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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

(continued from page 3)

Oxford also wanted, and got, a successful company that would continue to be actively managed by its original founders, not by the parent company in Atlanta. "It's been a great relationship, actually," says Dalla Gasperina. "They've been an awesome partner. They respect what we do, they respect our designs, our success, and they leave us alone to do what we do best."

While the purchase has provided a certain amount of financial freedom for the founders, the daily running of the company hasn't given them extraordinary amounts of additional time off. Yet. Still, Emfield insists that they do their best to live their lives with the same attitude they try to inspire in their customers. "'Life is one long weekend' is more than just a saying, you know," says Emfield. "We really do believe it and, within reason, try to live it."

For Emfield, that means spending a little more time in Naples with his golf clubs—his cell phone actually features a taped message from his wife saying that Bob can't be bothered right now; he's too busy putting—and Margolis professes to having taken up tennis in a serious way since his wife declared that golf made him too, um, grumpy. "I'm a perfectionist," shrugs Margolis, "and I just couldn't stand the pace of the game and the fact that not every ball was going to go exactly where I wanted it to."

For the Italian-born Dalla Gasperina, relaxation includes spending time in Napa and planning a future that includes growing more grapes and, perhaps, olives. "My wife and I bought the land a few years ago and it's beautiful country, beautiful land. I can relax there, definitely."

When the men relax together, it often involves a cigar.

"I don't think cigars are on the top of any of our wives' wish lists," says Emfield, with a grin, "so cigars are banished to the outdoors at our homes or to some other dark, dank place where our wives wouldn't go anyway. When I do smoke, I really like a Partagas Serie D No. 4 or maybe a Montecristo No. 2 for late afternoon or early evening. I prefer to smoke before dinner. I don't drink, but I like to sit down with my friends who have cocktails and let an hour pass, and in place of a Martini I smoke a cigar. And, of course, in Florida and here [in Naples] it's all about timing and the sun setting into the Gulf of Mexico."

Margolis concurs with the importance of sunset timing, but with slightly different parameters. "Unlike Bob, I do drink alcohol," Margolis says with a laugh. "I think a cigar goes really well with a Martini. I also like to smoke before dinner—sunset's a great time—but I prefer a Hoyo de Monterrey. I also don't mind an afternoon smoke sometimes, and I think Davidoff makes a good afternoon cigar. For me, a cigar is an unwind's similar to drinking [wine] and the enjoyment of wine in that it has a lot of the same tactile features of taste, smell."

For Dalla Gasperina, the aspiring winemaker with Cabernet, Sauvignon Blanc and Merlot grapes growing in his vineyard, an occasional cigar for celebratory purposes with "the boys" works just fine, as does pairing that cigar with some nice wine. "We're pretty fortunate in that we usually have access to a nice repertoire of cigars...the better Dominican or Cuban cigars, for instance. I like the Partagas Serie D No. 4 too. It's a nice way to recap a day's events when we're together, maybe in Las Vegas or in Hong Kong, and it's just wives! They hate the way we smell [after smoking], and when we smoke and go home, you know, we have to leave our clothes in the garage!"

Like anything else, cigar smoking is about lifestyle choices, and no one seems to know more about lifestyle choices than our man Tommy. Along with Dalla Gasperina's inspired apparel designs, what Tommy Bahama as a company seems to do best is define a particular lifestyle—casual but successful, affluent but low-key—that its customers have either already achieved in life, or aspire to. And if that means, in addition to clothing, outfitting a home with Tommy Bahama furnishings and proffering a bottle of Tommy Bahama Golden Sun Rum at the bar, well, the company has made its mark showcasing that lifestyle. Not to mention some very profitable licensing.

"Licensing has been extremely lucrative for us," admits Margolis, "but if Tommy wouldn't wear it or sit on it or have it on his boat or in his home, then Tommy's name doesn't go on it. It's that simple."

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