In 1995, Wolfe founded the first online coupon site, known initially as CouponsDirect.com. After growing the company, he sold it to a competitor for roughly $23 million in 2000, then reacquired it in 2002. Jason then began to build an affiliate tracking technology and platform called Direct Response Technologies. Wolfe sold the company to Digital River in 2006 for $22 million. In 2008, Jason launched GiftCards.com. That company was acquired by Blackhawk Network Holdings in 2016 for $120 million.
His current focus is GiftCardGranny.com, a discount gift card website.