Speaking to Denver's WestWord, Shepherd addressed his days as a "roadie" for Nirvana. Ben says, "I didn't really roadie with them. I just went on tour with them. We all did all that sh!t. It was a blast to get out."
In 1989, Nirvana's second guitarist Jason Everman left the band. Shepherd knew the band and actually introduced them to Chad Channing, Nirvana's drummer for their first album. So, Nirvana considered adding Shepherd as a second guitarist. However, when word got out, many other Seattle bands encouraged Nirvana to stay a three piece.
Soon after that, Shepherd auditioned to be the bassist for Soundgarden. But, ironically, Jason Everman was chosen over him. However, shortly after Everman joined the band, he was fired and Shepherd became Soundgarden's bassist.