568 Four Huge Startup Exits w/ Jason Wolfe

Going Deep with Aaron Watson

Jason Wolfe is the definition of a serial entrepreneur. He sold MyCoupons.com for roughly $23 million in 2000, shortly before the DotCom bubble burst.

Jason rolled over his proceeds into successive wins with his companies Direct Response Technologies (acquired by Digital River for $22 million), Jambo Media (for $15 million) and Giftcards.com (by Blackhawk Network for $120 million).

Pretty impressive. Even more so when you consider how he grew up. After growing up in the Milton Hershey School, an orphanage founded by Milton Hershey, Jason was living out of his car.

He taught himself how to code by using books at the local library and CompUSA's 'Building the Perfect Web'. This led to building the first coupon website and launching his first internet business. From 1995 to 2000, Jason built the business, raising $500k in VC from Jupiter Media and garnering >$1 million in annual sales and 20 million page views per month.

Today, he is building GiftYa, GiveInKind, and PerfectGift, which have the potential to be his biggest businesses yet.

​Jason’s Challenge; Give more. Be Kind. Pull someone else up.

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