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General Information


US Air Force Academy, BS
Engineering Mechanics
University of Pennsylvania, MBA
Wharton School
University of Pennsylvania, JD
Law School

Current Companies

Advisor and Mentor

Former Companies

President and COO

Web Presences


Chuck Wallace

Few entrepreneurs can say they founded an Internet business that grew from zero to a billion dollars in revenue. Chuck Wallace is one of those rare entrepreneurs. In 1999, a year before the dot com implosion, Chuck co-founded Esurance. It not only survived the bubble burst, but through innovation and unheard of customer service strategies, Esurance aggressively grew by introducing a new business model to the stale, unimaginative world of insurance. Chuck helped build Esurance into the fastest growing auto insurance company in the US with revenues approaching $1 billion, 500,000 current customers, 2,000 employees, and 11 offices nationwide.

Today, Chuck is bringing the same vision and expertise in building innovative ecommerce companies to Upstream Worldwide. As President and COO of Upstream, Chuck is helping to create the first true Consumer Cash Commerce Platform – a new category of business enabling consumers to exchange everything from cell phones and consumer electronics to precious medals for much needed cash. And like Esurance, Upstream is changing the game by elevating service levels to a new high through its “100% Max Cash Guarantee.” At Upstream, Chuck oversees every department that impacts a customer’s experience – marketing, customer care, operations, technology and operational finance.

In between Esurance and Upstream, Chuck served as CEO of Ustream TV, the leader in live interactive video broadcasts, enabling anyone with a camera and an internet connection to broadcast easily to a global audience. As Upstream’s CEO, Chuck led the company through 30% monthly growth and angel, venture debt and private equity financings by top funding partners.

Chuck started his career as an Air Force instructor pilot, first teaching young men and women to fly at undergraduate pilot training in Lubbock Texas, and then flying the C-130 Hercules in Frankfurt Germany and Willow Grove Pennsylvania. Outside the office, Chuck is passionate about building strong communities and has held Director positions for Peninsula Family Services and Swords-to-Plow Shares, both non-profit social service agencies helping to improve the lives of families and neighborhoods in need.

Chuck holds a BS in Engineering Mechanics from the US Air Force Academy, an MBA from the University of Pennsylvania’s Wharton School, and a JD from the University of Pennsylvania Law School.

Recent Milestones



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Last Edited 6/25/13

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