Jayson is a fifth-generation Vermonter who grew up in the Northeast Kingdom and was introduced to horses when he met and fell in love with Bekki in 2014. He shared a few of Bekki's other interests (adventure & nature) before then, and spent the first decade of his adult life traveling by foot, bicycle, and bush plane around Kenya, Alaska, Spain, and 33 other countries and US States, before returning to northeastern Vermont. There he worked for 20 years as a Forester and Operations Director of the NorthWoods Stewardship Center (East Charleston, VT), pursuing his interests in ecology, teaching, and stewardship of the land.

Jayson and Bekki were married at Round Robin Farm (South Royalton) in 2016, where he miraculously survived their gallop away at the end of the ceremony. In 2017, he started a new consulting forestry business "Saw-Whet Forestry, LLC", which serves mainly central Vermont clients. He also shares Steve and Bekki's love for mountains, but has his hands full trying to keep up with them on the ski slopes.