While growing up in Mechanicville, N.Y., Brown frequently attended the summer meet at nearby Saratoga Race Course with his family. He got his first experience around horses during high school working with Standardbred trainer Paul Kelley at Saratoga Raceway. While he was a student at Cornell University, where he was headed toward a career as a veterinarian, Brown worked summers for Hall of Fame trainer Shug McGaughey. By the time he graduated from Cornell, Brown had decided that he would rather train horses and continued working for McGaughey.
He took an internship with a veterinarian then accepted an opportunity to work for Hall of Fame trainer Bobby Frankel in 2002. Brown earned promotions in Frankel's high-profile operation and was handling a division when he decided to go out on his own in November 2007. Brown has had a meteoric rise to national prominence, winning with the first horse he started at Saratoga Race Course and his first Breeders' Cup starter, Maram, in 2008. In 2011, Brown earned his first Grade 1 victory, trained his first champion, Stacelita, winner of the Beverly D., and finished 16th nationally with $5.2 million in purse earnings. In 2012, Brown trained his second champion with Zagora, winner of the Breeders' Cup Filly & Mare Turf.
Brown ran his first horse in the Kentucky Derby in 2013 and finished a good fourth with Normandy Invasion. Brown has won such races as the Arlington Million and Sword Dancer Stakes but his biggest weekend of racing in his career so far had to come at the 2014 Breeders' Cup where he won three races, including Lady Eli's win in the Juvenile Fillies, Bobby's Kitten's Turf Sprint tally and Dayatthespa and Stephanie's Kitten running first and secodn in the Filly & Mare Turf. In 2015, he won the Breeders' Cup Filly and Mare Sprint with Wavell Avenue and the Breeders' Cup Filly and Mare Turf with Stephanie's Kitten.