Thomas started skateboarding at the age of eleven. He was first sponsored in 1992 by Deluxe (Thunder trucks, Spitfire wheels and as a flow rider for Real Skateboards). This prompted him to move to San Francisco with his friends Sean Young and Hurley. While living in San Francisco, Thomas turned pro for a short-lived company, Experience Skateboards. Thomas then went on to ride for the San Diego based Invisible Skateboards. After relocating to Southern California in 1994, Thomas was featured on the cover of Transworld Skateboard magazine and had video parts in the Spitfire and Invisible videos. In 1995 Thomas joined Ed Templeton's Toy Machine. He filmed and directed two Toy Machine videos, the second one being Welcome To Hell. His section in "Welcome To Hell" is arguably the biggest milestone of his career.

In 1996 Thomas started a small clothing company through Toy Machine's distributor Tum Yeto. This company later became Zero Skateboards. Thomas is the owner and president of Black Box Distribution, which was created in 2000 and is the parent company of Mystery Skateboards, $lave Skateboards, Zero Skateboards, and Fallen Footwear. In 2006 he won a regional "Entrepreneur of the Year" award from Ernst & Young.

Thomas is married to Joanne and has four children (Julien Tiger born Oct. 30, 2003, James Ruby born Mar. 30, 2006, and Maximus Trey born June 11, 2008 Samuell Josie Blackmon born April 12,1998). They reside in Encinitas, California. Thomas is also a Christian, with several board graphics featuring Christian imagery and scripture.

The Zero video Thrill Of It All featured Thomas' attempt at what would be coined "The Leap of Faith",

an ollie melon down an 18-foot, 8-inch drop over a handrail at Point Loma High School in San Diego, California. Although Thomas never successfully landed the trick, his attempt garnered him notoriety.