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1. Mark successful moments with a watch
O’Leary links purchases to business milestones rather than buying only because a model is fashionable. “Whenever I closed a deal or had something successful happen in business, I would buy a watch to associate that deal with the timepiece,” he told Kenyon.
The useful lesson is emotional documentation: decide what an occasion means, then choose a watch that will keep that memory visible. It is a collecting ritual, not evidence that milestone purchases will appreciate.
2. Buy deeply into a brand—if the commitment is genuine
When O’Leary enters a maison, he says, “I always buy two, up to four sometimes.” He recalls buying four F.P. Journe watches at once. Kenyon explains that an established relationship and purchase history can sometimes matter when sought-after allocations are discussed, but that is not a guaranteed access formula.
For most collectors, buying several expensive watches at once is neither necessary nor prudent. Consider the difference between the two approaches:
| Approach | What it requires | Main risk |
|---|---|---|
| One watch at a time | Patience, research and a clear budget | Slower development of a retailer relationship |
| Multiple watches when entering a maison | Substantial cash, genuine interest in several references and comfort tying up money | Buying pieces you would not otherwise choose in pursuit of access |
O’Leary’s example reflects his resources and collecting scale, not a default rule for everyone.
3. Diversify instead of chasing one trend
O’Leary recommends variety across brands, periods and styles rather than concentrating on whatever combination is currently popular, such as steel cases with blue dials. He recalls discussing changing metal preferences over the decades with Hank Edelman, identified in the interview as Patek Philippe chairman.
This is a collecting principle, not a promise of financial diversification. A broad collection can simply give you more ways to enjoy watches:
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- Book - a man and his watch: iconic watches and stories from the men who wore them
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| Collecting axis | Narrow approach | Broader approach |
|---|---|---|
| Brands | One favored maker | Several makers with different design languages |
| Period | Only current releases | Contemporary and older watches |
| Materials | One case metal | A considered mix of metals and, where appropriate, other materials |
| Dial style | One fashionable color or layout | Different colors, complications and visual treatments |
| Personal interest | Trend-led purchases | Pieces connected to your own taste and stories |
4. Do not buy a poorly considered watch
O’Leary attributes a lasting lesson to his mother: save for quality and understand what a watch represents before spending. That means learning about the maker, the watch’s history and why the piece matters to you. He summarizes his respect for watchmaking plainly: “I mean, these watches are pieces of art.”
Quality is not a universal appraisal formula. A less expensive watch that fits your interests can be a better choice than a prestigious piece bought without understanding its design, construction or place in the maker’s history.
5. Do not keep the entire collection in one place
O’Leary says two of his collections were stolen and that he now distributes his watches. Kenyon also reports that O’Leary told The Hollywood Reporter he used two insurers so that no single location had a complete inventory. That insurance detail is a report of another interview, not an independently confirmed policy arrangement here.
Distribution can reduce the consequences of one burglary, but it does not guarantee safety. A sensible security plan should also include a current inventory, photographs, serial numbers, purchase records, appropriate storage and insurance terms that match your location and collection.
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6. Learn the historical context before judging a watch
O’Leary uses Audemars Piguet’s CODE 11.59 launch to make a broader point: new watches can be criticized before their place in design history is understood. He compares that reception with early criticism of the Royal Oak and says he chose to own one of the first 100 CODE 11.59 Perpetual Calendar models.
The “first 100” figure and the historical interpretation are claims from his 2021 interview. They should not be turned into current production data, a scarcity guarantee or a forecast of appreciation. Research the design’s intended context, the maker’s earlier work and contemporary critical response, then decide whether the watch interests you.
7. Respect craftsmanship and personalize carefully
O’Leary wears red straps on television because continuity requires a consistent appearance: “Because I have to have continuity for television, I have to have a red band.” He adds, “On weekends I may want to put back the original band.” The interview says manufacturers made custom red straps for him; it does not establish that those bespoke straps are commercially available.
The practical takeaway is to personalize without compromising fit or the watch itself. Before buying an ordinary aftermarket red strap, confirm the lug width and attachment type for your specific watch. A color change can make a watch feel personal, but it should remain reversible and mechanically compatible.
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What O’Leary’s rules do—and do not—claim
Taken together, the commandments favor deliberate buying, historical curiosity, variety and personal meaning. They do not establish a reliable method for predicting prices, securing limited allocations or choosing watches that will outperform the market. The only source for these seven rules is Kenyon’s July 12, 2021 interview and distillation in Time+Tide; no independent market study or performance statistic accompanies the advice.
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