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The Tommy Bahama Boys

Tommy Bahama's three creators rhapsodize about making their fantasy a successful reality
Betsy Model
From the Print Edition:
Cuba, May/June 2007

In the late 1980s, apparel executives Bob Emfield and Tony Margolis wished for weekends that never ended and days filled with teak-decked boats, lapping waves, rum-spiked drinks and chaise lounges angled just right to catch the last rays of a Gulf Coast sunset. SPF 8, please. They dreamt of a lifestyle where Hawaiian shirts, deck shoes and a pair of silk-blend shorts served as appropriate attire for any event this side of black-tie. • What they wished for, really, was to be Tommy. Somewhere in all their fantasizing, a collective alter ego was born, a fellow who, unlike them, didnÕt have to go to work on Monday or when a vacation ended.

Someone who had a little money put away (there were vague rumors of a trust fund and some highly paid, intermittent consulting contracts) and who could indulge in a Florida Keys kind of lifestyle with the equally well-dressed girl of his dreams. A man who always looked stylish but never slick, who looked as if he could close a multimillion-dollar deal with panacheÉusing a Blackberry. From the deck of his boat.

Tommy had everything that Margolis and Emfield, or anyone else, could possibly want, including a casual wardrobe to die for. He had everything, it seemed, but a last name.

Tommy. Tommy. Tommy...Bahama.

What Would Tommy Want?

For most of us, fantasies are just that: fantasies. Whether it's having a Ferrari in the driveway, a perfectly balanced stock portfolio that doubles in value overnight or taking Tiger on the 18th hole, our fantasies rarely intersect with our careers unless they have to do with profits, paychecks or golden parachutes.

Emfield and Margolis, who had met years earlier in management positions at Britannia Ltd. (later a division of Levi Strauss & Co.), decided to make their fantasy a reality in 1992. They recruited another good friend, Union Bay apparel designer Lucio Dalla Gasperina, and the three men then parlayed $2 million in start-up funding toward introducing their friend Tommy Bahama to consumers.

One of the more interesting challenges the men faced was where to base their new company. At the time, Margolis, now 64, lived in New York City. Emfield, now 65, lived in Minnesota and Dalla Gasperina, now 50, lived in Seattle, Washington.

Interestingly enough, the three men still live in New York, Minnesota and Seattle—at least part-time. Margolis has another home in Connecticut, and both he and Emfield have purchased homes near Naples, Florida—a sure way to beat the wintertime blues of their two frigid home states—and Dalla Gasperina has a small vineyard in Napa.

Still, if it seems a little odd that the three founding partners of a business that's now worth an estimated $460 million live in three different states, the trio insists that it was a Tommy-worthy business decision; after all, if the company was really selling a lifestyle, and the founders all had families happily ensconced in their respective cities, they'd simply divvy up the company's functions based on the expertise of each founder.

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