Kevin “Mr. Wonderful” O’Leary, the high-flying investor of Shark Tank fame, is known for his impeccable grooming. He shows up on every episode looking meticulously dapper in a tailored suit, trademark red tie and matching pocket square, gleaming collar pin and gold cuff links. So it stands to reason that he would also be wearing a luxury watch.
His choice for Season 13 was a rare “Eye of the Tiger” Rolex Daytona, with a diamond-encrusted tiger-striped pattern on the dial and a diamond bezel. The entrepreneur is known to own an extensive collection, so when Robb Report caught up with O’Leary during Dubai Watch Week last November, we pressed him on his latest acquisitions.
The business mogul is, however, cagey about his collection. O’Leary won’t say how many watches he has anymore, because he’s been robbed, twice, but he will reveal that he wears three different watches every day. And his watches travel solo—he has them shipped ahead to his destination where they will be waiting for him upon arrival in a hotel safe.
When we sat down with O’Leary, he had traded his tailored suit and tie for a kaftah, the traditional white cotton robe worn by men in the UAE. He’s wearing it partly in honor of having just received his UAE citizenship that day (his mother is of Lebanese descent), and partly because it’s the best way to dress in the extreme heat—in Dubai, it qualifies as acceptable business attire. On his wrist was number 18 of a 71-piece limited-edition Montblanc Star Legacy Orbus Terrarum world timer created for the Middle East to celebrate the 50th anniversary of the UAE’s formation in 1971. “It’s going to look like Christmas when I put a red band on it,” he says of the green-dialed watch. O’Leary has a thing for red wristbands because they match his signature tie and pocket square and, naturally, they are eye-catching on TV.
“I pull three or four watches per day,” he says. “I know it sounds eccentric, but that’s what collecting is.” On that day, his choice for the morning was an iconic status watch: a steel Rolex Daytona with a white dial. For the party later that evening, he donned an F.P. Journe Chronomètre à Résonance, one of several Journes in his collection. “These have appreciated like crazy,“ he comments. “He doesn’t make them anymore. That’s the thing about Journe, he gets passionate about one and then produces it, and then he gets passionate about something else and moves on to that. Drives you crazy.”
O’Leary’s Journe journey began several years ago when, as he puts it, “a good friend of mine, a minister in Dubai, and one of the world’s largest collectors, saw an Instagram post I did mentioning I was in NYC. He called me and told me about an F.P. Journe event that I should go to, and that he could get me an invite. I said who the hell is F.P. Journe? He said ‘Oh, it’s a brand you never heard of but you will. Let me make a phone call. You should go there and look at the collection.” So I went to the boutique and I met him, and I met Pierre [Halimi, his business manager] and they showed me the Centgraphe Souverain, and I said ‘that watch was made for me.’ I realized after a while, since he makes so few of them, that it wasn’t going to be easy to get one. I said, ‘How many Journe watches do I have to own to get this?'” Shortly thereafter, he was a proud owner of four F.P. Journe watches.
That may sound excessive, but unlike most collectors, O’Leary is not coy about acknowledging that at least part of his agenda is the investment. “Collectors are allocating capital to their watches. It’s a better investment than a house. Put a watch in a bank vault for two years, and there’s no maintenance, the roof doesn’t leak, the pipes don’t burst, there are no taxes, and it goes up 30 percent,” says O’Leary. “It’s way better than a house. It’s way better than a lot of things.”
But he also recognizes the hobby as a serious commitment and there is some sentimental motivation. “I didn’t do it for money,” he says later in an apparent reconsideration of his motives. “I did it because of my stepfather. He worked for the ILO (International Labour Organization) in Geneva, and he used to walk me through the city’s boutiques and show me the Patek Philippes, the Rolexes, the Omegas.” His first watch was an Omega Moonwatch from 1975. But these days, he’s in love with his new Ming, an independent brand that “got hot overnight,” says O’Leary. “The floating dials are stunning. I’m a dial guy so when I saw the Ming, I said okay, I need to have that in my collection.”
Although O’Leary has amassed a portfolio of over 50 companies that he has invested in, he has never invested in a watch brand. “I’ve thought about it but I’ll tell you what I’m worried about. If I invest in one company, will the others support my habit? Right now, I get access to incredible pieces, because I’m neutral. I’m Switzerland; I support all the brands. Also—you don’t have to invest in a watch company to make money off their watches. You just have to buy the watches.”
He also stresses that he buys watches because of the culture surrounding them. “The watch market is the most fascinating market in the world,” says O’Leary. “It’s got the passion, it’s got the people, it’s got the artists, it’s got the technical side of it and it’s got these crazy collectors. I travel quite a bit and the common language with people I meet is always watches. You meet the most incredible people.”
Those closest to him aren’t always so interested in his obsession. “Linda thinks I’m insane,” says O’Leary of his wife. “It’s to the point where now I have to hide them. She said, “You have to stop. I’m going to get someone to work on you. You’re broken, there’s something wrong with you.’ She once called Paul [Boutros, head of the Americas for Phillips in Association with Bacs & Russo] and said, ‘I need to keep your number handy because if Kevin gets run over by a truck, I’m going to need to sell some of this stuff.’”
Now you know where they’ll end up should you want to get your hand’s on a timepiece from O’Leary’s vault…but if you believe in his business acumen, you might be paying significantly more for it than he did.