Born and raised in the Kittitas Valley, Toby graduated from Central Washington University with a degree in education. He taught for a short while before transitioning to opening and operating a successful restaurant, which he later sold. Toby then ventured into general contracting, specializing in remodels for clients. After a few years, he began "flipping" properties and investing in real estate, ultimately leading him to a full-time career in the real estate industry since 2011.