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Moving Forward un-Wonderfully

The watch community has attracted a wide range of impressive characters.
An AI generated image of a Rolex Cosmograph Daytona on a red rubber strap. Much of this article will discuss a particular collector who is fond of such straps.
I'm all on board with the idea that inclusion should be at the center of the watch community. Regrettably, though, there is always this background matter that's become known as the Paradox of Tolerance, which was developed by philosopher Karl Popper. Here's the paradox: does tolerance extend to those who are intolerant? Relatedly, do you need to be inclusive towards those who are not inclusive?

A bit of a warning here, in what follows I explore the topic of mysoginy and describe some potentially upsetting material. I also discuss loss of life in an accident.

I'm not a philosopher and, admitedly, I haven't read Popper's work beyond a short excerpt I encountered online. But my understanding is that Popper's solution to the paradox was based upon the long-run implications when anyone tolerates intolerance: it will lead to the loss of tolerance. For that reason, Popper suggests that those adhering to tolerance must engage in rational debate to counter intolerant behavior. If rational debate won't work, Popper even advocates for direct action against those who are intolerant.

It would be fair to ask what all this has to do with the watch industry and watch community. Well, I think these questions are extremely relevant when it comes to a character who has a somewhat high profile in the watch community: Kevin O'Leary, aka Mr. Wonderful. O'Leary is on television a lot and he touts a carefully cultivated persona of business success. He's also active in watch industry commentary. If you search for "Kevin O'Leary watches" on YouTube, you get a lot of results. Some of the videos have millions of views.

Here's the thing: knowing what I know about O'Leary, I'm just not certain his approach is aligned with some very important efforts in the watch community. For example, I think work towards bolstering inclusion in our community is extremely important and, quite frankly, way overdue. We need to be honest: the watch industry has a history which has fallen short when it comes to inclusion. For example, in my book on Rolex I discuss the development of a 1965 advertising campaign by J. Walter Thompson in which a hypothetical Rolex owner is featured alongside prized posessions like a car and a horse. Notably "his wife" fell after the horse in the list of "possessions."

I'm honestly concerned that O'Leary's philosophy is more aligned with this outdated, mysoginistic industry legacy.
Screenshot of a tweet posted on Twitter by Kevin O'Leary.
My concern is based upon O'Leary's own words, which I've reproduced in the screenshot here. In February, on Twitter, Mr. O'Leary wrote, "You may lose your wife, you may lose your dog, your mother may hate you. None of those things matter." The tweet has over 12 million views and it is still online two months later. It would be one thing if O'Leary realized the post was a mistake and deleted the Tweet. But he has vigorously defended it. I'm not an expert in this subject, but it sure looks like the tweet has been ratioed, which suggests the general reaction to O'Leary's tweet has been quite negative.

There is probably more to O'Leary's philosophy than a single tweet. But his sentiment is plausibly more disturbing in light of recent legal developments. Roughly seven months before O'Leary's tweet, a Supreme Court case, "Dobbs v. Jackson Women's Health Organization" eliminated a right held by American women for three decades. To tweet something about the irrelevance of women in that context is failure to read the room par excellence.

The tone deafness of O'Leary's tweet has more layers.
An AI generated photo from a prompt involving Kevin O'Leary in a boat at night.
On August 14, 2019, two people were killed when Kevin O'Leary's boat hit another vessel at night on a lake in central Ontario, Canada. O'Leary's wife was charged with careless operation of a vessel. Ultimately, she was acquited of those charges. But just imagine if you were a family member of one of the people who was killed in this tragic accident and you read O'Leary's tweet about how losing a family member is irrelevant. I can't know how that would feel with certainty, but I think I'd be pretty upset.

Finally, let's also discuss the importance of authenticity in the watch industry. It's really really important. Buying an inauthentic watch is potentially disastrous. Buying from an inauthentic source is also potentially disasterous. The list goes on. In 2016, Canada's National Observer (a publication receiving a "High" accuracy rating by Media Bias / Fact Check) published an expose providing a fair bit of evidence that O'Leary was perhaps not as successful in business as his persona might suggest. This certainly leaves open questions regarding whether O'Leary's prominence in watch collecting helps advance authenticity in the watch industry.

In sum, Kevin O'Leary is a high-profile dynamic person who draws attention to the watch industry, which is unquestionable a good thing. There is a question, though, about whether his influence might make it more difficult for the industry to progress to a new, better plane. I don't know the answer, but I think it is a question worth asking.
My book on the history of Rolex marketing is now available on Amazon! It debuted as the #1 New Release in its category. You can find it here.

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