From the Orphanage to the Penthouse

Jason Wolfe grew up in an orphanage. In his 20s, living out of his car, he came across a CompuServe book. Inside its contents, laid the foundations for a career in technology and entrepreneurship.

With his newfound coding abilities, he built a website for buying and selling gift certificates online. It was a great time to know how to a build website.

Shortly before the DotCom bubble burst in 2000, Wolfe sold MyCoupons.com for roughly $23 million.

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).

At each venture, Wolfe was generous with employee equity grants and much of the talent that helped him accomplish his past wins. This made his team eager to saddle up time after time to chase an even bigger prize.

Now, Wolfe is building GiftYa and PerfectGift.com, which he believes will be his most successful companies yet.

Knowledge, skills, and great people compound. Over twenty years in the same industry have molded Jason into an entrepreneur capable of standing companies up quickly, targeting market opportunities precisely, and recruiting top talent.

Most of your peers aren’t planning to be in the same industry and work with the same people for 20-plus years. They’re just thinking about the next big payoff.

Think about the long game.

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