Raised on his family's expansive Thoroughbred operation, Live Oak Stud, Chester Weber came about his love of horses naturally. Consistently among Florida's leading breeders by the earnings of its Thoroughbred race horses, Live Oak has been in the Weber family since 1968. The farm is situated in Ocala, the heart of Florida's horse country which boasts an abundance of champions in many different breeds and disciplines.

Surrounded by the exploits of Live Oak's successful runners, as a child Weber dreamed of becoming a jockey, although he physically outgrew that possibility. Soon it became clear that it wasn't the race horses which stirred his heart and ignited his competitive nature. In the 1980s and early 90s, Live Oak bred and raised quality show Clydesdales. It was in working with the draft horses that Weber first discovered his passion was not in the saddle but in the carriage.

With perseverance and practice, he honed his driving skills, quickly advancing from showing draft horse teams to the speed and challenge of combined driving. The Clydesdales initially launched Weber's driving career, but it has been his stable of top European warmbloods which has enabled him to compete successfully at the highest levels.

In addition to a full competition schedule, Weber works diligently to organize the annual combined driving event, CAI Live Oak, which is held at the farm every March. One of only two international events in the United States which is sanctioned by the Federation Equestre Internationale, CAI Live Oak regularly serves as a USET and Canadian Equestrian Team selection trial for the various driving divisions. As one of the country's largest carriage driving events, the show draws high praise from contestants who travel from around the world to compete there. The event continues to attract a growing number of enthusiastic spectators