The Emperor's New Watches: Kevin O'Leary's Rolex Obsession Reveals a Deeper Truth Kevin O'Leary, the self made billionaire and Shark Tank investor, has built a reputation as a no nonsense advocate for disciplined investing.
However, his recent confession about weeping over a rare Rolex Daytona may raise more questions than it answers about the allure of luxury watches as an investment asset class.
In a 2023 interview, O'Leary recounted how he "got on my knees and begged" for one of the most coveted timepieces in the world.