The Master Collector: Kevin O’Leary On Time Being His Most Valuable Asset

MASTERING THE ART OF COLLECTING

With an unparalleled reputation in the watch industry, Kevin O’Leary has a relationship with watches that transcends far beyond the dial — as time is Mr. Wonderful’s most valuable asset.

BY ADRIENNE FAUROTE

PHOTOGRAPHY ALBERTO GONZALEZ

Kevin O’Leary’s passion for watches is palpable.

A brief digression: in mid-July, I connected with O’Leary a few weeks prior to our shoot to discuss the creative direction and story we wanted to tell. He was beaming with such enthusiasm about showing his watch collection in a new, fun way that for a moment, I thought he was going to burst through the phone. Fast forward to late August on our cover shoot with his beloved timepieces, and his passion practically became infectious. Being in this industry, it’s clear that some collectors and enthusiasts were just destined for it — and I quickly discovered O’Leary is one of those folks.

His aptitude for watchmaking is a part of his early upbringing. When O’Leary was just a teenager around 15 years old, he moved to the watch capital of the world, Geneva, Switzerland. It was there he discovered the biggest players in the industry, which sat along the streets lining Lac Léman (or Lake Geneva). “Lake Geneva is where the watchmakers were, and where they still are today,” O’Leary explains. “I took a fascination with watchmaking in Geneva, and at that time, in the late 60s, there were remarkable dials I was beginning to learn about, in addition to the history of watchmaking. I developed a passion for watches, realizing they are an unusual piece of art,” he recalls.

There is a hint of nostalgia in O’Leary’s voice, while he also reflects on his early days in Geneva so fondly — as if it were yesterday. “We were just getting a man to the moon around this time, and Omega launched the Speedmaster, which was a watch selected by NASA to be worn in space,” O’Leary says as he references his first-ever watch. And yes, that is the 1969 Speedmaster that made history when worn by Neil Armstrong and Buzz Aldrin on the moon.

The second watch to grace his collection proved to be a classic: the Rolex Submariner. “I was going down the classic route,” he remembers. “And some of these [early] pieces, I still have in my collection today. They are priceless to me, yet they have appreciated in value because they are vintage. And while I have collected so many watches since, these are so special to me because of what they meant and when they were made.”

Some years later, his passion — and collection — have only grown.

“When starting a collection, most people go down the so-called ‘three horsemen’ path, which consists of the three core brands of every collector’s collection: Audemars Piguet, Rolex, and Patek Philippe,” O’Leary explains. Indeed, these are the big three: think of the Patek Philippe World Time, the steel white-faced Daytona from Rolex, and the Audemars Piguet Royal Oak as your founding fathers, if you will. However, O’Leary came to a point in his collecting career where he had reached great heights in the classic category from these three industry pillars. He began to question where he would go next.

The answer was simple: dials. “I got captured in the dials. I wanted to get more diversification in dials because what you see on your wrist — and what starts the conversation — is the dial. And the thing is, Patek has a look, Audemars Piguet has a look, and Rolex has a look. Those are dials I can spot from 20 feet away. I wanted to explore new watchmakers and new dials. For example, the F.P.Journe dials are unmistakable,” he suggests with a smile spreading across his face.

There is no doubt O’Leary is in awe of ​​François-Paul of F.P.Journe and the meticulous craft with which he creates his dials. “People look at those dials and ask how I tell the time with them, and I say, ‘I don’t!’ I am wearing this as a piece of art. This is a dial you have never seen before and may never see again. It is no different from a piece of art — like a Picasso,” he adds.

Speaking of which, O’Leary’s collection is itself a true work of art. Teeming with both classics and timepieces that are synonymous with one-of-a-kind art masterpieces, some would say his collection is invaluable. “To me, [watches] are one of the most successful asset classes I have — compared to all of the other things I do in private equity, gold, crypto, stocks, and bonds. Nothing has beat my watch collection over the last five years,” he states with pride.

A proven expert in both watches and entrepreneurship, I do not doubt his claim. In fact, as an incredibly successful businessman and investor who spends his time as an original “shark” on Shark Tank, evaluating and investing in dynamic business proposals, his strategic thinking has infiltrated his keen eye and mindset in watches. Ultimately, he has mastered the minutia of collecting through his investment in watches — emotionally, physically, and beyond.

