That Really Ruins Thanksgiving Dinner' – Here's Why Kevin O'Leary Has A Tough But Fair And Generous Policy When Family Asks Him For Money

When family asks for financial help, things can quickly get awkward. Kevin O’Leary, the famous entrepreneur from Shark Tank, has learned from experience that mixing family and money is a slippery slope. To avoid tension and protect relationships, O’Leary has developed a simple, tough, but generous policy that balances helping out and setting boundaries. Here’s why it works.

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The Problem With Lending Money to Family

O’Leary thinks that money gives you freedom but can also complicate things, especially when family members ask for it. “A lot of people want some of it from you for free,” he says, noting that family can put you in a tricky situation by asking for financial help, like to start a business or cover personal expenses. 

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For example, if a family member asks for $150,000 to open a restaurant, O’Leary doesn't want to get caught in a business partnership that could strain the relationship. As he puts it, "That really ruins Thanksgiving dinner."

The One-Time Gift Rule

Instead of lending money or investing in a family member's venture, O’Leary offers a one-time gift. If a relative asks him for money, he’ll give them a portion of what they need, say $50,000, as a gift. 

There's just one catch: it's a gift with a clear condition. The relative can never ask him for money again – ever. In his own words, “Never ask me for money again ever ever. You never come to me again for money and we never talk about this again, ever.”

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It's not a loan, and O’Leary clearly says he doesn't want the money back.

Instead of saying “no” to his family, he offers what he feels comfortable giving and prevents future conflicts or financial entanglements that could create long-term resentment.

O’Leary draws a firm line between helping and overextending himself by offering a one-time gift. This lets him support family without being dragged into potentially risky ventures, like a failing restaurant or other business ideas. And by setting the rule that money won't be discussed again, he keeps family gatherings about family, not finances.

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O’Leary’s approach to handling family requests for money ties into his overall philosophy on smart money management. He's all about making wise investments and being careful with your spending.

“You can live off half a million bucks in the bank and do nothing else to make money,” O’Leary said. “Do not invest in your brother’s bar. Or a bowling alley, or a bar, or all that other crap, you’ll lose your money.”

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