It’s still all about the people! Nothing makes me happier than getting together and talking watches with old friends and new acquaintances, and this past autumn it was a pleasure meeting and chatting with entrepreneur, television personality, and enthusiast collector Kevin O’Leary at the F.P. Journe New York Boutique anniversary dinner.

O’Leary made his first fortune in the educational software business and has founded a number of other businesses including private equity and fund management ventures, but is perhaps best known as a panelist on the popular television series “Shark Tank.”

In the hit TV show, he and fellow investors evaluate – and sometimes buy stakes in – the businesses of aspiring founders. Part of O’Leary’s on-screen persona is his practice of wearing a different watch from his collection each week, always with a signature red strap tailored to the piece.

Two watches from Kevin O’Leary’s collection: Audemars Piguet Royal Oak and Patek Philippe Nautilus (photo courtesy Kevin O’Leary)

With the kind assistance of Quill & Pad contributor and watch pal Nick Gould, I was able to schedule an in-depth discussion with O’Leary; our far-ranging conversation covered topics, from his origins as a collector, to how he selects watches and who pays for them, to advice for others as they build their own collections.

First things first: in conversation

GaryG (GG): Let’s get started! What watch are you wearing today?

Kevin O’Leary (KO): Today I’m wearing the Vacheron Constantin Overseas blue-dial watch that I recently purchased with a red band that they made for me. It’s a spectacular watch for television!

Vacheron Constantin Overseas with blue dial

I’ve known Vacheron since I was 14, though I’d never included them in my collection. But when I recently saw the blue-dialed Overseas in person, I knew I needed to add a “third horseman” to my Audemars Piguet Royal Oak Jumbo and Patek Philippe Nautilus 5711/1A.

GG: I don’t think we’ve seen that Nautilus on TV, have we?

KO: I have what on TV is called a continuity challenge! I’ve been wearing watches with red bands on television for the past 11 years, and despite several attempts I haven’t found any way of fitting a Patek Philippe red band to that watch so it’s just not going to happen.

But by tonight I’m probably going to switch! I believe that the soul of a watch is kept alive by wearing it, and I often wear three different watches in a day. Tonight it will probably be a gold Grand Seiko maki-e dial watch with red urushi lacquer that I’ve been enjoying lately.

I love Grand Seiko and I think it is probably the most underappreciated watch brand in the market right now.

Underappreciated, but not by Mr. Wonderful: Grand Seiko Elegance Collection (image courtesy Grand Seiko)

GG: When you are looking in the safe in the morning, how do you decide which pieces to wear that day or take on the road?

KO: The first thing is deciding whether to go with steel or gold; I’ll pick out the right cufflinks and tie pin accordingly to match the case. When I travel, I’ll usually take two gold and one steel watch with me and a variety of matching accoutrements.

On my current trip, my other gold watch is a controversial one, but an amazing piece: the Audemars Piguet Code 11.59 Perpetual Calendar, one of 100 made in the first year of production.

I think that the Code 11.59 Perpetual Calendar with the aventurine dial is going to be the first one of the Code line to really take off; we have to remember that in the 1970s the Royal Oak was not well received when it first came out, and yet look at it today. Social media doesn’t tell the story when a new line is launched; it’s the views of collectors and people wearing them that matter.

Kevin O’Leary’s choice: Code 11.59 Perpetual Calendar from Audemars Piguet (photo courtesy MichaelH)

GG: Collectors obviously have different preferences when they buy; for some it’s primarily about aesthetics, for others mechanical interest, and for some it’s about brand or exclusivity. What really matters to you?

KO: I really start with the dial. It’s one reason that I was really drawn to the watches of F.P. Journe when I discovered them recently; I bought four watches in one day, which I’d never done before.

The amazing color of the dial on the Chronomètre Bleu and the combination of colors on the New York Boutique Anniversary limited edition were the basis of my negotiation with them to acquire those watches; I even tried to buy the boutique manager’s Chronomètre Bleu right off her wrist!

GG: You do seem to have taken to F.P. Journe!

KO: Well, you know how I feel about Journe’s watches; but the main thing is that it’s a crazy group of people that I want to be a part of. And their dial and case factory is the most insane place in the world.

