Guinness grew up on his family's farm in Northern California, where his father grows grapes,herbs and raises cattle. He spent much of his youth working on the farm, driving tractors and working in the farm shop. While in college at the University of Nevada, Reno, Guinness worked at Northstar ski resort in various capacities- a stint as a landscaper and operating heavy equipment.
After college, Guinness moved to Kentucky and began working at Three Chimneys Farm in November of 2004 in the Old Bradley broodmare division. He spent a number of years on the farm before joining the sales team in 2007. Guinness spent 5 years as the Director of Sales at Three Chimneys Farm before moving to Blackwood full-time in the spring of 2014.
The first thoroughbred race Guinness attended was in 1996, at Belmont park with his Aunt and Uncle. He was always a huge sports fan, but it was then he found his love for racing and handicapping.
Guinness lives in Lexington with his wife Lisa, daughter Olivia, son Tripp, and their two dogs.