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 completing 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 more than 30 years. He has held key positions with respected dealerships and organizations including Yamaha of Killeen, Texas Motorsports, Woods Fun Center, America’s Powersports, Honda of Houston, New Braunfels Cycle Country/Woods Cycle Country, and most recently Woods Indian Motorcycle. His expertise and dealership focus have also led him to serve on the boards of the Texas Motorcycle Dealer Association, the National Powersports Dealer Association, and Massimo Motors.

Currently, Sheffield serves as Strategic Advisor for Woods Cycle Country and Woods Indian Motorcycle, and works on workflow optimization with several large dealers.

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