Episode #58: Jason Wolfe, CEO of GiftCards.com

In this episode, I interviewed Jason Wolfe, CEO of GiftCards.com. Jason has an incredible story. He grew up in an orphanage and attended Milton Hershey School.  He graduated high school with a suit case of clothes and $100. He ended up bring in a horrific car accident and had to get two major spine surgeries. After the surgeries, Jason started to teach himself how to code and started his first online company, mycoupons.com. In the interview Jason will share how he went from there to where he is now with 95+ employees and well over $100 million in annual sales. He also shares the leadership lessons he learned along the way.

You can find the questions that I asked, my key takeaways, ways to connect with Jason below in the show notes. I know that this interview will add value to your life! Enjoy!

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Episode #58: Jason Wolfe


 Connect with Jason:

Jason Wolfe is an online visionary, entrepreneur, and businessman. Jason created MyCoupons.com in 1995, the first online coupon site. In 1997, he started DirectLeads.com, one of the first online lead generation networks. In 1999, he developed DirectCertificates.com, now called GiftCards.com, as a leading online gift card service. In 2002, Jason launched DirectTrack.com which became the world’s #1 affiliate tracking and ad serving system. In 2003, he introduced KeywordMax.com, which became one of the world leaders in keyword bid management. In 2004, his company created and patented the Cross Publication and Network model.

Jason was able to raise venture capital from Jupiter Media (NASDAQ: JUPM) in 1999, and an expansion investment from the State of North Dakota in 2002. He successfully sold MyCoupons.com to Valassis (NASDAQ: VCI) in 2000 and sold Direct Response Technologies to Digital River (NASDAQ: DRIV) in 2006.

Jason owns Wolfe.com, LLC as his holding firm that owns in whole, or in part, 7 ventures at various stages. MyCoupons.com (estb 1995), GiftCards.com (estb 1999), Swapagift.com (estb 2003), Jambo Media (estb 2006), OmniPrepaid (estb 2007), GiftCodes.com (estb 2009), and WRL.com (estb 2010). All businesses are profitable and growing. Jason attends and supports Orchard Hill Church of Wexford, PA. Jason has a son, Morris James Wolfe, and they live in Sewickley, PA.


  • Could you share your story with us? It’s an incredible story!
  • From the ages of 10 to 18 you were in an orphanage that was founded by Milton Hershey that was a private school for the economically poor? How did that experience shape your life?
  • You’ve had some high highs and some low lows in your life. In one interview you said, “I think when things fall apart, it creates great opportunities.” Can you talk about that? How come you see things falling apart as an opportunities and others see it as the end of their life?
  • You started the You Gift We Gift campaign for a very specific reason. Can you share the story the caused you to start it and why it impacted you so much as a 7 year old. What are you doing and what have you done to ensure you continue to grow and develop as a leader?  
  • You give back to your community a lot. What goals do you have around giving?
  • In listening to your story, it seems that you’ve always emerged as a leader and had great work ethic. Where did you learn those things?
  • In one video, your coach said that you’ve learned that nothing happens automatically. You saw an opportunity with the Internet and bought a book and taught yourself how to code. Can you talk about the importance of initiative in pursuing our dreams? We really do live in a world where we can learn how to do pretty much anything we’d like to do.
  • You’ve had moments in your life when you’ve had nothing and you’ve had moments when you’ve had plenty – What have you learned about money? What advice would you give to young leaders in their pursuit of money.
  • Could you talk about one or two of your greatest leadership failures? What did you learn from them?
  • Can you name a person who has had a tremendous impact on you as a leader?
  • Maybe some one who has been a mentor to you? Why and how did this person impact your life?
  • You love to travel, what has travel taught you?
  • Can you talk about the process of taking an idea for a business and making it happen?
  • What advice do you have for young entrepreneurs who have an idea for a business?
  • What has been the most challenging thing in starting and running your own business?
  • What have you learned about leadership from your experience starting and running your companies?
  • I recently read a book called the Hard Things about the Hard Things, as CEO and Founder, you’ve had to make some tough decisions. What are the hardest parts of leading at the level you’re at?
  • What have you learned about building a team?
  • How do your companies stay on the cutting edge of technology and creativity in a culture where both seem to move so quickly?
  • What’s next for Giftcards.com – What’s the future of gift cards (if you’re allowed to tell us)?
  • How can people get connected with and help Giftcards.com?
  • Out of everything you’ve accomplished in your life, what are you most proud of?
  • Where do you see yourself in 5-10 years? What do you want your legacy to be?
  • Any last pieces of advice for young leaders?

Key Takeaways: 

  • Out of catastrophe comes opportunity
  • Persistence is extremely important… the ability to not quit
  • If you want to be an entrepreneur, prepare to sacrifice a large portion of your life.

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