Jaimee grew up in her family's restaurant in Maryland, on the East Coast of USA. She moved to California to pursue her love of painting at university, with the aim of becoming a college professor one day. She was living in San Francisco, and while figuring out her career options, she worked back on the floor in a restaurant. While working as a server at the famed RN74 restaurant under the tutelage of Rajat Parr, she started to bury herself in wine books, meeting winemakers who would visit the restaurant.
She remembers, "I just fell in love with the idea of wine. I'd always loved being outside, and working with my hands, that tactile element. You find that in the winemaking environment too."