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The 'holeshot' is a term used primarily in motorcycle racing (but also motorsport racing in general) for the rider who is the first one through the first turn. In some cases a holeshot award will be given, which is a prize separate from winning the race. In drag racing, it refers to a heads-up race where the slower car beats the faster car by leaving the line (legally) first.
Many motorcycle racers consider the start to be the most important part of a race, and it is particularly important in those forms of the sport where the tracks are very small, tight and difficult to pass on. This is particularly relevant in motocross where racers line up in alongside each other rather than behind each other in tarmac-based sports. The term had also found its way into Bicycle Motocross racing by the early 1970's due to the fact that BMX is a bicycle derivative of Motorcycle Motocross and have inherited many terms from that sport. In BMX the holeshot is even more important since BMX races are single lap 25 to 45 second races with only a few opportunities to pass in that time period. Achieving the holeshot in BMX will earn you a victory the majority of the time.
This term can also be used to describe the starting performance of a vehicle. A vehicle that is fast off the line (though not necessarily fast overall) is said to have a good "holeshot".