When Mr Ben Clymer was 16, his grandfather removed an Omega Speedmaster from his wrist and gave it to him. Thus began an obsession with vintage timepieces that has since swallowed much of Mr Clymer’s time and money. That comparatively modest watch remains the most cherished piece in what is now, 16 years later, an extensive and expensively assembled collection.

Mr Clymer’s online watch magazine HODINKEE (the name is a bastardisation of the Czech word for wristwatch) began seven years ago as a Tumblr, the product of “pure boredom at work”. Today, it is the go-to site that helps stave off boredom at work for a growing cult of like-minded, rare-watch enthusiasts: more than 500,000 of them currently visit the site each month to read watch news, in-depth reviews and entertaining interviews.

“Back in 2008, work was totally different for me than it is now,” says Mr Clymer, 32, as he looks out onto another rarity – his own private garden in New York’s West Village. “I was sitting in a cubicle working as an analyst for a giant, completely soulless bank. The financial crisis had just hit. My boss told me I had to come in each day but since there was literally nothing being done operationally at the time, he said I could do whatever I liked as long as I was there. I liked watches, I liked to write, I liked the web and thus HODINKEE was born.”

Not long afterwards Mr Clymer was given the option to either move into another division within the firm he was working for, or take redundancy. He chose the latter, using his severance package to help fund his Masters at Columbia University’s Graduate School of Journalism. “When I left my high-paying banking job with health insurance to go and be a watch blogger, my parents were a little upset,” he says. “But for the first time in my life I really loved what I was doing.”

It was a high-risk move at the time but it has since paid dividends. Having resisted increasingly aggressive offers from media heavyweights to buy HODINKEE, last month Mr Clymer announced that he had partnered with Silicon Valley tech entrepreneur and fellow watch nerd Mr Kevin Rose (co-founder of news aggregator site, Digg) to expand and develop the site with the support of $3.6m of investment from Google Ventures, Twitter’s Mr Evan Williams, Basecamp’s Mr Jason Fried, as well as musician and HODINKEE contributor Mr John Mayer.

In a short space of time, HODINKEE has grown to become the most respected online resource within what remains a very traditional watch industry. “We’ve been successful because we write about things that are often perceived as pretentious and slightly obnoxious, and ridiculously expensive and overpriced, in a way that explains them to normal people so that they can understand and appreciate them,” says Mr Clymer. The site is credited with helping to spark and sustain a vintage watch craze, which has seen prices for investment pieces soar in the past decade. “I believe that within five years many of the world’s elite art collectors will also turn to mechanical watches,” he predicts. “The market is there.”

Mr Clymer has become quite the collector himself. “To some extent it’s problematic because I spend every last cent I make on watches – to the detriment of other things at times.” He is not so gauche as to reveal the size and value of his collection. “I’m really looking for pieces with a great story behind them rather than being influenced by price. A great watch isn’t about bling: the best $8,000 watch beats the worst $300,000 one.”

What is it about watches that is so fascinating? “They are such emotional objects that I think they really tend to pull on the heartstrings,” he says. “These things are truly multigenerational, which almost nothing else is. There is just nothing as lasting, as personal, or as complex as a great watch.”

In this short film we take a ride in Mr Clymer’s vintage Porsche as he drives from his apartment to HODINKEE’s new offices in SoHo, where he talks us through the stories behind some of his favourite pieces.