Phelps personified the Thrasher brand. He started skateboarding in Massachusetts when he was 13 and never stopped. One of his first jobs was at a Massachusetts skate park in 1977. He moved back to California in the early 1980s and was working at a San Francisco skate shop when he met the owners of Thrasher, a fledgling magazine started in 1981.
Phelps started writing a product review column for the magazine in 1986 before he was moved to the magazine’s warehouse where he boxed T-shirts and hats. He was constantly asked his opinion as the issues were being published and was eventually tapped to be editor in 1993.
Although the last few years he did not oversee day-to-day operations, Phelps served as ambassador and figurehead as the magazine expanded its digital footprint as well as opened a brick and mortar Thrasher skate shop in San Francisco, the San Francisco Chronicle reported.
Phelps, who nearly always had a skateboard with him, suffered many injuries over the years. He fell, suffering a serious head injury in 2017, KNTV reported. He still continued to skate.
"I've been bit by a horse, bit by a camel, fell off a camel, fell off a horse, hit by an elevator, hit by a horse, hit by a bus, hit by a car, hit by a van," Phelps said in a 2016 interview with California Sunday. "I've been a projectile pretty much forever."
Phelps referred to his career as a “cavalcade of gnar.”
A pair of his signature, thick-rimmed Ray Ban glasses are embedded in the concrete at Potrero del Sol, a skate park near where Phelps lived and visited daily.
“I don’t like when people candy-coat skateboarding or make fun and games out of it,” Phelps told California Sunday. “It’s sacred to me.”