I took my father there, and we couldn’t believe the amount of effort – and the reject rate – that goes into making those gorgeous blue dials. The Chronomètre Bleu is one of the greatest watches for television; depending on the light, the dial can look like anything from bright blue to black.

F.P. Journe Chronomètre Bleu (image courtesy F.P. Journe)

Rewinding the time machine

GG: Let’s go back in time a bit to your origins with watches. You spent much of your youth in Switzerland, but not all Swiss are watch lovers! Was there a pivotal event or important watch that started your love affair?

KO: I’ve been a science enthusiast since my youth, and when the Omega Moonwatch came to market it was the watch that I coveted the most. I still own a 1970s Speedmaster, and that’s the piece that got me into watch collecting.

I couldn’t afford the expensive watches of the time but I could still learn, and I immersed myself in the products of the various maisons. I loved visiting the Patek Philippe Museum as frequently as I could, and every weekend I would be in the watch stores seeing what was new.

It was frustrating to want the watches and not have the capital to buy them, of course. When young people on my staff and the entrepreneurs I meet ask me about which watches to consider my immediate question is, “Are you sure you want to catch this disease? This is going to be a big problem.”

Kevin O’Leary wearing a Panerai with one of his trademark red straps (photo courtesy ABC/Beth Dubber)

When to buy and whether to sell 

KO: My practice for a long time, and what I advise young collectors to do, is to buy watches as a celebration of a liquidity event. It’s an expensive hobby, and while many, many collectors say that they are going to buy and trade, in reality they mostly end up building up their collections without selling. They’re hard to part with, especially if they are hard-to-get pieces.

GG: Do you ever sell?

KO: No, among other reasons as a sign of respect for my relationships with the brands and their CEOs. I do buy some watches and present them as gifts to my companies’ CEOs, but I’m completely transparent about it and even bring the recipients to the store to have the papers executed in their names and bracelets sized.

And when I give a watch, the requirement is that the new owner isn’t allowed to sell it or give it to someone else! You’d be amazed at how many young entrepreneurs want to get their hands on a steel, white-faced Rolex Daytona when they could have anything – I totally respect that, but once I give the watch as a memento of our deal, I expect that it will be kept.

If he gives it, you keep it: Kevin O’Leary’s Rolex Daytona with matching accessories (photo courtesy Kevin O’Leary)

Lure and allure of exclusivity

GG: What is it that draws you to watches, like the Journes we discussed earlier, that are hard to get?

KO: To me, that’s the journey of watch collecting. As I mentioned, for me it all starts with the dial; and if there’s a unique dial I see that will capture attention and start a conversation it really intrigues me. I really enjoy it when a watch leads to a conversation between two people, either because the other person is knowledgeable or because they’re curious and eager to learn more.

When it comes to getting access to special watches from a brand, it comes down to one thing: either they believe I’d be a good ambassador for their brand or they don’t. Some don’t, and I totally respect that!

But when I start collecting a brand I buy several watches, and the watches I wear on television are seen by tens of millions of people. I think I’m a pretty good advocate for brands and the organizations and cultures behind them; if a brand wants the advocacy that I can bring, I want access to the pieces that I personally love.

Special access: F.P. Journe New York Boutique Anniversary Centigraphe, one of 10 made

KO: I will not accept a watch for free! I want to buy it; I don’t want to owe anybody anything, I want to pay what everybody else pays. People ask me all the time, “Did you get that watch for free?” If anyone wants to see the invoices, I have them.

Lure of independents

GG: Other than F.P. Journe, are there additional independents getting your attention?

KO: A collector friend of mine from the Emirates has been introducing me to H. Moser and Cie. The pieces are interesting and very modern looking; the fumé dial in red – or blue – could be very appealing onscreen.

I showed a few of them to the head of our wardrobe department, and she was really intrigued. The camera sees things differently than the eye: the dials of many of the Moser watches are big pieces of real estate, but often that’s what you want.

I’ll be interested to talk with Moser’s CEO Edouard Meylan to learn more about the brand. One of the things I love most about the journey of collecting is meeting these creators who have horology in their blood. I appreciate their stories and really enjoy celebrating them to a large audience.

It seems that the independents have the freedom to do things with the dial of the watch that some of the big guys won’t, and I can see myself moving more toward independents as I learn more. And I’m not worried about whether the small makers can survive; even in the face of industry consolidation, as long as a small maker focuses on quality and uniqueness in building a brand and establishes credibility with collectors they will be around for a long time.

