Growing up in Seal Beach, Simon's interest in surfing was sparked by watching the crew at Harbour Surfboards build boards in the back of their shop. In the early 90s, he started shaping and building custom blanks working with legends like Hap Jacobs, Donald Takayama, and Dale Velzy, among others.

By the end of the decade, Simon had his own factory producing nearly 100 boards per week before being offered a job shaping at Channel Islands headquarters in Santa Barbara, where he would be working in the shaping bay next to the legendary Al Merrick. Simon honed his shaping skills at Channel Islands and spent a decade as "Senior Shaper" for some of surfing most elite athletes, including Kelly Slater, who rode Simons boards on his championship tours in 2010 & 2011.