It’s difficult to pinpoint who an entrepreneur is. Some are risk-takers looking for an idea to run with, while others are risk averse, but believe too much in something to let it go. Many are business school graduates, while others learned business out of necessity. But there are common threads running through the tale of every entrepreneur—a mixture of hard work and cleverness, the grit to overcome challenges and the willingness to take advantage of what good fortune comes their way. Executive Travel spoke with seven entrepreneurs, ranging from young to old, from modest means to fabulously wealthy. In each of their stories are lessons for entrepreneurs and those who have the vision to become one.

The Pennysaver

David Gold

Some ideas are so simple, they’re almost overlooked. Amazingly, Dave Gold didn’t act on his until he was 50 years old. A long-time shop owner in Los Angeles, Gold, now 73, had wondered at length why no one ever opened a dollar store. One day in 1982, an exasperated friend pointed to an empty storefront and yelled at Gold to finally do it. He walked in and signed the lease that day on the first of what are now 227 locations of 99 Cents Only stores dotting the Southwest. The everything-for-a-buck concept is so prevalent now, it’s hard to fathom it was one man’s idea. But credit Gold with the saved pennies, which built a company with $1 billion in sales and vaulted Gold onto the Forbes list of America’s wealthiest people in 2002.

Far from lining his own pockets, Gold has never sold a share and instituted options for every non-family employee, including cashiers. “A business should be run like a family,” he says. And not just in terms of treating employees well, but also in watching costs. “Don’t FedEx something you wouldn’t FedEx from home. Look to save money where you can and, eventually, it even becomes fun. But don’t hold down costs that help the bottom line,” he warns.

Gold’s stores are bright, clean and stocked with brand-name merchandise. Like at his most profitable location in Beverly Hills, shoppers are drawn from every economic level. “Everyone loves a bargain,” Gold says, repeating his business mantra; “But nothing is a bargain if it isn’t good quality.”

Sweet Success

Dany Levy

For most of the dot-com boom, Dany Levy toiled in the decidedly old-tech world of New York publishing. Ironically, it was her experience at monthly magazines that spawned the idea for one of the true Internet winners, DailyCandy, a daily email that goes to one million subscribers in nine cities (plus a national and a weekly travel edition). DailyCandy details one trendy, in-the-know item, be it a hip shampoo available at a London boutique or the best undiscovered restaurant in Manhattan. “Everyone is on information overload, there is so much to weed through. The idea of delivering one very concise, intelligently written heads-up to what’s going on in your city seemed a no-brainer,” explains Levy, 33.

Ignoring naysayers claiming she couldn’t be profitable or compete with offerings from VC-backed dot-coms, she launched DailyCandy in 2000. Levy gave herself nine months to build a subscriber base before even thinking of making money. After 18 months, DailyCandy turned a profit (revenues aren’t disclosed). After three years, she took on investment from MTV founder Robert Pittman. Despite a barrage of competitors, Levy’s publication remains the fix of choice for young, well-educated readers who appreciate the editorial voice she likens to “your best friend whispering in your ear.” Keeping that closeness to subscribers is paramount: Editorial remains independent, with ads sent in separate emails clearly labeled as purchased content. Says Levy, “It’s become a brand that people trust.”

Tuscan Son

PierLuigi Tolaini

The morning he left his native Tuscany, PierLuigi Tolaini knew his father was watching him take the mile walk to the train station, wishing he would turn around. Despite his own urge to turn back, Tolaini resisted, telling himself, “I will never eat polenta, I will never drink bad wine, and I will never—never—be poor again.”

The train eventually led the hardscrabble 19-year-old to the oilfields of Western Canada, where he realized he would never be financially successful working for others. At 25, he purchased a truck with his $25,000 in savings and began hauling freight in Manitoba. “If I lost it all, so what, I could make it again.” Tolaini built the company, TransX, into a $500 million (revenues) freight corporation, emphasizing good service and controlled 8 to 10 percent annual growth. Despite handing over many day-to-day responsibilities to his sons, Tolaini, 69, still tends to long-time clients like Cargill himself, lest they feel TransX has become impersonal.

Recently named a commendatore, Italy’s equivalent of a knight, “Louie” has allowed himself the pleasure of starting a super-Tuscan winery called Tolaini, with the goal of making the best wine in Italy. “You must have a dream,” he says. “Dreaming is the beginning. It must be a realistic dream. And the dream must become part of your vision.”

