Born in Letchworth Garden City, Hertfordshire, England, Sheffield traveled extensively before eventually settling in Beaumont, Texas. After graduating from Lumberton High School in 1989, he took a brief six-day break before enlisting in the U.S. Army. He completed basic training at Fort Leonard Wood, Missouri, followed by advanced individual training (of all things as an M1 Abrams Tank Systems Specialist) at Fort Knox, Kentucky. His military service included a combat tour in Iraq during Operation Desert Storm. Upon fulfilling his four-year enlistment, Sheffield transitioned back to civilian life.

The day after leaving the military, Sheffield embarked on what would become a distinguished career in the Powersports/Motorcycle industry, now spanning over 30 years. He has held key positions with a variety of respected dealerships and organizations, including Yamaha of Killeen, Texas Motorsports, Woods Fun Center, America’s Powersports, Honda of Houston, and New Braunfels Cycle Country/Woods Cycle Country and most recently Woods Indian Motorcycle. His expertise and focus on dealerships have also led him to serve on the boards of the Texas Motorcycle Dealer Association, the National Powersports Dealer Association, and most recently, Massimo Motors.

Currently, Sheffield continues his work in the industry as the Strategic Advisor for Woods Cycle Country and Woods Indian Motorcycle. In addition, he collaborates with Spader Business Management and NCM Associates, where he facilitates 20 Groups within the Marine, RV, and Powersports sectors.​

In 2016, at the request of Dave McMahon, Sheffield began contributing articles to Powersports Business, which eventually expanded into daily posts on his LinkedIn account. A passionate advocate for dealerships, he actively works to counter the overreach that dealerships often face from certain industry vendors. His goal is to establish a balanced, equitable environment where both dealerships and OEMs can thrive long into the future.

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