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The Tommy Bahama Boys

Tommy Bahama's three creators rhapsodize about making their fantasy a successful reality

By Betsy Model

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.

Dalla Gasperina oversees production and design from the 79,000-square-foot office space in Seattle that houses 250 of the company's employees. Emfield handles the company's sales and marketing from Minnesota, and Margolis, the company president and CEO, manages the company's finances, partnerships and licensing from New York.

Having the three principals of a major company spread across six different locales, not to mention being acquired by a company based in Atlanta, has to cause confusion and chaos, right? "No, not at all," says Margolis. "When we need to be together for meetings or planning sessions, we're there. We're probably all together in one room or on one trip together a dozen or more times of the year. The rest of the time we're in constant contact."

They also, occasionally, finish each other's sentences. When asked if, with business partners, absence makes the heart grow fonder, the men laugh. "Well, I wouldn't exactly go that far," says Margolis, "but we're friends. We've been friends, great friends, for the duration of our company. Longer than that. I think there's something to be said about trust, and when you're not all in the same building together, day in and day out, you'd better trust each other. You'd better like each other. And, when we do spend time together, it's great fun."

That the three men have maintained not only a cohesive working relationship but a strong friendship in the course of building a company is a testament to their business savvy and work ethic. But, Emfield admits, it's also due to a stubborn insistence on doing things their way—Tommy's way—even when, during those first few crucial years, department store buyers told them that, not unlike Jimmy Stewart's 6-foot rabbit in Harvey, they just couldn't see Tommy.

"We don't put a pony or an alligator or any other embroidered symbol on our clothing," explains Emfield, referring to the logos used by Lacoste, Ralph Lauren, Tommy Hilfiger and others for easy recognition and status appeal. "At that time, anything without a brand name or designer's logo in a prominent position on a piece of apparel was suspect."

"We spent our first two years in business going out of business," Dalla Gasperina admits with a smile. Tommy's creators were, perhaps, a few years ahead of their time. The concept of "casual Fridays" hadn't caught on yet with corporate America, and the dot-com crowd at the time was interested in nothing more stylish than T-shirts featuring the name of a grunge rock band or the logo of the local ISP.

After a couple of bleak years, some corporate restructuring and the infusion of additional capital, the three founders found their niche: what wasn't cookie-cutter enough for the major department stores was perfect for upscale men's boutiques, especially those in tropical climates.

The clothing line—featuring loose, flowing lines, natural fabrics like cotton, silk and linen, and a color scheme straight out of Margaritaville—was a hit with consumers looking for attire that said "casual chic" and hinted at tan lines acquired on Caribbean shores.

By the mid-'90s, Tommy had clout.

From Camp Shirts to Crab Cakes

If the three men earned a reputation for staying true to a very specific market niche—affluent, male, age 35-55—that's due in part, they've explained, to constantly asking themselves a question that sounds like the punch line to an inside joke, but which nevertheless has become practically a mantra for any serious business decision that the company makes involving product or style: What would Tommy want?

Apparently, clothes shopping makes Tommy hungry, and what Tommy wanted was a laid-back café offering fried plantains, crab cakes and maybe a Caribbean-inspired pulled pork quesadilla. A cold brew would be good, too, along with plenty of open-air seating, palm trees, rattan and an expansive wooden bar that Jimmy Buffet would be proud of.

Tiki, yes. Tacky, no.

Deciding that building brand identity and loyalty was more important than building additional clothing lines, the men launched their first retail/restaurant compound in Naples, Florida, in 1995. It was, says Margolis, "a huge gamble. Huge! Any accountant or savvy investor will tell you that the last thing you want to do if you want to make money or keep money is to open a restaurant. What shocked a lot of people was that it was also an immediate hit [and] bigger than we ever imagined it could be. In many ways it opened our eyes to additional retail opportunities that were out there for Tommy."

The executives outfitted that first retail store the way they envisioned Tommy would: with warm wood tones, rattan and bamboo fixtures, soft colors, island music, and old crates and travel trunks used for props. And suddenly, the clothes were in a setting that complemented the whole ensemble.

"I think it became easier for people to see Tommy Bahama as an attitude, a lifestyle, as opposed to just a collection of clothing," muses Margolis. "It became easier for people to drop into the experience when they were surrounded by an ambience that fit the clothing."

This seemed especially true for women shoppers who, it was discovered, had been frequenting the store and buying extra-small sizes for themselves. The lesson told by the cash register wasn't lost on the men, and a complementary—and highly successful—Tommy Bahama women's line was added.