“The thing about collecting,” he starts to explain, “is people always ask me how I am getting these pieces. So, I think it is important to cover this topic for collectors who are just starting to understand how it works. The watch industry has not changed in 250 years. It has grown on the back of its collectors. Those who get into watches and spend a lifetime collecting are the backbone of the industry. And there are certain unwritten rules to follow,” O’Leary reveals.

“Watchmakers have to get to know you as a collector and know that you cover their work and support the art,” he continues. “For example, I am a member of the Horological Society of New York; I support watchmaking, and I am a patron of young watchmakers. But one thing I will never do is sell a watch. I never flip a watch. I never trade sideways,” he says with a stern level of confidence.

It’s true; O’Leary is a man of his word. He is so serious about his unwavering commitment to not selling, trading, or bartering any of his watches that he confesses they will likely go with him when he dies (lightheartedly, of course), as he will undoubtedly need them in his afterlife. As they say, watch enthusiasts are die-hards.

All jokes aside, O’Leary is not wrong; this is the golden rule of watch collecting. And once you earn the watchmaker’s trust, the fun can be had. “When I covet a piece, I let a brand know that a particular dial is of interest to me; however, I do not bug them or call them 40 times — I call once. At their election, they may eventually call me up one day and say they have that dial in North America, asking if I want to take it. My answer is always yes,” he admits.

You may be wondering if O’Leary is a ‘yes man’. He is. When he makes that phone call asking for that one specific model, he is good for it. He has made it to the point – and well beyond the mark — where he can have fun.

“Now, watchmakers hold me as an important collector and want to make one-of-a-kind pieces where we design together. That is truly where I am now, and I feel incredibly fortunate,” he explains. Case in point: most recently, Audemars Piguet delivered a one-of-a-kind watch to O’Leary, a steel Royal Oak circled in rubies that notoriously brought him to tears. “I cried when it arrived because I had worked on it for nearly two years; you cannot rush these things,” he says. And spoiler alert, the watch is set to be a major star in the upcoming season 15 of Shark Tank.

O’Leary then points to a rather interesting watch on set, the Chopard L.U.C Quattro Spirit 25 “Mexican Laughing Skull” – another one-of-a-kind watch he bought in December at the Paul Boutros auction with Phillips. “I bought that specifically for charity, knowing it never had an owner.” He pauses, then says playfully, “I was fortunate Claude Sfeir did not want it.”

Like Sfeir’s, O’Leary’s watches have seamlessly become a part of his identity.

“I wear 3 or 4 watches a day,” O’Leary admits — a rumor which I have heard, and am now glad to confirm. He starts his day with one watch, swaps it out at noon and in the afternoon, and then wears one final model at night. If he is going to an event in the evening, he is likely opting for something over-the-top. And while he is constantly keeping us on our toes with his wrist game, the one constant throughout his pieces is the red band.

“Ah, the red band,” O’Leary sighs. “I learned something over a decade ago: I showed up on the set of Good Morning America wearing a different-colored suit and tie than my normal white shirt, black suit, and red pocket square I wore every day on Shark Tank. I was wearing a blue suit and a yellow tie, and the producer, shocked, asked what I was doing. She then explained that on television, there’s the Q Score — people want you to know how they recognize you,” he explains.

“The same thing happened on Shark Tank. One year, when I did not wear the red band, the producer insisted on me wearing it, saying the show needed continuity. Now, I think I am well-known for the red band. I think most brands are now creating it, and I like to think I caused that,” O’Leary proudly admits. Now whether watchmakers loved the red band at first is up for debate, but the collector insists that if one can experiment with dials, why not the band? And to that we say, touché.

A trendsetter nonetheless, he is excited about where the industry is headed at this very moment. “I am excited that even the most conservative watch companies — like Rolex and Patek — are getting more creative with their dials. For instance, the Rolex Day-Date Puzzle Dial that just dropped this year is off the charts,” he says with his passion shining through his words again. “That watch came right out of left field, causing a massive controversy among collectors. They thought Rolex was out of its mind, but I think it’s a brilliant move, bringing excitement to a classic.”

Of course, O’Leary secured the Puzzle Dial — in yellow gold. He was on his way to pick it up in New York, following our cover shoot, joining Tom Brady and John Mayer, the other two to be allocated some of the first models. (Small disclosure, O’Leary does claim he thinks he secured his before both Brady and Mayer — healthy competition.)

