Harry Whitewolf grew up in the tiny town of Kernersville, North Carolina. He went to college at Appalachian State University where he majored in English and minored in Psychology. He moved to Raleigh to work for an advertising agency where he conducted market research and developed advertising campaigns for Fortune 500 companies. He served as a public affairs officer in the US Army during Operation Desert Storm
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While in the military, Harry studied creative writing at a local community college and a program at the National Defense University. Afterwards, he moved back to North Carolina where he worked as a copywriter and creative director for a public relations firm. At 44 years old he decided to take control of his life and pursue his dream of having his own business.
In 1992, Harry opened his own company that provides online marketing training for small businesses.