Gossling's brother, Eric, once threw a Chinese star at him in retaliation for hyper-extending his knee during a pickup basketball game when they were children.
Gossling's favorite comics to watch growing up were Steve Martin, Albert Brooks, Bob Newhart, Richard Pryor, Eddie Murphy and Sam Kinison.
After failing to get recruited by Nebraska to play football for the Cornhuskers he declined to go straight to college and instead joined the military and enlisted in the Louisiana Army National Guard.
He acquired an associate degree in Advertising design then enrolled at Southwest Texas State in San Marcos, TX.
Gossling left Southwest two semesters short of his degree when he got involved in stand-up comedy in San Antonio at River Center Comedy Club 1994 where he met Chris Duel, now a radio personality in San Antonio, then the house MC at the club.
Gossling has been seen nationwide on Comedy Central's Premium Blend, also Comics Unleashed with Byron Allen and the Game Show Network's National Lampoon’s Funny Money.