When it comes to wristwear, most people are satisfied with one good watch. Kevin O’Leary, the investor, Shark Tank star, and outspoken business mogul known as “Mr. Wonderful,” is not most people.

In a recent interview with Brew Markets, O’Leary revealed that he doesn’t just collect watches  — he lives them. “This is what I'm going to wear in the next two days,” he said, gesturing to a sleek travel box containing 10 timepieces. “I wear six pieces a day. Two in the morning, two at lunch,” then presumably two in the evening. 

Let that sink in.

The Daily Watch Ritual

While others might rotate a favorite Rolex or Omega throughout the year, O’Leary rotates six watches — daily. His practice isn’t about showing off wealth (at least not entirely), but about maximizing exposure to the vast and often personal stories his collection tells.

Each day is a carefully orchestrated display of horological storytelling. He begins his morning with two watches, changes to a new pair at lunch, and finishes the day with yet another duo. For O’Leary, the extensive watch wardrobe changes aren’t just indulgence; they’re a ritual.

And as the interview went on, he explained his reasoning for this peculiar ritual and how he chooses which watch to wear on each side. 

The Watches Themselves

The Brew Markets interview gave us a close-up of what that six-a-day regime looks like for Mr. Wonderful:

• A 1950s Patek Philippe that’s set to appear in the upcoming movie Marty Supreme (in which O’Leary has a role).
• A vintage Seiko with its own screen time.
• A one-of-a-kind F.P.Journe Souveraine vertical tourbillon with a red “K” replacing the 12 — a nod to his first initial.
• A Rolex Daytona made from meteorite, one of the rarest versions of an already elusive icon.
• A Patek 175th anniversary world timer, a holy grail piece for collectors.
• A custom Tudor made of silver with the Shark Tank logo, created specifically for O’Leary.
• And several experimental Tudors in carbon and ceramic — pieces that play with material innovation in a way Rolex never has.

It’s a lineup that even seasoned collectors would envy, and one that suggests O’Leary isn’t just a watch guy — he’s a curator of mechanical art. The watches Kevin O’Leary showcased in his Brew Markets interview represent some of the rarest and most coveted timepieces in the horological world.

In fact, the watches revealed during his Brew Markets interview represent a staggering level of horological prestige, with a combined estimated value between $659,000 and $1.2 million. 

Among them, the vintage 1950s Patek Philippe is likely worth between $80,000 and $150,000, while the screen-worn Seiko, although modest in origin, could command $5,000–$10,000 due to its film role. And his unique vertical tourbillon, featuring a red “K” at the 12, is a true one-of-one creation, estimated conservatively at over $500,000. 

The meteorite Rolex Daytona adds another $100,000 or more in value, while the rare Patek 175th Anniversary World Timer is known to fetch over $125,000. The one-of-a-kind Shark Tank Tudor brings an estimated $20,000–$40,000, and his experimental ceramic and carbon Tudors, while more accessible, still contribute another $10,000–$20,000, depending on edition and rarity. 

Together, the eye-catching collection is a high-value testament to O’Leary’s deep dive into the world of luxury timekeeping. Those are just some of the highlights, but in total, the small collection he brought with him for just two days likely fetches close to $1 million. 

The Power Play of Wearing Two at Once

If you’ve seen O’Leary on Shark Tank, you’ve probably noticed the quirk: he always wears a watch on each wrist, almost always with a red band. It’s become part of his visual identity, almost like Steve Jobs' black turtleneck or Zuckerberg’s hoodie. But in this interview, he takes it a step further — not only does he wear two at once, he cycles through six watches a day.

It’s the kind of excess that could come off as absurd, but from O’Leary, it lands with conviction. He wears these watches like armor — symbols of craftsmanship, rarity, and sometimes even cinematic prestige.