Jason Wolfe is an American Entrepreneur. Grew up in the Milton Hershey School (originally an orphanage), founded by Milton Hershey in 1909, one of America's greatest Entrepreneurs and creator of Hershey chocolate. Jason was Alumnus of the year for Milton Hershey School in 2014. In his mid-20's Jason was a homeless (living in his car) self-taught programmer and created the first coupon web site in 1995. Jason focused on the coupon sites from 1995-2000. Grew to 20m visitors per month. He raised $500k in venture capital from Jupiter Media (NASDAQ: JUPM) in 1999 and sold MyCoupons to Save.com (then owned by Valassis (NASDAQ: VCI) in 2000 for $23m. Jason went on to build Direct Response Technologies, Inc (from 2001 to 2006) which provided DirectTrack affiliate tracking technology. Received expansion capital from the State of North Dakota in 2002 and sold Direct Response to Digital River (NASDAQ: DRIV) in 2006 after reaching 16 billion transactions per month and employing 75 people for $22m.

Jason focused on GiftCards.com and OmniCard from 2008 - 2015. GiftCards.com had 120 employees, and was the #1 gift card site in the world. GiftCards.com sold over 10 million gift cards, value of over $1 billion. On January 6, 2016, Jason sold GiftCards.com and OmniCard to Blackhawk Network (HAWK) for $120m. Today, they do over a billion in card value loads per year.

Jason is now focusing on Wolfe, LLC an incubator company – and specifically focusing on GiftYa, his next generation gifting solution, fixing the brokenness of the gift card product as he calls it. Wolfe owns several companies in startup mode, and Jason invests and sits on several boards for the investments made by Wolfe. Wolfe is the Chairman of the Board of the Pittsburgh Technology Council - a council of over 1,000 member companies in Pittsburgh accounting for over 35% of the region’s payroll.

Some awards and recognitions:
  • Ernst and Young Entrepreneur of the Year winner for 2011 for W. PA and WV
  • Judge for EY Entrepreneur of the Year award in 2012, 2013 and 2014 for our region
  • Top 5 Entrepreneurs in Prepaid in 2010
  • Top Workplace award #11 – 2011
  • Governor’s impact award 2012
  • Finalist for Entrepreneur Magazines Top National Entrepreneur in the USA in 2014
  • Winner Pittsburgh Business Ethics Award 2014
  • Winner of Business Times CEO Diamond award Pittsburgh 2014
  • Winner Tech 50 top CEO in Pittsburgh 2015
  • Pittsburgh Business times for 100 fastest growing companies 7 times.
  • Alumni of the Year Milton Hershey School – 2014
  • Pittsburgh Venture Capital Association, 2017 Outstanding Entrepreneur Award
  • Carnegie Science Award Winner – Entrepreneur of the year - 2019
  • On News shows like Bloomberg, Morning Joe on CNBC, MSNBC + others