Born in Montana and raised in Phoenix, Jesse was introduced to the sport by his grandfather Burton Farley, a trainer in the Northwest and at Turf Paradise, and by his aunt, longtime racing official Coralee Farley. At 19, he became the Track Announcer at Fair Meadows in Tulsa, Oklahoma, in 2007 and was named Track Announcer at Will Rogers Downs and Blue Ribbon Downs the following year. He also served as Director of Racing at Fair Meadows and Will Rogers Downs in 2013 – 2016. Since 2018, Jesse has served as Sales Announcer at Fasig-Tipton in addition to his role as Account Executive. Jesse also serves as the President of the Board of Directors of the Blue Grass Farms Charities.