Holly Dai was born in Seattle, Washington and grew up in San Diego, California. Her family was artistic and they were always making something to decorate the house for different holidays. She confesses to not being very athletic in high school but she did take four years of dance classes as a way of getting out of high school PE. She shares that she has always loved vintage patterns and clothing, collecting vintage patterns on eBay in her youth. She got her start sewing when a neighbor taught her to read a pattern, cut fabric and build a Renaissance dress for herself in high school.
In 2008 in Seattle, a friend introduced Holly to Burlesque. She began to help out at Burlesque shows by kittening. At a Burlesque show, the kitten is the person who picks up clothes and props after an act is done. After being around Burlesque shows for a year or so, Holly decided she would perform. When she moved to Portland around 2009, she found a group of performers to work with. They did shows at the Hawthorne Theater. Soon she organized qualified Burlesque people to teach different aspects in the art of striptease, and they started the Rose City School of Burlesque. She gives credit to Charlotte Treuse for pushing her toward the Classic Burlesque style. Subsequently, in 2011, Holly won the Most Classic Award at the great Boston Burlesque Exposition.
Holly started her costume boutique shop on Etsy in 2010, and in 2013 she founded the All That Glitters Burlesque Academy. That same year, she and a collection of other performers decided to organize a big event, the Oregon Burlesque Festival in Portland. At the time, there was no other Burlesque Festival happening in Oregon.