While in high school, Brown got his first experience around horses working with standardbred trainer Paul Kelley. While at Cornell University, Brown worked summers for Hall of Fame trainer Shug McGaughey. While intending to undertake veterinary studies - even interning with Steve Allday - he instead took fulltime employment with Hall of Fame trainer Bobby Frankel following graduation.

Brown opened his own racing stable in November 2007. In ten years, Brown has achieved over 1,000 wins including eight Breeders Cup races and the 2017 Preakness Stakes. Last year’s Preakness success follows a career year for Brown. In 2016 he was the leading trainer in America by earnings and number of graded stakes wins, and earned the Eclipse Award for Outstanding Trainer.