In 2007, he left a career in corporate finance and accounting to pursue his passion of standup comedy. His comedy is a mix of social commentary and satire through a unique perspective based on his background: born in Baghdad to Catholic parents before moving to a town of 500 people in Georgia where he grew up on a farm. In the past few years, he has participated in several festivals, including the Laughing Skull Festival where he was a semifinalist in 2013. In 2014, Gilbert was the opening act in several theatre shows for both Aziz Ansari and Dave Chappelle.