Canadian businessman and Shark Tank star Kevin O’Leary has secured a significant legal victory in a Florida federal court, being awarded $2.8 million (CAD $3.9 million) in a defamation lawsuit against former cryptocurrency influencer Ben Armstrong, known online as “BitBoy.”
The ruling, finalized on 16 February 2026, concludes a high-profile legal battle sparked by Armstrong’s false allegations against O’Leary, which included doxxing and unfounded claims of criminal activity. The judge’s decision included damages for emotional distress and punitive measures, marking a major win for the investor often referred to as “Mr. Wonderful.”
Financial Strategy and Retirement Advice
Beyond the courtroom, O’Leary has been active on the financial circuit this week, promoting a series of aggressive wealth-building strategies aimed at both young investors and those nearing retirement. His latest “rules for riches” have sparked debate across social media and financial news platforms:
- The $100 Weekly Rule: O’Leary asserts that consistently investing $100 per week in a diversified stock index can make the average worker a millionaire by retirement through the power of compound interest.
- The $500,000 Retirement Threshold: He recently claimed that Canadians can retire on $500,000, provided they follow a strict rule of achieving a steady 5% return from safe assets and avoid dipping into the principal.
- The “Sandwich” Critique: In a viral segment, O’Leary lambasted the habit of buying $15 lunches, stating, “What are you, an idiot?” He noted that a home-made sandwich costs approximately 99 cents, and the savings should be diverted into the market.
- Separate Marital Finances: O’Leary continues to draw mixed reactions for his staunch advocacy of prenuptial agreements and maintaining separate bank accounts from spouses, a view recently challenged by hosts of The Ramsey Show.
Housing and Political Advocacy
O’Leary also took his expertise to Washington recently, testifying before the House Financial Services Committee regarding housing affordability. He addressed the rising costs of real estate and the impact of interest rates on the “American and Canadian Dream” of homeownership. Meanwhile, his outspoken nature continues to draw fire from the entertainment world; actor Mark Ruffalo recently criticised O’Leary’s public stance on celebrity political advocacy, following O’Leary’s comments regarding Billie Eilish.
Born in Montreal, Quebec, O’Leary remains one of Canada’s most recognisable exports in the world of venture capital. Despite the conclusion of his 2017 bid for the leadership of the Conservative Party of Canada, he remains a frequent commentator on Canadian fiscal policy and global market trends.