They say you can tell more than the time from a man’s watch. It’s no surprise, then, that Kevin O’Leary’s timepieces exude boldness and sophistication. Take, for example, the watch he’s wearing during this interview – a stunning F.P. Journe four-dial watch, number six of ten in the world. It’s a piece befitting one of this country’s most well-known and successful business exports.
But to call O’Leary a bold and sophisticated businessman is only half the story. He has a complex suite of interests, spanning the arts, music, cooking, wine-making and philanthropy. While the businessman seeks utility and efficiency, O’Leary waxes poetic about his watches: “The truth is, nobody needs a watch anymore, the best time piece you have is your phone, it gives you the perfect time in every jurisdiction, and geography in the world, and yet we still wear watches. Why is that? Well, for some of us, we’re celebrating the artistry of manufacturing these incredibly complex mechanical devices, which you have to dedicate your life to, which I find fascinating. It really goes to that idea of yin and yang. Why would you do that? Why would you do something that actually nobody needs? Because it’s art, and it’s beautiful, and it’s something people appreciate.”
Even so, O’Leary manages to find a commercial angle to his watch collection. Some of O’Leary’s best-performing investments have been watches from his collection. Like any collector, O’Leary’s challenge is finding the time to wear them all: “I have to wear three different watches every single day just to rotate through the collection, which I do. A morning watch, a lunch watch, and an evening watch.” I couldn’t help but wonder which watch he’d be wearing later that day, and whether it could possibly outdo his F.P. Journe.
Although O’Leary could make a fortune selling some of his most rare pieces, he is not interested in selling his collection. Rather, he has generously decided to merge two of his passions: fashion and philanthropy, by donating one of his beloved watches to One Drop Foundation, a global non-profit organization that was founded by one of O’Leary’s friends, Guy Laliberté. One of its aims is to ensure sustainable access to safe water for vulnerable communities around the world, “I don’t sell my collection and I don’t trade it. I’m not interested in buying watches that are very hard to get, and then selling them, that’s not of interest to me. But when I heard about “One Drop Foundation” – it interested me.” Along with O’Leary, Bono, and Prince Albert of Monaco are also amongst the men who are donating to the charity auction.
When O’Leary started thinking about which piece out of his collection would be best for the auction, it came down to one that he really did not want to let go of: The infamous Shark Tank Daytona. “It’s a Rolex Daytona, steel white-face Daytona on a red strap, that’s been on more episodes than any other watch on Shark Tank. I mean, it’s a legendary watch. Everybody knows the red watch-band story…I think it’s kind of a great story about this piece, and a great watch, beautiful watch, and also, a television legend.”
The “red watch-band” that O’Leary is referring to is his signature bold fashion accessory that draws even more attention to his incredible watches. The band is made by the Swiss company Rubber B. O’Leary is going into filming the twelfth season of Shark Tank, which means he is selecting his “Shark Tank 8,” which are eight watches that will rotate on and off of his wrist through Season 12, “I rotate through eight watches and they all have red bands, and so each year it’s a different eight, with the exception of that steel Daytona, which has pretty much been in every single episode of Shark Tank. If they [watch manufacturers] want me to buy one of their watches, they have to make me a customized red band so that I can wear them on television.” There is a practicality when it comes to wearing red bands on television. O’Leary decided in the early seasons of Shark Tank, circa season one and two, to standardize a “look” in order to cut the time that it takes to film outtakes. O’Leary’s signature crisp white shirt, black tie, and red band are what add to his Mr. Wonderful persona, “I’m very meticulous about what I wear. These are Deakin & Francis skull cufflinks. I work with them directly to make iconic pieces. My tiepin is silver or gold depending on what the dial of the watch is. Either I have gold or silver, accoutrements. I care about that stuff.”
If you thought O’Leary couldn’t become more cultured and multi-dimensional, his other interests reveal just how cosmopolitan he is. His other non-watch-related passions allowed him to escape from the business world even in the pre-pandemic days, “It takes my mind off the gruel of the challenge of business all day. I think it makes you more creative in business, so, I’m a big believer in that concept of yin and yang. A little craziness in the arts, and then discipline in business on the other side of the brain.” When O’Leary isn’t immaculately dressed up in his signature suit, he’s Chef Wonderful in the kitchen, wearing another type of crisp white shirt with the most unexpected pants: Vietnamese fishing pants. “I actually have a very large collection of Japanese fishing pants [aka Vietnamase fishing pants]. When I grew up, my dad worked in the United Nations, and we lived in Phnom Penh, Cambodia, where I learned how to cook Asian-French Fusion.” If you’re interested in seeing Chef Wonderful’s fashion ensemble, you can find him on QVC selling some of his pastries and his sous-vide meats, “I want to be comfortable, and so it’s a different fashion look completely. They are essentially day time pyjamas.”
One of O’Leary’s other loves in his life is wine. O’Leary likes to indulge in his favourite wine, “I make wine, and have my own O’Leary fine wines. I’m very proud of mine. My favourite out of all my wines is my unoaked chardonnay. It’s very crisp, apricot, peach, appley flavour overtones, just delicious, goes with everything. I have a glass of wine every day.”
O’Leary’s love for watches and wine is fascinating. With O’Leary fine wines, and many of O’Leary’s other businesses, the strategy to maintain sales during the pandemic was key to maintaining its success. Part of the issue surrounding selling wine was that retail and restaurants weren’t ordering wine anymore, and so O’Leary went to direct shipping in 42 states. O’Leary’s advice when it comes to other business owners or aspiring entrepreneurs during this unprecedented time is clear, “The ones that survived the pandemic were the ones that were able to change their strategy of distribution. They went digital, they went to social media, they set up their own website, they shipped their product directly to customers. They’re the ones that escaped going to zero because they were not relying on retail which got shut down. The ability to show your product online, and to tell a story on all the social media platforms, to attract customers back to the website, when they used to buy the product in retail. And that required us to change our strategy completely. To enrich our digital video, our audio, our photography, our story-telling, we set up sites, we set up our own shops using Shopify, we did all kinds of things.”
O’Leary is hopeful and encouraging when it comes to the innovation and the business ideas that have risen from the pandemic, “Great entrepreneurs aren’t stopped by pandemics or chaos in the market – they find solutions to problems that people have everyday. These entrepreneurs, particularly the ones that are showing up on Shark Tank this year, have come up with all kinds of solutions. It just shows that entrepreneurship exists and continues to grow and no matter what the adversity is, there are men and women coming up with great ideas, and I’m always investing in them.”
Given that Mr. Wonderful has done it all and has nothing left to prove, does he have any plans to slow down? I wouldn’t bet on it: “The older watches get, the more valuable they are.” I could’ve told you that just by looking at him.
