Kevin O’Leary is many things: investor, entrepreneur, media personality, and unapologetic luxury connoisseur. But “Mr. Wonderful” isn’t immune to a little soul-searching — even when it comes to the prized collection of timepieces that he wears strapped to both of his wrists.

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.

The Call-Out That Hit Hard

The story begins with what was likely just another day of filming for Shark Tank.

O’Leary, dressed in his usual sleek suit and dual-watch setup, was approached by one of the show's producers with unexpected feedback: “You know, Kevin, you're wearing these red bands. You've got two watches on all the time. It's your whole schtick. Everybody knows about it. But when people see you, you wear watches that no one can buy. Nobody can either afford it, or they just don't exist because they're one of a kind. So you're coming off as a watch a**hole.”

The words landed with weight. At first glance, it might sound like a throwaway jab — but O’Leary took it seriously. 

“It really hit me like a ton of bricks,” he admitted. “Because you should be inspiring young people to get into horology, not show them what they’ll never have.”

The Philosophy Shift: Two Wrists, Two Worlds

Since that moment, O’Leary has adopted a new approach to his signature style: “Ever since that day, on my left I wear a piece unique — something insane…. On this side though, is a ren, a watch you can buy for under $1,400.”

That subtle act of balance — pairing the ultra-rare with the accessible — became his way of inviting everyone into the world of watch collecting. On one wrist, he still sports the museum-grade marvels: meteorite Daytonas, one-off tourbillons, or custom Shark Tank Tudors. But on the other, he deliberately wears watches that young collectors, aspiring entrepreneurs, and everyday fans can find and afford.

This practice isn't about false modesty. It's about representation. It says, "You can get started in this world too."

A Lesson in Accessibility from the Pinnacle of Luxury

For a man whose public persona is built on wealth, power, and precision, O’Leary’s response to the “watch a**hole” critique is surprisingly humble. He didn’t double down on exclusivity. He opened a door.

It’s a moment that resonates beyond horology. In a culture obsessed with flexing, O’Leary’s adjustment sends a powerful signal: true leadership doesn’t just show what’s possible — it makes others believe they can get there too.

So yes, he’ll still wear six watches a day. He’ll still star in films where his watches have cameos (Marty Supreme, coming Christmas Day). And he’ll still drop phrases like “piece unique vertical tourbillon” without flinching.

But these days, one of those six watches will always be within reach — for someone just getting started.