Bolder Options was established in 1993 as a response to a community needs assessment that determined there was an urgent need for mentoring programs in the Twin Cities. As a result, the Minneapolis Jaycees Charitable Foundation (MJCF) established a task force of representatives from Hennepin County Probation, Operation De Novo (Hennepin County's diversion program), the Minneapolis Police Department, public school authorities, and other citizens from the community to conduct a needs assessment of high-risk youth in the Twin Cities. The task force agreed unanimously that a void in one-on-one mentoring opportunities existed and recommended the creation of a youth mentoring program that would use structured activities and athletics to motivate at-risk youth. Bolder Options became an independent 501(c) 3 in June of 1998.

In 2004, a growing need for quality mentoring and intervention programs in St. Paul drove representatives from St. Paul Public Schools (SPPS), SPPS Truancy Intervention Program (TIP), the St. Paul Police's juvenile unit, and Ramsey County Attorney's office to meet with representatives from Bolder Options to discuss the possibility of expanding its innovative mentoring program to the St. Paul community. After Bolder Options was recognized as one of the best charities in the nation on the Today Show in 2006, Bolder Options gained the capital, funding, and political and community support to pursue this expansion. St. Paul Mayor Coleman hosted a number of meetings and events to announce the arrival of Bolder Options. The agency hired a St. Paul Program Coordinator and began serving youth from the Ames Lake Neighborhood on St. Paul's East Side in January 2007.

In 2008, Bolder Options expanded to the Urban League in North Minneapolis. The agency now serves Twin Cities youth from 3 locations.

So far in 2010, Bolder Options has hired a Rochester Regional Director. The agency expects to begin serving youth in the Rochester area in Summer of 2010.