 In 2008, Strain participated in his first professional skateboard contest for the original "Battle at the Berrics" where he won his first round match against Sean Malto, only to be knocked out of the contest in the second round by Eric Koston.He received his first signature skateboard with the brand Sk8mafia in 2008 before a split with the brand and receiving his next signature skateboard with City Skateboards in 2009.In 2010 Donovan got involved with the Make-A-Wish foundation when he was able to help grant a wish for a kid from Florida named Alex that requested to meet him.