[7] Webb was born in Newport, North Carolina where his father Robert a professional surfer raced motocross in the 70s.

[2] He won his first AMA National race on June 28, 2014, in the 250 cc class at the Muddy Creek Raceway in Blountville, Tennessee and, was named the 2014 Monster Energy Supercross Rookie of the Year.

After Webb's second supercross championship, he was nominated for his first ESPY Award in the Best Athlete, Men's Action Sports Category.

From then on, Webb would be the main rival to Honda rider Jett Lawrence, who was making his debut in the 450 SX class.

Webb picked up four wins and five additional podium finishes on the season, which placed him second in the 450 SX points standings, later revealing he’d been dealing with a thumb injury sustained at round 9.