Dr. Phil McGraw built a media career giving blunt relationship advice on daytime television. Kevin O’Leary built his public brand giving blunt business advice on “Shark Tank.”
So which one told a young entrepreneur that his girlfriend might be easier to replace than a $5 million business?
It was, of course, O’Leary during a 2022 podcast interview. It is hard to imagine Dr. Phil reducing affairs of the heart to money in quite that way.
What exactly did Kevin O’Leary say?
During a June 28, 2022, appearance on the podcast “Impaulsive with Logan Paul,” O’Leary recalled teaching a night class for graduating engineering students.
According to O’Leary, one student said he had built a cloud business from his dorm room. The business, he said, provided compliance software for hedge funds with less than $250 million in assets and generated about $5 million a year in free cash flow.
The student also said his fiancee was threatening to leave because he was not spending enough time with her or her family.
O’Leary claims his response was: “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 then suggested that if the student could not work it out, he would “do just fine.” Presumably, he was talking about the relationship not working out.
The student’s story itself remains unverified. There is no public evidence confirming that the student existed, that the business generated $5 million in annual free cash flow, or that the classroom discussion unfolded exactly as O’Leary described.
Is it relationship or money advice?
O’Leary’s point was not that a high-earning business is more valuable than a relationship. He was arguing that the student had already built something rare: a profitable company, before graduation, in a niche market with wealthy clients.
For O’Leary, the question was whether the student should risk that momentum for a relationship that might not fit the demands of the business.
The money question is not whether a business matters more than a partner. It is whether both partners are on board with the sacrifices required to build it.
Does building wealth mean making trade-offs?
O’Leary has long argued that financial success rarely comes without sacrifice. Whether it is starting a business, paying off debt or building an investment portfolio, reaching long-term goals often requires giving up something in the short term.
That does not mean neglecting relationships. It does mean recognizing that time, like money, is a limited resource. Every hour spent growing a business is an hour not spent somewhere else.
You don’t have to give up your girlfriend
Most people are not choosing between true love and a multimillion-dollar business. But almost everyone has to decide how much time, effort and help they are willing to put toward building wealth.
If managing investments is not your strength, working with a financial advisor could be worth considering. A Vanguard study found that advisor guidance may add about 3% in net returns over time, though results vary.
Kapitalwise matches investors with fiduciary advisors who build around their goals. It is designed for serious investors with $100,000 or more in investable assets. Claim your free advisor match now.
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