Object of interest: Endeavour Centre Seconds Blue Lagoon by H. Moser et Cie.

Kevin O’Leary’s watch buddies

GG: Tell me about your community of watch friends – how does that work?

KO: I have contacts in the financial community around the world and travel frequently to see them. Then it’s back to the watch dial: someone will notice my watch and say, “Hey, I’m a collector too!”

Sometimes clients are just beginning their journeys in collecting and they’ll send me photos of watches they’ve just bought or are considering. Wherever I am in the world, it’s easy to find friends who will go down the rabbit hole of watch conversation with me.

Sometimes I can help friends to avoid making mistakes in terms of collectability; often they want to buy a whole lot of commodity production watches and that’s fine if they just want daily watches to wear. But if your goal is to build a collection you need to listen to other collectors who have more experience than you have. I’ve always listened to other collectors; I certainly don’t assume I know everything.

Vintage watches and patronage

KO: Some collectors go really deep on one brand, particularly in the vintage world; vintage Rolex for instance. My collection is much more diverse: if you were to see all of the watches in one place you’d immediately notice that not one looks much like another.

I do have a few vintage pieces, but for me it’s much more interesting to talk with watchmakers and companies and ask, “What’s next? What do you have coming down the line?”

GG: Your collection does seem to be much more focused on contemporary pieces; how important is the concept of patronage of living watchmakers and the watchmaking arts to you?

KO: I want to support the entire industry. I support my authorized dealers; I support the watch companies and watchmakers. I will buy direct if I have to, but I prefer to buy through the established dealer network.

As an established customer of Audemars Piguet, I wanted to support the launch of the Code 11.59 from the start, and they responded by customizing a red band for me and expediting shipment of the watch to me in time for my next filming session.

I love being in on the first round of a new direction!

Switzerland vs. Germany

GG: Speaking of being in on the first round, I just took delivery of one of the first examples of the new A. Lange & Söhne Odysseus.

Leading edge: the author’s A. Lange & Söhne Odysseus

KO: Oh, I love that thing! There are some guys who say, “Well, Lange’s not Swiss . . .”

And I say who cares? I can’t believe that sort of snobbishness exists among collectors, but I hear it all the time. The Lange style, and German watchmaking overall, has a distinctive character that’s all its own and makes it very interesting.

Looking to the future

KO: In today’s world, if you want to wear a piece of consumer electronics on your wrist, you can go ahead; but I’m never going to wear one of those watches – ever! I’m going to be collecting for the rest of my life. If others don’t get it, they don’t get it and that’s fine, but I’m not worried about the future of the industry.

Ready for prime time: Kevin O’Leary with his Rolex Daytona (photo courtesy ABS-CBN News/Nadia Trinidad)

GG: What’s the one piece of advice that you would give to your fellow collectors?

KO: Diversify! I really find that many people go too far into one brand – to me that’s not collecting. Collecting is about diversification and appreciating the art of watchmaking and the different artists that make different kinds of watches. If you’re a real art collector, you don’t just buy the work of one artist.

If your first three watches are from one maker, your fourth can’t be – just can’t be!

GG: Many thanks for your time and your insights, Kevin. It’s been good fun talking with you.

KO: See you soon in Geneva!

Quick Facts Grand Seiko Elegance Collection Ref. SBGK002
Case: 39 x 11.6 mm, pink gold; dual-curved sapphire crystal with anti-reflective coating; display back, screw-down crown
Dial: curved with Suki-urushi lacquer over a Mt. Iwake pattern; markers with maki-e lacquer and gold powder finishing by Mr. Isshu Tamura
Movement: manually wound Caliber 9S63; 72-hour power reserve; 4 Hz/28,800 vph frequency; accuracy +5 to -3 seconds per day (when static)
Functions: hours, minutes, subsidiary seconds; power reserve
Limitation: 150 pieces
Price: €31,400/$29,000
Production year: March 2019

* This article was first published February 8, 2019 at Collector Conversations: Shark Tank’s ‘Mr. Wonderful,’ Kevin O’Leary, Reveals Watch Collecting Philosophy To GaryG.

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