student had confided. “I just can’t because I’m so busy. I’ve got to keep my business going; I’ve got to graduate my degree. What do I do?” O’Leary didn’t mince words. “Wow. OK. I’m not Dr. Phil, but let me give you some advice here: Which one is easier to replace — the girlfriend or the business?” He elaborated further, “She’s not the right person if she’s not supportive of this journey you’re on. You’re obviously going to be wildly successful; you’re going to get somebody else,” as per Business Insider.
O’Leary even told the student to think about it carefully, pointing out that he was already making $5 million, and was popular enough among the women in his class. O’Leary didn’t hold back as he offered more reassurance to the student. “I’m going to guess that if you can’t work this out, you’re going to just do fine,” he said, stressing that his success wouldn’t be derailed.
Beyond this specific advice, O’Leary also shared his broader philosophy on relationships and finances. He believes that combining finances is a mistake no matter how much you love someone. “You should never combine finances,” O’Leary stated firmly as per CNN.
O’Leary firmly believes that financial independence is essential for a strong relationship, and he has long advised couples to keep their finances separate—even after marriage. “What I tell everybody to do in a relationship is: Have your own account, your own credit card — never merge your finances together,” he said in an interview with Fox News. “I don’t care how in love you are, you keep your account to yourself.”
For O’Leary, a healthy relationship isn’t just about emotions—it’s also about how money is managed. He stresses the importance of discussing finances early in a relationship to understand each other’s spending habits, goals, and plans for the future. “Before you get serious with somebody, you really should ask them, ‘What are your goals? How do you see yourself in 20 years? Who do you want to become, and how do you want to treat money? Do you want to save it, do you want to spend it, do you want to splurge it? What are your goals with your financial future?’” he explained during an interview with CNBC.
O’Leary’s own marriage to Linda serves as a prime example of this approach. When they were dating in the ’80s, they aligned their financial priorities and values, even keeping their wedding simple with pizza and beer. Over the years, they grew together financially, and for their 25th anniversary, O’Leary surprised Linda with a beautiful diamond, symbolizing their shared financial success. “The best marriages are built on pillars that both sides agree on,” he added.