Cole gained attention following the completion of a number of difficult tricks: 360 flip, Switch Frontside flip and Backside 360 ollie down the staircase at Wallenberg High School in San Francisco, California. Backside
360 Kickflip down the
Carlsbad gap in
Carlsbad, California, &
Martin Place Amphitheatre in Sydney, Australia. But most notable a Backside flip, Switch Frontside flip and a Backside 360 ollie down the "Love Park" fountain in Philadelphia as seen in his Transworld In Bloom, and Fallen Ride the Sky Video Parts. Cole was formerly a member of the G-Spot Skate and Snow team, before being sponsored by
Enjoi and
Zero Skateboards. Reflecting on the early stage of his career, Cole stated in a 2009
Thrasher interview: I really like Enjoi. The brand is a breath of fresh air. I was on the East and detached from any team member so I was kind of a guy who rode the products, but not on the team. Especially 'cause they are a group of friends. I hung out with Marc Johnson a couple times. He was totally cool. I have always been a huge fan of his, so that was great. Cole's other past sponsors include
World Industries, Axion Footwear,
Tensor Trucks, Ezekiel clothing, Speed Demon Bearings,
Enjoi,
Circa Footwear, eS Footwear, Omit Apparel, but the most significant were
Zero Skateboards and
Fallen Footwear. In May 2013, following a bet between Cole and professional skateboarder
Mike Mo Capaldi, Cole became a team rider for the Glassy brand—Capaldi and Cole, who are teammates on the DC Shoes team, agreed that Cole would join the Glassy team if he lost to Capaldi in any contest. The pair competed in the
Battle at the Berrics 6 contest on May 18, 2013, with Capaldi being the winner; however, as of July 9, 2014, an announcement had not been made regarding the new sponsorship arrangement and Cole does not appear on the brand's "Team" page. A segment on
Tony Hawk's RIDE Channel, published on July 6, 2014, asked Cole—who was riding a blank, black-colored skateboard deck at the time—if he knew of any possibilities for his next skateboard deck sponsor and he indicated that he was not aware of any options at the time. On June 27, 2014, Cole posted an announcement of his departure from Zero on the social media platform
Instagram, without a corresponding reason; however, a reply from the Zero Instagram account thanked Cole for his "loyalty & dedication." Cole is perceived as an "ambassador" for skateboarding, representative of the generation that he is a member of, and he explained his perspective on the matter in an October 2014 interview: When I started getting asked to talk about skateboarding in front of people, I found that my love for skateboarding wasn't the same as everybody else's. I have a skate rat mentality, much like the kids that are out there skating, and less like the older, more jaded people that get paid to do it. I love it so dearly, and I feel like the people that get paid to do it and represent it in the public eye, they should really love it too ... I also just wanna live a full life and it not to be all about just tricks at spots ... Who should represent this sport? Someone that dedicated their life to it and loves it. ==Company owner==