Apr 1, 2026
When wealth accumulates, so does the ask. In an interview on the Fifth Column with Michael Moynihan, Montreal-born businessman and Dragons' Den and Shark Tank personality Kevin O'Leary was candid about one of the most uncomfortable realities of financial success (1). One of the "worst parts about being a rich guy," he said, was "your own family hitting on you for money."
O'Leary admitted he made several early missteps when handling money requests from family members before eventually finding what he calls "a path to success." His solution is simple, firm and, by his account, highly effective: it's a one-time-only gift. The money is offered with a clear understanding that all future requests will be declined.
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It's a blunt strategy. But as O'Leary has framed it, it's also a compassionate one — it draws a firm line, closes a door that might otherwise stay perpetually open, and removes the ambiguity that often poisons these financial arrangements.
And this problem isn't limited to the ultra-wealthy — everyday Canadians can learn a thing or two.
Hidden costs of 'helping' loved ones
You don't need a private jet or a television deal for family members to start viewing you as a resource. Across the income spectrum, many Canadians face the same uncomfortable situation: a relative or close friend in need, a genuine desire to help and the growing risk that lending money could damage — or even destroy — the relationship.
The financial stakes are real. A 2025 survey conducted by Fig, in partnership with the Angus Reid Forum, found that 84% of Canadians currently carry debt and that financial stress is now deeply entangled with mental health and personal relationships (2). According to the same survey, 45% of Canadians say a single unexpected expense could throw their finances off course — leaving many one emergency away from asking someone they love for help.
The parent-child financial relationship is one of the most common fault lines. A 2024 survey by TD Bank Group found that nearly 3 in 5 Canadian parents (57%) expect to financially support their children after they reach adulthood (3) — even as two-thirds of those same parents say they're not very confident in their ability to do so. The top reasons: a belief that the future cost of living won't be manageable for their children, and the concern that their kids may not be able to afford a first home.
However, a written contract or verbal agreement may not be enough to capture all the nuances of a financial arrangement between loved ones. If you're thinking about lending money to a sibling or asking a parent to co-sign a loan, it may be worth pausing before you proceed.
And if you're struggling to set boundaries with a persistent relative or friend, O'Leary's one-time gift rule isn't the only tool available.
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How to set boundaries (without burning bridges)
Turning down a money request is genuinely hard — especially when the ask is sincere and the person inquiring means a great deal to you. Saying yes without conditions can enable a pattern of dependency. Saying no too bluntly risks real relational damage.
To find the right balance, personal finance expert Ramit Sethi — Netflix host of How to Get Rich and founder of I Will Teach You To Be Rich — offers a framework worth applying (4).
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His first recommendation: know your own numbers. Without a clear picture of your own budget, monthly cash flow and longer-term financial goals, it's dangerously easy to lend more than you can actually afford to lose. Once you have a clear snapshot of your finances, you can determine what, if anything, you can genuinely spare — without stretching yourself.
From there, Sethi recommends placing a firm ceiling on your generosity based on your personal situation. You might replicate O'Leary's one-time-only policy, set a fixed annual dollar amount you're willing to give across all requests, or decide that you'll only ever offer money as a gift — never a loan — so that repayment never becomes a source of resentment.
If a loan is unavoidable, document it. Put the terms in writing: the amount, a repayment schedule and what happens if payments stop. It may feel overly formal between people who trust each other, but the formality is precisely what protects that trust.
For requests that cross a line — ones that feel uncomfortable or lay beyond what you can responsibly provide — Sethi is direct: practise saying no, and say it firmly. Clear communication about your limits, delivered with care, is far healthier in the long run than grudging compliance that breeds quiet resentment.
Finally, consider whether financial help is even the right kind of support. Offering to review someone's budget, connecting them with a financial counsellor, or helping them research debt management resources can be far more valuable than writing a cheque — and far less likely to cost you the relationship.
Setting financial boundaries isn't about withholding care. It's about making sure your generosity doesn't come at the cost of your own financial stability — or the health of the relationship itself.
Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
The Fifth Column (1); GlobeNewswire (2); TD Bank Group (3); I Will Teach You To Be Rich (4)
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Vishesh Raisinghani is a financial journalist covering personal finance, investing and the global economy. He is the founder of Sharpe Ascension Inc., a content marketing agency focused on investment firms His work has appeared in Money.ca, Moneywise, Yahoo Finance!, Motley Fool, Seeking Alpha, Mergers & Acquisitions Magazine, National Post, Financial Post and Piggybank. He frequently covers subjects ranging from retirement planning and stock market strategy to private credit and real estate, blending data-driven insights with practical advice for individuals and families.
