Jennifer Ashley was born in the Chicago area. Raised in Brookfield Illinois, her early years were filled by lessons in dance and piano, singing popular hits with record player and the joys of living the idyllic suburban life. From a young age, it was clear that Jennifer possessed an incredibly creative mind and a vibrant personality.

Jennifer’s academic journey began at her public schools, and she eventually went on to obtain a BBA in Finance at Loyola University Chicago and later earned her JD from Loyola University Chicago School of Law.  Jennifer is a current member of the Illinois Bar Association.  

After completing her education, Jennifer dedicated herself to family. During this time, she raised three wonderful daughters. She was an active member of the Hinsdale Women’s Club, serving in many capacities including a term as President of the organization.  She maintained her piano abilities while continuing to develop additional skills in graphic arts, guitar, and songwriting.

In 2015 Jennifer’s career reached new heights when she began performing and teaching private piano lessons.  In 2016, she became a full partner in Randomosity Records.  The business operates a commercial recording space in Downers Grove and includes lesson space, a Record company and a music publishing company.

In addition, Jennifer is a member of the folk duo Ashley & Simpson.  The duo has released two full length albums, several singles, performed in the US and Canada and been featured at many local premier folk venues and folk festivals. Their 2019 album, “Off To Here Land,” debuted at #7 on the folk DJ charts.

Beyond her professional endeavors, Jennifer enjoys time with her daughters, nature walks and creating visual art in a variety of mediums. She is co-director at Two Way Street Coffee House in Downers Grove (a non-profit music venue) and volunteers with various folk music festivals and organizations.

Whether recording her next album, creating art, spending time with her family or volunteering in support of live music, she remains dedicated to bringing beauty to the world through art and musical performance. Jennifer Ashley’s life is a testament to how enthusiasm for creativity, community and the arts translates to meaningful and fulfilling work.