Jason Wolfe, chief executive of Giftcards.com.
Courtesy: Joe Appel Photography
By Maxine Wally
November 7, 2014

Deep within the recesses of the DoubleTree Hotel in Pittsburgh, Jason Wolfe is mentally preparing himself to deliver a speech at his company’s quarterly meeting. He’s stationed in the back of the hotel’s ballroom, seated, swiping through slides, reviewing his talking points. He looks up, takes a breath, and begins to make his way toward the front. Wolfe, the 45-year-old chief executive of GiftCards.com, is hardly shy. But there’s always something a little unnatural about speaking to—and answering questions from—a hundred or so employees gathered in a single room.

In the back of the hotel’s ballroom, servers are passing out bottles of Yuengling lager and cans of soda. The crowd seemed to be in relatively good spirits. Josh Miller, a former punter for the Pittsburgh Steelers football team, was in the house signing copies of his new book, It’s Always a Home Game, co-written with one of the company’s employees. Still, there were some dark clouds. Carlos Tribino, the company’s chief marketing officer, had just signaled that GiftCards.com would scale back on some of its initiatives, mostly related to marketing. Even though the company’s annual revenues were up 40 percent over the year before, it would soon be forced to retrench and invest in product development.

For Wolfe, that fact isn’t much cause for much concern—but he worries that the message would make his employees nervous that the company’s fortunes were shifting. And a nervous crowd is much harder to present to than a carefree one.

The speech went fine, of course. Wolfe’s prepared remarks went off without a hitch, and none of the questions asked of him were unexpected. For a man who built his e-commerce company from scratch—and at one point lived out of his Jeep Cherokee—a little public speaking isn’t the end of the world.

Wolfe first launched CouponsDirect.com in 1995, a concept that ultimately evolved into his current multimillion-dollar business, GiftCards.com. The website sells to its customers personalized, pre-paid Visa gift cards. The company banks on the experiential nature of buying, using, and giving gifts. Personalized details on the cards’ plastic—photographs and messages—lend a feeling of permanence to an otherwise intangible gift. Wolfe says he wants his customers to keep the cards, hold them in wallets, even put them up on refrigerators to keep long after their face value is spent.

A composed man with heavily lidded eyes and a sharp intuition, Wolfe knows what the opposite—transience—is like. He spent ages 10 through 18 in an orphanage (or more appropriately a school for disadvantaged children, now that the term has come to mean a child whose parents have died) called the Milton Hershey School in Hershey, Penn. His father left when he was four years old. His mother, disabled and struggling to take care of two sons and a daughter, needed help. When she heard about the free, private school from a nun at a Catholic educational facility in Torrington, Conn., she submitted an application for Jason. He was accepted.

In Hershey he was thrown into a life of structure and organization. Classes were serious, and came with the risk of getting what Wolfe calls “swatted.” After graduating with “a suitcase of clothes and $100,” Wolfe enrolled at the Bloomsburg University of Pennsylvania. He emerged at 23 with the stark realization that he had nowhere to go. After two years as a whitewater rafting guide in West Virginia, he moved to Pittsburgh. That’s when the hits started coming: Three months in, he was in a car accident and underwent two major spinal surgeries. The next year, thieves stole his Jeep. “I was stupid—I kept the title inside the glove box,” he says. (Wolfe recovered it months later.) A year after that, his girlfriend dumped him. Disheartened, he sold most of his belongings and spent the summer sleeping in the Jeep and working long days—sometimes 18 hours—at the office.

Along the way, Wolfe had taught himself how to code from a book he’d bought from CompUSA called Building the Perfect Web. It would prove to be the basis for his resurgence. His first true company, called MyCoupons.com, slowly grew to a million dollars in annual sales. In 2000, Wolfe sold it to Save.com and prepared for his next step.

Then the dot-com bubble burst. Save.com stopped making payments to Wolfe. He was forced to slash his staff of 40 to 14. As he mucked through the dot-com detritus, Wolfe picked up the domain for GiftCards.com and used it to rebrand the business he had at DirectCertificates.com. Today, the new company is his crown jewel, with 95 employees and well over $100 million in annual sales.

“After the dot-com bubble burst, there was a year or two of being scared—’Maybe this wasn’t going to be what we all thought it was,'” he says. “It was a slow comeback.”

As the quarterly meeting at the DoubleTree winds down, Wolfe answers a few lingering questions from employees. They want to know when he expected to ramp up the company’s advertising again. The cutbacks were going to happen, he explains, but these kinds of oscillations—taking a hit, retrenching, capitalizing on a glimmer of an opportunity, expanding—have never sunk him in the past. They wouldn’t start now.

“I think whenever things fall apart, it creates great opportunities,” Wolfe says. “We’re continuing to grow, and even though you see a little bit of cutback, that’s normal. Companies go up and down. It’s a cycle. But we will continue to move forward.”

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