boss: From orphanage to entrepreneur

Jason Wolfe

"To tell the truth, I didn't think I'd be alive," says Jason Wolfe, chief executive of - the biggest gift cards website in the world - when asked if he ever dreamt he would end up as a successful entrepreneur.

That's because it is hard to imagine the future when you are 10 years old and your mother - disabled, on welfare, and struggling to cope with several children - sends you to live in an orphanage.

Mr Wolfe, now 45, says he spent his early years just wondering if he would make it into adulthood.

Today Mr Wolfe is the head of a successful firm that allows customers to buy pre-paid Visa or Mastercard gift cards that can then be personalised with a photograph.

Start Quote

I can remember lying under a blanket one Christmas Day because there was no heat in the house”

End Quote Jason Wolfe

And it's a booming business - between 2010 and 2013 Pittsburgh-based saw its annual revenues rise by 72%, from $64m (£37m) to more than $110m last year.

Mr Wolfe says that while his upbringing might not have allowed him to dream about his future, it definitely helped prepare him for it.

"Going through difficult times as a young kid makes you resilient - so I felt like I could overcome pretty much anything," he says.

Chocolate inspiration

Mr Wolfe says that while he never set out to be an entrepreneur, he was inspired by the man who established his orphanage - the Milton Hershey School in Hershey, Pennsylvania.

The founder, Milton Hershey, was also the creator of Hershey, the famous US chocolate and confectionery company which is now worth an estimated $20.8bn.

Jason Wolfe with his mother Jason Wolfe grew up in Connecticut with his mother until he was 10

"Probably subconsciously it was inside me that I wanted to walk in his footsteps," says Mr Wolfe.

He adds that the inspiration to get into the gift-giving business specifically came from memories of his childhood.

"I can remember lying under a blanket one Christmas Day because there was no heat in the house.

"Somebody knocked on the door and we looked outside and there was a box outside of gifts for us."

A fateful accident

In 1994 Mr Wolfe graduated from Bloomsburg University determined to set up a coupons business, initially thinking he would sell them door-to-door to video stores.

However, he was then involved in a serious accident which put him in hospital.

line break sample facts
  • The average buyer is a 35-year-old woman
  • Each customer buys on average 2.5 cards per year
  • Average card value is around $100
  • Customers can buy Visa or Mastercard gift cards, or ones for a range of shops
line break

Mr Wolfe says: "It was lemons to lemonade - I was recovering from spinal surgery, getting fusion in my neck, and I was just lying there.

"So I got a book and taught myself how to [computer] code," he says.

Milton Hershey school The Milton Hershey School today has 1,925 students from diverse backgrounds

With his new found programming knowledge, Mr Wolfe decided to ditch his plans to focus on video stores, and instead be more ambitious and develop his coupons idea as a website. And so his first business was born -

This was a a prescient move in 1995, when the internet was just getting off the ground.

Yet Mr Wolfe struggled to get the company up and running, making just $1,000 (£586) that first year. And then his girlfriend dumped him.

"I don't think she thought I was going to make out too well in life," he says.

As Mr Wolfe had been living with his girlfriend he suddenly found himself homeless, living out of his car for two months while renting office space from a friend.

Jason Wolfe on high school basketball team Jason Wolfe (top row, fourth from left) says his upbringing at the Milton Hershey school inspired him

Finally, he made a sale - to the owner of a company selling Italian espresso machines, who wanted to put a coupon on his website.

When the businessman said how much he was willing to pay for the coupon - $1,500 - Mr Wolfe said he knew the internet was his future.

From there, things picked up, and sister company was founded in 1999 under its original name

But only a year later near disaster struck when Mr Wolfe agreed to sell - which was by then getting 20 million page views per month - for $20m just as the dot-com bubble burst.

With the purchaser suddenly finding itself in financial difficultly, the payment was delayed, and Mr Wolfe ultimately only received $2m.

"I had to figure out how we were going to survive," says Mr Wolfe, who eventually trimmed his then workforce of 40 people to 14.

Growing market

Mr Wolfe then successfully launched and ran a data tracking company, before taking a back seat from his business interests to help raise his son who was born in 2004.

"I grew up thinking that my father was dead - but he really took off when I was just four," says Mr Wolfe, adding that spending time with his own son was incredibly important.

Jason wolfe in haiti Today, Mr Wolfe also spends part of his time working with impoverished children in Haiti

However, when his son started going to school in 2008, Mr Wolfe decided to refocus his time and efforts on running

Last year, gift cards accounted for $118bn in sales globally - 90% of which was offline, at grocery stores and the like.

Mr Wolfe says he thinks sales will shift further to the internet in the next five years, and that is well placed to take advantage.

And so far, he has refused any outside investment in the business.

"I want to control the outcome of it - I feel like we have something special," he says.

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