How Wolfe LLC founder and CEO Jason Wolfe went from orphanage to entrepreneur

The most popular gift item at the holidays is not a toy, a piece of jewelry or an electronic device. For the last 16 years, the majority of people surveyed by the National Retail Federation said the gift they most want to receive is a gift card.

That leads to a colossal amount of money spent on gift cards, and, unfortunately, a colossal amount of money wasted on gift cards. The Mercator Advisory Group has estimated that as much as 3 percent of total gift card funds are never redeemed, whether it’s because the gift card is lost or forgotten or expires. That’s billions of unused dollars.

“The whole industry is broken,” says Wolfe LLC founder, president and CEO Jason Wolfe. “People don’t use their gift cards, there’s criminal activity that goes on with them, and landfills are filled with the one-time-use plastics.”

So, Wolfe has set out to fix what’s broken.

For nearly 30 years, Wolfe has used his entrepreneurial acumen and work ethic to build, grow and sell some of Pittsburgh’s biggest financial technology and ecommerce businesses, including, and Gift Card Granny. Now, the 54-year-old’s main motivation is to disrupt the gift card dilemma with a system in which gift card funds can be linked to your credit card and automatically debited when you shop at that particular retailer.

“Gift cards have been around since 1994, and nothing is new about them,” Wolfe says. “It’s old technology. People buy them, and recipients are stuck with a plastic card. Why has it not evolved? We’re going to evolve it, and, over the next five to 10 years, a company like ours has a good chance to really make a difference.”

Despite meager beginnings and adverse circumstances, Wolfe has long found a way to make a difference in a fascinating, fruitful and philanthropic career.

Hershey help

Wolfe’s story of success in the gift card business begins with the gift he and many other students have received from chocolatier Milton S. Hershey.

In 1909 — nine years after the sale of the first Hershey bar — Hershey and his wife, Catherine, established the Hershey Industrial School in Hershey, Pa., to provide free education to orphan boys. In 1918, Hershey, who did not have children of his own, put most of his fortune into a trust for the school, which came to be known as the Milton Hershey School, and has since expanded to include boys and girls who are “social orphans” with single or divorced parents.

Wolfe was one such student. His father left the family when Jason was just 6, and his disabled mother struggled to raise her three children on welfare. Wolfe was enrolled in the Hershey school at age 10, and there he learned the principles that would shape his career.

Though Hershey passed away long before Wolfe was born, the candy tycoon became a role model for Wolfe, who was awed by Hershey’s business acumen and humanitarianism.

“As I grew up, I had to look at somebody as my mentor,” Wolfe says. “I had no father figure. Milton Hershey was this figure that built the company and then gave everything to these kids. As an entrepreneur, what better person to idolize than the person that built Hershey’s and then gave the funds to the kids who went there? I’m one of them, and I’m in the gifting business. I mean, it’s crazy. He gave me a gift, and it’s destiny.”

Destiny, though, did not come without difficulty.

Desperation leads to inspiration

Wolfe graduated from the Milton Hershey School in 1987, then received his bachelor’s in marketing from Bloomsburg University of Pennsylvania in 1992. He spent two years as a whitewater rafting guide before moving to Pittsburgh, where he planned to sell coupons door to door. However, he was involved in an accident that required two spinal surgeries.
Now unemployed and temporarily immobile, Wolfe was desperate.

“I was down on my luck,” he says. “I needed to find some way to make money.”

While laid up in recovery, Wolfe began to read computer coding books he borrowed from the local library. The Internet was just taking off, and Wolfe sensed opportunity. In 1995, he created his first website — an online coupon site known as (later renamed

It was not a smashing success at first. Wolfe estimates that he made about $4,000 in the first year. His girlfriend, with whom he lived, thought he was chasing a pipe dream and dumped him. That left Wolfe without a home for a few months. He slept in his car while renting office space from a friend.

Eventually, though, businesses caught on to the concept. The coupon site took off, and, by 1999, had more than $1 million in annual sales and three million registered users.