His recent excitement within the industry continues. “When I look at what Jacob & Co. bring to the market — straight from outer space with some of the craziest designs — I realize there is a diverse range in dials now. It brings a raging debate between collectors and watchmakers on what is too aggressive or too conservative. But I think that this narrative is what has made collecting so fascinating in the last decade. It is all in the diversity of my dials,” O’Leary says.

Spending the morning with a snippet of his collection, there is no denying his dials are special. From the Rolex “Eye of the Tiger” Daytona and the F.P.Journe Chronomètre Bleu to the same Patek Philippe Aquanaut Luce “Rainbow” Messi was spotted wearing earlier this year, his repertoire is impressive. As I admired not only his collection, but his insane level of expertise and knowledge, I couldn’t help but ask “Mr. Wonderful” what his best piece of advice would be for collectors.

Without hesitation, he answers, “Never borrow money to buy a watch.” He preaches that a watch is not something you go into debt for. On the contrary, the reason you own a watch is because you have achieved an important life milestone. “You want to link your achievement to a dial so that for the rest of your life, when you wear that certain watch, you will remember why it is on your wrist and how you got there.” A sentiment both he and I share.

“As you work harder and get luckier in life, your collection will change alongside your success,” he explains. For new collectors, he suggests starting with the basics, suggesting a brand near to his heart, Grand Seiko.

“Grand Seiko has extraordinary quality for the price point it offers its pieces at, like the Superman. They are incredible pieces, with a polished look and beautiful dials. The Japanese don’t get enough credit for what they bring to the market through that brand,” he feels.

On set, another major callout for O’Leary is Credor. The ultimate “if you know, you know” brand for him, he admits that if most watches were rated a 10, a Credor would be an 11. “Winding a Credor, you know a master genius put it together; when I see another Credor, it’s like we have a mind link,” he says.

The mind-to-watch phenomenon is real. Some refer to it as the emotional link that is intrinsically wound into each watch, but the connection between the wearer and their watch is unmatched.

“When you match the dial to a moment in your life — a marriage, the birth of a child or a deal you closed — it’s a milestone. It becomes the milestone of where the watch comes from and why it was bought. Everything is crystallized into the timepiece,” O’Leary explains. And after speaking with him, I see he has a lot of milestones.

One of the most significant at this moment is still a work in progress. As Shark Tank has been on air for 15 years now, he and the team went back to the pilot, quickly realizing that there are 23 people still working on the show today who were there for the very first episode. To celebrate the 23 integral people behind the scenes of the show, O’Leary tapped Tudor to collaborate on a special timepiece.

“I approached Tudor as I was in awe of their use of rare materials. For example, they make a pure silver watch that I would wear on set and that the crew loved. I asked if they would consider making one-of-a-kind pieces with each person’s name engraved on the back and with the Shark Tank logo on the front, and they agreed.” O’Leary hinted that they would be going into production, and gift them this season. Taking it a step further, he will also auction with Phillips in December his silver Tudor watch as his annual Shark Tank auction piece, on the heels of his steel white-faced Daytona that sold at $65,000 last year.

With such a vast collection, I supposed it would be hard for O’Leary to pick just one favorite. Proving me right, he rattled off a few classics he simply could not live without like the Patek Ref. 5711, the Audemars Piguet Jumbo Royal Oak, and his F.P.Journe Chronomètre Bleu he wore during our interview. But watches that transcend into the mind-to-watch realm hold the most importance.

Thinking about his most prized possession as of late, O’Leary reveals that his happiness lies in the success of others. “I am most proud when a team that I have backed and have been working with for years has a great liquidity event. Last year, that happened with Shark Tank. Anna Skaya, the founder of the company Basepaws, sold to Zoetis Animal Health, a split-off of Pfizer. It was a huge win for all of us. That day, I decided to sit down at the F.P.Journe boutique in Miami and convince ​​François-Paul to make a one-of-a-kind Vertical Tourbillon on which the 12 hands would be replaced with a red K. That will forever be my Basepaws watch,” he says endearingly.

With season 15 of Shark Tank in full swing and a few other ventures in the queue (he teased a culinary endeavor on the horizon in Miami), we can’t wait to see which milestone he reaches next — in life… And on his wrist.