When he was sixteen, he bought his first dirtbike and started to race as an amateur in New York and Florida. In 1993, after graduating from Wellsboro High School in Pennsylvania, he moved to California. It was there that he met up with Dana Nicholson who had just founded Fleshwound Films with fellow filmmakers Jon and Cami Freeman. In 1994, they released their first film Crusty Demons of Dirt showcasing the underground motocross movement out in the deserts and badlands in the United States. The film gave Enslow notoriety for overjumping a sand dune and crashing hard. The distance he traveled was never measured but it is speculated to be around 200 to 250 feet (61 to 76 m). The movie quickly spawned a sequel and, once again, Enslow made an impact by coming up short on a jump and landing on supercross racer Jeremy McGrath's practice bike. This notoriety made Enslow one of the first bike riders to receive sponsors without having a racing career.
Enslow, who by this time was making a living riding bikes, decided to break the world record of 251 feet (77 m) set by Doug Danger. He started practicing by jumping ramp jumps over kegs of beer, cars, motorcycle and other big objects at different events. In 1999, he broke Robbie Knievel's (son of Evel Knievel) 226 feet (69 m) record for most motorcycle jumps. However, Enslow's triple clamps broke, which disconnected his front end from the frame, resulting in Enslow diving head first into the asphalt. But Enslow was soon on his feet and even signing autographs before leaving the venue.
