Because jobs were – and continue to be – few and far between, especially for youth with no formal experience, our first program was an advertising service for teens selling odd job services called the Odd Job Squad, a program since replicated in other cities and towns and soon to scale nationally online. This was followed by BizVenture!, our 70-hour entrepreneurial training program. Jerry Whaland – a local teen who ignited the idea for YES in 1997 -- joined YES' teaching staff after completing the first BizVenture! program, later joined by YES alumni, Dan Richards.

In 2000, YES moved out from under ORP's umbrella by incorporating, receiving our tax-exempt 501(c)3 status, and moving into a storefront donated by local entrepreneur. With funding from the Community Foundation of Western Massachusetts and a unique partnership with NFTE, the National Foundation for Teaching Entrepreneurship, and local schools, organizations, business associations, and youth groups, YES trained 36 NFTE teachers to teach youth in in Athol, Greenfield, Turners Falls, Charlemont, Shelburne/Buckland, and Cummington.

In 2001, with funding from the Public Service Endowment at UMass, Amherst, we piloted our Co-op BizTeam effort, a 140-hour social enterprise planning project for BizVenture! alumni. The BizTeam developed a plan to launch a cyber cafe and copy shop in downtown Orange. Their plan edged out 25 others to win the National 4H Council/USDA Cooperative Business Plan Competition and enabled YES to acquire a mortgage to purchase two adjoining buildings in downtown Orange in 2003 and launch the YES BizCenter and Teen Cyber Cafe in 2004. These ventures continue to prepare youth for the workplace and business ownership and to generate funds to support YES' programs.