Rob Dolan's career began in South Australia, where he learned the art of making wine from the ground up. He developed and refined his skills under the instruction of two of Australia's most distinguished teachers. It was during this time that the budding winemaker and towering sportsman, known as "Sticks", was also a dual premiership player for the Port Adelaide Football Club.

In 1991, Rob Dolan became the winemaker at Yarra Ridge. The small family winery provided Rob with the opportunity to experiment, which enabled him to hone his winemaking skills. His efforts were immediately recognized on the international show circuit. Rob proceeded to plant his first 'sticks' grapes in the mid 1980's.