- Dropped out of college after one year, but was inspired to study improvisational comedy after seeing the iO (aka ImprovOlympic) 15th-anniversary show in Chicago.
- Worked for the Chicago Transit Authority while studying and performing improv at iO, Second City and the Annoyance Theatre.
- Spent two years in Amsterdam with the comedy troupe Boom Chicago.
- Hired to be a writer (along with his high-school classmate and writing partner, Dave Stessen) on The Mindy Project after series creator Mindy Kaling noticed him on HBO's Eastbound & Down; joined the cast when Kaling created a character especially for him.
- A founding member of the improv group the Lindbergh Babies.