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“Two years ago I got this crazy idea to drive my truck out to the local Amphitheater, set my speakers up, and play right off the back of my tailgate…I’ll never forget those sunburned, 100 degree summers…that’s where it all really started for me.”
Montgomery was just out of high school when he decided to park his truck in the middle of thousands of country music fans and perform right off the back of his tailgate for the crowd tailgating outside the Coral Sky Amphitheater in his hometown of West Palm Beach, Florida. Little did he know at the time, that he would be performing on the main stage and in the lineup at one of South Florida’s largest country music festivals inside that very same amphitheater just 2 short years later.