Kevin O’Leary explains that instead of investing in family members’ businesses, he’s giving away cash with a caveat

Kevin O’Leary, a renowned investor known for his no-nonsense approach to business, has a unique strategy for dealing with family members who ask him for money. He’s had relatives come to him with big ideas and high hopes, looking for a solid investment. And given O’Leary’s financial situation, it’s not surprising. The Canadian business owner and Shark Tank star has a net worth of approximately $400 million.

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But while he is generous, he also has limits that help prevent family and finances from colliding. In a short YouTube video, O’Leary explained his actions when family members ask him for money. He recognizes the old truth: “More money, more problems.” O’Leary says: “It’s a fantastic thing because it gives you freedom, but it complicates your life because a lot of people want a piece of it for free from you – especially family members. This is a huge problem.”

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O’Leary makes it clear that people come to expect something for nothing just because you have money. And to deal with that, he’s developed a simple method that keeps things straight and avoids awkward Thanksgiving dinners.

When a family member approaches him for money—whether it’s starting a restaurant or launching a new business—he gives them a unique gift. In the case he mentions, it is $50,000. Not a loan, not an investment, just a gift. But there’s a catch: “Don’t ever ask me for money again. Never”. O’Leary’s rule is simple: after that check, there will be no more paperwork, no more future expectations, and no more financial problems. As he humorously adds, he hands over the money and then “goes back to grinding eggs.” It’s a clean break that leaves no room for future financial disputes or awkward family interactions.

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For those without a portfolio like O’Leary’s, his approach still offers a valuable lesson. Setting clear boundaries is crucial when lending or giving money to your family. It’s easy to get caught up in the emotions and obligations that come with helping loved ones, but things can get messy without clear rules. A good approach for the rest of us might be to only give what we can afford to lose—whether it’s $50, $500, or $5,000—and make it clear that it’s a one-time deal. No loans, no strings attached, no awkward family gatherings.

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Managing family and money can be difficult, but O’Leary’s approach shows that it’s all about setting expectations and meeting them. And maybe, just maybe, it’s also about having a little humor to keep things from getting too tense.

It’s always smart to consult with a financial advisor before making any big decisions, especially when family is involved. They can help you determine what makes the most sense for your situation and set appropriate boundaries. It’s not just about money, it’s about keeping relationships intact while making choices that work for everyone. A little guidance can go a long way in ensuring that your finances and family ties stay strong.

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This article ‘Never ask me for money again’: Kevin O’Leary explains that instead of investing in family members’ businesses, he’s giving away cash with a caveat originally appeared on Benzinga.com

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