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‘You’re Becoming a Watch A**hole’: Why Kevin O’Leary Went From Wearing One-Of-A-Kind Watches to ‘Inspiring Young People’

Equities

Caleb Naysmith

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August 9, 2025

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Barchart

In a candid and surprisingly self-aware moment during a recent Brew Markets interview, O’Leary recalled a confrontation on the Shark Tank set that permanently changed how he thinks about watches — and the message he sends by wearing them.

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