1998–2006: First sponsors, Round Three Sheckler's sponsors were the
Etnies skate shoe company and
Oakley, Inc., both of which made contact with Sheckler when he was around seven years old. Etnies invited both Sheckler and his brother Shane to the company's California headquarters, where he was given his first pair of Etnies shoes; however, his official relationship with the brand ended in 1998. In 1999, Sheckler was featured on the cover of
Big Brother magazine's controversial "Kids Issue". He was not allowed to read the issue by his parents due to the graphic material contained in it. Backlash of the publication resulted in lawsuits forcing the magazine being labeled as 'for adults only' due its inclusion of inappropriate interview questions of the teenage skateboard subjects, instructions on drug use, how to commit acts of self harm, and explicit photos throughout the magazine. In 2003, professional skateboarders and entrepreneurs
Rodney Mullen and
Daewon Song founded the skateboard company
Almost. Sheckler, together with
Greg Lutzka, was a foundational member of this team and was promoted to professional status during his time with the company. Almost team member
Chris Haslam explained in January 2012: "Almost is when Rodney [Mullen] came together with Daewon [Song] ... and Lutzka, and Sheckler." Sheckler appeared in the inaugural Almost video
Almost: Round Three alongside Cooper Wilt, Haslam, Lutzka, Mullen, and Song; Sheckler's video part is edited to the
Cure song "
Why Can't I Be You?"
2007–2012: Plan B, Life of Ryan, Superfuture After appearing in
Almost: Round Three, Sheckler resigned from the company to join the relaunched
Plan B Skateboards deck and apparel company in 2007—at that time, the team consisted of Brian Wenning,
Pat Duffy, Ryan Gallant,
PJ Ladd,
Paul Rodriguez,
Colin McKay, and
Danny Way. Sheckler's MTV reality series,
Life of Ryan, premiered in August 2007. Jason Carbone and Sarah Kane were the show's executive producers, and both of Sheckler's brothers starred in the series, alongside his childhood friends Tony, Casey and Taylor. Following his recruitment into the ranks of Plan B, Sheckler successfully cleared a gap on
Bob Burnquist's
Mega Ramp construction (a segmented ramp that typically consists of , , or -foot gaps, and a -tall "quarterpipe" ramp) in April 2008, with Way also in attendance. Sheckler appeared in the final section of Plan B's
Superfuture promotional video, released in 2008, which also consisted of footage from Sheckler's Mega Ramp skateboarding. The
Superfuture part also featured a historic trick that Sheckler completed at a location known as the "Costco gap." Skateboard photographer Atiba Jefferson and filmer Ricki Bedenbaugh were present when Sheckler completed the trick, and both recalled in 2013 that they were very nervous due to the
degree of difficulty involved. The trick was finalized on the fourth try and led to Sheckler appearing on the cover of
The Skateboard Mag magazine, which Jefferson shot. Jefferson later described what he observed: "No hands down, no nothing. He just, like, once he caught it, he just ... set it down." The Red Bull online series "Sheckler Sessions" was launched in June 2012 and the first episode featured the Plan B team at the Zumiez "Couch Tour" event. In an online interview that was published in September 2012, Sheckler revealed that, at the time of the interview, he was in the process of building a new skateboard training facility.
2013–present: Teasers, Dew Tour Streetstyle, True By the beginning of 2013, discussion continued, among both skateboarding fans and the industry, regarding whether the relaunched Plan B team would release its first full-length video. Way confirmed that the production process was underway in a January 2013 interview for the online magazine
Jenkem, during which time he mentioned Sheckler: They [Plan B team] are doing the best tricks consistently with every variation of it down the biggest stuff. And it doesn't take them long, so they have a lot of it. For example when we went to China recently, Sheckler alone has more footage from his one trip than all of the Girl team from their China trips combined. I'm not trying to diss on Girl, just trying to put it in perspective, what I think his strengths are. Sheckler then appeared in the second teaser for the inaugural full-length video, which was published online in February 2013. Sheckler is filmed performing a kickflip in a street-based setting, while teammates
Torey Pudwill and Duffy are also present. A promotional video was released in May 2013, commemorating Sheckler's 15th year with the Etnies brand. Sheckler explains in the video that he received his first pair of free skate shoes from the company and skated in Etnies shoes ever since. The final episode of the second season of the "Sheckler Sessions" online series was aired in November 2013 and signaled the conclusion of the entire show. Titled "Southern Comfort," the episode was filmed in the U.S. state of
North Carolina, and featured fellow professional skateboarders Zered Bassett and Bobby Worrest. The
Volcom clothing and apparel company announced in January 2014 that Sheckler rejoined the brand's team of sponsored skateboarders after a period of sponsorship during the early part of Sheckler's career. The announcement was made in the form of a 15-second online video in which Sheckler signs the Volcom contract on January 21, 2014. The first official trailer for the Plan B full-length video was published in July 2014, and served as the announcement of the video's title: "True." Following victories at the 2012 and 2013 Dew Tour Streetstyle events, Sheckler won the contest for the third consecutive time in August 2014. The Streetstyle event was a new downhill concept added to the tour in 2012 and spanned across four blocks above San Francisco's Bay Bridge. The event returned to San Francisco in 2013 and was held in Portland, Oregon, U.S., in 2014. On January 10, 2022, Sheckler announced his departure from Plan B after 16 years of sponsorship. ==Video games==