Watch collector, race car driver, and car collector Drew Coblitz continues his discussion with Tim Mosso. In the second installment of our two-part series, Tim and Drew discuss the challenges and rewards of building careers around their shared passion for performance cars and luxury watches. Drew is both a collector and a consultant whose day job involves pairing clients with luxury products of enduring value; he helps his friends pursue cars and watches as alternative classes of investment.

Drew's watch collection began with his inheritance of his grandfather's gold Jaeger LeCoultre, but his current collection reflects a preference for sports watches, vintage sports watches, and watches that carry the romance of memorable histories. He also voices enthusiasm for ultra thin watches including the new Jaeger LeCoultre "Kingsman's Knife" and modern watches that effectively channel the personality and charisma of vintage watches.

Although his collections are not price-sensitive, the 2020 watch that most excites Drew is the Rolex Oyster Perpetual 41 (124300) with green dial, and he has placed an order for one of the first examples.

Regarding critiques of the watch collector community, Drew believes that too many watch enthusiasts are choosing to buy watches because they're "hot" rather than because the individual earnestly loves the model. For example: he turned down a dealer's offer of a 42mm Rolex Sky Dweller because he didn't love the fit. Drew hopes that dealers will make a greater effort to match watches to clients who can best appreciate a given model rather than simply offering every new debut to the highest spenders. Moreover, the advent of immense waiting lists at authorized dealers has undermined the cultural traditions of marking life milestones with a spur-of-the-moment watch purchase.

"Grail watch" is a term thrown around casually by watch collectors, but the definition varies from person to person. In Drew's view, a grail watch isn't defined by model or price but by the human story associated with the watch. Watches -- especially Rolex -- owned by Paul Newman, Steve McQueen, and other notable race car drivers, actors, and watch collectors are the ones that Drew most would like to own. While he has a fondness for Patek Philippe grand complications, he ultimately prefers a watch with documented provenance and an exceptional ownership history. Moreover, in a possible world-exclusive, Drew describes to Tim a firsthand witness' account of Steve McQueen verifiably owning a Rolex Explorer II 1655.

Drew also adds the Richard Mille Airbus Corporate Jets RM 50-02 tourbillon split-seconds chronograph and the Audemars Piguet Royal Oak Perpetual Calendar Openworked Black Ceramic.

When it comes to selling watches from a collection, Drew only considers selling a watch when it fails to see enough wrist time. Also, he shies away from keeping too many watch winders in motion, and he prefers not to keep more watches than he can quickly keep wound and set by himself. Drew also describes his changing preference for brand and style; his interest in Panerai watches waxed and waned with the novelty of the brand and his own enthusiasm for large watches.

Drew's collection also includes a "grail car." The Porsche 911 (964) as modified by Singer Vehicle Design (Singer Reimagined) is his grail, and he realized his dream by custom-ordering a Porsche 911 Singer. Every detail of Drew's Singer 911 was designed and executed to his exacting specification. Perhaps co-equal with the Singer, Drew regards the landmark Porsche Carrera GT as a grail, and he added one to his collection shortly before the production of this feature.

Tim Mosso and WatchBox will return to Drew's garage to document his new arrivals on four wheels and four lugs.