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A native of New South Wales, Australia, Simon grew up in a small country town with a population of roughly 500 people. Initially interested in architecture in high school, once he found out more about engineering, he was hooked. He began his design engineer career working on numerous projects for the Sydney 2000 Olympic Games, including the Olympic Athletes Village, a large rail tunnel, and a 20-kilometer sewer overflow project, which tunneled under Sydney Harbour.

Eventually following his steady love from Sydney to the Bay Area, he began working for BKF in 2000. The transition to life on the Peninsula took some time. He jumped right in to learn design, read numerous books and plans, and sought out those in the office who were working on interesting projects and were willing to provide mentorship.