At that time, Wolfe decided to create a sister site called, where merchants could sell gift certificates.

“Within a year or two, I started seeing plastic gift cards showing up,” he says. “Let’s say we had 100 merchants. All of a sudden, we had five of them that were this little plastic card instead of paper. I’m like, ‘Oh, that’s cool. You swipe it, and then you can use it again.’ Because [paper] certificates were a pain in the neck.”

As with the Internet itself, Wolfe could see where things were headed. He bought the domain name Within a decade, the site was pulling in more than $40 million in sales.

“Most people don’t realize it, but it’s very hard to get into the gift card space,” Wolfe says. “The gift cards are a form of currency, so there’s a lot of crime involved in that. And the margins are very thin. So, it’s risky. But if you know how to do it and can do it on a larger scale, you’ll be successful.”

Adding value

Wolfe’s understanding of his business models has allowed him to create and sell a number of companies and products, including,, DirectTrack (an affiliate tracking technology and platform) and others. In 2007, he founded Wolfe LLC as a holding company for his subsidiaries, which are called the Wolfe Companies.

Currently, Wolfe operates a number of innovative business units, including (but not limited to): Gift Card Granny, which allows consumers to purchase gift cards for a discounted price or sell them for below face value;, which provides businesses with incentive and gifting solutions; and Give InKind, a platform where family and friends can organize support for loved ones going through challenging moments such as a hospitalization or a death in the family.

But in addition to building companies, Wolfe has focused on building company culture. The Pittsburgh Leadership Foundation helped him articulate the values he prioritizes — teamwork, integrity, drive and caring.

“When you have a value for caring,” he says, “you’re going to help other people and be a good team player. You’re going to do things not just for yourself. You’re going to be humble.”

Wolfe has used employee engagement tools such as Officevibe and Bonusly to survey and reward employees. The 20,000-square-foot company headquarters in Green Tree has no cubicles, and the roughly 160 employees are given flexible work hours and a profit-sharing program.

The combination of hiring based on values and listening to and recognizing employees has led to growth and retention. The company’s revenue has grown by triple digits for each of the last four years, and after bringing in $231 million in revenue in 2022, Wolfe LLC’s companies were on track to achieve about $350 million in 2023.

“I’ve seen way more success [with the Wolfe Companies] because I’m not doing it for the money anymore,” Wolfe says. “Our growth has been crazy high, because I decided I’m going to hire people based on cultural fit first.”

And just like Milton Hershey, Wolfe is using his success to give back. Not only was he a volunteer board member for Voce, which co-administers the Statewide Adoption and Permanency Network program for the Pennsylvania Department of Human Services, but he has adopted three children of his own. He was also chairman of the Pittsburgh Technology Council and is currently on the Board of Managers for the Milton Hershey School.

Patents and patience

Wolfe’s innovative career path has taught him a lot about patents but also a lot about patience.

“I look at the things I’m trying to accomplish now with a longer lens,” he says.

His primary focus now is the aforementioned “broken” system that he aims to correct with GiftYa, a gift credit service that allows users to send e-gifts to one another using a mobile phone app or web interface. The recipient links their e-gift to their Visa or Mastercard, making it impossible for the gift to ever be lost or stolen.

“I got passionate about this,” Wolfe says. “Well, I didn’t realize it was going to take 1,058 days, 367 e-mails and 55 phone calls to Visa to let me have access to the APIs [application programming interfaces] at the point of sale. I had to convince Visa and MasterCard to do this. It took me three years to convince them, but I finally did.”

GiftYa was launched in 2019 but is only beginning to reach its potential. Wolfe is as excited about it as he was about that first company he dreamed up while sleeping in his car.

“That’s what really drives me every day is this idea,” Wolfe says. “My hope is that, over time, the platform that I built to change the gift card space gets used by everybody else that’s doing gift cards.” ●

Jason Wolfe

Founder and CEO
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