Also highly successful was the company's target-specific print ad campaign. Following a national search for a model, the three men compared notes and agreed on a face and demeanor that personified Tommy: tanned, fit, of indeterminate age but prematurely gray. Virile and playful but a one-woman man, Tommy was also, they determined, sensitive and romantic but definitely confident in his masculinity. The model had to exude confidence and a certain élan without appearing too...wimpy?

"We wanted a consistency in our ads and our look, and [model] Andy [Lucchesi] was exactly what we had in mind," explains Margolis. "Tommy's very clear on who he is and, while his activities and locale might change—and customers can watch those changes take place in the ads—Tommy's still Tommy, and we want to stay true to that."

Actually, Margolis might just as well be referring to the changes the three founders have experienced together in the last few years. In 2003, Oxford Industries purchased Viewpoint International's Tommy Bahama Group—including the clothing lines Indigo Palms and Island Soft—for a mix of cash, stock and shareholder payouts totaling $325 million. What Oxford got in return was a company whose successful licensing agreements include Tommy Bahama-branded products as diverse as furniture, rugs, ceiling fans, fashion accessories and, most recently, rum. Want some mood music to accompany that Piña Colada? Heck, there are even CD compilations with music that, you guessed it, Tommy chose.

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 moment...it'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 us...no 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."

Besides the myriad product lines, Tommy's name is on over 60 retail stores around the country. The men hope to expand into international locations next, with plans to create more compounds similar to their original one in Naples.

That the 20,000-square-foot compound in Naples continues to be their most successful venue makes sense. Naples' sun-drenched climate and demographic are a perfect match to the clothing line; locals and tourists alike seem perfectly willing to wait an hour to be seated at the café, and Margolis and Emfield are, for the most part, considered hometown boys, even if they only reside there part-time.

Then again, Tommy Bahama has proven to be a good neighbor, sponsoring and building an impressive garden within the campus of the local NCH Hospital and NCH Regional Cancer Institute. Opened to the public last fall, the Garden of Hope and Courage was the dream of Bob Emfield's first wife, Jan, who died of breast cancer in 1994.

To raise money for the garden, Tommy Bahama's employees held fund-raisers, the company donated proceeds from specific promotions and, together with individual donations, the company raised more than $3 million to make the Garden of Hope and Courage a reality.

And it's a physically beautiful reality. Emfield chose the park as the setting for this interview and, with its small lake and lush landscaping, the park is a tranquil respite for patients at the adjacent hospital and a popular meditation spot for locals.

The company is equally committed to the other communities where it has stores, raising millions each year through golf tournaments and similar events that benefit organizations as diverse as the University of Washington Breast Care Research Center, the Muhammad Ali Parkinson's Research Center, the Elizabeth Glazer Pediatric Aids Foundation and the Children's Cancer Research Fund. Explains Dalla Gasperina, "For every company that has the good fortune to succeed to any degree, there is a responsibility that goes beyond your own little world. To contribute through our success to make people's lives better is a duty and, equally, a pleasure."

So, what's next for the three men and Tommy? The three men offer three different answers, but none expounds any further than his own plans for that afternoon: Margolis is headed to a tennis game, Emfield has plans for a barbecue and Dalla Gasperina is off to a business meeting.

As for Tommy, well, there are a few high-end products that he might like to see added to his branded collection—golf clubs, maybe, or the right yacht or automobile—but what would really rock Tommy Bahama's boat is a resort. A really, really, high-end resort.

"We've been approached," Margolis admits, "but it hasn't been the right deal, the right resort concept. I think a Tommy Bahama resort is a natural extension of what we've done and what we're doing. We've already broken the mold with successful, profitable restaurants and we're perfectly situated for the next step, which would be a beachfront resort or golf resort. Tommy Bahama is known for its clothes, yes, but we're really about an entire lifestyle, and what better way to advertise that than at a resort that offers all the opportunities that Tommy would take advantage of?"

Ah, yes, the "What would Tommy want?" litmus test.

When asked if they ever worry about sounding a little like they're talking about an imaginary playmate, the men laugh.

"No," says Emfield. "Tommy may be fictional but he's also very real. It's about lifestyle. There's a little bit in all of us that wants to be Tommy and a little bit of Tommy already in each of us. Be honest, given a choice, wouldn't you rather be on a beach right now?"

Betsy Model is a frequent contributor to Cigar Aficionado.

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