The release of the Milestones series is not only about Ryan and the stand out moments in his life, but all the people who contributed to each one. “There are certain days you wake up, and you know it’s a good day to jump off something really high (Costco Gap). There are other days that catch you off guard (Bust or Bail San Francisco), and the energy of your crew gets you hyped to go for it (Hollywood High). Sometimes, you spend years throwing your body down an embankment before it ever happens (Encinitas Gap). And other days, you are skating for fun with the people you look up to and you pull off something insane (First X Games Medal at 13).  This series is a reminder that "you never know what day is going to be a milestone” says Ryan.

In 2003, at the encouragement of World Industries, Sheckler turned pro, at the age of thirteen. He immediately put an end to any uncertainty of his ability with first place finishes at the Gravity Games, Vans Triple Crown, Slam City Jam and the X Games. His success in the Skateboard Park event also earned him a Guinness World Record as the youngest participant ever to earn a gold medal at the X Games at just 13 years of age.

"It’s crazy what happens when you have fun doing what you love." - Ryan Sheckler

Who remembers Thrasher's Bust or Bail? Winning Thrasher’s Bust or Bail put Ryan on the map as a street skater at age 16. Watch the original footage from San Francisco.

Sometimes you wake up knowing it’s a good day to jump of something really high. Skateboarding is about community, just getting together and seeing what happens. This was a milestone day.

The energy was right. The right crew, the right spot, the right day. For me, this Hollywood High milestone is a reminder that who you surround yourself with can make all the difference. Torey Pudwill gets the Hollywood 16 Tre Flip Sequence.

3 Years. 65 Tries. Encinitas drop 🛹️ Relive that moment of rolling away after this battle.