During his teenage years in Akron, Ohio, Hollendorfer learned his racing lessons at Acton Park in Cuyahoga Falls, Ohio. The track is long gone, but Hollendorfer, a Hall of Fame inductee in 2011, continues on. He is the dominant trainer in Northern California and consistently develops national-caliber graded stakes horses. Hollendorfer became the fourth trainer in history to reach the 6,000-win milestone, on September 3, 2011.
Hollendorfer's graded staked winner list includes King Glorius, his first two Kentucky Oaks winners - Lite Light and Pike Place Dancer - Event of the Year, Tuscan Evening, Heatseeker, Kentucky Oaks winner Blind Luck and Breeders' Cup winners Dakota Phone and Songbird.
Hollendorfer's racing career started during a visit to San Francisco when he was in his early 20s. He talked his way into the backstretch at Bay Meadows and talked his way into a job with trainer Jerry Dutton. He later worked for Jerry Fanning and began saddling horses in his own name in 1979.