Travel Teacher

Rick Steves

A disappointing seminar about taking a bus from Istanbul to Nepal spurred Rick Steves to start his own business. The class “showed me the frustration and lost opportunity of a traveler who had the experience, but was too lazy and disorganized to share it effectively,” he explains. Marrying his love of travel with the potential value of a well-run tour company, Steves launched Europe Through the Back Door in 1976, building his one-man guidebook business into a 70-person, $30 million (sales) tour company and travel guide publisher, and making Steves host of his own popular PBS show.
Yet even pursuing one’s passion comes with its own set of challenges. For Steves, now 50, it was making the transition to manager with a paid staff. It was such a struggle that he mulled becoming a high-school teacher instead. “Then I realized I am a teacher, free as a bird with the best students anywhere: smart people who slept through their history and art classes … who are now Europe-bound and wish they knew who the Etruscans were. I haven’t looked back since,” he says.

Steves now pleasantly labels himself one of a five-person team known as “virtual CEO” of the firm. As a traveler, Steves tells fellow roadies: “Sure, you’ve got plenty of reasons to be homesick, but for now, you live there. Immerse yourself in it all.” As an entrepreneur, his advice is simpler: “Don’t hire relatives.”

Towering in Babel

Liz Elting

When Liz Elting tells people she owns a translation business, “Most people imagine I’m a translator working out of my apartment.” The reality is that her mastery of French and Spanish isn’t good enough to make her a living. But that hasn’t stopped Elting from building TransPerfect Translations into the world’s third largest translation services company, with $75 million in annual revenues and 400 employees in 30 offices. Since founding her company in 1992 with fellow NYU business school grad Phil Shawe, Elting (who is now 40) has separated the firm from thousands of competitors by focusing on expertise needed by businesses in areas like telecommunications and pharmaceuticals.

After college, Elting worked in sales for a translation company, where she recognized that corporations weren’t finding the professional level of service and quality they required. After NYU and a brief, uninspiring stint in finance, Elting decided to exploit the opportunity she saw years before, pooling $5,000 with Shawe to start the business. “It’s very difficult to think of something that hasn’t been done. Instead, we thought, ‘What do clients need that needs to be done better?’” The philosophy continues to benefit the company, which has expanded to include document management and transcription services. “There are so many things out there that can be done better. That’s how we continue to build the company.”

Hotel Rebel

Chip Conley

Sometimes opportunity comes through flouting common wisdom. For Chip Conley, that realization came in the 1980s, as he was looking for a way to make his mark in the hotel business. That didn’t seem easy; it was an established industry rule that customers valued predictability more than anything else. But Conley, now 45, realized there were a number of travelers who wanted unique experiences, instead of cloned properties. Striving to meet that need would also complement strengths he identified in himself: managing people and creatively packaging products.

This realization spurred him to launch Joie de Vivre Hospitality, now a collection of 28 boutique hotels in northern California. Each property has its own personality, ranging from “funky irreverence” to “elegantly world-class.“ “Each hotel’s brand is a mirror for how customers see themselves,” he explains. That’s led to fiercely loyal customers and booming business—sales are $125 million a year, up 150 percent in five years.

Conley attributes his success to hiring “rebel spirits” who approach the hotel business from a non-traditional perspective. The focus is on touching the four points of the company’s heart: creating a unique corporate culture that in turn builds an enthusiastic staff, which leads to strong customer loyalty resulting in sustainable profitability. To Conley, the only way to be great in business is to do your best at what you do best.

Lucky Duck

Ariane Daguin

A duck changed Ariane Daguin’s career. The academically bent Gascony native was heading a division of a New York wholesaler in the mid-1980s when an upstate moulard duck farmer came in, looking for a distributor. Her bosses weren’t interested, but for Daguin, now 47, it spelled opportunity. “It was historical, the first time someone was raising ducks for foie gras in America. I couldn’t pass it up,” she says. Soon after she (and a fellow grad student she eventually bought out) founded D’Artagnan, distributing foie gras and other specialties like squab and venison. Business was hard at first: She had to convince farmers to raise the animals and adhere to humane standards. “We had to work with people who had the same vision and grow little by little with them,” Daguin explains.

D’Artagnan dovetailed with the awakening of the American palate. No longer is it just Manhattan chefs taking deliveries, but grocery stores, too. Annual sales now amount to $45 million. Part of her success stems from sheer luck, Daguin insists: “We arrived with the right product at the right time.” But, she adds, it took lots of hard work to capitalize on the luck of finding that first duck. “If you know in your heart it is the right thing and that your product is good and that people will like it for legitimate reasons, you cannot fail.”

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brendan coffey is a freelance writer based in New Jersey. Email Brendan at editor@executivetravelmag.com.