Shark Tank's O'Leary On Tough Love: Fiancee Is 'Easier To Replace' Than A Thriving Business

Kevin O’Leary doesn't sugarcoat things – especially regarding business over love. The “Shark Tank” star has made his views on tough choices very clear. In a story he recently recounted on the Impaulsive with Logan Paul podcast, as reported by Business Insider, O’Leary shared his advice to a young entrepreneur struggling with a life-altering decision: his fiancee or his thriving business?

Don't Miss:

• The global games market is projected to generate $272B by the end of the year — for $0.55/share, this VC-backed startup with a 7M+ userbase gives investors easy access to this asset market.
• ‘Beating the market through ethical real estate investing' — this platform aims to give tenants equity in the homes they live in while scoring 17.17% average annual returns for investors – here’s how to join with just $100

O’Leary recalled a student coming to him with a problem. The student had built a successful software company, generating $5 million in annual free cash flow, all while juggling school. But there was a catch: his fiancee wasn't happy. She felt neglected, claiming that he wasn't making time for her or her family and ultimately issued an ultimatum – her or the business.

O’Leary didn't hesitate. “Which one is easier to replace – the girlfriend or the business?” he asked, much to the class's silence. The answer seemed obvious to him. “You’re making $5 million and every woman in this class now knows it. I’m going to guess that if you can't work this out, you'll do just fine.” 

Trending: This Adobe-backed AI marketing startup went from a $5 to $85 million valuation working with brands like L'Oréal, Hasbro, and Sweetgreen in just three years – here's how there's an opportunity to invest at $1,000 for only $0.50/share today.

O’Leary’s advice didn't end there. He pointed out that if the fiancee wasn't supportive of the student’s journey and business success, she might not be the right partner for him. “You're obviously going to be wildly successful. You'll get somebody else,” O’Leary added bluntly.

The statement sparked a 45-minute debate in the class. O’Leary said it wasn't just about the relationship but about how people value their time, priorities and future. For him, the take-away was simple: find a partner who understands and supports your goals. “That's ultimately how you're going to be personally free one day,” O’Leary explained.

Trending: ‘Scrolling to UBI': Deloitte's #1 fastest-growing software company allows users to earn money on their phones – invest today with $1,000 for just $0.25/share

This isn't the first time O’Leary, known as “Mr. Wonderful” on Shark Tank, has offered similar tough-love advice. He's been known for his pragmatic and often harsh views on personal finance and relationships. From warning couples not to combine their finances to advising against lending money to family, O’Leary's perspective always comes down to ensuring financial stability and business success.

As for the student? O’Leary didn't follow up but joked, “I bet you he's making a fortune and I'm sure he's got plenty of options.”

O’Leary's advice, though blunt, captures a core belief he's held throughout his career: business comes first and success will open up more opportunities – including in love. Whether or not everyone agrees, no doubt O’Leary's words stick.

Read Next:

• This Jeff Bezos-backed startup will allow you to become a landlord in just 10 minutes, and you only need $100.
• These five entrepreneurs are worth $223 billion – they all believe in one platform that offers a 7-9% target yield with monthly dividends