"5 million bucks a year"- Shark Tank's Kevin O'Leary recalls giving a wake-up call to an entrepreneur

Shark Tank investor Kevin O'Leary recently shared an X video of him in an interview about a story where he advised a student entrepreneur who was faced with a difficult decision between his business and his fiancée. The student was running a successful software company generating "$5 million in cash a year" while completing his engineering degree.

However, his fiancée was unhappy with the time he dedicated to his business and gave him an ultimatum. O'Leary responded by asking which would be easier to replace—his fiancée or his business—implying that the entrepreneur should carefully consider his priorities.

The Shark Tank investor emphasized the potential consequences of prioritizing personal relationships over financial success, adding:

"And I would think by now, all these beautiful women in this class over here just heard you make five million bucks a year."

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Shark Tank Kevin O'Leary's advice on choosing business over personal relationships

A student's business dilemma

During a class session, O'Leary recalled how the student, who had remained quiet throughout, spoke up near the end of the discussion to share his concerns. The student explained that he was operating a cloud-based software company designed for hedge fund managers while also pursuing his degree. His fiancée, frustrated by his demanding schedule, had given him an ultimatum.

The entrepreneur detailed the sacrifices he was making, stating,

"I sleep four or five hours a night because I have to run both things. I got to graduate...I have no time for her on the weekends. I don't go to any soccer games with her family. I missed last weekend's picnic."

After listening, O'Leary immediately questioned why the student viewed this as a problem.

"You're still in school and you've got a five-million-dollar business out of your dorm? I don’t hear a problem," he stated.

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O'Leary's direct advice

O'Leary provided a straightforward response, advising the student to reconsider his priorities. The Shark Tank investor posed a critical question:

"Which one is easier to replace? Your fiancée or your business?"

The Shark Tank investor underscored the importance of having a supportive partner, stating,

"She is clearly not the right one for you. She doesn’t understand your mandate. She doesn’t support you."

O'Leary suggested that the student’s success would naturally lead to more opportunities. He explained that achieving financial success often expands personal options and emphasized that an unsupportive partner could create obstacles to long-term goals.

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The aftermath and entrepreneurial lessons

Following the conversation, Kevin O'Leary observed that his statement caused a strong reaction within the class. The Shark Tank investor noted that the case was compelling enough that he wanted to follow up on the student's outcome. However, he acknowledged:

"We tried to find out what the outcome was because it was such a great story. I wanted to do a case of it."

O'Leary highlighted the importance of being around people who are supportive and comprehend the entrepreneurial process. He clarified that entrepreneurs need to find partners who appreciate and value their efforts, as this eventually leads to personal freedom.

While he did not confirm the final decision made by the student, he concluded that the entrepreneur likely continued on a successful trajectory.

"I think he didn’t marry her. He was wildly successful," O'Leary stated.

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