Get the FREE WatchSmarts Beginner Buyer's Guide. Steve Bollar joins David to discuss how a childhood admiration for his father's professional attire cemented the idea that success is signaled by the watch on your wrist. From a Kmart triathlon watch funded by a paper route to a high-end collection featuring a Tudor Root Beer and the iconic square TAG Heuer Monaco, Steve shares his journey as a "secret watch looker." He reveals his unique strategy for spotting timepieces on airplanes and explains why he actually enjoys the bulky charm of working watch cufflinks. With practical advice on building a collection with a plan, Steve emphasizes that while watches all tell the same time, the right one serves as a personal rite of passage or a celebration of how far you have come.

⏱️ Timestamps

00:40 : Early Inspiration
• Steve remembers his father as a symbol of achievement who always wore a suit and a watch. • He learned early on that success means having a quality timepiece on your wrist.

02:45 : The Kmart Breakthrough
• Buying a multi-time zone triathlon watch with money earned from a newspaper route.
• Drawing pictures of his first watch because he thought it was the coolest thing in the world.

04:00 : The Cruise Ship Turning Point
• How a 45-minute lecture on luxury brands sparked a ten-year obsession with collecting.
• Transitioning from looking for good looks to understanding the heritage of Omega and TAG Heuer.

06:17 : The Everyday Essential
• Why the Hamilton Khaki Field watch remains Steve's lightweight go-to for daily wear.
• The story of an impulse buy at the Philadelphia airport that became a timeless classic.

07:35 : The Tudor Root Beer Quest
• Dealing with credit card fraud alerts while trying to buy a watch in Saudi Arabia.
• The satisfaction of finally finding the Root Beer GMT at the Mall of America.

09:02 : The Iconic Square Case
• Adding the TAG Heuer Monaco to the collection after seeing it in a ship's gift shop.
• Why the Steve McQueen classic is his favorite piece to wear during professional speaking engagements.

11:27 : The Swatch Planet Craze
• Collecting the Moonswatch series across different cities including New York and Amsterdam.
• Why fun, plastic pieces can be just as rewarding as high-end mechanical watches.

14:39 : The Seiko GMT Experience
• Purchasing a Seiko 5 GMT on Amazon to satisfy a craving for a vibrant orange dial.
• Why the convenience of online shopping cannot replace the experience of an in-person purchase.

17:45 : The Secret Watch Spotter
• Steve's tactical airplane seating strategy used to identify watches on fellow passengers.
• Striking up conversations with strangers about their Breitlings and Rolexes at 30,000 feet.

21:51 : Working Watch Cufflinks
• Discovering functional Submariner and Daytona style cufflinks from a Kickstarter project.
• The "flick of the wrist" technique used to make sure people notice his extra timepieces.

23:51 : Advice for New Collectors
• The importance of having a plan so you do not spend frivolously on every trending blog post.
• Why beginners should look at Seikos as the reliable "Japanese cars" of the watch world.

38:05 : The Lightning Round
• Why Steve prefers five good watches over one "great" one to maintain variety.
• The preference for quiet, understated designs over loud and flashy timepieces.

A watch is a personal indulgence that captures who you are and where you are going.

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